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

This episode is brought to you by Capchase, helping software and hardware companies close deals while accessing TCV upfront. Learn more at Capchase. http://www.capchase.com/20vc?utm_source=lp&utm_campaign=2025q1-all-POD-pay-20sales&utm_medium=paid-podcast& ---------------------------------------------- Julian Teixeira is the Chief Revenue Officer at 1Password, where he has grown B2B revenue over 8x and scaled a team of more than 450 in go-to-market. 1Password set the record for the largest raise in Canadian history at the start of 2022. Prior to 1Password, Julian served as the head of global sales at Lightspeed Commerce, a company he helped scale from startup to IPO and through over 10 acquisitions throughout his decade-long tenure. ---------------------------------------------- In Today’s Episode We Discuss: (00:00) Intro (02:58) How to Create and Master a Sales Playbook (05:56) Lessons on First Sales Hires (08:01) Setting Goals and Targets for Sales Teams (12:29) The Reality of Tech Sales Today (16:14) Evaluating and Managing Sales Reps (19:49) Outbound Prospecting and Pipeline Generation (23:36) Hunter vs. Farmer Sales Models (25:51) Compensation and Specialization in Sales Teams (31:08) Outbound vs Inbound Sales (35:25) Pipeline and Deal Reviews (41:12) Sales Tech Stack and Tools (42:28) Maintaining Sales Morale (49:30) Are Remote Sales Teams Less Effective (51:36) Final Thoughts and Advice ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow 1Password on X: https://twitter.com/1Password Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #julianteixeira #1password #cro #sales #lightspeed #remotework #playbook

Julian TeixeiraguestHarry Stebbingshost
Mar 7, 202554mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 2:58

    Intro

    1. JT

      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. Like, without the right skills development, your playbook isn't worth shit. You're not hiring people to take orders. You're, you're hiring them to sell. You think about what outbounding really is. It's about captivating interest. It's about getting to the point quickly. There's something that matters to the individual that 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.

    2. HS

      Ready to go? 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.

    3. JT

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

    4. HS

      Not at all. But I wanna start with your entry. You ha- 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?

    5. JT

      Uh, it, yeah. It was really interesting, in a way. 'Cause like, on, on the one hand, it, it, you know, it didn't prepare me at all, uh, for, for what sales could sorta look like. But, on the other hand, um, I learned to appreciate very early on that, uh, when done right, uh, marketing can really serve as the guard rails for repeatable success, uh, in sales. And so, you know, aligning the outside-looking-in perception of the company and the brand with what the field is presenting, um, is critical, uh, to establishing that trust and credibility. So that, that was sort of my appreciation, uh, as I went into sales, is understanding that, you know, when it's done right, it could, it could be really effective.

    6. HS

      You had 10 years at Lightspeed. That's a phenomenal amount of time. And you also, like, incredibly accomplished, in terms of position, at a young age. I just wanna ask, what are the biggest sales leadership, specifically, takeaways for you from 10 years at Lightspeed in that period of hypergrowth?

    7. JT

      Yeah. It, it, it was a long journey. Um, and, you know, the, the company I joined, uh, at the top of 2011 was not the company I left, um, uh, you know, sorta halfway through 2020. Um, but I, you know, I learned very on and at every stage that, uh, connecting with people was the key to motivating them, uh, and keeping them engaged. You know, you know, building and scaling companies is hard work. Uh, you're taking people through some really, really hard changes. And so, the ability to connect with them on a very personal level and understand what motivates them, um, was really-

    8. HS

      What are the hardest changes, Julian?

    9. JT

      You know, people are sort of used to going through change and then living with it for extended periods of time. Um, but, you know, the reality is, when, when you're part of a scale-up or a startup, like, you know, the thing you implemented three months ago can very well go stale, uh, shortly thereafter. And so people get a lot of fatigue with that. Um, you know, they, they, they like for things to remain constant and consistent. Um, and that's just not the case when you're scaling

  2. 2:58 – 5:56

    How to Create and Master a Sales Playbook

    1. JT

      rapidly.

    2. HS

      You were 30 leading all sales in GTM for Lightspeed a year pre-IPO. Did you have any imposter syndrome? It's a big role. It's a young age.

    3. JT

      Yeah. Uh, loads of it. Um, I, I still make eye contact with it, uh, today. Uh, you know, I, I was always fortunate to have been surrounded by people who believed in me, uh, more than I did in myself.

    4. HS

      At what extent does imposter syndrome make you better or worse?

    5. JT

      I'd say it's the, the constant pursuit of more and better. Um, you know, I, I look to people that are more successful or who have accomplished more than I have in a shorter timeframe. Um, and that's my bar. And so, you know, being in this constant state of good isn't good enough, um, just keeps you grinding.

    6. HS

      Uh, listen, I have it too. Uh, you know, I was about 12 years old when I raised my first fund.

    7. JT

      (laughs)

    8. HS

      Uh, and, uh, I, I definitely felt that. Um, but it's what drives me to go up and go and work at, you know, 2:00 AM when everyone else is going to bed. So, I, I actually think imposter syndrome's good. I wanna dive right in, though. We always hear in sales, like, sales playbook, sales playbook. What is a sales playbook to you, first? How do you define it?

    9. JT

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

    10. HS

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

    11. JT

      You know, the, the, the playbook's gotta start with hiring the right people, um, with the right level of intellect, the right level of curiosity, the right level of discipline. Um, and it's from that base that you develop skill and industry knowledge, and then start applying the winning formula to close deals, whether that's deciding whether, uh, you know, proof of concept is appropriate or not, at what stage in the cycle, how and when to get the executive team involved, things like that. But it, it's gotta start with having the right people for the right phase of the journey. Uh, no playbook is gonna solve for that.

    12. HS

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

    13. JT

      I believe strongly that it's gotta be the founder. Um, you, there are definitely situations where, uh, that maybe isn't the case. Um, but I, I, I think you do yourself a disservice as a founder. Like, being able to get on the front line, um, and get firsthand exposure, um, to how customers are reacting to whatever it is that you're, you're pitching or, or selling, I think is an important leverage that you then need to call bullshit on anyone else that you're ultimately gonna trust sales to in the future. So, um, you know, a, a capable go-to-market first hire can certainly do that, but getting involved as a founder, I think, early

  3. 5:56 – 8:01

    Lessons on First Sales Hires

    1. JT

      on is critical.

