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AJ Tennant: How to Build a Sales Machine and Where Most Go Wrong | E2118

AJ Tennant is the Vice President of Sales & Success at Glean, Glean has more than 20x'd its revenue and 100x'd its user base in the just two and a half years he's been there. Before Glean, AJ had incredible runs at Slack and Facebook. At Slack, AJ helped grow revenue from $6 million to more than $1 billion. ----------------------------------------------- Timestamps: (00:00) Intro (01:45) The Hardest Sales Skill To Learn (02:48) What Do Young Reps Struggle to Learn Today? (04:51) The Sales Playbook (07:22) Sales Team Structure (09:22) Takeaways From Working at Slack (12:08) Moving Upmarket (17:50) Small Contracts for Big Customers (22:01) Buzzwords (23:19) How to Sell AI Tools in 2024 (30:14) When Does It Make Sense to Scale Up CS? (34:02) Should CSMs Be Compensated for Upsells? (35:24) What Would You Change About Glean’s Sales Comp Plan? (36:01) Hiring Sales Team (40:05) Are Sales Reps Truly "Coin Operated"? (50:18) How To Improve Glean’s Interview Process (54:32) Hiring Mistakes (57:52) Quick-Fire Round ----------------------------------------------- In Today’s Episode with AJ Tennant We Discuss: 1. How to Sell AI Tools in 2024: Are we still in the experimental budget phase for AI? How does selling AI tools differ to selling traditional SaaS? What are enterprises biggest concerns when it comes to adopting AI tools? What buzzwords get enterprises most excited in the sales process? Will we see a massive churn problem when the first renewal cycle for many of these AI products comes? 2. Outbound, Discounting, Closing: Is outbound dead in 2024? What does no one do that everyone should do? How does AJ approach discounting? Biggest lessons and advice? What can sales teams do to create a sense of urgency in a sales cycle? How does AJ do deal reviews and post-mortems? What is the difference between good and bad post-mortems? 3. How to Master Customer Success: What are the biggest mistakes founders make today in managing their CS teams? Should CS be compensated for upsell? How should the comp structure of CS teams change? What can be done to create a good handoff experience for the customer when handing from AE to CS? What are the most common ways CS teams break over time? 4. Hiring the Best Sales Teams: How does AJ structure the hiring process for all new sales hires? What questions does AJ always need to ask when hiring sales reps? What are clear signs of outperformers when hiring new reps? Does AJ give candidates a take-home assignment? What does he want to see from them? How quickly do you know when you have made a bad sales hire? What are the signs of a bad sales hire? What goes wrong first? ----------------------------------------------- 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 Twitter: https://twitter.com/HarryStebbings Follow AJ Tennant on Twitter: https://twitter.com/ajtennant 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 #ajtennant #glean #sales #hiring #customersuccess #slack #tmobile

AJ TennantguestHarry Stebbingshost
Oct 23, 20241h 8mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 1:45

    Intro

    1. AT

      You can very quickly know when you've got an AE that's all they're doing is coming to you with problems and not coming with solutions and ideas. If you do not have the ability to collaborate effectively in a way that's driving your point of view, that does require some tension, and you are steamrolling people, people don't want to work with you, you're gone. It just doesn't work.

    2. HS

      Ready to go? (upbeat music) AJ, I am so excited for this, dude. We get to do this in person. This is so ... 'Cause we were planning on doing it remote-

    3. AT

      Yeah.

    4. HS

      ... and then when you said you were in London, I was like, "Yes, this is it." Thank you so much for doing this.

    5. AT

      Thank you. I'm- I'm stoked to be here.

    6. HS

      Now, I want to start with sales leadership skills and sales skills. A lot of people suggest that they are born, you're a natural salesperson. Do you believe that sales skills are born or they can be learned?

    7. AT

      I fundamentally believe they can be learned. Uh, uh, you know, I think a lot of people would say it's innate, you know, you're born with it, it's that personality of someone that's outgoing. But my- my philosophy is that pretty much humans can learn anything if they're taught and they have the motivation to do it. And so I've seen in my career someone that's joined, you know, both Facebook and Slack that many people are like, "Oh, they're not outgoing. They don't have that gregarious nature," but they were able to navigate just, like, figuring out how to do sales because they had the work ethic, they had the desire to learn. And ultimately, it's about, it's about inputs and it's not just about being a personable, like, gregarious person.

