Julian Teixeira, CRO @ 1Password: How to Hire and Train Your First Sales Hires

I think of it as breaking down the anatomy of a win: what steps should one be repeating to have a higher rate of success in winning deals? That’s just part of it. Without the right skills development, your playbook isn’t worth shit. You’re not hiring people to take orders; you’re hiring them to sell.

You think about what outbound really is: it’s about captivating interest, getting to the point quickly, and saying something that matters to the individual you’re speaking to. That in and of itself is valuable. Even if all you’re getting is an inbound call, that makes you more effective at that first discovery call, that first meeting.

Julian, I am excited for this, dude. I’ve been looking forward to this one for a while, so first, thank you so much for joining me.

Likewise. Thank you for having me, Harry. This is great.

Not at all. I want to start with your entry. You started in marketing, and I think it’s a really interesting entry point. How did your entrance from marketing impact how you think about sales today?

It was really interesting. On the one hand, it didn’t prepare me at all for what sales could look like, but on the other hand, I learned to appreciate very early on that, when done right, marketing could really serve as the guardrails for repeatable success in sales. Aligning the outside-looking-in perception of the company and the brand with what the field is presenting is critical to establishing that trust and credibility. That was my appreciation as I went into sales: understanding that, when it’s done right, it can be really effective.

You had 10 years at Lightspeed. It’s a phenomenal amount of time, and you were also incredibly accomplished in terms of position at a young age. What are the biggest sales leadership-specific takeaways for you from 10 years at Lightspeed during that period of hypergrowth?

It was a long journey, and the company I joined at the top of 2011 was not the company I left halfway through 2020. I learned very early, and at every stage, that connecting with people was the key to motivating them and keeping them engaged. Building and scaling companies is hard work. You’re taking people through some really, really hard changes, so the ability to connect with them on a very personal level and understand what motivates them was really what helped me through the hardest changes.

1. How to Create and Master a Sales Playbook

Julian, people are used to going through change and then living with it for extended periods of time. But the reality is, when you’re part of a scale-up or startup, the thing you implemented 3 months ago can very well go stale shortly thereafter, and people get a lot of fatigue with that. They like for things to remain constant and consistent, and that’s just not the case when you’re scaling rapidly.

You were leading all sales and go-to-market for Lightspeed a year pre-IPO. Did you have any imposter syndrome? It’s a big role at a young age.

Loads of it. I still make eye contact with it today. I was always fortunate to have been surrounded by people who believed in me more than I believed in myself.

Does imposter syndrome make you better or worse?

I’d say it’s the constant pursuit of more and better. I look to people who are more successful or who have accomplished more than I have in a shorter timeframe, and that’s my bar. Being in this constant state of “good isn’t good enough” just keeps you grinding.

Listen, I have it too. I was about 12 years old when I raised my first fund, and I definitely felt that. It’s what drives me to go up and work at 2:00 a.m. when everyone else is going to bed. I actually think imposter syndrome is good.

I want to dive right in, though. We always hear in sales, “Sales playbook, sales playbook.” What is a sales playbook to you? First, how do you define it?

I hate the term because of what it stands for. It usually ends up looking like some 20-page document that you use to check a box. I think of it as breaking down the anatomy of a win: what steps should one be repeating to have a higher rate of success in winning deals? That’s just part of it. Without the right skills development, your playbook isn’t worth shit. You’re not hiring people to take orders; you’re hiring them to sell.

What do you mean by the skills-development element, and how do you think about that in relation to sales playbooks?

The playbook has to start with hiring the right people, with the right level of intellect, the right level of curiosity, and the right level of discipline. It’s from that base that you develop skill and industry knowledge, and then start applying the winning formula to close deals.

That might mean deciding whether a proof of concept is appropriate or not, at what stage in the cycle, how and when to get the executive team involved, and things like that. But it’s got to start with having the right people for the right phase of the journey. No playbook is going to solve for that.

Before we dive into the who, in terms of the what and the when, should the founder be the one to create the first sales playbook, or can you bring in a head of sales to do it for you?

I believe strongly that it’s got to be the founder. There are definitely situations where that maybe isn’t the case, but I think you do yourself a disservice as a founder by not being able to get on the front line and get firsthand exposure to how customers are reacting to whatever it is that you’re pitching or selling.

2. Lessons on First Sales Hires

I think that’s an important leverage point that you then need to call bullshit on anyone else that you’re ultimately going to trust sales to in the future. A capable go-to-market first hire can certainly do that, but getting involved as a founder early on is critical.

We now need to hire our first go-to-market person. Julian, you’re an angel in my company. I don’t know what to look for. Should I go for a tenured sales leader, or should I go for junior reps? What do you advise me on for that first GTM hire?

I’d say that, if you’re very early on in your journey, you need somebody who’s going to have humility, patience, low ego, and high curiosity. Sometimes the person with the fancy cover at the front of the book, who’s touched the right companies at the right times, is not what you want.

You want somebody who has something to prove, has a chip on their shoulder, and is motivated to build something greater than anything they’ve ever been a part of. You’re largely looking for somebody who’s going to be patient, not somebody who’s going to blame a lack of success on all the things the company doesn’t do or doesn’t have.