    2. HS

      So 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, like, a tenured sales leader or should I go for, like, junior reps? What, what do you advise me on that first GTM hire?

    3. JT

      Yeah. I- I- I'd say, you know, uh, if you're very early on in your journey, um, you, you need somebody who's gonna have the humility, the patience, low ego, high curiosity. You know, sometimes the person with the fancy cover at the front of the book that's touched the right companies at the right times, um, is- is not what you want. You want somebody who has something to prove, has a chip on their shoulder, and is- is motivated to build something greater, um, than anything they've ever been a part of. Um, and so I think you're- you're largely looking for somebody who's gonna be patient, not somebody who's gonna, you know, blame a lack of success on all the things the company doesn't do or doesn't have, or, "Hey, if only we had these systems or this much more money to invest." They should be the type of person who's gonna focus on, "Hey, what's in the art of possible? What can we do? How do we push the envelope further?" Um, so th- that's the kind of person that I think of as- as, uh, as a salesperson one. And look, there- there's a company, um, you know, I advise for, um, that- that started off with founder-led sales that's now looking, you know, or staring down the barrel of making that same decision of, "Hey, who should that first sales person be?" Uh, and- and ultimately, they- they landed on an individual who, um, you know, had found success at other companies, but ultimately felt like they had something to prove, felt like, "Hey, I wanna be in the driver's seat now. I wanna create it from A to Z," and loves a good underdog story.

    4. HS

      Should we hire two at a time? Everyone always says, "Hey, you wanna hire two at a time and pit them against each other."

    5. JT

      Absolutely. I think that's critical. Um, you know, having someone to sort of chase, creating that- that sense of competition, I think is really important. And it also gives you a good barometer to understand like, hey, um, you know, are- are there patterns or things that are getting in the way of these individuals succeeding, or is it really linked to the person? I think if your sample size is one of one, um, it- it can be really challenging to draw

  4. 8:01 – 12:29

    Setting Goals and Targets for Sales Teams

    1. JT

      that conclusion.

    2. HS

      How do we think about target setting for them? Again, we've got these two new reps now. I'm the CEO, but I'm a young founder. I- I'm quite naïve. How do I think about goal setting and targets for them?

    3. JT

      Yeah. I- I'd say, you know, uh, in both the early days of, uh, Lightspeed and 1Password, uh, we actually started with team goals. Um, you know, we- we- 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, very short period of time. Um, but it- it was important for us to sort of establish an in it together while we started to figure out, um, you know, what sort of capacity can we get out of these individuals? Um, you know, without any sort of historicals on, hey, I know that a rep should be able to close this many deals at this value, you kinda need to figure that out. So, you know, we would leverage spiffs and incentives to get the most out of people and understand, hey, w- w- you know, where does that back wall live, um, but- but focus them on one common goal. I think as you- as you think about, uh, putting guard rails and defining what that comp plan is gonna look like, the simpler, the better. Um, especially in the early days. Like your, you know, your reps should be able to understand how much they're gonna earn and how they're gonna pay their mortgage without having to go through a ton of gymnastics. Um, and you should be open to changing the comp plan as your focus as a company changes. Um, you know, anchor the people that are responsible for driving revenue to, uh, the things that are gonna be best for the business, whether that's a multi-product story, whether you need them signing multi-year deals. Whatever that thing may be, their comp plan should be i- intrinsically connected to that.

    4. HS

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

    5. JT

      Oof. I'd say within the first year. Um, you know, at- yeah, at- at 1Password, we moved a little bit-

    6. HS

      I- I- I mean this respectfully to you. I don't even understand how team goals can work, 'cause if we wanna have the competitive element between them, you need to have a metric of measurement. And if you have team goals, you don't have the metric of measurement.

    7. JT

      Well, we'd still measure them as individuals, you know? So I can st- still sit there and say, "Harry has sold more than Julian has this week. You need to catch up," um, right? But, you know, a- as people are starting to figure out what works and what doesn't very early on, having that team goal pushes absolutely everyone. 'Cause especially in a small team, you don't wanna be the one who's dragging everyone else behind. And so, you know, a team goal is not meant to mask individual performance. Um, it's just meant to give you a proxy for, um, how people get paid in addition to spiffs and things like that while you're trying to level set and determine, how far should I be pushing people at an individual level? You know, what is acceptable and, you know, what does overachievement look like? So, um, you know, uh, that can last anywhere from, you know, uh, a couple of months, uh, you know, to maybe six or seven months. Um, but, uh, you know, I've seen that be very effective, um, you know, at the last two companies. Um, you know, it may not necessarily work everywhere, but I- I found it really helped us to ground ourselves in keeping momentum on, hey, we've gotta just get here as a company. As opposed to having people, you know, either- either judge or criticize the targets we've set, uh, or the plans that we've put in place.

    8. HS

      When it comes to forecasts ... This is great. I'm just like, pummeling you with quickfire questions.

    9. JT

      (laughs)

    10. HS

      When it comes to forecasts, do you rather have the unachievable that we hit 80% of? Do you rather have the achievable that we hit? How do you think about that stretch?

    11. JT

      Yeah. Y- look, we- we typically build plans so that, you know, 70% of people can achieve them. Um, you know, it- it's gotta be challenging enough, um, that it's- it's forcing you to push boundaries. But, you know, we don't design them so every single person, uh, will attain them. Um, uh, the acceleration is often much greater than deceleration. So when, you know, when- when people are having, uh, you know, really strong quarters and months, they can- they can really overachieve. But, uh, you know, the- the- the goal is not to set the bar just low enough so everyone makes it across. Um, it's- it's gotta be a challenge. And- and every time that 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, um, you know, than- than the goal that we initially set or- or thought was realistic. And so, there- there is a- a mental element of this that is like just pushing people to think creatively and outside of just the art of what they see in front of them to- to achieve a goal.