  2. 1:45 – 2:48

    The Hardest Sales Skill To Learn

    1. AT

    2. HS

      What was the hardest sales skill to learn for you?

    3. AT

      I think rejection. J- just this idea that, man, like, I- I- it feels... I feel a little bit of, you know, shame. You know, c- like, my s- I started my s- just to give some background, I started my sales career doing outbound, almost in-person sales doing print ad sales in Cambridge, Massachusetts. I was selling to mom and pop shops on buying ads in this guidebook called The Unofficial Guide to Life at Harvard. I felt bad interrupting, like, a small business owner who was trying to make, like, a l- money. And so just the- the- the sort of, like, sh- almost the shame of, like, interrupting their life and then that rejection of them saying, "Hey, look, I am not interested. Get- you know, please get away," like, that is just, like, a really hard thing because it's- it's just failure, failure, failure, failure.

    4. HS

      When you look at ... Yeah, it's super tough and it actually just makes me think of why Mormons tend to actually be such good sellers-

    5. AT

      Yes.

    6. HS

      ... 'cause they actually have to go and, you know, sell the Book of Mormon to, like, Africa.

  3. 2:48 – 4:51

    What Do Young Reps Struggle to Learn Today?

    1. HS

      But, uh, you know, my question to you is, you see this, like, generation of new young reps coming in today-

    2. AT

      Yeah.

    3. HS

      ... are there commonalities in what you see them struggle to pick up/learn?

    4. AT

      I would say AEs are really struggling is being super creative and, uh, flexible and nuanced when you're engaging in a live conversation with someone. So, everyone has an idea when they're going into a call of what to say. They first think they're gonna get rejected, then they find a way to, like, convince someone to be engaged in the conversation. And what happens is the customer is actually interested or the prospect's interested and people go into this very specific structured prescriptive approach, where I- I think that the best sellers navigate and adjust to the- to the- to the customer, the specific situation. And so I'd say that's where I see more junior sellers struggling the most is they're not actively listening and morphing and changing to the conversation.

    5. HS

      The thing I'm always amazed by also is, like, the desire for volume over depth and, like, the- they wanna send a thousand outbound messages versus 20 really well crafted ones.

    6. AT

      I think what we're seeing now is just this spam to some extent. What- where I see the best outbound and ways to do messaging is what you're saying, which is tailoring it very specifically, doing the research, but more important, it's come in with a point of view and then listen to the customer and- and adjust from there.

    7. HS

      Do you think AEs should be doing their own outbound?

    8. AT

      Absolutely. We- we at Glean, you know, we have a, you know, and- and every company I've been a part of, like, I want AEs to be joining expecting that they have to do outbound and they're not gonna have a BDR. Now, th- the reality is is you're gonna have a lot of help from product marketing, content marketing, you know, just you're gonna get the support you need in the field marketing. But the AEs that do the best are the ones that are also spending the time and the cycles to do the outbound

  4. 4:51 – 7:22

    The Sales Playbook

    1. AT

      themselves.

    2. HS

      You mentioned the playbook there, 'cause they obviously run the playbook with different clients-

    3. AT

      Yeah.

    4. HS

      ... so you need to be flexible with it. How do you define the sales playbook?

    5. AT

      The whole concept of the playbook, um, for me, is- is one that it ... Like, I'm gonna be a little controversial. Like, I'm- I'm not a huge playbook person.

    6. HS

      Why?

    7. AT

      My view is that playbooks are really ... It's like a fancy word for what is your strategy, what is your outbound messaging. Like, what is your plan? (laughs) Like, a play ... So I- I guess, you know, it can be semantics a little bit, but what I- what I view as ... Sales is very simple. You have prospects that are in a certain target ICP, you have messaging, you have a really good product, you have content marketing that's going around that product, and you need to go outbound, get someone interested, convert that interest into an opportunity, and then start someone through a sales funnel. And so I- I think kind of building it up as more than it is sometimes I think, like, complicates it, and so I like to bring it down to just very simple things, like are you getting net new meetings?... are you then converting those to op- opportunities and then working those through a funnel?

    8. HS

      Should the founder be the one to create that process/plan, or is it okay for me to say, "Listen, AJ, I'm a, I'm a product person. Um, I've built this beautiful product. Eh, you go create the sales playbook"?