They should be the type of person who’s going to focus on, “What’s in the art of the possible? What can we do? How do we push the envelope further?” That’s the kind of person I think of as a salesperson.

There’s a company I advise for that started off with founder-led sales and is now staring down the barrel of making that same decision: who should that first salesperson be? Ultimately, they landed on an individual who had found success at other companies but felt like they had something to prove. They felt, “I want to be in the driver’s seat now. I want to see it created from A to Z,” and they love a good underdog story.

Should we hire 2 at a time? Everyone always says, “Hey, you want to hire 2 at a time and pit them against each other.”

Absolutely. I think that’s critical. Having someone to chase and creating that sense of competition is really important. It also gives you a good barometer to understand, “Are there patterns or things that are getting in the way of these individuals succeeding, or is it really linked to the person?”

If your sample size is 1 of 1, it can be really challenging to draw that conclusion.

How do we think about target-setting for them? We’ve got these 2 new reps now. I’m the CEO, but I’m a young founder and quite naive. How do I think about goal-setting and targets for them?

In both the early days of Lightspeed and 1Password, we actually started with team goals. We anchored the team to deliver what was most important for the company and what the company was looking to achieve. That works for a very, very short period of time, but it was important for us to establish an “in it together” mentality while we started to figure out what sort of capacity we could get out of these individuals.

Without any historicals on, “I know that a rep should be able to close this many deals at this value,” you kind of need to figure that out. We would leverage spiffs and incentives to get the most out of people and understand, “Where does that back wall live?” But we focused them on one common goal.

As you think about putting guardrails in place and defining what that comp plan is going to look like, the simpler, the better. Especially in the early days, your rep should be able to understand how much they’re going to earn and how they’re going to pay their mortgage without having to go through a ton of gymnastics.

You should be open to changing the comp plan as your focus as a company changes. Anchor the people who are responsible for driving revenue to the things that are going to be best for the business. Whether that’s a multi-product story or you need them signing multi-year deals, whatever that thing may be, their comp plan should be intrinsically connected to it.

Okay, so we have these reps and these team goals. How fast do team goals break, and when do you need to move to individual goals?

Within the first year. At 1Password, we moved to individual goals.

I mean this respectfully, but I don’t even understand how team goals can work. If we want to have the competitive element between them, you need to have a metric of measurement. If you have team goals, you don’t have the metric of measurement.

We’d still measure them as individuals. I can still sit there and say, “Harry has sold more than Julian has this week. You need to catch up.” But as people are starting to figure out what works and what doesn’t, very early on, having that team goal pushes absolutely everyone.

Especially in a small team, you don’t want to be the one who’s dragging everyone else behind. A team goal isn’t meant to mask individual performance. It’s just meant to give you a proxy for how people get paid, in addition to spiffs and things like that, while you’re trying to level-set and determine how far you should be pushing people at an individual level.

What is acceptable, and what does overachievement look like? That can last anywhere from a couple of months to maybe 6 or 7 months. I’ve seen that be very effective. The last 2 companies may not necessarily work everywhere, but I found it really helped us to ground ourselves and keep momentum: “We’ve just got to get here as a company.”

That’s as opposed to having people either judge or criticize the targets we’ve set or the plans we’ve put in place.

3. Setting Goals and Targets for Sales Teams

When it comes to forecasting, this is great. I’m just pummeling you with quick-fire questions. Do you rather have the unachievable target that we hit 80% of, or do you rather have the achievable target that we hit? How do you think about that stretch?

We typically build plans so that 70% of people can achieve them. It’s got to be challenging enough that it’s forcing you to push boundaries, but we don’t design them so every single person will attain them.

The acceleration is often much greater than the deceleration, so when people are having really strong quarters and months, they can really overachieve. The goal is not to set the bar just low enough so everyone makes it across. It’s got to be a challenge.

4. The Reality of Tech Sales Today

Every time I’ve set a goal that is at least 20% or 30% higher than I think we’re capable of achieving, even when we don’t achieve it, we always end up doing 10% more than the goal that we initially set or thought was realistic. There is a mental element to this that is about pushing people to think creatively and outside of what they see in front of them to achieve a goal.

Dude, 70% hit it and 30% don’t. We chatted before, and you said something about the bottom dropping out of sales. What did you mean by that?

Working in tech sales has been such an interesting proposition for so many years. For the last decade and change, it’s been up and to the right. If you can prove that you’ve got a real solution to a real problem that exists, companies were willing to throw money at it.

I think the world of tech sales that we’re living in today is akin to what it was for many people who have been in this industry for 20 or 30 years, and a lot of people just aren’t ready for it. A lot of people got into sales because they figured, “I don’t really need a degree. I can just find my way into it. If I’ve got some form of charisma or charm, I can probably sell software, and the earning potential is there.”

I think there are a lot of incredibly talented people in tech sales today, but I think many are looking at this and thinking, “Wait a minute, this isn’t what I signed up for,” and are just going to give up and drop out. I just think the mentality around what it takes to be successful, not just in sales but in the world of work in general, has changed.