  5. 12:29 – 16:14

    The Reality of Tech Sales Today

    1. HS

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

    2. JT

      I think that working in tech sales has just been such an interesting proposition for so many years. And I think that, you know, for the last decade and change, it's been up and to the right. Um, you know, if, if you can prove that you've got a real solution to a real problem that exists, um, companies were willing to throw money at it. Um, I, I think the world of tech sales that we are living today is akin to what it was for many people that have been in this industry for 20, 30 years. Um, and a lot of people just aren't ready for it. You know, a lot of people got into sales because they figure, "Hey, like, you know, I don't really need a degree, I can just sort of find my way into it. If I've got some form of charisma or charm I can, you know, I can probably sell software." And the earning potential is there. So, um, I think there's a lot of incredibly talented people in tech SaaS sales today. But I think there's many that are sort of looking at this and thinking, "Wait a minute, this isn't what I signed up for." Um, that are just gonna give up and drop out. Um, I, I, I just think the mentality on, you know, what it takes to be successful, um, you know, not just in the world of sales but in the world of ge- in, in general-

    3. HS

      Do you not think that's r-

    4. JT

      ... that, it's just-

    5. HS

      Do you think that is right? I mean this in the nicest way. I don't think the majority of sales people are very good. I don't think the majority of sales leaders are very... dude, I, 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 met.

    6. JT

      Yeah, but y- yeah, I, I, I w- I don't disagree with you at all. Um, I, I think that, you know, companies are pushed to scale very quickly. Uh, they're, they're, they're pushed to get, you know, capable sets of hands in roles, uh, to keep things moving forward. Um, I, I think it's just been easy to, for too long, and I think those easy times have, have sort of bred a, you know, just a lot of mediocre talent, um, unfortunately.

    7. HS

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

    8. JT

      We look for, um, skill versus will, is something that we think a lot about. Right? It, you know, if, if somebody lacks the skill to meet the needs of, um, an evolving business, whether that's, you know, hey, your, your, you know, your product portfolio has changed, your sales motions are changing, uh, and people are catching up to that, and that's the reason that 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 ones that just sort of lazily blame, um, you know, their, their failures, um, o- on anything but themselves that, um, you know, un- unfortunately are gonna drop off over time. Um, it, i- i- it's, it's hard work.

    9. HS

      Super hard one. People who are laid off are often laid off for a reason. Do you hire people from layoffs?

    10. JT

      I think there are some good people, um, that have been laid off. Um, but I have to imagine that most companies that have done layoffs have looked at just the bottom performers on the team. The, the r- the reason I say that, that, you know, it's not all created equal is within that bottom you may have individuals who are either new to the organization, um, and still getting their bearings, um, they may have had an off month or an off quarter. And so if anyone's doing Excel math to determine who falls at the bottom as opposed to taking the time to really evaluate the people as individuals, um, I, I, I do think you can find some, uh, some good talent that, you know, unfortunately fell victim to a layoff.

    11. HS

      I always say look for shutdowns. Which is like, if you shut down a whole product division-

    12. JT

      Right.

    13. HS

      ... and the sales team are gone, that may not have been that, that they were shit. It may have been that the product didn't have product market fit, the product team won't work with... so many things. If everyone's gone, that's not a-

    14. JT

      Yeah.

    15. HS

      ... it's not a layoff really. Do you see what I mean? So like being-

    16. JT

      Totally.

    17. HS

      ... more nuanced in how you look at it I think is so important. Um,

  6. 16:14 – 19:49

    Evaluating and Managing Sales Reps

    1. HS

      okay, so we have that target setting, we have that goal setting. How quickly do we know when we've hired a not great rep?

    2. JT

      Oh, within the first three months, um, you know-

    3. HS

      What are the signs?

    4. JT

      You know, we, we, we tend to look at, in the first three months, we've, we've got ramp targets, um, you know, w- which everybody does. Um, but we look for a certain set of both behaviors, um, and l- uh, you know, leading indicators of whether or not they're gonna be successful over the course of the next three months. And so their ability to generate pipeline...

    5. HS

      How quickly do we expect them to generate pipeline?

    6. JT

      Oh, from day one. I mean, i- as, as soon as you're out of training and you've got an understanding of the product, you've gotta get out there, you've gotta get the reps in. It's-

    7. HS

      So I come in to you... Sorry, it's, it's just this is where people love it. So I come to you, "Hey, I'm on your team. I'm young and enthusiastic." Um, day... what does week one look like? How should we spend the first seven days?

    8. JT

      Yeah, so look, so your first seven days you're getting set up. I'd say really your first two weeks, um, you're, you're getting to understand the product, the systems and tools, how the job gets done, you're meeting the team. Um, you're in listen and learn mode. Um, you should be asking a lot of questions about what you don't understand, not just nodding your head up and down and going, you know, going through the training. Um, but we look for that curiosity in the first two 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, "Hey, someone's gonna give me a headset and a laptop, uh, and a 20 page playbook, uh, you know, and, and suddenly I'm gonna hit my target." So that's what the first two weeks look like. But the steps you take after that, whether that is reaching out to top reps on the team to understand what they're doing, whether that's shadowing calls, whether that's, you know, spending time in Gong, um, whether that's seeking out more training, one-on-one time. Um, all of these are really in- important indicators to me that say, "You're engaged. You're in it."

    9. HS

      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, where they seek out the extra learning post-hours, where they're researching the latest AI tools they can use to, to have more pipeline generation? For, 'cause for me, it's like none.

    10. JT

      Well, I- I-

    11. HS

      Maybe I'm hiring the wrong people and I'm in the UK.

    12. JT

      (laughs) It- it- it happens. I mean, look, it's certainly not the case with everyone. Um, um, but, you know, you know, this year, uh, you know, our non-regrettable, uh, attrition is probably in the realm of 29 to 30%. Um-

    13. HS

      Not bad.

    14. JT

      And, um, you know, we- we- we come to that conclusion rather quickly. Uh, we started putting, uh, especially at scale, putting a lot more emphasis on the hiring process and sort of how we vet that out early on, um, even before they started. But some people are just great interviewers. Um-

    15. HS

      Okay, so w- we have the two weeks of listen and learn. After that, we're expected to do pipeline generation straightaway. And when do we speak to customers first, especially if we're selling to enterprise?