    9. AT

      I think that the founders need to be very involved, and the CEO needs to be very involved in that, that zero to 10 million, um, on, on kind of, like, how you're getting those initial customers to product market fit. You know, at, at Slack and at Gleen, you know, at Slack, Stewart was very involved on figuring out how to get those first customers and making them successful. Arvin, the same thing at Gleen, and I think it, it, what it helps to do is also show your sales team that your CEO and your founder's gonna be in the trenches, in the weeds to figure out how to get them to suc- to, to s-success. Um, but I think there's a stage at which you need to have that founder and CEO not necessarily, like, be deciding exactly what is the messaging, exactly what is the, the, the s-sales play that you're running, and they need to, you need to leverage them, but they shouldn't be the one determining

  5. 7:22 – 9:22

    Sales Team Structure

    1. AT

      the strategy.

    2. HS

      How do you feel about verdict... I'm just completely freewheeling here at this point-

    3. AT

      Yeah.

    4. HS

      ... so how do you feel about verdict-clad sales teams? When you think about, like, uh, a relatively horizontal product like Gleen, which is like, you sell to enterprise, sure-

    5. AT

      Yeah.

    6. HS

      ... but there's many different types of enterprise, from fintech to healthcare to consulting to the financial services. How do you think about specialization of sales teams and advice to founders there?

    7. AT

      The way I look at is when you're, when you're first sort of going to market, you can't all of a sudden just try to sell to everyone. (laughs) Right? If you all of a sudden are trying to go to the Fortune 100 and also sell to S-SMBs, you're gonna fail. I think, like, for c- technology SaaS products, a really good place to sell to is in that middle market space, and going after that and getting to product market fit, you get more cycles, more at-bats.

    8. HS

      Can we just unpack that? The, what is the middle market space? Like, what, what is that contract size?

    9. AT

      Like at gle- like at g- you know, you look at Gleen, like, when we got started in selling the product, it was going to technology SaaS companies that were between 500 employees to 2,000, 3,000, 4,000 that, you know, weren't these sort of what I would consider true enterprise, but, like, on that cusp. So that's-

    10. HS

      And so, and so it's like 100K ACVs?

    11. AT

      Yeah, little, little north of that, like, you could get. Um, you know, in that, in that, that segment right now, we're well north of that, but when we were getting going, early, early days where even before I was there, that's, eh, even, that's what it would be.

    12. HS

      How long is the sales cycles in that? I know it's varying, but just kind of average.

    13. AT

      Yeah, average is about four and a half, five months in that segment.

    14. HS

      Wow.

    15. AT

      Yeah.

    16. HS

      That's still quite long.

    17. AT

      It is, but, uh, I, I w- on the, on the sub-1,000, we're getting it down to, you know, 90, 90 days. So it's, it's, wh- it's closer to the four if you blend in that fi- below, like, that

  6. 9:22 – 12:08

    Takeaways From Working at Slack

    1. AT

      below 1,000.

    2. HS

      Yeah. I do wanna retain some sense of, you know, structure. Otherwise, my mind just goes-

    3. AT

      Yeah, yeah.

    4. HS

      ... everywhere. Slack was an incredible journey for you. Uh, it really shapes a lot of how one thinks when has, when one sees such a transformational journey. What are one or two of the biggest takeaways for you from Slack and how did that impact how you think as a sales leader?

    5. AT

      The number one, number one takeaway that I, I've, I've brought to Gleen, it's what I give to other, you know, founders I advise and just is how important it is to have the collaboration and, like, collaborative tension between R&D and GTM. So when I was at Slack early days, it was interesting. Like, I was struggling to get the organization to think about supporting the enterprise. We were so focused on just, like, the, like, the inbound and the PLG that we were starting to r-run into challenges with supporting and getting to customer success on the Comcast, the Walmarts that were some of those early, earlier enterprise customers. And so I think driving feedback to the product organization, challenging them, getting them on calls-

    6. HS

      What are the biggest points of tension between GTM and research and product?

    7. AT

      In that example, uh, there was a, there was a fundamental question of how much do we wanna actually go upmarket to enterprise?

    8. HS

      Mm.

    9. AT

      So it was almost even a, not a research question, R&D question, it was company strategy question. But there were challenges where there was different parts of the engineering team that were like, "Hey, I don't think we should be supporting or we can't support right now customers that have over 5,000 users on Slack." And I was like, "We gotta find a way to solve that." And bringing them on those calls, having them hear from those customers the challenges helped us push through. So that was number one.

