How to Build a Sales Machine | Max Freeman, Ramp
- Ramp treats sales hiring as a Moneyball exercise in finding “undervalued assets” and then paying for disproportionate output. Freeman hired investment bankers for their work ethic, business fluency, and credibility with CFOs; their background also reduced the need to train concise cold-call and email communication. Ramp could pay an SDR roughly 2x market if that person scheduled 40–60 qualified meetings, 4–6x the conventional expectation. For experienced technology sellers, he targets top performers at companies that reached nine-figure revenue despite weak NPS, premium pricing, and little inbound demand.
- The best career decision is usually the strongest market, talent density, and founders—not the grandest title or equity package. Freeman left a mid-level account-manager role to become an SDR again because Ramp addressed trillion-dollar card, bill-pay, travel, and banking markets with what he viewed as an exceptional product and engineering team. Joining a mediocre company growing 20–30% for a vice-president title is, in his framing, “the wrong exchange.”
- Freeman’s central operating thesis is that “sales is largely an engineering problem.” Ramp began building OATS—its outbound sales automation infrastructure—in late 2020 or early 2021 to assemble lists, surface account signals, find contacts, and automate distribution while sellers concentrated on customers. The system must remain recursive: A/B-test continuously, learn from high-quality manual outreach, and optimize for meetings rather than replies; just under 1% email-to-meeting conversion is “a very, very strong standard.”
- Shorter sales cycles come primarily from qualification, not persuasion or premature verticalization. Freeman tests whether a buyer can influence change and is motivated to act within 12 months, then asks that person to bring the relevant executive into the next meeting while Ramp contributes its own technical resources. He would verticalize only when market coverage becomes constrained—using a transition from roughly 3% to 5% share as an arbitrary example—and faster conversion matters more than broad capture.
- Early compensation plans manufacture false precision, so Freeman recommends 100% OTE for at least the first two quarters. A guessed quota can either produce an accidental six-figure windfall or make a solid seller feel like a failure; founders should wait for pipeline and sales-cycle data and hire sellers in pairs for comparison, competition, and shared onboarding. Once a company has multiple products, however, he supports excessive incentives, including setting quotas 2–3x higher for new products.
- Ramp turns onboarding into a gated, 60–90-day production system whose rigor is itself a talent filter. Reps must master product, buyer personas, competitors, and internal operations; pass discovery and demo certifications “flawlessly”; and receive their lead routing and accounts only afterward. Freeman says the strongest leading indicator is an “annoying” new hire who asks thoughtful questions constantly, while silence—or questions any AI or Notion bot could answer—is usually weak signal.
- Ramp’s execution advantage extends beyond closing deals into customer success, forecasting, and AI-assisted seller productivity. Technical customer-success specialists help drive NDR and earn future cross-sells; forecasting is reportedly kept within 5% through systems plus individual accountability; and Ramp Revenue cuts pre-call research from 15–30 minutes to at most 90 seconds. Freeman’s leadership constraint is now resisting the urge to rescue every deal: “Maybe we’ll win, but I won’t necessarily make my sales team better.”
1. Ramp pays for output, not conventional sales pedigrees
Freeman’s early hiring arbitrage was investment bankers: they were “programmed to work,” understood business, and could cold-call a CFO by credibly saying they had just left Goldman TMT investment banking for a credit-card startup. Their backgrounds also reduced the need for early teams to train concise cold-call language and correct cold-email grammar. Mike Webber from Citi and Sam Buck from Goldman subsequently came to run substantial parts of Ramp’s business.
The economics were deliberately aggressive: Ramp paid roughly twice a typical SDR’s compensation but expected 40, 50, or 60 qualified meetings—4–6x conventional output. When Stebbings called 50 monthly meetings unimpressive, Freeman clarified the role distinction: lower-end SDRs could book more than 50 rigorously qualified meetings monthly, while inside sales reps were described as making 10–12 calls daily. He later said AEs make about 8–10 calls daily and that some Ramp sellers exceed 15, so the transcript does not cleanly reconcile the different AE figures.
Freeman’s technology-company filter is pure “Moneyball”: find the number-one or number-two sellers at businesses that surpassed nine figures of revenue despite low NPS, weak third-party reviews, premium pricing, and limited inbound demand. Those sellers learned to manufacture pipeline and navigate difficult cycles; after moving to a product that generates unsolicited customer praise, “that’s where the magic happens.”
A résumé number is never enough. Freeman decomposes quota attainment into inbound, outbound, expansion, founder-sourced business, and inherited accounts, then makes candidates replay two deals chronologically and diagnose a painful loss. Even an unavoidable relationship disadvantage should have been surfaced early and confronted directly—not discovered after the seller consumed the company’s resources.
Freeman says his hiring mistakes came from overvaluing pedigree and famous brands. Candidates still need the independence and “x-factor” to operate without excessive internal support, plus genuine obsession with Ramp and the willingness to give it their all.
2. Candidates should diligence the market before negotiating status
Ramp’s business case tests three dimensions: knowledge of Ramp, research into the prospect—including its 10-K where relevant—and core selling ability. Freeman looks for managerial confidence, second- and third-level questions, quantified pain, and articulated value, then applies two blunt tests: “Would I buy a product from this person?” and, for managers, would he personally work for them?
Freeman argues that a startup seller should prioritize market, talent density, business quality, and founders over cash, shares, or title. He voluntarily moved backward from mid-level account manager to SDR because cards exceeded $1 trillion annually and bill pay, travel, and banking were each multi-trillion-dollar markets: broad structural growth could create a career boost.
Technical founders need not arrive as gifted sellers, but they must be sales-minded and receptive to market feedback. The practical test is whether they will devote engineering capacity to growth systems and evolve the product for demanding customers. Freeman credits Ramp’s technical leadership—especially Karim’s early engineering support for OATS—with doing this; the early engineering bench felt “more like a science lab or SpaceX.”
3. Outbound advantage is becoming proprietary infrastructure
Ramp began building OATS—“outbound sales automation team”—before the AI wave, in late 2020 or early 2021. Engineers studied Freeman’s manual workflow and automated account lists, contact information, templates, and signals such as new hires, shared universities, and common investors, leaving sellers to discuss customer problems and implement solutions.
Freeman’s pitch to founders is direct: assign one or two excellent engineers because “the coolest product in the world” is worthless without paying customers. A three-to-six-person go-to-market team manually sending a few hundred emails and perhaps making 100 calls lacks the reach, brand exposure, and leverage required across a large TAM.
Stebbings’ pushback—worth keeping—was that 20 deeply researched, personal messages might outperform automation. Freeman agreed, but argued for a recursive system: continuously A/B-test, preserve room for manual outreach, identify why it performs, and apply those lessons at scale. Ramp now has at least half a dozen growth engineers dedicated to go-to-market products.
Reply rate is the wrong objective because a 5% response rate filled with unsubscribes or requests never to be contacted creates nothing. Freeman tracks meetings booked; slightly below 1% email-to-meeting conversion—roughly one meeting per 100 messages—is “a very, very strong standard.”
4. Qualification creates speed; value protects price
Freeman believes businesses commonly verticalize too early while they should still capture broad market share. He would introduce vertical specialization when opportunity coverage begins tightening—using a move from roughly 3% to 5% market share as an arbitrary example—and the next source of leverage is converting leads faster, as he says Oracle, Workday, and SAP did.
The strongest sales-cycle compressor is stricter qualification: determine whether the buyer can influence implementation and is motivated to change within 12 months. To test that authority, offer senior technical resources for the next demonstration and ask the contact to invite a relevant executive—“give in order to receive.” Whether Susan, the purchasing VP, attends is an immediate test of the contact’s influence.
Freeman resists early discount negotiations because price talk after an initial call usually signals an inexperienced buyer, except in very small, one-call transactions. In larger deals, seller and buyer should quantify ownership cost, margin impact, accounting efficiency, and staffing leverage; if the product creates seven-figure value, saving two dollars per seat should not govern the decision.