    16. JT

      Um, you're- you're speaking to customers nearly straightaway, and- and- and that can come, uh, in varying different forms. Either you are joining a call and listening in and interjecting where you feel you can, and slowly taking the training wheels off. But from day one, um, you should be able to go out there and have a conversation. Um, this is well before we've given you, uh, a book of business, well before we've given you any leads. Like, you- you've gotta get out there.

    17. HS

      Okay, so I've gotta get out there. Uh, (laughs) yeah, it's,

  7. 19:49 – 23:36

    Outbound Prospecting and Pipeline Generation

    1. HS

      uh, it's tough. And so as an AE then, you expect me to generate my own pipeline. How do you think about me generating my own pipeline versus relying on demand gen?

    2. JT

      Um, the- the difference that I see there, um, is that you're going to identify companies and individuals within a company that fit squarely within our ICP and- and you're gonna reach out to them cold. Um, you're- you're going to try different approaches to reaching out, whether that's on- on LinkedIn or via email. Um, but you're gonna start establishing those connections early on. And some of that- some of your emails are gonna be crap, some of your outreach is just not gonna work. You're- you're gonna get no responses. But you're gonna have to develop muscles very quickly to say, "Hey, how do I get Harry's attention?" Um, it's certainly not an email in his inbox that I walk away from and wait for a response on that's gonna get him. Um, how do I tap into what Harry gives a shit about, what's relevant to him in that moment? Um, you know, some of it is borderline just stalking to understand, like, what's Harry talking about? What's he interested in, right? What is he surfacing? Who is he following? And try to get into that. And so before you even reach out, you know, show that you give a shit. Show that you've done some research and that you're not just blasting off a template to a thousand people hoping that 10 of them get back to you. So that's the muscle that I think, and ultimately ends up making you far more effective, uh, before I've handed you a lead, or an opportunity, or a meeting that I've paid real dollars to go out and generate that you just blunder.

    3. HS

      Do you believe outbound is still a viable strategy in '24? With the proliferation-

    4. JT

      I do.

    5. HS

      ... of AI tools, the immense supply side of content that we're able to shift now, is outbound viable?

    6. JT

      I think it's viable. I think it's gotten a lot harder. Um, but it- it is viable. Um, look, I- I'd say 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. Uh, if it's- if it's not a priority, it's- it's easy to move it out of the way. I think AI should make, uh, should actually make it a lot easier, right? You 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 just, you know, work on autopilot, um, you know, and- and fill your inbox with leads and responses. But I think it could help the job of outbound prospecting become a lot more effective. And I do think that, um, you know, BDRs and- and AEs, uh, can actually do a sharper job at prospecting with- with a lot less effort.

    7. HS

      If AEs are meant to generate their own pipeline, what the fuck are BDRs doing?

    8. JT

      (laughs) So they're doing the same, and I- and I think that outbound prospecting does become a team sport, um, especially when you're selling in a high enterprise, um, especially when you're selling cross mid-market. I think that for the AEs, it's a matter of keeping some of those muscles sharp. Like, you think about what outbounding really is. It's- it's about captivating interest. It's about getting to the point quickly. There's something that matters to the individual that you're speaking to. Like, that in and of itself is valuable, even if all you're getting is an inbound call, right? That makes you more effective at that first discovery call, that first meeting. So it's an important muscle that people need to exercise, period. And I also think there's a certain amount of appreciation and gratitude that you have when you've got a BDR, you know, working their butt off to generate pipeline for you. If you understand what goes into getting that meeting set, um, you're- you're gonna- you're gonna treat that opportunity accordingly. I think that's the difference. I still expect the majority of pipeline to be generated from the BDR team. But AEs who don't self-gen, um, j- just doesn't work. And I think it does them a- a personal disservice over time.

  8. 23:36 – 25:51

    Hunter vs. Farmer Sales Models

    1. JT

    2. HS

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

    3. JT

      I think ultimately it depends on, um, how your customers are buying. So I'll, you know, I'll give you a concrete example. Um, we, you know, we started off with the hunter-farmer model at 1Password. Um, and the main reason for that is when we landed here and started building the team, the company had already acquired 50,000 businesses that were using our product. Um, but we had less than a 2% penetration rate within those businesses because these were fanatical users that were bringing our product into the workplace. So if all we did was have one flavor of sales individual, they would favor expanding across the base. Um, and they would likely be a lot less efficient with any inbound demand, and they certainly wouldn't be pushing themselves to go out and generate outbound demand. So early on, we decided to create that friction on both ends to say, "Right, we're gonna 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. And the reason for that is we now have a multi-product portfolio. Uh, our customers are landing and expanding with us far more. And what we, what we saw was that we were actually losing new business deals 'cause we were pushing too hard to get too much upfront. And so now we've sort of aligned the sales motion and model to how our customers buy, and take a far more segmented and, and territory view to how we split the team.

    4. HS

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

    5. JT

      (laughs) Um, I think it depends on the context. You know, like, you know, farmers are, um, you know, they're a lot more patient. Um, you know, they, they'll, they'll really take the time to explore all four corners, uh, build a meaningful connection. They're a lot more curious. Uh, I'd say they're way better active listeners. Um, hunters are just used to operating in an environment where, you know, uh, they're trying to outrun a whole bunch of other lions for the same gazelle. And so you've got this fast-twitch muscle that's sort of working at all times. And, uh, you know, sometimes you might miss something. Uh, sometimes you might hurry and leave money on the table. So, it really depends on the context. Um, you know, one will always tell you that the other's job is, is much easier

  9. 25:51 – 31:08

    Compensation and Specialization in Sales Teams

    1. JT

      than theirs.

    2. HS

      Should CS be comped for upsells?

    3. JT

      Yes. I think CS should be comped on net dollar retention. They've got a role to play, um, in the process. And I think it's important that there's overlap between, uh, how they're compensated and how the AE is compensated. And ultimately, how I've seen that model be successful in the past is when both are working together to serve the customer. And I know there's, there, you know, there, there are really polarizing views on CS. And, uh, you know, I've heard a few folks on this show sort of bash on it. But ultimately, I think the body of work needs to get done. So whether you're in the camp of saying, "Well, I think one person should do all of it," well, naturally they're gonna be able to handle fewer accounts. Or you sit there and say, "Well, actually I, I want a cleaner division of labor, um, and I expect individual capacity to be much higher," I think you get to the same net result. In our world, you know, customer success is sort of this impartial, uh, person who the customer sees as a trusted advisor, not as somebody who's just trying to cram more product down their throat. And they are. They're ultimately thinking about how they're using the product, what more benefit they could be getting, and are sort of playing the role of orchestrator, bringing the right people in at the right time, uh, while the AEs are just strictly revenue-focused.