    10. HS

      You gotta feel for these product teams when it's like, "Yeah, yeah, I hear you. Now do it." (laughs)

    11. AT

      Yeah. I mean, that, uh, you, and I, my, my lesson was bringing those individuals onto the calls. Get R&D onto the calls to hear the feedback. We needed to get engineers and R&D and, and product leadership to hear and have empathy for the customer.

    12. HS

      Mm.

    13. AT

      I think the, the s- the second-biggest lesson from just the, the ex- experience at Slack, um, you know, and for context, I was their, kind of, employee 50. We had six million in revenue. I left at, at, when we were at about 1.5 billion. My other biggest learning from the experience at Slack is it is important when you have, like, such a horizontal product like Slack that has product market fit to move upmarket faster and more aggressively.

  7. 12:08 – 17:50

    Moving Upmarket

    1. AT

    2. HS

      How do you know when is the right time to move upmarket? It's a hard one. You don't wanna get distracted too early, but you also don't wanna leave great and big contracts on the table when you could take them.

    3. AT

      My, my view is that if you are delivering-... like, clear repeatable success in that middle market segment, and you're, you are, and you're now kind of getting experimentation into that upper end of, of, uh, what I- like, let's call it 5,000 to 15,000 employee size companies, and you are getting success and deals done, at that point, the moment that you are getting customers to value and success, and you can repeat it once, twice, three times, at that point, you just need to go fast upmarket.

    4. HS

      The trouble with going fast upmarket is I don't think it's, like, an easy transition for the company. You do need to move whole scale product needs SOC 2, it needs compliance, it needs permissioning. It's not like a, "Tomorrow, we're going to be also an enterprise company." Is it possible to just move fast upmarket and what do you need to do to do that?

    5. AT

      I think it is possible to move fast upmarket from a sales segmentation, obviously from a marketing you can do that. I think your point around the product side and how do you get tho- that part of the organization there-

    6. HS

      On that. Sorry.

    7. AT

      Yeah.

    8. HS

      Let's just start on that. Sales segmentation. Does that need to change as you move upmarket?

    9. AT

      Absolutely. Yeah. I mean, when I-

    10. HS

      How so?

    11. AT

      ... when, when, you know, when I came into, at both Slack and Glean. When I joined Slack, I immediately, after we got to about 10 million in revenue, cut the team into SMB and enterprise, and I basically said, "Enterprise is 1,000 employees and above, SMB is below." And that way we just sort of put the resourcing, the more expensive sales resourcing on those bigger accounts.

    12. HS

      Mm-hmm.

    13. AT

      Now, at Slack it was a lot of inbound, but even that segmentation is important to do so you at least get your true s- like your sellers starting to think about a m- upmarket inbound at, at a minimum. At Glean, when I joined, we had real great success in that mid-market segment. We had strong sellers, about, like, eight of them, and we decided very quickly with the team to say, "We've got to move upmarket. Let's cut it at 2,000 employees and above, and, and the below will be serviced by a smaller subset of the team." And that helped us start to accelerate moving up. But you're right. It's not like because you only have eight AEs or ten AEs, you're not all of a sudden touching every Fortune 100 and able to do deals overnight. And so what we did was strategically pick one or two key bets that we wanted to get to prove success in. T-Mobile became that account for us at Glean. Not just a sales team, as a company and leadership team we said, "We are gonna prove success at a Fortune 100 like T-Mobile, get it to get a win, get value, get success." And that's what we did. And then as soon as we did that, that's when the momentum of the business started to take off because then we said, "Let's move upmarket even more. Let's go after more traditional, like Microsoft accounts, and start to build out the sales team in a more aggressive way."

    14. HS

      What are the biggest challenges to going upmarket?

    15. AT

      Security. (laughs) N- number ... I mean, i- in our business, and I would-

    16. HS

      Don't, don't hold back, mate. (laughs)

    17. AT

      Yeah, I won't h- I think people underestimate, especially, uh, R&D organizations, like, how you're gonna navigate security, deployment, POCs, pilots, like, all of that nuance of getting through that, not to mention legal (laughs) and contracting becomes just, it's, it's, it's like molasses. And, you know, I remember having conversations with Vish, one of the co-founders of Glean. He's like, "AJ, I've been on 20 hours of calls with, you know, with this account for the same conversation about security issues. What are we doing?" And I'm like, "Vish, this is what it takes to figure out the playbook on how to navigate the largest companies in the world. I commit to you, we are not gonna do this for every account." But the detailed questions and how deep they're going into, like, how do we protect their data, the security, you know? Um, y- yeah, all of that.