5. Pipeline and Deal Reviews

Do you think that—I mean this in the nicest way—I don’t think the majority of salespeople are very good. I don’t think the majority of sales leaders are very good. I interview them from doing the shows that I’ve done. I think I’m a better sales leader than most of the sales leaders that I have.

I don’t disagree with you at all. Companies are pushed to scale very quickly. They’re pushed to get capable sets of hands in roles to keep things moving forward. I think it’s been easy for too long, and those easy times have bred a lot of mediocre talent, unfortunately.

Should you then fire the bottom 30% that don’t hit goals?

We look at skill versus will. That’s something we think a lot about. If somebody lacks the skill to meet the needs of an evolving business—whether your product portfolio has changed, your sales motions are changing, and people are catching up to that, and that’s the reason they’re falling behind—that, to me, is acceptable if somebody is willing to put in the reps and the time to get better.

It’s the people who just lazily blame their failures on anything but themselves who, unfortunately, are going to drop off over time.

It’s hard work. Super hard. People who are laid off are often laid off for a reason. Do you hire people from layoffs?

I think there are some good people who have been laid off, but I have to imagine that most companies that have done layoffs have looked at just the bottom performers on the team.

The reason I say it’s not all created equal is that, within that bottom group, you may have individuals who were either new to the organization and still getting their bearings, or they may have had an off month or an off quarter. If anyone is doing Excel math to determine who falls at the bottom, as opposed to taking the time to really evaluate the people as individuals, I do think you can find some good talent that unfortunately fell victim to a layoff.

I always say, look for shutdowns. If you shut down a whole product division and the sales team are gone, that may not have been because they were bad. It may have been that the product didn’t have product-market fit, the product team didn’t work, or so many other things. If everyone’s gone, that’s not really a layoff. Do you see what I mean? Being more nuanced in how you look at it is so important.

Okay, so we have that target-setting and that goal-setting. How quickly do we know when we’ve hired a not-great rep?

Within the first 3 months. In the first 3 months, we’ve got ramp targets, which everybody does, but we look for a certain set of behaviors and leading indicators of whether or not they’re going to be successful over the course of the next 3 months.

How quickly do we expect them to generate pipeline?

From day 1. As soon as you’re out of training, you’ve got an understanding of the product, and you’ve got to get out there and get the reps in.

I come to you—sorry, this is where people love it—and say, “I’m on your team. I’m young and enthusiastic.” What does week 1 look like? How should we spend the first 7 days?

Your first 7 days are about getting set up. I’d say, really, your first 2 weeks are about getting to understand the product, the systems and tools, how the job gets done, and meeting the team. You’re in listen-and-learn mode.

You should be asking a lot of questions about what you don’t understand, not just nodding your head up and down and going through the training. We look for that curiosity in the first 2 weeks. It’s an indication of how engaged someone is and how willing they are to be an active participant in their success, as opposed to thinking, “Someone’s going to give me a headset, a laptop, and a 20-page playbook, and suddenly I’m going to hit my target.”

That’s what the first 2 weeks look like. The steps you take after that—whether that’s reaching out to top reps on the team to understand what they’re doing, shadowing calls, spending time in Gong, or seeking out more training and 1-on-1 time—all of these are really important indicators to me that say you’re engaged and you’re in it.

I totally agree with you. I just have the question of how many are like that, where they stay late to listen to extra Gong calls, seek out the extra learning after hours, or research the latest AI tools they can use to have more pipeline generation. For me, it’s none.

Maybe I’m hiring the wrong people, and I’m in the UK.

It happens. It’s certainly not the case with everyone, but this year our non-regrettable attrition is probably in the realm of 29% to 30%. We come to that conclusion rather quickly. We’ve started putting a lot more emphasis, especially at scale, on the hiring process and how we vet that out early on, even before they’ve started.

But some people are just great interviewers.

Okay, so we have the 2 weeks of listen and learn. After that, we’re expected to do pipeline generation straight away. When do we speak to customers first, especially if we’re selling to enterprise?

You’re speaking to customers nearly straight away, and that can come in varying forms. Either you’re joining a call, listening in, and interjecting where you feel you can, and slowly taking the training wheels off, or, from day 1, you should be able to go out there and have a conversation.

This is well before we’ve given you a book of business and well before we’ve given you any leads. You’ve got to get out there.

Okay, so I’ve got to get out there.

6. Outbound Prospecting and Pipeline Generation

Yeah, it’s tough.

As an AE, you expect me to generate my own pipeline. How do you think about me generating my own pipeline versus relying on demand gen?

The difference I see is that you’re going to identify companies and individuals within a company that fit squarely within our ICP, and you’re going to reach out to them cold. You’re going to try different approaches to reaching out, whether that’s on LinkedIn or via email.

You’re going to start establishing those connections early on. Some of your emails are going to be crap, and some of your outreach just isn’t going to work. You’re going to get no responses, but you’re going to have to develop the muscles very quickly to say, “How do I get Harry’s attention?”