    4. HS

      How do you think about the specialization or verticalization, more importantly, of sales teams? And what I mean by that is, 1Password is a horizontal product. Amazing, because you can serve so many different people, but also difficult because you can serve healthcare, banking, consumer, b- you name it. Um, I like verticalized sales teams. How do you think about verticalized sales teams?

    5. JT

      I, I think there's a time and place. Um, and again, it'll, it'll vary from company to company. Uh, we're not verticalized today, and the main reason for that is we looked at our success across every vertical. We look at win rates, ACV, time to close, um, and we found very, very little difference, um, across these different segments. Um, and we have yet to reach any sort of saturation, um, in any one segment really. And so 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 yet. But we're absolutely gonna get there. Um, I think our journey is such that, you know, we're looking at segments first and foremost, because SMBs buy very, very differently than large enterprise companies. Um, territory-based splits are sort of where we're at right now, making sure that we've got the right people, right language, right timezone, and so on and so forth. The next step will be to verticalize the team so that we go deeper and wider.

    6. HS

      I had Matt Plank at Rippling on the show recently, and he said that 5 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?

    7. JT

      It varies by segment. Um, and-

    8. HS

      So enterprise ACV is...

    9. JT

      Yeah, I'd say like, you know, enter- enterprise deals for us, um, you know, are in the six figures. We actually landed our first seven-figure customer, uh, earlier this month, which we're really excited about. But yeah, so- somewhere between six to seven figures. Uh, you know, mid-market's somewhere between 50 to, you know, 100K or well into the six figures. Um, and SMB deals will vary, you know, anywhere from, um, you know, a few thousand dollars for a very small business to, uh, you know, 25 or 30,000.

    10. HS

      Can you have a sales motion like we discussed with that SMB structure? If you're paying 5 to $15,000, you can't afford the outbound, the AE, the CS. Can you?

    11. JT

      No. You, you, you need to be very intentional about where you deploy those resources. Um, most of our outbound motion right now is invested in mid-market and enterprise, 'cause that's where we get the biggest bang for our buck. The SMB teams are a lot more transactional. Uh, they work on high volume, high velocity. You know, most of, most of them pay for themselves four times over, um, you know, even if I load in all costs. And then from a, a CS and onboarding perspective, um, you know, we rely on low-touch models, um, with smaller customers to get them going. Ultimately, we'll get someone on the phone working with them if they need the help. But it isn't the default switch of the team to just unload the mega-machine for every single customer and deal regardless of size.

    12. HS

      If they pay for them four times over, why don't you 10 times them? And what I'm trying to get at here is like, where is that asymptote of value where you no longer get four times payback?

    13. JT

      I think there's, there's a point at which, um, you, you reach a ceiling. You know, I think today, that team is largely driven by the inbound demand that we get for our product. And so as we think about investing in that further, um, the unit of economics need to make sense. And at a certain point, we're gonna have to make a decision to say, "How do we wanna serve this segment?" Um, conversations we're having now are to sit there and say, "Well, can we start to leverage a different distribution model?"... for that cohort. Um, and we've recently got into working with MSPs and MSSPs, as well as distributors to achieve that. So there definitely is a point at which, um, 10Xing constantly starts to make less and less sense, um, which is a big part of why companies need to think about moving up market and building that motion early

  10. 31:08 – 35:25

    Outbound vs Inbound Sales

    1. JT

      on.

    2. HS

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

    3. JT

      We're probably, uh, just over 50% outbound. Um, so 54/46 split. Um, and I'll say that a year ago today, uh, we were probably 99% inbound.

    4. HS

      Wow.

    5. JT

      Yeah. Yeah. Big shift. And it's not just about hiring BDRs either. Um, it's, it's r- really about, um, getting the sales team to not only participate, um, in generating pipeline, but understanding that the level of intent of these customers is vastly different than when you're getting an inbound lead. So, um, these deals take longer to close. Um, they-

    6. HS

      What's-

    7. JT

      ... they close at half the rate-

    8. HS

      ... what's the time to close on an enterprise deal today?

    9. JT

      Um, there's a great deal of variance but I'd say, on average, two quarters.

    10. HS

      Two quarters?

    11. JT

      Yeah. Yeah.

    12. HS

      Okay.

    13. JT

      So we usually think about the pipeline about two quarters out. Um, it may be closer to three to four quarters, uh, when, when we're generating outbound pipeline. Outbound deals typically close at half the rate, but they close for twice as much. And so, you know, the person we're reaching out to doesn't have a preconceived sort of notion of what they want to buy. We are defining that from the get-go. So that is the ... um, that is the advantage, um, of outbound pipe gen over inbound.

    14. HS

      I've always been taught that when you have to educate the customer, don't bother. They don't ... it's gonna be too hard a sell. Uh, it's like when you're fundraising. When you have to persuade a VC to invest in, like, the category itself, don't bother. Is that wrong? You know, they, they, they can believe that they need password management and it's really important. Now, they've got many options and they can choose lots of them, but ... and that's up to you. But if you're having to persuade them that password management is important, uh, you know, no mass.

    15. JT

      I think that, in and of itself, can sometimes be the problem. Um, y- y- y- you need to be able to educate them on the problem. And if, if the problem isn't clear to them or they don't agree with it, um, then I'd agree, you're, you're ... you've got an uphill battle ahead of you. So, uh, uh, a lot of companies tend to anchor to their product, "I'm gonna explain the product and why it's different," um, as opposed to attaching themselves to the problem, which, if you've done your job right, the person that you're speaking to should understand very, very clearly. And now you've got their interest, and now they're leaning in, and your product is just proof that the solution that you're talking about, uh, is real and exists. Um, so I, I, I tend to think that leading with the problem and familiarization with the problem is the most important way that you get them to lean in. No one will sit there and disagree that, um, you know, reused or weak credentials, um, is a problem. Right? 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 on what the problem is, and then ideate closer to how you're going about solving for it.