5. Compensation should follow evidence, then shape strategic behavior
For the first AE or SDR cohort, Freeman recommends 100% OTE for at least two quarters: “You simply don’t know what you don’t know.” A guessed quota can accidentally owe someone six figures, while an unattainable number can turn a respectable 250 against a 500 target into lost confidence that is difficult to recover.
Once a sub-six-month sales cycle produces enough evidence—ramp progress, stage progression, pipeline, and expected outcomes—the company can set an ambitious but defensible quota. Founders should hire in pairs: onboarding one person is expensive, a lone rep cannot be benchmarked intelligently against the founder, and two hires create both cooperation and competition.
Early companies should concentrate on making 20 customers excited about one product rather than weakly serving six customers across many products. At Ramp’s later stage, incentive design becomes more aggressive: Freeman considers over-rewarding launches vital and may set quotas 2–3x higher for new products to build reference customers, use cases, and momentum.
6. Onboarding is a gated operating system, not a training presentation
Ramp’s curriculum covers four things in sequence: product and technology, buyer personas, competitive environment, and internal operating machinery. Freeman says modern buyers possess an “immunity to nonsense”; they can retrieve answers quickly and expect sellers to do the same, making shallow product knowledge professionally useless.
The program lasts 60–90 days by segment, with an intense first four weeks combining hands-on work and independent study. Reps must pass discovery and demo certifications flawlessly before entering the lead router or receiving accounts, although they can begin communicating with customers within two to four weeks. Preparation includes Gong recordings, live calls, team meetings, funnel reviews, forecasting, and close manager support on the first call.
Freeman says roughly 70% of reps impress him and 30% fall below Ramp’s standard. He reviews calls personally and brings the rep and manager together when quality misses; relying solely on enablement is failure because line managers must help create the future “killers” who will expand their own capacity.
Ramp’s ramp periods reflect sales-cycle length: 60 days for mass-market inside sales, 90 days for sales reps, four months for mid-market, five for enterprise, and six for strategic enterprise. The positive leading indicator is the “annoying salesperson” who asks thoughtful questions constantly, seeks deal coaching, and asks for help with customer and product issues; the reverse correlation is weaker, but silence is concerning.
Freeman agrees that many young professionals want a different balance of remote work, mission, and burnout avoidance, but says leaders are responsible for building a contagious high-intensity culture. Ramp has young sellers who come in on Saturdays and Sundays without being asked; that culture also filters out people unwilling to follow it.
7. Accountability turns customer success and forecasting into engines
Freeman rejects the blanket claim that customer success should become paid professional services. Ramp’s team includes highly technical specialists and certified accountants fluent in ERP and accounting systems; the product economics can subsidize that support, while excellent implementation drives NDR and earns the right to cross-sell and upsell an expanding product set.
Ramp’s finance partner Asher reportedly built forecasting models that keep the overall business within 5% deviation. The cultural mechanism is accountability: forecast discipline affects performance reviews, individual meetings, and quarterly reviews at rep, frontline-manager, and segment-leader levels—even if compensation is not calculated directly from forecast accuracy.
Pipeline reviews happen weekly and are run by segment managers, with line managers present and individual contributors rotating through their most important deals. Freeman eliminated separate forecasting meetings because system-based forecasting made them duplicative “imitation of work.” Reviews instead concentrate on deals at risk and losses that might be controlled.
Ramp most often loses to the status quo, which Freeman calls its own failure: the team did not connect to a sufficiently important problem, create urgency, or reach someone with career and political capital at stake.
Brand marketing also helps outbound as an informational backdrop. Sports events, private dinners, and Ramp’s musical about paying bills give sellers and prospects reasons to engage; Freeman says the effect is difficult to substantiate with data but correlates with cycle times and customers’ willingness to expand their use of Ramp.
8. AI increases capacity, but leadership remains the scaling constraint
Ramp Revenue automates research that once consumed 15–30 minutes before a call—perhaps 10 for an exceptional rep—and reduces it to at most 90 seconds. It also closes the skill gap by surfacing product launches, financing changes, sponsors, and prior Ramp users that an average seller might miss, converting saved time across hundreds of reps into additional selling days and eventually higher quotas.
Freeman can imagine commercializing internal products, but warns that enterprise software cannot simply be switched on to “see how it goes.” Ramp Revenue would need dedicated salespeople, implementation, customer success, and marketing; timing and sequence must match the organization’s capacity. His indispensable current tool is Inspect, an internal coding agent on Harness used for custom demos and customer-configuration analysis.
Freeman’s own development challenge is resisting personal intervention in every consequential account. Taking over might win an individual deal while teaching the organization that “when something gets important enough, Max will just step in.” He instead wants leaders to be a “dual threat”: operate at a high level while staying in the trenches; he still sends at least five cold emails every day.
Working directly for Eric early on felt like earning “50 MBA degrees in nine months.” Dave Schneider’s mentorship, Colin’s experience taking companies public and selling businesses, demanding accountability, and the need to prove his value daily all accelerated Freeman’s development.
Dave Schneider gave Freeman the memorable formulation that sales effectiveness has three categories: “First: you are God. Second: I don’t know yet. Or third: you’re damn fired.” Freeman’s advice to new hires follows naturally: obsess, solve problems, bring a diagnosis and proposed fix when seeking feedback, and “take the blame and give the credit to others.”
Full transcript
There are 3 categories of effectiveness in sales. First, you are a god. Second, I don't know yet. Or third, you're getting fired.
Today, we're joined by Max Friedman, VP of Sales at one of the fastest-growing companies in the world, to explore how to think about onboarding and how to attract the best talent. By the way, he believes that the best sales managers come from bankers. We'll discuss how to think about employee retention and how to motivate sales managers with new products. All this and more in one of the most thorough and detailed shows on how to build a sales machine.
We pay twice as much as a regular SDR earns. But you know what? You have to schedule 40, 50, 60 meetings, which is 4–6 times more than a typical SDR has to do. Some salespeople at Ramp make over 15 calls a day. You should approach hiring for a go-to-market team like Billy Beane. Sales is largely an engineering task if you break it down into parts. This is the task of the data infrastructure. This is a mathematical problem.
1. Why Ramp Hires Investment Bankers Into Sales
Ready to start? Max, I'm so excited about this, man. I think when people think of the fastest-growing companies, they immediately think of Ramp. Eric told me that all the accumulation of income is your merit, so no pressure, but the next hour is going to be a real treasure trove of wisdom, okay?
I like it. I am charged. But I think I get too much credit. The Ramp team has great professionals, and I am very lucky.
Well, that's great, because I was just talking nonsense. He said you were a complete idiot.
But quickly moving on to the show, a sales team is nothing without the people in it. When we talked before this, I said we don't do preparatory calls.
No, Harry is too old for preparatory calls.
But you made me do a prep call, and I'm so glad you did, because you said you like to hire bankers and turn them into salespeople. Why?
Not just bankers. I believe there are many undervalued assets in the market whose résumés don't reflect their true alpha. But let's start with the bankers.
When we were forming the first go-to-market team at Ramp, we hired quite a few investment bankers, and now they run pretty large parts of the business. That's why I tend to take that approach.
First, bankers are programmed to work. The concept of a 9-to-5 schedule is completely foreign to these people. Secondly, they have intelligence, business acumen, and a tremendous drive, which you don't always find when hiring sales professionals.
The third point for our business is that we sell services for the CFO's office. In the early stages, when we had no brand recognition and no one knew who we were as a company, the ability to cold-call the CFO and say, “Hi, I just left Goldman TMT IB to join this credit card business,” was a big plus. This made a huge impression on us, so I think those were real benefits.