It’s certainly not an email in his inbox that I walk away from and wait for a response on that’s going to get him. How do I tap into what Harry gives a shit about and what’s relevant to him in that moment?

Some of it is borderline stalking to understand what Harry’s talking about, what he’s interested in, what he’s surfacing, and who he’s following, and then try to get into that. Before you even reach out, show that you give a shit. Show that you’ve done some research and that you’re not just blasting off a template to 1,000 people, hoping that 10 of them get back to you.

That’s the muscle that ultimately ends up making you far more effective before I’ve handed you a lead, an opportunity, or a meeting that I’ve paid real dollars to go out and generate that you just blunder.

Do you believe outbound is still a viable strategy in 2024, with the proliferation of AI tools and the immense supply side of content that we’re able to shift now? Is outbound viable?

I think it’s viable. I think it’s gotten a lot harder, but it is viable. The easiest part of my day is marking a whole bunch of emails as unread in my inbox that are clearly people trying to sell me stuff. If it’s not a priority, it’s easy to move it out of the way.

I think AI should actually make it a lot easier. Think about the amount of time it would take for you to do proper research and discovery on a company before reaching out. AI can accelerate that dramatically.

I don’t think AI is necessarily going to work on autopilot and fill your inbox with leads and responses, but I think it could help outbound prospecting become a lot more effective. BDRs and AEs can do a sharper job at prospecting with a lot less effort.

If an AE is meant to generate their own pipeline, what the fuck are BDRs doing?

I think outbound prospecting becomes a team sport, especially when you’re selling into high enterprise and when you’re selling across mid-market.

For AEs, it’s a matter of keeping some of those muscles sharp. Think about what outbound really is: it’s about captivating interest and getting to the point quickly with something that matters to the individual you’re speaking to. That in and of itself is valuable, even if all you’re getting is an inbound call. It makes you more effective at that first discovery call and that first meeting, so it’s an important muscle that people need to exercise, period.

7. Hunter vs. Farmer Sales Models

I also think there’s a certain amount of appreciation and gratitude that you have when you’ve got a BDR working their butt off to generate pipeline for you. If you understand what goes into getting that meeting set, you’re going to treat that opportunity accordingly. I still expect the majority of pipeline to be generated from the BDR team, but AEs who don’t self-generate just doesn’t work. I think it does them a personal disservice over time.

It makes me think of the hunter analogy, and I’m fascinated by it. How do you think about the hunter-versus-farmer analogy and knowing what structure you want at what stage?

Ultimately, it depends on how your customers are buying. I’ll give you a concrete example. We started off with the hunter-farmer model at 1Password. The main reason was that, when we landed here and started building the team, the company had already acquired 50,000 businesses that were using our product, but we had less than a 2% penetration rate within those businesses.

These were fanatical users who were bringing our product into the workplace. If all we did was have one flavor of sales individual, they would favor expanding across the base and likely be a lot less efficient with any inbound demand. They certainly wouldn’t be pushing themselves to go out and generate outbound demand.

Early on, we decided to create that friction on both ends: “We’re going to have a team of hunters and a team of farmers.” Today and going into next year, we’re actually bringing those functions back together in a hybrid sales model.

The reason is that we now have a multi-product portfolio. Our customers are landing and expanding with us far more, and what we saw was that we were actually losing new-business deals because we were pushing too hard to get too much upfront.

Now we’ve aligned the sales motion and model to how our customers buy, and we’re taking a far more segmented and territory-based view to how we split the team.

Do you agree that you never want your farmer against someone else’s hunter?

I think it depends on the context. Farmers are a lot more patient. They’ll really take the time to explore all 4 corners and build a meaningful connection. They’re a lot more curious, and I’d say they’re way better active listeners.

Hunters are used to operating in an environment where they’re trying to outrun a whole bunch of other lions for the same gazelle. You’ve got this fast-twitch muscle that’s working at all times, and sometimes you might miss something. Sometimes you might hurry and leave money on the table.

8. Compensation and Specialization in Sales Teams

It really depends on the context. One will always tell you that the other’s job is much easier than theirs.

Should customer success be comped for upsells?

Yes. I think customer success should be comped on net dollar retention. They’ve got a role to play in the process, and I think it’s important that there’s overlap between how they’re compensated, how the AE is compensated, and ultimately how I’ve seen that model be successful in the past.

That’s when both are working together to serve the customer. I know there are really polarizing views on CS, and I’ve heard a few folks on the show bash it, but ultimately the body of work needs to get done.

Whether you’re in the camp of saying, “One person should do all of it,” in which case they’re naturally going to be able to handle fewer accounts, or you sit there and say, “Actually, I want a cleaner division of labor, and I expect individual capacity to be much higher,” I think you get to the same net result.

In our world, customer success is an impartial person who the customer sees as a trusted adviser, not as somebody who’s just trying to cram more product down their throat. They’re ultimately thinking about how the customer is using the product, what more benefit they could be getting, and playing the role of orchestrator by bringing the right people in at the right time.

The AEs are strictly revenue-focused.