    16. HS

      (laughs) I'd love someone to take the argument against, like-

    17. JT

      (laughs)

    18. HS

      ... strong credentials (laughs) -

    19. JT

      (laughs)

    20. HS

      ... you know what I mean? He's like, "I disagree." You're like, "Okay?" (laughs) .

    21. JT

      Yeah.

    22. HS

      Like, uh, what if they just don't care? I don't mean that badly, Julian, but I'm just like, like, "I don't care about credential strength." Like ...

    23. JT

      Yeah. And, and, and we get that. Um, you know, the, the security practitioners that we sell to have a number of different priorities. Uh, they've gotta think about everything. It's like me telling you that, like, you know, that microphone six inches from your mouth is probably gonna give you cancer. You're like, "Yeah, sure. Well, everything will." So it's, it's really about contextualizing what not solving that problem, um, is gonna, is gonna mean for them. Right? And, um, connecting with something that they care about. Like, 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 at first conversation that, you know, solving for credential management is gonna be the solution to that. But that's your job as a seller, to sort of guide them there. But I think 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, um, uh, and w- and, and working with them in that way.

  11. 35:25 – 41:12

    Pipeline and Deal Reviews

    1. JT

    2. HS

      So we have this great prospect and for whatever reason, it doesn't full land, whatever, or it does land. We need to do deal reviews. Crucial part of a, a sales process. Uh, dude, I'm a young founder again. I don't know how to do deal reviews. I don't know what to expect from my go-to-market for deal reviews. How often do you do deal reviews?

    3. JT

      Uh, we do them weekly.

    4. HS

      Okay.

    5. JT

      Uh, so we do pipeline inspection, uh, on a weekly basis.

    6. HS

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

    7. JT

      So I, I, I'd say that from an SMB perspective, you're often looking at pacing. You're often looking for pattern matching on what's going on that month relative to the previous month, relative to the same period last year. Um, and oftentimes when we're looking at those daily. Um, we're also looking at the pipeline, like, how does a drop in pipeline this week impact us next week? So it's a very, very data-driven approach and you need to obsess over it. Um, and 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 up market, you know, the classic is like, well, you know, enterprise deals take two quarters to close. What on earth could we possibly be talking about, you know, on a week-to-week basis? But the reality is, is you still need to have some form of objective or goal, um, that you're working towards, even on a weekly basis. Right? What outcomes are you trying to drive? What needs to be true as part of this deal in order for us to win it? And what progress have we made towards checking off those items this week? Right? How much pipeline have we built? Um, even if you're looking at things sort of, you know, two quarters in arrears, what does our pipeline look like for the second half of...... next year, and how are we trending there. So we do this inspection weekly regardless of segment. But I'd say the larger the deal, um, the more focus you're putting on sort of the account level or deal level as opposed to just looking at the sum of how that segment is performing. It's really critical.

    8. HS

      Who's invited to this meeting? Is it the whole sales team, only leads, only AEs? How do we think about that?

    9. JT

      So I, I think it'll vary on company size, right? If your team is small enough, I would get the whole team involved in the process. Um, I think then it's an important part of how you drive accountability. As you grow, though, it's about creating a cadence, right? So, you know, every Monday, every AE is gonna sit down and look at their pipeline. They're gonna take inventory of what they've done that week, how they've progressed, what's fallen out, what's moving ahead. Um, and then the following day they're gonna report that to their frontline leader. Their frontline leader is then gonna go ahead and inspect that work, ask probing questions, ensure that there's proper hygiene, and then roll that up then to their second line leader. So typically, by the time we have our weekly forecast call, um, I'm usually having it with my directs, and we've got folks from marketing, folks from our FPNA team that are joining us as well. And then we roll a summary to the executive team.

    10. HS

      Can I be a bit blunt? Does this not seem a bit ridiculous? And I don't mean that horribly in any way. But like, an AE rolls it up to a sales lead, who rolls it up to someone else, who rolls it up to someone el- oh, for fuck's sake, 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 of just valuable. Like, is this really how businesses are run today?

    11. JT

      I think you reach a certain size and scale where, you know, um, you, you'd end up having an eight-hour meeting if every AE had to sort of come and, and sort of run you through, um, you know, w- what-

    12. HS

      But can we not just, can we not just hire AEs where we trust that pipeline?

    13. JT

      (laughs)

    14. HS

      And so when you hire ... No, I'm being serious. But like, where you say to me, "What's your pipe?" And I go, "Dog shit. I got 200K this week and actually I think I'm gonna have a 50% dropout rate, so 100K." You're like, "Great, thanks." It's all done by message.

    15. JT

      Yeah. No. Unfortunately not. I think there's just, there's too many moving parts. There's too much emotion that's involved in selling. There, there, there's too much that can be driven on a feeling. "Hey, I just had a great conversation with Harry. I think he's gonna buy." Having someone to keep you honest throughout that process I think is mission critical.

    16. HS

      I've seen so many AI sales coaches where they are continuously prompting, "Really? What makes you think that? Oh, oh ..." Continuously pressing. Do you think that will continue to be human or AI led?

    17. JT

      I think the landscape of that is gonna change dramatically. Like, we started using a product called Momentum that, uh, not only does notating on the call and sets follow-ups, but it also gauges the customer sentiment on that call. Um, it also gives you suggestions on, you know, things that you could have done, that you should have done that you didn't do on a call by call basis.

    18. HS

      Why has Gong fallen asleep at the wheel?

    19. JT

      That's a great question. Look, I, I, I was one of Gong's first 50 customers, um, you know, uh, you know, back in, back in the early days of. I, I think that they, they led the charge on, um, siding with the salesperson and saying, "Hey, 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. Um, but candidly, you know, a, a lot of sales leaders that I speak to, um, are using it as a coaching tool, as a way to sort of go back and instant replay. Some are using it to manage pipeline. I think it's tough. Um, I, I mean, I can spend ages talking about the sales tech stack in and of itself, 'cause I, I do think it's gotten very, very messy. But I, you know, my, my hope is that, um, 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, that instead I'm gonna work through the existing channels and existing products that you're using and just augment what you're getting from them," right? So like, I don't want another thing I need to log into to get customer segment. Feed me that through Slack. Populate it in Salesforce, right? Surface this in the areas where I'm already getting work done.