Perhaps the last additional component that I think is important is that I didn't have the time—and early sales teams don't have the time—to train people on how to use concise language in a cold call or how to use grammar correctly in a cold email. We had to act, so involving such people helped significantly reduce these risks. We were just in task mode.
Today, for example, Mike Webber—we lured him from Citi—runs a huge part of the business. Sam Buck runs a huge part of the business. He came from Goldman.
I spoke to Sam before this show, and he gave some great advice. My question to you is: I literally feel the pain of founders listening and thinking, “Seriously? How can you even afford these investment bankers?”
We made a bet at the very beginning to pay significantly above the market rate for such specialists. But instead, we expected a much higher return than the market average. In this way, we make the unit economics work.
We pay twice as much as a regular SDR earns. But guess what? You have to schedule 40, 50, 60 meetings, which is 4–6 times more than a typical SDR has to schedule.
Do you schedule 40–50 appointments? What are the actual expectations regarding the number of appointments scheduled?
It depends on the segment. Of course, the higher you move in the market, the smaller the numbers, and we pay attention to quality. But at the lower end of the market, we still have SDRs who schedule over 50 appointments per month.
That's not that much, man—50 meetings per month for an SDR.
You should schedule a meeting with a clear purpose. There should be strict qualifications. This requires a lot of effort and precision. I think you're underestimating it.
No, because when we talked earlier, I said that Chris Denyan thinks, “You can't hold more than 7.” And you said, “People do a lot more. They spend about 10 a day.”
These are account managers who conduct 7 real meetings—that is, closers—not people at the beginning of the funnel who are booking appointments for salespeople.
You wouldn't expect them to do much more than 12 even at low ACVs? These are small businesses and startups, for example. I mean, SDRs.
On the AE side, yes, of course they do more than 12 meetings per week, especially in a market with low ACVs. Our inside sales reps, our sales reps, make 10–12 calls a day.
That's what I'm talking about.
Yes. Sorry, was that a misunderstanding?
So, are there people who make 10–12 calls a day?
Absolutely. Some sellers at Ramp have over 15 calls a day.
Okay, that's exactly what I'm talking about.
Okay. Yes, of course.
And, excuse me, are they AEs or SDRs?
Account executives—AEs. They make about 8–10 a day.
Got it. Perfect.
But there is another component to teams: we can't just have investment bankers. They must come from some technology company. There are tech companies that are good to hire from, and there are others that aren't. I'm not asking for specific names, but rather profiles that I, as a founder, should think about.
2. How to Hire Great Salespeople
I like it. I am obsessed with this topic. I'm a big fan of Moneyball (The Man Who Changed Everything). You need to approach recruiting in the go-to-market space like Billy Beane.
There is so much alpha in finding companies that have significantly increased revenue. I'm talking about over 9 figures, but they did it despite a low NPS score.
Why are there so many sources of alpha here? Several reasons. You have to create most of the demand yourself. If you are the 5th or 6th player in the market, the inbound funnel is not very fruitful, so you have to go and do it yourself.
Second, you have to overcome many complexities in sales cycles. There are probably a lot of weak reviews on third-party resources like G2 or Capterra, so you need to be as focused as possible to pursue opportunities. Third, you usually have a premium price compared with other players in the market who cost significantly less.
If you can be the number 1 or 2 seller there, you come into a system like Ramp, and that's where the magic happens.
If you don't name the company, I can't reveal the secret ingredient.
I will name one: 6sense.
Former 6sense. The NPS and products may not be very good, right?
That's right. In fact, just yesterday, one of our top salespeople for enterprise clients sent me an email from a client with a huge testimonial that they had sent out internally. They want to propose a case study, and we didn't even ask them to.
Alex said, “I've never seen anything like this in my 15 years in sales.”
I said, “We get this 10–20 times a month at Ramp. You were just selling crappy products.”
When you're trying to determine a candidate's level based on their previous experience, how do you figure out if it was truly their merit or if they were just taking orders?
You may encounter 2 different situations. First, they just take orders, and it's not very difficult. Or, second, they're at Twilio, they sign up Uber when they're just starting out, and then the company grows, and they take credit for it. How do you define true quality versus randomness or just taking orders?
3. How to Tell a Great Seller From an Order Taker
You have to decompose their score. You made $2 million—that's great. How many of those were inbound requests? How many were outbound contacts? How much of this was expansion? How much of this was brought in by your founder? How much of this came from existing capabilities that you inherited?
Then you really have to dig deep to understand whether someone is trying to trick you. To test their sales acumen even further, say, “Tell me about 2 deals.”
You have to make them walk through them in chronological order. The best candidates give so much detail, and you really try to understand: How did you push this? What was that? Have you clearly articulated the business value? Was there some kind of workflow that you linked to a business outcome? They'll know it, and if they can't describe it, that's a bad sign.
The reverse is also true. You want to understand: Tell me about the deal that kept you up at night. Why did you lose it?
If they can't explain why they lost the opportunity—did they only have 1 contact, didn't find a champion, was there no business value, wasn't the product good enough, or did they qualify the customer poorly?—finding this out and checking it is extremely important during the interview.
What if I told you, “Hey, I understand you. One of the decision-makers is friends with a competitor, and that's exactly why”? I don't like it, but I understand it.
Blame-shifting can also be sincere. How do you determine what is good and what is bad in such cases?
Absolutely, but you have to be able to detect it early enough in the sales cycle. You have to face it head-on.
“Hey, Harry, I know you're considering us and another competitor. I see that you have a common board member with that competitor. Will this interfere with your decision? How do you actually rate us? Do you evaluate us on merit or not?”
The seller should be able to clearly communicate this to me.
They shouldn't find out about it at the last second, after they've deployed all their internal resources to push the deal forward.
Okay, so I did pretty well with this series of questions. I'm going through this hypothetical interview process with you. What's next? Do I need to do a demo? Do I need to make a case for you? What happens next in our process?
Yes, you definitely need to complete what we call a business case, where you play the role of a seller at Ramp. You need to make an introductory call. We give assignments in advance and check 3 things.
The first is Ramp as a business and as a product. The second is the potential company in question. Are you already conducting research? Do you know what is happening? Have you read their 10-K report? Things of that nature.
The third is simply the basics of sales. Do they have managerial confidence? Can they ask second- and third-level questions? Can they quantify the problem? Can they articulate value? Most importantly, without oversimplifying, would I buy a product from this person? If I can't say that with certainty, I won't hire them.
I feel the same way about hiring leaders. If I'm trying to hire a manager but I don't think I would work for that person myself, I wouldn't make that choice.
So, you sit down with me, realize you would buy a product from me, and you really want to work with me. What does the proposal stage look like? What do you notice in my reaction to promotions, positions, or compensation? What then?
4. What Salespeople Should Look for When Joining a Startup
I have so many thoughts on this. It really depends on what stage of your career you're at. If you're a salesperson looking to join a startup, thinking about shares, cash, and bonuses is the wrong direction.
The right things to evaluate are the market, talent density, the business, and the founders. This is how you should evaluate it. Why the market? Because there are structural advantages if you choose a business that can continue to find growth vectors.
In my story with Ramp, the reason I left—I was a mid-level account manager. I resigned to become an SDR at Ramp again, and people looked at me like I was crazy. The reason I did this was because the market had unfair structural advantages.
The card business is a market worth over $1 trillion a year. The costs are the same. Bill payment is a multitrillion-dollar-a-year market. Travel is a multitrillion-dollar-a-year market. Banking is a multitrillion-dollar-a-year market.
You don't even have to be a good business to find a way to grow, given this dynamic and having a market-leading product. You have the most talented engineering team, which is more like a science lab or SpaceX. You will definitely win. That's why you get a career boost.
If you're worried about, “I want a vice president position and a bunch of stocks,” but you're going to work for a mediocre business that's growing 20%–30% a year, then who cares? You're making the wrong exchange.