How do you think about the specialization, or verticalization more importantly, of sales teams? 1Password is a horizontal product, which is amazing because you can serve so many different people, but also difficult because you can serve healthcare, banking, consumer—you name it. I like verticalized sales teams. How do you think about sales teams?

I think there’s a time and place, and again, it will vary from company to company. We’re not verticalized today. The main reason is that we looked at our success across every vertical. We looked at win rates, ACV, and time to close, and found very, very little difference across these different segments.

We have yet to reach any sort of saturation in any one segment, really. We’re not yet at the stage where we need to hire individuals who have built a career selling to specific verticals and have deep vertical and specialized knowledge. We’re absolutely going to get there.

Our journey is such that we’re looking at segments first and foremost because SMBs buy very, very differently than large enterprise companies. Territory-based splits are where we’re at right now, making sure that we’ve got the right people, right language, right time zone, and so on and so forth.

The next step will be to verticalize the team so that we can go deeper and wider.

I had Matt Plank at Rippling on the show recently, and he said that $5K to $25K ACVs is where SaaS companies go to die. How do you feel about that, and what’s your ACV today across the different segments?

It varies by segment. Enterprise ACV is—I’d say enterprise deals for us are in the 6 figures. We actually landed our first 7-figure customer earlier this month, which we’re really excited about. Somewhere between 6 to 7 figures.

Mid-market is somewhere between $50K and $100K, well into the 6 figures. SMB deals will vary anywhere from a few thousand dollars for a very small business to $25K or $30K.

Can you have a sales motion like we discussed with that SMB structure if you’re charging $5K to $15K? You can’t afford the outbound, the AE, and the CS. Can you?

No. You need to be very intentional about where you deploy those resources. Most of our outbound motion right now is invested in mid-market and enterprise because that’s where we get the biggest bang for our buck.

The SMB teams are a lot more transactional. They work on high-volume, high-velocity deals. Most of them pay for themselves 4 times over, even if I load in all costs.

From a CS and onboarding perspective, we rely on low-touch models with smaller customers to get them going. Ultimately, we’ll get someone on the phone to work with them if they need the help, but it isn’t the default switch to the team to unload the whole machine for every single customer and deal, regardless of size.

If they pay for themselves 4 times over, why don’t you 10X them? What I’m trying to get at here is: where is that asymptote of value where you no longer get 4X payback?

I think there’s a point at which you reach a ceiling. Today, that team is largely driven by the inbound demand that we get for our product. As we think about investing in that further, the unit economics need to make sense.

At a certain point, we’re going to have to make a decision: how do we want to serve this segment? Conversations we’re having now are about whether we can start to leverage a different distribution model for that cohort. We’ve recently started working with MSPs and distributors to achieve that.

9. Outbound vs Inbound Sales

There definitely is a point at which constantly 10Xing the investment starts to make less and less sense, which is a big part of why companies need to think about moving upmarket and building that motion early on.

What’s your inbound-to-outbound ratio today on converted deals?

We’re probably just over 50% outbound, so a 54%-46% split. I’ll say that a year ago today, we were probably 99% inbound.

Wow. That’s a big shift.

It’s not just about hiring BDRs. It’s really about getting the sales team to participate in generating pipeline and understanding that the level of intent of these customers is vastly different from when you’re getting an inbound lead.

These deals take longer to close.

What’s the time to close on an enterprise deal today?

There’s a great deal of variance, but I’d say on average, 2 quarters.

2 quarters?

Yeah. We usually think about the pipeline about 2 quarters out. It may be closer to 3 to 4 quarters when we’re generating outbound pipeline.

Outbound deals typically close at half the rate, but they close for twice as much. The person we’re reaching out to doesn’t have a preconceived notion of what they want to buy. We’re defining that from the get-go, so that is the advantage of outbound pipeline generation over inbound.

I’ve always been taught that, when you have to educate the customer, don’t bother. They don’t know, and it’s going to be too hard to sell. It’s like when you’re fundraising: when you have to persuade a VC to invest in the category itself, don’t bother. Is that wrong?

They can believe that they need password management and that it’s really important. Now they’ve got many options, and they can choose lots of them. That’s up to you. But if you’re having to persuade them that password management is important, no mas—I think that in and of itself can sometimes be the problem.

You need to be able to educate them on the problem. If the problem isn’t clear to them or they don’t agree with it, then I’d agree that you’ve got an uphill battle ahead of you.

A lot of companies tend to anchor to their product: “I’m going to explain the product and why it’s different,” as opposed to attaching themselves to the problem, which, if you’ve done your job right, the person you’re speaking to should understand very clearly.

Now you’ve got their interest, and now they’re leaning in. Your product is just proof that the solution you’re talking about is real and exists.

I tend to think that leading with the problem and familiarization with the problem is the most important way to get them to lean in. No one will sit there and disagree that reused or weak credentials are a problem. But how you go about solving that problem is often what the debate is. Don’t start there. Get on the same page with them first about what the problem is, and then get closer to how you’re going about solving for it.

I’d love someone to take the argument against strong credentials. You know what I mean? I disagree. I’m like, “Okay, what if they just don’t care?” I don’t mean that badly, Julian, but I’m just like, “I don’t care about credential strength.”