  12. 41:12 – 42:28

    Sales Tech Stack and Tools

    1. JT

    2. HS

      Sorry, there's a couple of things. What are the core tools that you think every sales team and leader should be using today? You said about tech stack. Which are the like, Hail Mary, regardless of what sta- stage sector you're in, you have to have this?

    3. JT

      Yeah. I mean, look, a, a, a good CRM to start ... I, I implemented Salesforce early on here. I've done CRM migrations before. It's a pain in the butt. Um, just start with what you know you're gonna need to scale and be done with it. Uh, Outreach and Gong I was quick to implement. Uh, and 1Password as well. Um, you know, we leverage both of those. Um, and then some form of sales enablement tool. Um, you know, there, there's tons of great ones out there. Flock J, Highspot, Seismic. Um, I think inherently, you, you're gonna end up with a lot of different collateral, uh, and information to feed your sales team. They'll digest it and then it goes into a repository, uh, that they'll never reference ever again. And so having, uh, a tool that surfaces the right content at the right time for the right opportunity based on stage and so on and so forth I think is, is pretty important.

    4. HS

      I, I totally agree with you. Uh, when you are in those reviews and it's, "I don't have much. Yeah. No, um, Notion dropped out. Next one. Rippling dropped out. Yeah, I don't have

  13. 42:28 – 49:30

    Maintaining Sales Morale

    1. HS

      much," how do you maintain morale when sales teams are not performing?

    2. JT

      I think it's important to, um, see the positive and call it out, right? I think that when the results are shit, it doesn't mean that everything is shit. Um, I think you need to be able to call out the good. I mean, ultimately selling is a very emotional sport. And so if you've got a group of deflated, uh, salespeople out there, uh, trying to get people excited about your product, uh, it's really hard to do if they're not believing in themselves. So, I think it's about being positive about the things that have gone right. But I think it's about being brutally honest about the things that are not working, and getting comfortable assessing that, um, attacking the problem and not the person in that scenario, right? And so we do inspection w-... often enough. And if you're doing inspection often enough, there should not be any surprises. And if there are, then there's something you missed as part of that process. There's something you didn't inspect for. There's a risk you didn't assess, or that you didn't call out.

    3. HS

      What is the most common risk people miss that leads to deal at- attrition?

    4. JT

      More often than not, it's an understanding of what the procurement process looks like within the company end-to-end. There's always some surprise budget committee individual who needs to weigh in. And so not going wall-to-wall on understanding what it's gonna take to get a deal done is the biggest mistake that I see oftentimes and one of the leading causes of deals slipping. Um, sometimes things'll happen that are completely outside of the rep's control. I get that. Um, we can only control for- for- for what we can control. But, um, uh, more often than not it's about, uh, missing something in the procurement chain or not getting the right amount of value established with the right individuals in the organization. Like, if you're attempting to sell a half million dollar deal to a manager in a department and their, you know, superior or their budget holder is not even aware that these conversations are taking place, that's a huge red flag, um, because people are inherently bad (laughs) at then going back and selling the business case internally. So we actually find that we- we end up coaching a lot of our reps to do exactly that. Like, not just sell the product to the person that you're working with, but coach them and help them sell this internally.

    5. HS

      How do you do that without being so fucking obvious? So, listen, Julian, I- I ... we both want 1Password in Notion, Rippling, Vanta, you name it, whatever. Okay? We both want that there. This is a pack of information that I would use. This... How do we do it?

    6. JT

      I think it comes, like the subtle art there is not just loading them up with technical jargon, even if they understand it, but thinking, "What are the questions that their CFO is gonna ask them when you try to go and justify spend for this product? What are they gonna ask?" Right? And it's about giving them those answers throughout the process, right, so that they've got it. It's at the tip of their tongue. They can answer it right away. And most of the time, they can't anticipate what their CEO, what their CFO is gonna ask of them. So we give that to them without asking anything in return, knowing full well that they're gonna- they're gonna end up facing that challenge at some point. So we... even if we don't get access to those individuals throughout the sales process, I mean, o- our CFO often says, like, "Please don't have me speak to a salesperson," but we make sure that our champion is armed with the right answers to the right questions to be able to justify it. Uh-

    7. HS

      It's so funny what you said there about the CFO. "Oh, don't nod the salesperson."

    8. JT

      (laughs)

    9. HS

      Are people still buying software like they used to?

    10. JT

      No. No, they're not. Uh, the CFO suddenly has an interest in absolutely everything. You know, there used to be a time where, you know, while you're in your envelope of spend, I'm not really gonna question it, or, well, you know, you've presented a logical case for why we would need this thing. That just isn't the case anymore. They want to understand. Because ultimately, their boards are holding them accountable to managing spend efficiently. Um, you know, even as a- as a fast-growing, profitable business, uh, we still run through cost rationalization exercises on the tools that we use constantly.

    11. HS

      I remember when it was good times, huh?

    12. JT

      (laughs)

    13. HS

      Wasn't that nicer? Wasn't that so much more fun?

    14. JT

      Well, I think w- I think we're being a lot more intentional about the things we're investing in. Uh, we're looking for overlap across different products that we use. We're thinking like, "Well, wait a minute, could this other thing we're using do it 80% as well for the same cost?"

    15. HS

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

    16. JT

      I think we had the opportunity to be a lot more aggressive investing in product and engineering, whether that's sort of like a- a build or buy scenario. Um, again, I- I think we had the benefit of being a profitable business with a lot of cash at a time when, um, many companies were struggling. And so I think there was a window of opportunity there for us to substantially accelerate, uh, our pace of growth. And we chose to err on the side of caution or a middle ground. Um, and so, you know, look, hindsight's always 20/20, uh, and who knows where we'd be today had we- had we sort of made that decision. But that's, um, that's probably one regret that I have is not pushing a little bit harder for us to do that as a company.

    17. HS

      Uh, listen, I wanna do a quick fire. I've so enjoyed this. This has been so much fun. You gotta understand, for me, like, we put the schedules together, and that's fine. But I just wanna have a great chat, be interested myself, learn myself. That's why I did this show. So like, amazing. But I'm gonna say a short statement, you give me your immediate thoughts. Does that sound okay?