With all due respect to the people who are working on, say, AI sales tools, I'm like, “Seriously? You're doing revenue forecasting using AI.” I'm not trying to be rude; I'm just being honest. I think that's actually quite—
That's right. That's exactly what I mean. It's like the moment with John Sculley at Apple: “Are you really going to spend the rest of your life selling sugar water?”
That's all. If you don't believe and have no conviction that it can become something that can match Salesforce, then of course, please try to achieve the highest goals, but it's hard. I completely understand you.
Sorry, the market came first. What were the second and third?
Talent density.
Talent density?
Among the current lineup.
Yes.
And third, the founders.
Okay, so in terms of talent density, if you break it down further, it just means how good a team is? What does this really mean?
Working in sales, you want to get the advantage of working with incredible engineers. The first engineers I met at Ramp were simply cosmic. One was the youngest person ever to graduate from MIT, someone who had already created and sold the Apple business in his Stanford dorm room.
You had the Olympic medalists in computer science from the International Olympiad in Informatics. This is what you want to sign up for. And the fact that Eric and Karim have already built and sold the Capital One business is no coincidence. That's a pretty solid engineering team to start with, right?
The youngest guy to graduate from MIT. Oh my God. Okay, I understand. My 4 weeks at university are already making me feel guilty. That's why we're sellers, Max, understand?
That's right. That's right. I went to public school, little one.
Yes, that's all. Okay, so it's talent density, I get it. The third is the founders. When we say “founders,” can we break that down a little bit? We're seeing a rise in founding engineers who are terrible at sales, have definitely not created a sales strategy, and have no idea about sales at all. How do you feel about such a potential founding team to join?
This is perfectly acceptable, and I think we'll see this more and more often, as many engineers want to start their own AI-focused businesses. I think you need to check a few things. Are they sales-oriented? And second, are they willing to interact and engage in feedback so that the product can evolve and become sophisticated enough to meet sales demands?
5. Why Sales Is Really an Engineering Problem
But I will dwell on the first example in more detail. Being sales-minded—what does it mean? Will your technical co-founder provide you with engineering resources to help build the system?
Sales is largely an engineering problem, if you look at it that way. This is a data infrastructure problem. This is a mathematical problem. You need to build systems that will give you the edge and automation so you can create a ton of opportunities.
I am very grateful to Karim for providing me with the engineering resources to build our OATS app at the very beginning, even in the early stages of the business.
Sorry, what is the OATS program? Why is this a data infrastructure problem? Why is this a math problem? Can you help me seriously figure this out?
In the past, outbound sales were mostly a matter of writing texts and making calls. I think this is increasingly becoming an engineering problem. In late 2020 and early 2021, even before the advent of AI, we built our own internal infrastructure to automate many of the backend processes. That's what the acronym Oats stands for: Outbound sales automation team.
Let me explain this in more detail. The team studied what I do to go to market and how I create signals within accounts. These signals can be limitless. This could be a new employee who has just joined the business, or the fact that I graduated from the same university as this person. We might have shared investors on the company's cap table.
It was a very manual process. You had to create templates and look for contact information. Why should our sales department do this? They should be focused on communicating with the customer, solving their business problems, and implementing the product.
Our engineering team built a lot of automation for list collection and email sending, and that was—
Sorry. So, if I'm a founder who's listening to this and wants to do the same, what do I do? Do I tell my engineers to buy ZoomInfo?
No, that's just part of it. You tell 1 or 2 of your best engineers, “Hey, we can build the coolest product in the world, but it's not worth a damn if it doesn't get into the hands of paying customers.”
Therefore, we must be obsessed with growth, as it is vital to our business.
What are we trying to solve here? I didn't understand. Are we looking for new leads or trying to reach them? How do we handle integrations? Should it be an email or a LinkedIn message?
Yes, you're trying to solve the reach problem. In the early stages of your business development, you won't have an army of go-to-market specialists. You might have 3 to 6 people responsible for outbound sales.
And you know what? If you do it manually, you might be able to send a couple hundred emails and maybe make 100 calls. This is not enough. Especially in today's markets, where TAMs are becoming increasingly limitless, you need leverage.
The problem you're solving is reach, brand awareness, and getting your name out there. You simply cannot rely solely on vendors in this matter.
Do you know what I'm thinking? You're losing efficiency. In other words, outbound sales become less effective at scale, whereas if I sent 20 really great, thoughtful messages with research, a joke about our alma mater, and a picture of my mom and me hanging out on the weekend, my efficiency would skyrocket.
This is a sincere question, not a statement.
This is a valid observation. You have to make the system recursive to really understand what works so that it can optimize over time. If you just rely on automated emails being sent nonstop, it doesn't make sense.
You should constantly conduct A/B testing and implement what will really give the best results. You still leave room for manual contact from your sales team because, as you rightly pointed out, if you send 20 incredibly well-chosen emails, the likelihood of them being responded to is, of course, higher.
Then the system can identify that, get that feedback, learn from it, and start applying it at scale.
Do you have engineers on your sales team on a permanent basis? This is not just a one-time development of a sales tool.
Yes, there are. We have a team of growth engineers, which is—I think—at least 6 engineers who are really obsessed with building products to market.
What response rate is considered good when you send outbound messages using a tool like this?
Response rates have actually declined quite significantly over time, following the acceleration of AI development.
The response rate is not the criterion you should be guided by. It’s an indicator of scheduled appointments. You might get 5% of responses, but if they say, “Please never write to me again,” unsubscribe, or send it somewhere far away, it’s not helping in the right direction.
So, the main thing is how many of them convert into a meeting?
Yes. It should be a little less than 1%. I think this is a very strong standard. That means that for every 100 emails you send, 1 converts into a meeting—that’s great.
6. How Quickly Can You Tell if a Sales Rep Will Be Great?
How quickly do you implement verticalization in your sales team? All of this can become better, more efficient, and more accurate through verticalization.
Hey, we have clients including British Airways, Delta, and Ryanair.
7. When Should You Verticalize Your Sales Team?
Wow, wow. Okay, we’re focusing on the travel industry, specifically airlines. Do you understand what I mean? When is the right moment, and what do you think about it?
Yes, I believe that the right time to verticalize a business comes when you need to use leverage to accelerate conversion. I think companies are actually starting verticalization too early, especially if you have a huge addressable market and are in the market-share capture phase.
I believe that verticalizing the business may even be counterproductive to this. But when you take a larger market share—let’s say, arbitrarily, from 3% to 5%—the total number of opportunities you can cover starts to get limited. Therefore, the leverage you need to apply is the ability to convert leads into closed deals faster, and I believe that this is the moment when verticalization should begin.
If you look at the companies that I think have done this well, like Oracle, Workday, and SAP, that’s exactly what they did. One of the reasons I like verticalizing sales teams is the impact it has on sales cycles. Often, messages become better and more targeted, value propositions become clearer, and I see a reduction in the sales cycle when I see this verticalization.
What are your biggest lessons on how to shorten sales cycles?
8. How to Compress Enterprise Sales Cycles
It depends on the nuances of the segment you’re targeting, but the best way to shorten sales cycles is through stricter qualification.
Mhm.
At the initial stage, you need to understand: does this person have the influence to actually implement changes? Are they motivated enough to do it within 12 months? If you can check those boxes, go for it.
How do you actually define it? Many people want to comfort their egos and say that they’re very important, and many want to please you by promising to do everything quickly. How do you actually define it?
You should test them. The way to check is that if they’re not in top management or don’t have a vice president position, you should know who their boss is in the organizational structure. If you had an incredible conversation and earned the right to bring in another interested person, you should ask for it.
There’s a subtle way to do this where you give in order to receive: “Hi, Harry. Today was great. I strongly believe that we can solve this problem for your business. We’re going to hold this demonstration at the highest level, and I’m going to bring in a number of my technical experts to add to the call. My request is that you invite Susan, your vice president of purchasing, to the next conversation.”