    18. HS

      But, but that's my point, which is like, is it possible to go upmarket fast when you look at all of those different elements and suddenly, like, you need someone for legal, you need like... I mean, the sales team changes dramatically. You definitely need customer success people, you probably need security people. We've built out a whole nother company.

    19. AT

      I hear you, but there's a way to phase it. What we did was we said, "Okay, this, this team that's going after the 2,000, 3,000, 4,000, 5,000," maybe even we were starting to sell into like 10,000, 15,000 person accounts. We said, "We're gonna give you one or two of these key accounts that we're gonna try to get into." And it's not, and, and it's not like we're saying, "This is the only account you're on." They're still trying to m- progress and move the ball down the field with that huge account, but still doing the more clear product market fit accounts. I think the worst thing you can do early stage as a, as a sales organization and a go-to company is segment too early, and move way up, way upmarket. And just, like, let's say, let's say we rewind the clock. If I all of a sudden moved all my sellers to just focus on the Fortune 50 or Fortune 100, that would have been a nightmare because we would never get revenue for nine, 12 months, right? Because you still got to feed your reps while you're slowly

  8. 17:50 – 22:01

    Small Contracts for Big Customers

    1. AT

      moving upmarket.

    2. HS

      Quite often, even the very large companies, they're not that confident when they sign the first land deal.

    3. AT

      Yeah.

    4. HS

      How willing are you to do small contract- and what would your advice be to do small contracts with mega customers where they're like, "Hey, land and expand"?

    5. AT

      I think you need to be very willing to do that. Now, the, the key thing that we've learned, and I, you know, learned this at Slack as well, but at Glean, you've got to have success criteria. You've got to have, okay, we're gonna do, let's say for a Fortune 100 company, we're gonna do 100,000, 150,000 land deal, but you have-... commercial alignment and executive alignment on what are the success criteria that we need to hit to get to that seven-figure contract. That's how we try to do it and structure it. It's a very timely topic, because we're, like, debating it even more as a, as a go-to-market team. We had one Fortune 100 company say, "We want to test how your- how we're lowering call resolution time with Gleen relative to the other solution we had and the competitors." It was very time-bound, it was very specific, and we were able to tie that back exactly to dollars so that land/paid POC, in some ways, turned into the seven-figure contract.

    6. HS

      Aren't we still in the experimental budget phase for AI tooling?

    7. AT

      Ab- Absolutely. (laughs) I, I think like n- Any company that's gonna say, "Oh, we've figured out what we're doing with AI," I don't think they're, I don't think they've figured it out.

    8. HS

      So when you go to enterprises today, they're like, "Ooh, shiny, cool."

    9. AT

      Yeah.

    10. HS

      "Let's see what we can do."

    11. AT

      Yeah, and that's what we're weary of. So, you know, our, our strategy is to capture that AI demand, but then turn it back into clear business value that has success criteria. Because if, if we just-

    12. HS

      And you're defining that value for them, in a lot of cases.

    13. AT

      For them. I mean, uh, e- even here. I was in London meeting with a large telecommunications company, and they were like, "I need you to tell us (laughs) and be prescriptive for us in how we should be deci- de- defining success criteria, because I have my board and CEO asking me to do something."

    14. HS

      Is that even more a case for specialized sales teams, though? Because it means you need to have a much clearer understanding of specific verticals. "Okay, the core problems for telecoms businesses today are these three things. The core problems for healthcare providers-" You can only get to that granular level of insight where you can show them the value if you are deep in that domain.

    15. AT

      I hear that argument. I still think staying generalist is important until you get to a certain scale. I think you need to be at 200 million, 250 million to go that granular, because just the number of AEs that you would need to hire to get to vertical ... Just bec- And it becomes complicated to manage that. So, there's a time where you start to edge into it. So right now, we're seeing success in, like, financial services. So, we have started more financial services enablement, but we're not at the point where we all of a sudden want to just say, "All we're gonna do is have one financial services team."

    16. HS

      Because I'm like ... And this is wh- You know, I'm a podcaster and you're a very successful sales leader, so this is where you push back on me. But I'm like, "You know what? We have T-Mobile, one of the biggest brands in telecoms in the world, with real data on how they've used us effectively. Fuck, I want one AE who is just purely focused on telecoms." And they show explicitly with just the biggest telecoms providers a FOMO, "Do you wanna be like T-Mobile? Great, this is us." And that is a great ... Now, you need the entry point, you need that anchor into-

    17. AT

      Yeah.