We get that. The security practitioners that we sell to have a number of different priorities. They’ve got to think about everything. It’s like me telling you that the microphone 6 inches from your mouth is probably going to give you cancer. You’re like, “Yeah, sure, but everything will.”

It’s really about contextualizing what not solving that problem is going to mean for them and connecting with something that they care about. What are they prioritizing right now within their business?

Maybe it’s not credential management, but maybe it is keeping employees safe. Maybe it is minimizing the threats that exist within their company. They may not agree in the first conversation that solving for credential management is going to be the solution to that, but that’s your job as a seller: to guide them there.

The difference for me is not trying to create a new set of priorities or things for them to think about. It’s about tapping into what they already care about, what they’re already prioritizing and thinking about, and working with them in that way.

We have this great prospect, and for whatever reason it doesn’t fully land—or it does land. We need to do deal reviews, a crucial part of a sales process. I’m a young founder again. I don’t know how to do deal reviews, and I don’t know what to expect of my go-to-market team for deal reviews.

How often do you do deal reviews?

We do them weekly. We do pipeline inspection on a weekly basis.

What does pipeline inspection look like from a structural perspective? Can you walk me through it as granularly as possible?

From an SMB perspective, you’re often looking at pacing. You’re looking for pattern matching on what’s going on that month relative to the previous month and relative to the same period last year. Oftentimes, we’re looking at those daily.

We’re also looking at the pipeline. How does a drop in pipeline this week impact us next week? It’s a very, very data-driven approach, and you need to obsess over it. It’s not about reviewing it once a month or once a quarter. It’s about living in it every single day, but sitting down and reviewing it as a team every single week.

As you start to move upmarket, the classic question is, “Enterprise deals take 2 quarters to close. What on earth could we possibly be talking about on a weekly basis?” The reality is that you still need to have some form of objective or goal that you’re working toward, even on a weekly basis.

What outcomes are you trying to drive? What needs to be true as part of this deal in order for us to win it? What progress have we made toward checking off those items this week? How much pipeline have we built?

Even if you’re looking at things 2 quarters or a year out, what does our pipeline look like for the second half of next year, and how are we trending there? We do this inspection weekly regardless of segment, but I’d say the larger the deal, the more focus you’re putting on the account or deal level as opposed to just looking at the sum of how that segment is performing.

It’s really critical. Who’s invited to this meeting? Is it the whole sales team, only leaders? How do we think about that?

I think it will vary based on company size. If your team is small enough, I would get the whole team involved in the process. I think it’s an important part of how you drive accountability as you grow, though, and it’s about creating a cadence.

Every Monday, every AE is going to sit down and look at their pipeline. They’re going to take inventory of what they’ve done that week, how they’ve progressed, what’s fallen out, and what’s moving ahead.

The following day, they’re going to report that to their frontline leader. Their frontline leader is then going to inspect that work, ask probing questions, ensure there’s proper hygiene, and roll that up to their second-line leader.

Typically, by the time we have our weekly forecast call, I’m having it with my direct reports. We’ve got people from marketing and our FP&A team joining us as well, and then we roll a summary to the executive team.

Can I be a bit blunt? Does this not seem a bit ridiculous? I don’t mean that horribly in any way, but an AE rolls it up to a sales lead, who rolls it up to someone else, who rolls it up to someone else. Can we not just get the AE to present in a more direct way?

It feels like every stage is a gatekeeper, and every half hour is half an hour that’s valuable. Is this really how businesses are run today?

I think you reach a certain size and scale where you’d end up having an 8-hour meeting if every AE had to come and run you through their pipeline.

Can we not just hire AEs where we trust their pipeline?

No, I mean, being serious, but say you ask me, “What’s your pipe?” and I give you dog shit. I say, “I’ve got $200K this week, but actually I think I’m going to have a 50% dropout rate, so $100K.” You’re like, “Great, thanks.” It’s all done by message.

Unfortunately not. There are too many moving parts and too much emotion involved in selling. There’s too much that can be driven on a feeling: “I just had a great conversation with Harry. I think he’s going to buy.”

Having someone to keep you honest throughout that process is mission-critical.

I’ve seen so many AI sales coaches where they’re continuously prompting. Really? What makes you think that?

Do you think that will continue to be human-led or AI-led?

I think the landscape is going to change dramatically. We started using a product called Momentum that not only takes notes on the call and sets follow-ups, but also gauges the customer sentiment on that call. It gives you suggestions on things that you could have done, should have done, or didn’t do on a call-by-call basis.

Why has Gong fallen asleep at the wheel?

That’s a great question. I was one of Gong’s first 50 customers, back in the early days. I think they led the charge on siding with the salesperson and saying, “We get what you’re going through, and we’re here to help.”

I think Gong is leaning in that direction. I’m seeing more and more AI in their product, but candidly, a lot of sales leaders I speak to are using it as a coaching tool and as a way to go back and instant-replay calls. Some are using it to manage pipeline.

I think it’s tough. I can spend ages talking about the sales tech stack in and of itself because I do think it’s gotten very, very messy.