You’ll understand everything immediately. Is this person— is Harry—going to invite Susan to the call? Okay, great. Maybe you have a fan. Maybe you have someone who can influence change. If not, why not? Do you not have a relationship with your manager? You really can’t do this? This is a really good way to check it out.
I like it, and Susan would be happy to come. One thing that’s really important to us right now is cost control. So, Max, can you help me here? You say you charge $4 per card, $4 per seat, or $4 per unit of what we sell. Even more. I need it to be $2. Can you come meet me, Max? I’m mostly looking to buy something.
We haven’t even technically determined whether this will work for your organization yet. Look, we can deal with the economics. I think once you see how this product transforms and changes your business, it will have a much greater financial impact than saving $2.
But you don’t discuss discounts, because so many founders tell me, “I just don’t know how to do it. I want to close the deal, but they want a 20% discount.”
I think if we’re discussing economics and pricing early in the conversation, after the first call, that’s usually a bad sign. It usually means that the buyer isn’t very experienced.
Unless it’s a very low-end market and you’re talking to the founder of a 10-person startup and trying to close the deal in 1 call. Sure, maybe I’ll go for it and make a discount to seal the deal. But at a higher level, no—you have to jointly develop a business-value assessment.
You really need to understand what exactly they’re trying to solve and what the total cost of ownership looks like. Are you trying to get a margin advantage? Are you trying to make your accounting function more efficient and give yourself leverage over your staff? If you can come to an agreement on that, you can avoid any price concessions, because hopefully you’re creating 7-figure value.
9. Why Your First Sales Reps Should Have No Quota
Mhm. Speaking of creating 7-figure value, let’s get back to that great interview process, because I was really impressed with you. You were so excited for me to join RevGenius from day 1 that you wanted to offer me a job, and now it’s time to work out compensation. Can you help me with that? How do you advise founders on designing compensation for the first AE and the first SDR?
I usually advise against having a compensation plan. I usually recommend using 100% OTE for at least the first 2 quarters. You simply don’t know what you don’t know.
I’ve seen founders get into trouble when they set a quota that the salesperson overachieves in the first 6 months, and it’s like, “Oh my God, I owe this salesperson 6 figures.” I’ve seen the opposite, when you randomly point your finger at the sky and say, “I think this person will be able to close so-and-so or schedule so-and-so meetings,” and it’s unattainable. Then you try to gain momentum and get the wind at your back, and it hits confidence. I think lost confidence is hard to get back.
Right. Yes.
Even if they’re doing well, I’ve seen this happen. Let’s say they closed 250 and you set me 500. 250 would actually be pretty good. It was a solid, decent—not that bad of a start—but since it was half of what you set, I feel like I’m really bad.
This is true.
In a sense, there is a little bit of benefit in that. If you find the right person, they get fired up and feel like they don’t live up to expectations. There is a certain amount of healthy anxiety, but it depends on the archetype you’re engaging.
Well, we have 100% OTE. When does that change, and how do we initiate another discussion about adjusting this plan?
10. Why You Should Never Hire Just One Seller
Data. Typically, it depends on what segments you’re targeting, but if you have a sales cycle of less than 6 months, you should have enough data in the system to understand: this person has been in the position for 2 months, they ramped in the first 90 days, and we see progress in stages. We have reason to believe that the pipeline will be X.
Let’s set a quota that is both ambitious and somewhat reasonable based on the data available. You should never hire 1 salesperson or 1 SDR at a time, because the question becomes: how will you measure their performance? How do you know if they’re good? Will you compare them to yourself as the founder? I don’t think that’s smart.
Plus, as a founder, spending time onboarding a salesperson is exhausting and expensive. Do this in pairs. Competition and cooperation arise, and they’re not alone. I strongly advise against hiring 1 at a time.
Okay, I completely understand that. So, we strongly advise against hiring 1 at a time. Do we always fire 1, or do we sometimes leave both?
What do you mean?
What if someone isn’t doing very well? By the very nature of working together, 1 person will always be worse than the other. How often do you leave both behind rather than get rid of 1?
I think it depends on the situation. If someone is a complete outsider and is “destroying” another salesperson, yes, you should probably fire that person. If the difference is 10% to 20%, you need to dig deeper and figure it out. Why, exactly, does this person sell better? What structural advantage might they have?
Is this the pipeline I gave them? Is this a pipeline that came from our capitalization? Or something else? Do they know the product better? Are they more motivated? Do they just not care, and the other person doesn’t care? It’s the founder’s job to find out.
Going back to 100% OTE—I apologize—this is for AE sales. Does this change as we develop compensation for AEs?
No, this is universal for early go-to-market teams.
Yes. What do you think are the main mistakes founders make when designing a compensation system? Again, we have complex nuances. For example, when you have new products, you want to drive more sales and encourage people with bonuses for selling them. But I don’t want a bunch of people selling only that and nothing of the main thing. How do you look at this?
It depends on the stage. First, if you’re an early-stage founder, you’re probably still trying to get 1 product to market, and you want to focus on that. You really need to understand your ICP.
In other words, it’s much more valuable to have 20 customers who are excited about 1 product than to somehow serve 6 customers with many products who aren’t very excited. You need to create a tailwind of use cases, feedback, and positive momentum for your business.
But at later stages, like now at Ramp, incentive design is incredibly important, and I believe it is vital to provide excessive incentives for launching new products. When looking at executing quotas 2–3 times higher for new products, you have to, again, create momentum to earn more customers for many products, more examples, and more momentum.
When you make a mistake with a hire, Max, what don’t you see that you should see?
As for me, sometimes I’m quite openly aggressive. It’s very innate. I’m intense, and I’m going to, damn it, destroy the competition—and I’m having fun doing it. I’m happy to talk about it.
Silent killers are sometimes not so easy for me to spot. This is the talent I’m missing, and I’m trying to fix it.
When you make a hiring mistake, what are you missing that you should have seen?
11. The Biggest Sales Hiring Mistakes
People in sales, especially managers, are naturally inclined to do well in interviews. They are salespeople by profession. They know how to say the right things, and they know how to react extremely quickly during an interview to show their urgency and ability to relentlessly follow through on a case.
I think the only mistakes we made were overestimating the pedigree and origin of famous brands without truly understanding 2 things. First, do they have the initiative and that “x-factor” of independence to not depend on many different internal resources? And second, related to this, are they going to give it their all?
Will they be deeply obsessed with working at Ramp? This should become their identity. If both of these things are not made clear during the interview, it can go awry, and sometimes it’s a false hire.
Chad P, the legendary sales leader, said on the show that young people just don’t want to work. They have a different attitude toward what they want: working from home, work-life balance, a mission. They burn out quickly, and they want a different future. Is he right?
I love Chad so much. He is a real beast. I love Dagnan too. It was an interesting show.
I think he’s right. This is a bit provocative, but there are many young professionals who want to give it their all, and you need to find them. It’s your responsibility to build an internal culture so that people want to come to the office every day.
We have young salespeople who, at the beginning of their careers, come to the office even on Saturdays and Sundays. Nobody asks them to do this. But if you create that kind of culture, it becomes very contagious, and the advantage is that it filters out those who don’t want to follow it.
Look, if you want to work remotely and only make calls for 4 hours a day, the other individual contributors in the company simply won’t let that spread to the entire organization.
12. How Ramp Onboards New Sales Reps
Help me understand. I’ll gladly accept your offer. Thank you very much, Max. What are your biggest lessons on how to effectively onboard new professionals?
At the initial stage, you are all locked in one room.
Of course?
You go through 4 key components, and I’ll go through all of them in sequential order. The first is the product and technology you sell. The second is the personas of the customers you sell to. The third is the competitive environment. The fourth is internal operational chaos: how your systems work and what you need to know as a seller.