    18. JT

      Yeah, let's do it.

    19. HS

      So 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. So talk to me about your hair and how many people have cut it.

    20. JT

      (laughs) Uh, only three, um, and that number is three and not two because, uh, I ended up living, uh, in New York for four years and needed to find someone there. But, um, yeah, I'm very loyal in that sense, um, I like the ritual of going to the same person, somebody who's kind of like partway removed from the world that I live in that I can just sort of confide in in that one hour of therapy. Um, and, uh, you know, and so my hair's just become a thing over time, so I only really entrust it to one person these days.

    21. HS

      You've got great hair, by the way. Real volume (both laugh) and texture. Uh-

    22. JT

      Thank you.

    23. HS

      ... which is a line that I've never said in a show, but-

    24. JT

      (laughs)

    25. HS

      ... you know, there's a first for everything. Uh, what is your hotel cadence?

    26. JT

      (laughs) Oh my gosh. Uh, well, I spend a lot of time in hotels. Um, uh, bit of a germaphobe.

    27. HS

      Do you like that? Like, I- I don't travel.

    28. JT

      Yeah.

    29. HS

      I, you know ... I hate traveling. Do you like that?

    30. JT

      It, th- the hotel part is just like, when I'm not in my own bed, um, and I'm not in my own home, I'm sort of out of sorts. And so, um, yeah, it's sort of a weird one. I d- I love, you know ... the- the aspects of traveling that I love are getting out there and, you know, meeting people face to face. Um, I love that. I really, really do. And actually, in a lot of ways, when I'm traveling, uh, it just sort of shuts out everything else in my life and I can really focus on work. Um, but sleeping in hotels is probably my least favorite part.

  14. 49:30 – 51:36

    Are Remote Sales Teams Less Effective

    1. HS

      Do you buy remote sales teams?

    2. JT

      Well, I lead a remote sales team. Um, but I believe in the importance of in-person interactions. Like, we- we invest every year in getting every single individual together in one place. Um, I think it's important. Within 15 minutes, you can just tell who's engaged, who's in it, um, you know, who's- who's full of it. You just, like- you just- you get that sense. And, you know, part of my-

    3. HS

      I think it's so important though that you hear, you know, Julian on the call and close that deal and they're, "Yeah, we ha- we are winning." Or, "Oh, he lost it because of that reason. Hmm, I should watch out for that." Or, "Huh, she's doing really well. We should actually, like, promote her." Or, "Huh, they're really down. Like, we should actually, like, go for a beer after work with them and make them happy." Like ...

    4. JT

      Yeah. You lose that. It- it takes- it takes a lot more energy and work to actually go out and seek what's going on as opposed to just being in the room and seeing it. So, look, we- we get our sales teams together at the end of the month, at the end of the quarter. It's a subset of the team, it's not all of the team, but, um, it's definitely something that's top of mind for me as we continue to grow, is sort of this idea of building out centers of excellence for our talent so that we get a little bit more of that. Um, I get a lot of that with our leaders 'cause there's many points during the year where I can interact with them. But I miss that, man. I miss walking the halls, I miss the casual chats by the coffee machine. Like, uh, you know.

    5. HS

      Uh, dude, tell me about a deal you've closed where you've had to do something outside of the box to get it done.

    6. JT

      Oof. I- you know, I- I don't have like a ... I've heard some cool stories of people giving away their car to a prospect, um, to get the deal done. Um, that happened somewhere in Italy. Um, this was an old boss of mine who told me the story, but-

    7. HS

      Course it was Italy.

    8. JT

      (laughs) Yeah.

    9. HS

      Yeah, yeah. Only in Italy. "I gave my daughter." You know?

    10. JT

      Yeah. "You like the car? It's yours." Um, I don't have anything like ... I think- I think the closest is like, you know, we've definitely done, like, you know, tracking, you know, waiting for that last signature from the CEO who's on a flight, um, finding out which flight they're on, tracking their flight so we can get them right as they land. Uh, so we- we've done that and gotten deals in right at the 11th hour, literally, um, across the line. That's about as outside of the box as it's

  15. 51:36 – 54:02

    Final Thoughts and Advice

    1. JT

      gotten.

    2. HS

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

    3. JT

      Find a company where the biggest challenge that they have is one that you're actually passionate about solving for. Far too many people l- you know, judge companies based on what they are today, but I- 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 amount of value for yourself personally and for the company that you join. And I think that's a reflection, by the way, that sales leaders should have with themselves every single year as they're sort of sizing up, "Do I stay or do I go?"

    4. HS

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

    5. JT

      This discount expires at the end of the month. (laughs) Uh, I think- I think people are aware, well, that that's- that's just dead. That doesn't work anymore. Um, and- and pricing always-

    6. HS

      We always- we always grew up-

    7. JT

      ... becomes cheap.

    8. HS

      We always grew up with, like, TV ads in the UK and it's like, "Land of Leather or DFS," like sofa companies. And it was like, "70% off. Ends Friday." And then you're there on Saturday and it's like, "New sale, just 24 hours." And you're like, "Yeah?" (laughs)

    9. JT

      No, it- it's a bad thing to be trained on. Uh, even procurement teams have sort of wisened up to the fact that, "Hey, I'm gonna wait for the last day of the month, make the salesperson really, really sweat." Um, and then salespeople sorta get desperate and start dishing it all out. But yeah, I think that's- that's gone by the wayside. There was- there was a time and place for it, but not anymore.

    10. HS

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

    11. JT

      I'd say, uh, I- I ... Look, I've been really impressed with, uh, Wiz. And I- I guess like, you know, 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 zero to 500 million in revenue over that period of time, that is the impressive and remarkable part of- of that story. Um, 'cause the- the playbook of how you become a billion-dollar company is- is- is pretty well understood as far as just like the typical steps, whether that's international expansion, multi-product portfolio, working with partners, so on and so forth. Um, but doing that over a compressed timeframe, that's the impressive feat, um, that I think Wiz has accomplished. So, um, good on them.

    12. HS

      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.

    13. JT

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

Episode duration: 54:12

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