My hope is that somebody comes along and says, “Rather than adding another interface or tool that you need to log into to get insight or get work done, I’m going to work through the existing channels and existing products that you’re using and just augment what you’re getting from them.”

I don’t want another thing I need to log into to get customer sentiment. Feed me that through Slack. Populate it in Salesforce. Surface this in the areas where I’m already getting work done.

10. Sales Tech Stack and Tools

Sorry, there are a couple of things. What are the core tools that you think every sales team and leader should be using today? You mentioned the tech stack. Which tools are the “hell yes” tools, regardless of what stage or sector you’re in?

A good CRM to start. I implemented Salesforce early on here. I’ve done CRM migrations before, and it’s a pain in the butt. Just start with what you know you’re going to need to scale and be done with it.

Outreach and Gong were quick to implement at 1Password as well. We leverage both of those. Then some form of sales-enablement tool. There are tons of great ones out there: Flockjay, Highspot, Seismic.

I think inherently you’re going to end up with a lot of collateral and information to feed your sales team. They’ll digest it, and then it goes into a repository that they’ll never reference ever again.

Having a tool that surfaces the right content at the right time for the right opportunity, based on stage and so on and so forth, is pretty important.

11. Maintaining Sales Morale

I totally agree with you. When you’re in those reviews and it’s, “I don’t have much. Notion dropped out. Next one, Rippling dropped out. Yeah, I don’t have much,” how do you maintain morale when sales teams are not performing?

It’s important to see the positive and call it out. When the results are shit, it doesn’t mean that everything is shit. You need to be able to call out the good.

Selling is ultimately a very emotional sport. If you’ve got a group of deflated salespeople out there trying to get people excited about your product, it’s really hard to do if they’re not believing in themselves.

It’s about being positive about the things that have gone right, but it’s also about being brutally honest about the things that aren’t working and getting comfortable assessing that. Attack the problem, not the person, in that scenario.

We do inspection often enough that, if you’re doing inspection often enough, there should not be any surprises. If there are, then there’s something you missed as part of that process. There’s something you didn’t inspect for, a risk you didn’t assess, or something you didn’t call out.

What’s the most common risk people miss that leads to deal attrition more often than not?

More often than not, it’s an understanding of what the procurement process looks like within the company from end to end. There’s always some surprise budget committee or individual who needs to weigh in.

Not going wall-to-wall and understanding what it’s going to take to get a deal done is the biggest mistake I see, and one of the leading causes of deals slipping.

Sometimes things will happen that are completely outside of the rep’s control. I get that. We can only control what we can control, but more often than not, it’s about missing something in the procurement chain or not getting the right amount of value established with the right individuals in the organization.

If you’re attempting to sell a half-million-dollar deal to a manager in a department, and their superior or budget holder isn’t even aware that these conversations are taking place, that’s a huge red flag. People are inherently bad at going back and selling the business case internally.

We actually find that we end up coaching a lot of our reps to do exactly that: not just sell the product to the person you’re working with, but coach them and help them sell it internally.

How do you do that without being so fucking obvious? Let’s say you and I both want 1Password in Notion, Rippling, Vanta—you name it. We both want it. There’s a pack of information that I would use. How do we do it?

The subtle art is not just loading them up with technical jargon, even if they understand it. It’s thinking about the questions their CFO is going to ask them when they try to justify spending on this product.

What are they going to ask? It’s about giving them those answers throughout the process so they’ve got them at the tip of their tongue and can answer right away.

Most of the time, they can’t anticipate what their CEO or CFO is going to ask of them. We give that to them without asking anything in return, knowing full well that they’re going to face that challenge at some point.

Even if we don’t get access to those individuals throughout the sales process—I mean, our CFO often says, “Please don’t have me speak to a salesperson”—we make sure that our champion is armed with the right answers to the right questions and can justify it.

It’s so funny you said that about the CFO.

They don’t want to speak to salespeople.

Are people still buying software like they used to?

No, they’re not. The CFO suddenly has an interest in absolutely everything. There used to be a time when it was, “You’re within your envelope to spend, so I’m not really going to question it,” or, “You’ve presented a logical case for why we need this thing.”

That just isn’t the case anymore. They want to understand because ultimately their boards are holding them accountable for managing spend efficiently.

Even as a fast-growing, profitable business, we still run through cost-rationalization exercises on the tools that we use constantly. We’re looking for overlap across different products. We’re thinking, “Wait a minute, could this other thing we’re using do it 80% as well for the same cost?”

I remember when it was good times. Wasn’t that nicer? It was so much more fun.

I think we’re being a lot more intentional about the things we’re investing in.

What did you not spend money on at 1Password that you wish you had spent money on?

I think we had the opportunity to be a lot more aggressive in investing in product and engineering, whether that was a build-or-buy scenario. We had the benefit of being a profitable business with a lot of cash at a time when many companies were struggling.

I think there was a window of opportunity there for us to substantially accelerate our pace of growth, and we chose to err on the side of caution or take a middle ground. Hindsight is always 20/20, and who knows where we’d be today had we made that decision.