On the first point, in the era of artificial intelligence, especially as a new generation of buyers comes into the office, they have what I call an immunity to nonsense. They are straightforward, and they can find answers quickly. So the expectation is that if they’re talking to a salesperson, they also want answers quickly.
If you don’t technically own your product, you’re pretty useless as a salesperson.
The second is the personas of the buyers you sell to. This is very important. You need to know what their priorities are, and you need to understand their challenges.
This is different if you’re talking to the CFO of a software development venture than if you’re talking to the chief accountant of a construction business. You should understand that, too.
One level will be very high: they’re trying to achieve positive business results. An accountant may need a workflow related to month-end closing that creates a lot of tedious confusion for them. You must have the ability to switch between these contexts.
Third, the competitive environment. We obviously operate in an extremely saturated market, and many players claim to do many of the same things we do. You need to study these companies, understand their weaknesses, and address them in a diplomatic way, positioning your product in the best possible way for a specific buyer.
Do you have a training intensive where you go through these stages?
Yes, there is.
Can you tell me more about this? For example, how long does it last? Who conducts it? What materials do you use, and all of that?
We have Kyle, who leads the development and training direction at Ramp. He is fantastic. He is not a traditional training manager at all. He is a cool salesperson who became a sales leader, whom we invited to improve not only onboarding, but also the ongoing development of our salespeople so that they continue to hone their professionalism and know the product perfectly.
As for the intensive itself, depending on the segment, it lasts from 60 to 90 days. The first 4 weeks are quite intense, with many milestones to achieve. Part of this is hands-on-keyboard work, and part of it is independent mastery of the skills that our training team has developed in all of these areas.
As for the intermediate stages, great rigor is required. You have to pass the discovery certification, and you have to do it flawlessly. You have to get certified in demoing, and you have to do it flawlessly.
I like to check in on these sessions from time to time. If you don’t pass them, you won’t be connected to the lead router. You don’t get your accounts. So it is vital that you show good results; otherwise, your opportunities to grow and become a successful seller will be limited.
How soon will I be able to start communicating with clients or customers on my own?
2 to 4 weeks, depending on your segment.
Oh, I see. Do this as soon as possible. I’ll listen to a bunch of recordings of Gong calls by the time I get around to really understanding the tempo, the language, and the patterns.
Certainly. You will listen to the calls in Gong. You will join live calls. You will participate in team meetings, listen to sales-funnel reviews, forecasting, and everything in between.
After your first call, your manager should accompany you and support you from start to finish. If you manage a large sales team and depend solely on the training department, you will fail. Your line managers need to be actively involved and delve into the details as deeply as possible during the onboarding of new employees.
This is the part that sounds obvious, but it’s hard for a leader to get down to that level. I don’t mean to offend, but it’s like with groups of interns at venture funds, when you’re like, “100%. Everyone wants to help young people, but I have to close this damn huge deal.”
100%. But you have to do both. You have a plan that you are responsible for. So, yes, if there is a big, important deal and you are a line manager, then of course all your efforts are thrown at it.
But at the same time, guess what? Your plan will grow month by month, quarter by quarter, as these new sellers reach full capacity. So you have a vested interest in them becoming sales “killers”; otherwise, you as a leader will have problems.
What percentage of reps do you think you are impressed with, and what percentage disappoints you?
70–30. 70% are in the camp of those who impress, and 30% are in the camp of those whose level does not meet our standards.
And what happens to that 30%?
I dig into this pretty deeply, reviewing a lot of calls in Gong, especially with new hires, and frankly, even more so with our experienced reps. If someone doesn’t meet our standards, I call them and their manager in, and we discuss it.
This is difficult. It’s hard, but it’s right. If you join a sales team where the manager or vice president doesn’t delve into the details and doesn’t hold you accountable, it’s probably a bad sign.
13. What Is a Healthy Sales Rep Productivity Ratio?
Let’s talk about accountability. Let’s say I complete those 90 days. I’m ready. I’m going out on my own. Carlos, who was the head of sales at ElevenLabs, said they had a 20× quota. It was a pretty popular clip. How do you feel about this? What is a good indicator for you, and what advice would you give to founders who are listening to us?
I tend to agree with Degnan on this point: if you are that efficient, you are probably losing profit and need more managers. I think the old methods, like Snowflake or [?], where the ratio was 4:1 or 5:1, are too low.
Depending on the segments at Ramp, it’s anywhere from 7 to 12. I think that’s a pretty healthy number.
That’s a lot. I want you to pay me more if I do 12:1, man.
I know. You might have to cut that out.
Pay me twice as much, and then it’s 6:1. How do you like that?
We should probably cut that part out.
I don’t know if our inside sales reps know that some of them are 14:1.
I think they are 100%. I think that’s good. You want something like The Hunger Games in competition.
Good. For me, as an early-stage company, the range of 6 to 10 is what I need to achieve to have an effective sales team.
I think that’s right. Yes. Regarding ramp time, how much time do you give me after the boot camp? Boot camp is just about getting back on your feet, so how much time do I have to ramp?
Again, it depends on the segment. Our mass-market salespeople, our inside sales representatives, have 60 days. Sales representatives have 90 days. The mid-market segment has 4 months. The enterprise segment has 5 months.
And for strategic enterprise clients, the ramp schedule is 6 months. The reason these ramp schedules are the way they are is simply because of the length of the sales cycle.
How quickly do you realize that someone is not very skilled?
I think it's actually quite easy to check whether a person will be successful or not. I think there is a direct connection during onboarding between salespeople who are annoying and those who aren't. When I say “annoying salespeople,” I mean they're constantly asking questions 24/7.
They are very thoughtful. They discuss customer service strategy. They want advice on their sales funnel and ask you to send emails on their behalf. They want to ask questions about the product, and it never ends. There is a direct correlation to the fact that such a person will be incredible.
The reverse is not always true, but I think those who are silent, don't ask any questions, or ask things that any AI bot or Notion bot can answer are usually a weak signal.
I always say that the quality of a founder is very noticeable from the quality of the questions the founder asks at the end of an interview or meeting with a venture capitalist.
100%.
That's why I intentionally leave at least 10 minutes during the interview so they can bombard me with questions, because it shows how people think. My partners often say, “Why are we spending so much time answering this question?”
Because you don't understand this. I actually appreciate the questions. They ask me, “You have 4 partners. Do you have equal votes on the investment committee? Or how do you approach making investment decisions?” That's a smart question for a first-time founder.
That's right. I think about it the same way. I'm thinking about an interview where I need to intentionally give them at least 10–15 minutes to bombard me with questions, as if they're trying to sell me something.
Salespeople come to me and say, “Hey, Max, I spoke with Scott from your corporate team. I know he's number 1 now. The reason I think it works so well is because he showed me his process. That's how I look at sales, and why it's very similar to what Scott does, and why I'm a great fit for the role.”
Just like you're trying to reach a corporate client, if I'm a salesperson and I'm calling the CFO, I might say, “Hey, Mr. CFO, I spoke to your controller. Here are the pain points. Here are the challenges. Here's how I think Ramp can uniquely address some of these issues.”
14. Is Customer Success Actually Bullshit?
This is exactly what I'm trying to figure out. Can I ask? You've mentioned Doug a few times already. Doug always tells me, “I think customer success is complete nonsense. These should be paid professional services.” I'm not sure if he's right. Do you think customer success is nonsense that you just have to pay for?
I have a slightly different view on this. I really believe in customer success as an outcome, and as a result, we decided to make customer success an organizational structure in our business.
They are highly technical specialists. Some of them are certified accountants. They have excellent knowledge of ERP and accounting systems. So it's almost like an extension of the client's accounting function, which I don't think is possible through a professional services business.
The economics of our product allow us to subsidize a significant portion of this work. I think this team brings us a lot of value. While it might work for Snowflake, I don't think it's the right solution for us at Ramp.
You should view customer success as an economic engine that will drive net revenue retention (NDR), for your customer portfolio over time. That's why we want to work directly with customers. We want to control the outcome because, at the moment of the first transaction, implementation is extremely important.
If we do everything right and provide value, then guess what? We are earning the right to sell more and more products over time. There is no shortage of new products at Ramp today.
We must consider how to thoughtfully cross-sell, upsell, and expand, with the goal of increasing financial impact and operational efficiency for our customers. But if you don't do it perfectly from the start, it will be increasingly difficult for you to earn the opportunity to sell more products over time.
15. How Ramp Forecasts Revenue Within 5
The hardest thing I find in expansion is forecasting. It's hard to predict expansion, first of all, but I believe that predicting stages is simply impossible. The volatility inherent in our ecosystem is very high. The growth rate—we can never—
How do you think about forecasting today as a leader? What is your advice to founders and sales leaders on how to forecast in 2026?
I am fortunate to have an incredible colleague in the finance department. His name is Asher, and he has built some pretty impressive forecasting systems and models that consistently keep us within a 5% deviation for the entire business.
When was the biggest deviation you had, and what did you miss?
Nothing, because we are now subject to the law of large numbers. Years ago, before we introduced discipline into our operations, a lot of things were done by the sales department on its own, and there were disagreements.
The advice I would give, and the lever we used to make it much more consistent, is this: salespeople, you won't be paid or budgeted based on the accuracy and discipline of your forecasting, but it is part of your performance evaluation.
This is discussed during individual meetings. This is discussed during your quarterly business reviews. At the salesperson level, they are interested in taking care of this. The same goes for first-line managers. The same applies to segment managers.
If you don't make this part of your productivity culture, I think it will be difficult, because a lot of salespeople will be driven by emotion. “They told us we were a preferred supplier.” Well, they haven't even started a review by legal or the information security department. We have 3 days left until the end of the quarter.
Holding everyone accountable in this way is how I describe it.
How often do you conduct a pipeline review, Max?
Oh my God, we do pipeline reviews once a week. What's great is that I've eliminated forecasting meetings because everything is system-based. There was too much duplication and imitation of work. We don't need it.
Every hour counts, and as a leader, I have to provide as many resources as possible. Otherwise, it becomes an expensive problem.
Who comes to pipeline reviews? Who receives the invitation?
They are conducted by segment managers. All line managers are present, and individual contributors also come in turn to review their most important deals.
We try to focus on the fact that we're not so interested in deals that are going perfectly. What matters is which deals are at risk of slipping, and what we, as a team, will do to mitigate the risks and move forward.
I think it's also important to understand which deals we lost. How can we stop these losses? Could we have controlled it? Is this a gap in the product? Is this pricing? Or is it something else?
16. Why Most Enterprise Deals Lose to the Status Quo
When you lose, why do you lose?
I would say that most of the time we lose because of the status quo, and this is our fault. This is not a gap in the product. This is what we need to look at ourselves in the mirror about: we didn't create enough urgency.
You can create urgency as a salesperson. You have to get hooked on a big business problem. You have to find the right person within the company who is motivated enough to make the change because it will impact their career. They can gain political capital from this.
You may not get this from a low-level person. You may not get this from the CFO. So you need to use a multi-channel approach correctly.
Are we seeing brand marketing spending like never before from big brands like Ramp? Are you feeling the effects of this as a sales team? Do you feel the effect from customers when they say, “Oh, I saw you on the subway,” or “Oh, I saw you in a Boston Red Sox jersey,” or wherever you Americans watch sports?
Yes, it definitely helps. We have a lot of noise and excitement around us. This is difficult to substantiate with data, but it provides an informational backdrop for our outbound sales team, especially in certain markets and geographies.
It's a way for salespeople, along with customers—and, just as importantly, potential buyers in the funnel—to invite people to sporting events, to our musical about paying the bills, to private dinners, and other things like that.
This is clearly reflected in the cycle times and customers' willingness to expand their use of Ramp. This has a direct correlation.
What would you most like to change about your internal sales process today that you haven't already changed? Or can't you change?
I think if someone could describe what kind of interviewer I am, they would say I am thought-provoking.
Yes. Often wisdom comes through reflection. And that's the joy of how we do these shows. We cut out all the pauses, but I think reflection is very important.
17. How AI Is Changing Ramp’s Sales Machine
As the models have gotten better—this applies to the end of last year and the beginning of this year—we have done a lot for our sellers to unlock significant potential. I'll give you some examples.
Sales is largely an assembly line. You are a salesperson, and this is your first encounter with a business. There is work to be done before this meeting. You must conduct your own independent research.
What does this mean? You need to go to LinkedIn, their website, PitchBook, and all these different third-party sources and publications. When we calculated the time for this job, it came out to 15–30 minutes in the worst case. Maybe, if you're an exceptional specialist, 10 minutes.
If you quantify it, Harry, for hundreds of salespeople, this is a terrible loss of productivity. So we built our own internal revenue operating system called Ramp Revenue, which does a lot of this pre-call research. What's great is that it actually bridges the ability gap, in my opinion.
A great salesperson can do this: “Oh, cool. They just launched a new product. KKR has just come in. They are now the new debt sponsor. This random person, who isn't even in finance or accounting, used Ramp at a previous job.” The average salesperson can ignore all of this. So, first of all, this system bridges the skills gap.
During the call, you have everything you need at hand. You know exactly what to say and how to act. Secondly, it saves time. A maximum of 90 seconds will be spent conducting research before the call.
If you quantify this for the entire sales department, there is significant potential that I translate into additional sales days, allowing us to increase quotas over time. Increasing quotas means increasing revenue for businesses.
And will you ever open this to the general public?
Well, one thing that we're seeing, particularly with Deel and, actually, Revolut in some cases with their performance management software, is that they've built these internal tools and now they're selling them.
Will you reveal it, and how secret is the “secret sauce” really?
This can be monetized because you have a Ramp Router, right? You have an OpenRouter. So, for Ramp Revenue, I won't speak for Eric and Karim, but our ambitions go far beyond owning the CFO's office. I can totally imagine a time when we will bring these other products to market.
I think it all comes down to choosing the right timing and sequence so that our go-to-market organization can structurally handle all these changes. Here's the catch: this is not just a product solution. You can't just say, “Oh, yeah, why don't we do Ramp Revenue?”
Ramp Revenue actually needs salespeople to sell it, implement it, ensure customer success, and market it. I think that's what people often get wrong about the corporate sector. You can't just say, “Let's try.” It's like, you need it just to try it.
In the consumer segment, you can. You just turn on the light and that's it. Here, everything is different and very complicated. That's why, in my opinion, people are so wrong when they say, “Astra Law will destroy Harvey and Algorithma.”
Are you serious? Do you think the training and deployment methods will be the same for OpenAI and for Harvey and Legora, which have been flattering me for 2 years?
And finally, where do you fail as a sales leader, and where do you think you need to improve the most?
18. Max’s Biggest Weakness as a Sales Leader
I think the biggest thing I'm working on right now is resisting the instinct to personally intervene in every important issue. A lot of what helped me advance at Ramp was my incredible attention to detail. If there's an important deal or an important client, I'm all in, but it only works for a certain period of time.
As your workload gets bigger and bigger, this instinct can actually become a weakness. In other words, if I step in and decide every deal, maybe we'll win, but I won't necessarily make my sales team better. What's worse, I might inadvertently teach people that when something gets important enough, Max will just step in and take over.
This will become a limitation. I need to build more and more pillars in the go-to-market organization; otherwise, I will not do my job effectively as a manager. You don't build these supports if you're only busy with the operation of the mechanism. I think we need to do both.