That’s probably one regret I have: not pushing a little bit harder for us to do that as a company.

Listen, I want to do a quick-fire round. I’ve so enjoyed this. You’ve got to understand, we put the schedules together, and that’s fine, but I just want to have a great chat, be interested myself, and learn myself. That’s why I do this show. This has been amazing.

I’m going to say a short statement, and you give me your immediate thoughts. Does that sound okay?

Yeah, let’s do it.

I spoke to many of our mutual friends and some of your friends, and some of these are more personal than normal, which I love. Talk to me about your hair and how many people have cut it.

Only 3. That number is 3 and not 2 because I ended up living in New York for 4 years and needed to find someone there. I’m very loyal in that sense.

I like the ritual of going to the same person—somebody who’s kind of partway removed from the world that I live in, who I can confide in during that 1 hour of therapy. My hair has just become a thing over time, so I only really entrust it to 1 person these days.

You’ve got great hair, by the way. Real volume, which is a line I’ve never said on a show, but there’s a first time for everything.

What is your hotel cadence?

Oh my gosh. I’ve spent a lot of time in hotels.

You like that?

The hotel part is just that, when I’m not in my own bed and I’m not in my own home, I’m sort of out of sorts. It’s a weird one.

I don’t love traveling. The aspects of traveling that I love are getting out there and meeting people face-to-face. I really, really do love that. In a lot of ways, when I’m traveling, it shuts out everything else in my life and I can really focus on work.

Sleeping in hotels is probably my least favorite part.

12. Are Remote Sales Teams Less Effective

Do you buy into remote sales teams?

I lead a remote sales team, but I believe in the importance of in-person interactions. We invest every year in getting every single individual together in one place.

I think it’s important. Within 15 minutes, you can tell who’s engaged, who’s in it, and who’s full of it. You just get that sense.

You lose that ability to hear Julian on the call and close the deal: “We’re winning,” or, “He lost it because of that reason. I should watch out for that,” or, “She’s doing really well. We should actually promote her,” or, “They’re really down. We should actually go for a beer after work with them and make them happy.”

You lose that. It takes a lot more energy and work to seek out what’s going on as opposed to just being in the room and seeing it.

We get our sales teams together at the end of the month and the end of the quarter. It’s a subset of the team; it’s not all of the team. But it’s definitely something that’s top of mind for me as we continue to grow—this idea of building out centers of excellence for our talent so that we get a little bit more of that.

I get a lot of that with our leaders because there are many points during the year when I can interact with them, but I miss that. I miss walking the halls. I miss the casual chats by the coffee machine.

Dude, tell me about a deal you’ve closed where you’ve had to do something outside the box to get it done.

I don’t have a story like that. I’ve heard some cool stories of people giving away their car to a prospect to get the deal done. That happened somewhere in Italy. It was an old boss of mine who told me the story.

Of course it was Italy. Only in Italy: “I gave my daughter—”

“You like the car? It’s yours.”

I don’t have anything like that. The closest is that we’ve definitely tracked down and waited for that last signature from a CEO who was on a flight. We found out which flight they were on and tracked it so we could get them right as they landed.

We’ve done that and gotten deals across the line right at the 11th hour. That’s about as outside the box as it’s gotten.

13. Final Thoughts and Advice

What one piece of advice would you have for a sales leader starting a new role tomorrow?

Find a company where the biggest challenge they have is one you’re actually passionate about solving. Far too many people judge companies based on what they are today, but I’d encourage sales leaders to judge them based on their future potential and the belief that you have the ability to get them to that potential.

That will ultimately yield the most value for yourself personally and for the company that you join. I think that’s a reflection sales leaders should have with themselves every single year as they’re sizing up, “Do I stay or do I go?”

What current sales tactic will continue to reduce in importance over the next 5 years?

“This discount expires at the end of the month.”

I think people are aware that that’s just dead. It doesn’t work anymore. We always grew up with TV ads in the UK—Land of Leather or DFS, sofa companies—and it was, “70% off ends Friday.” Then you’re there on Saturday and it’s, “New sale, just 24 hours.”

It’s a bad thing to be trained on. Even procurement teams have wised up to the fact that, “I’m going to wait for the last day of the month, make the salesperson really, really sweat, and then salespeople start to get desperate and start dishing it all out.”

I think that’s gone by the wayside. There was a time and place for it, but not anymore.

What one company sales strategy has most impressed you over the last year?

I’ve been really impressed with Wiz. I guess it’s a typical answer in the sense that, yes, they’ve grown very quickly, and that’s admirable. But knowing the amount of talent and change-management cycles they likely needed to go through on that journey from $0 to $500 million in revenue over that period of time—that’s the impressive and remarkable part of the story.

The playbook for how you become a billion-dollar company is pretty well understood as far as the typical steps: international expansion, a multi-product portfolio, working with partners, and so on and so forth.

But doing that over a compressed timeframe is the impressive feat that I think Wiz has accomplished. Good on them.

Julian, as I said, I love shows like this where it’s much more natural than it was intended to be. You’ve been amazing. Thank you so much for joining me.

Thanks so much for having me, Harry. This was a blast.