What I pride myself on as a leader, and what I demand of all other leaders in the go-to-market organization, is the need to be a dual threat. You must be able to operate at a high level. You have to be able to compete with me, with Eric, with Will, and Colin on equal terms.
At the same time, you have to be in the trenches with your salespeople. To this day, I still make cold calls. I send at least 5 cold emails every day.
Are you really doing this?
Yes, I must. The moment we, as leaders, distance ourselves from the customer and from what our salespeople are doing, we lose. I don't think we are benefiting or adding value to our sales team.
There is nothing less inspiring for a salesperson than receiving guidance from someone you think can't do the job better than you.
19. How Ramp Creates a Founder Mentality in Employees
May I ask what you think Eric and Karim did to instill in you the founder mentality? When I talk to you now, it's a lot like talking to a founder.
I was just thinking, “Oh my God, I would like to lure Max away.” I spoke openly about alternative investments. I said, “We have to lure Max away.” I know what you would say: “Go to hell.”
So my question to you is: this is impressive, and I give credit to Ramp. What do you think Ramp, Eric, and Karim did to turn Max from Namely, who wasn't extraordinary, into a founder—no offense?
I think a few things. First, a lot of experience. When I joined Ramp, my boss was actually Eric. I saw him during sales calls. I saw him talking to investors. I saw him work through his mailbox. It was like I had earned 50 MBA degrees in 9 months. It was a crazy acceleration.
Second, it's the experience of communicating with investors who have been through this before. I am incredibly grateful to be able to call Dave Schneider my friend and mentor. I learned a lot from him.
Colin, my boss, is simply exceptional. He took companies public. He sold businesses. I think just being around him allowed me to absorb a lot of that knowledge. It also forced me to figure the hell out of everything myself.
I'm not naive, and I understand that I have to prove my worth every day. If I don't work productively, I could lose my job at any moment. If I'm not professional in my conversations with Eric, whether with a client or when discussing important issues with the board of directors, why should I stay in this position?
I think it's a combination of all the factors. The founders gave me a lot of opportunities. They hold me to a rigid framework of accountability, and I have a healthy dose of stress and paranoia that, if I don't show results and grow, it could all be over.
You know, Dave Schneider told me one of the best lines ever on one of the podcasts. He was coming to London. I love this guy. He says venture capitalists are like seagulls: they like to fly 100 feet in front of you, look down on you, and then just lay a big pile of shit on you.
20. The Three Categories of Sales Performance
I'll just say, honestly, I don't remember anything else he said, but that phrase stuck with me. He had the best catchphrases. I forget the topic, but it was something like, “How do you measure effectiveness? And how do you make ratings?”
He's like, “Max, there are 3 categories of effectiveness in sales. First: you are God. Second: I don't know yet. Or third: you're damn fired.”
That's true. This is very true. Yes.
But you know what else it taught me? If you listen to what I just said about the seagull giving you shit, sometimes it's better to be a purple cow, as Seth Godin said: being different sometimes means being better.
Dude, let's do a blitz, because otherwise I could talk to you all day, and you still have a plan to follow. What 1 sales tool could you not work without?
I don't know whether I should say this publicly, but I will: Inspect. Inspect is our internal coding agent in Ramp, implemented on the Harness platform. It feels like I always have an engineer and a technical sales specialist in my pocket.
Did you design all your own damn tools?
Harry, when I get to London, I'll show you this. What our sellers achieve with Inspect is simply crazy. For example, creating individual demos or analyzing current customer configurations in Ramp. This is epic.
Whose credit is this? Did the CTO develop these internal tools?
Yes, I would give credit to both Eric and Karim. It's just part of our DNA: to move forward and create.
You have a job offer that you definitely can't refuse. You can offer it to anyone in the sales world to join the Ramp team.
I really like Becca Lindquist from Clay.
I was literally going to say that. She was very good. Becca, or someone else who's on the rise right now?
I believe in finding someone who's going to take off right away. Again, my theory is about undervalued assets. There's this guy, Charlie Demuth, the head of corporate direction at Profound. He's a real beast, and I try to lure him back to us every 6 months. I hope Mark doesn't hear this, because he's the SVP of Sales at Profound.
What is your main advice to a new professional on their first day?
You have to give it your all. You have to be obsessed, because if you're not obsessed, you'll be mediocre. I would add: be someone who solves problems, not someone who only seeks them.
Anyone can look for problems in a startup. Something is burning here every moment. Few people can be problem solvers. As a new salesperson, you have a fresh perspective. You can see that there are structural errors in our process. Maybe you did something at a previous job that would help move the business forward. This is how you will accelerate your career and achieve success.
Regarding obsession, take ramping as seriously as possible. Get certified, reach out to clients, build your own pipeline—all these basic things that people ignore for some reason. I always say, “Listen, take the blame and give the credit to others.”
The worst thing for me is hearing, “Oh no, no, it's not my fault. It was Max's fault.” There's nothing worse than coming to your manager and saying, “Hey, do you have any feedback on me?” This is a terrible exercise for all involved.
Come to the conversation with your own point of view: “Hey, I noticed this in the last 2 deals.”
Here's how I plan to fix the situation. I would be happy to hear your opinion. I would be happy to get your advice. Am I looking at this correctly? Have you seen this happen to other sellers?
This is exactly the approach you need to be extremely effective as a new salesperson.
I agree with you. That's very fitting, because when they keep doing that to me, I always think, “Oh, fuck. I probably should have evaluated your work better.”
I know. I know.
Do you understand what I mean? It makes me feel like shit. It's like you're asking a horizontal question, rather than saying, “Hey, I need help with the closing process.”
Same with leaders. “Hey, do you have any feedback for me? I noticed this problem. Here's how I'm going to solve it. Here's a cross-functional resource that I'll need if I run into obstacles. Come help me.” That's it.
Do you know what pisses me off the most? Requests to meet are in the same spirit—horizontal. “I'd like to meet someone from Ramp.” Are you high? “With someone from Ramp. May I introduce you to Keith Rabois, a member of the board of directors, or Eric Gleyman?”
I can connect you with Max, the star sales leader, but I have no fucking idea why. On top of that, I get about 50 meeting requests a day. Maybe if you did a copy-paste, that would be helpful too. This horizontal, shitty nature of meeting requests amazes me.
If you're asking for an introduction, it should be to the point, and you should make it so simple that it's easy for the person to forward it to someone else with the appropriate context. Otherwise, don't wait for an answer.
“Max, I fully understand the point of the request, but I would really like to meet Colin. I would like to talk to him specifically about his experience at Axe. I have added a message below that you can copy and paste. By the way, I completely understand if that's impossible. Big hugs. Let me know when you're in London.”
Me too. Last question for you: What is the kindest thing someone has done for you?
I have to give credit to my wife. She was still my girlfriend then. Listen, it was the end of 2020, and I basically told her what this could turn into. This was 4 or 5 months after Ramp launched, but I deliberately warned her that it would ruin our lives.
I said we would have to go to great lengths for this. I would be absent from our social life, but I really wanted to do this, and I was really excited about the idea. She supported me a lot. She still supports it. She's not thrilled about weekend calls.
And a divorce would cost thousands.
Yes, I know. I think that was probably the kindest thing anyone has ever done for me.
Wow. Dude, listen, this Chanel solves a bunch of problems, you know. This is normal, you know? I learned it. I miss out on a bunch of family stuff, and my mom has 30 Chanel bags, so we both win.
Dude, I really enjoyed doing this. I really enjoy episodes like this, where everything is detailed, reflective, and fun—all in one. I really appreciate that, man.
Me too. That was cool. I'm a big fan of yours. This is the moment when everything came back to normal.
Actually, funny thing is, I should have said this at the beginning: when I was an SDR at Ramp, I always listened to your podcast and took stories from there. I did it all manually. I wrote to the founders who were your guests, trying to get them involved with Ramp, so it's funny that 6.5 years later, I'm sitting here.