    18. HS

      ... that market, but once you have it, (snaps fingers) "Hell, I wanna go."

    19. AT

      I think that you can solve that by educating some of the other generalist AEs. Because the, the problem with it is, sometimes, y- you know, those telecoms are all over the world, right? And you're not gonna have one AE who's based in the, you know, the Bay Area be able to service all glo- like, the global telecoms. And so at some point, you do have to scale the learnings from one account to, uh, another

  9. 22:01 – 23:19

    Buzzwords

    1. AT

      region.

    2. HS

      We've mentioned being in the experimental budget phase, and we mentioned-

    3. AT

      Yeah.

    4. HS

      ... kind of showing them the value that we can provide them. Bluntly, are there buzzwords ... You're a very smart and attuned sales leader ... Are there buzzwords where you see these boardrooms light up and go, "Ooh, that's exciting," or buzzwords where they're, "Mm, that's cynical"?

    5. AT

      I mean, the buzzword right now is generative AI.

    6. HS

      (laughs)

    7. AT

      You know, just saying generative AI, uh, and, uh, "How are you driving AI transformation inside your organization? How are you turning your employees into AI-centric employees?" That, th- those are, like, buzzwords that get people leaning in. Uh, a lot of the large accounts that we're in, like, w- we're kinda coming to the table saying, "Look, we have a differentiated solution, we have a unique value prop, but more importantly, like, we've got real, real customers that have gone through an AI journey. We can help you learn from those customers." So, that's, like, leaning into not, like, our speak of the ... Taking what our customers are saying. Like, even the example of, uh, the telecom I talked about, like, their CEO is talking about an AI-enabled workforce. So, we're taking that buzzword and bringing it to others.

  10. 23:19 – 30:14

    How to Sell AI Tools in 2024

    1. AT

    2. HS

      So, we say this "AI-enabled workforce", "AI-centric employee", and they're leaning in. Why do you say they're still in the experimental budget phase? Is it because of the size of their contract? The speed of their rollout? What makes you say that?

    3. AT

      I call it experimental because people are still not defining it all the way back to a business issue and an ROI that is, like, fully defensible. AI budgets that are based on just, "Hey, we need to, like, quickly enable our employees to be AI-centric" that aren't tying it back to business outcomes, impact, top line, bottom line, a year from now, two years from now are gonna churn. And so that's, that's how I, I view it as experimental.

    4. HS

      Aren't they willing to spend big on AI?

    5. AT

      Absolutely.

    6. HS

      Do they have urgency when it comes to AI tools? Are they like, "We need to get this in now," or is it, like, part of the innovation budget of excitement?

    7. AT

      Absolutely, they need to get it now. And, and I think they need to get it now because the companies that are doing it right are actually gonna be the innovators and, like, the accelerants in the space. And, and so what, what I think happens is, like, the herd mentality. Like, you've got a couple of these big, big brands and companies that are doing AI in the right way that's actually impacting their top line or bottom line already, that isn't experimental, right? And they're willing to spend ...Some of those accounts are willing to spend five, 10, 10 million dollars annually on these type of initiatives. Because of that, what happens is board members, you know, other CEOs of other companies are like, "We need to move quickly. We need to get in AI. We need to drive an AI initiative with- inside our company."

    8. HS

      Listen, if you're a public company CEO, you have to have an AI story. I had Vlad on from Robinhood the other day, and I said, like, "Do you have to as a public?" 100%.

    9. AT

      Yeah.

    10. HS

      Um, so I completely agree. C- you said I could ask anything.

    11. AT

      Yeah. I-

    12. HS

      You can say no to answering.

    13. AT

      Uh, g-

    14. HS

      Uh, what's the biggest contract that Gleen has, size-wise? Not name.

    15. AT

      You know, well, well north of five million.

    16. HS

      Wow.

    17. AT

      Yeah.

    18. HS

      That's real money.

    19. AT

      Yeah.

    20. HS

      That's not experimental budget shit.

    21. AT

      No.

    22. HS

      I was wondering, though, when it comes to this, it's one thing to get a deal done. It's another thing to get implementation done, (laughs) to get usage. We've seen Accenture and we've seen some big consulting firms post some amazing numbers when it comes to AI services. To what extent are these large enterprises actually able to implement new AI technologies, like Gleen or like-

    23. AT

      Yeah.

    24. HS

      ... many other tools?

    25. AT

      This is where I would say the space is, like, falling down.

    26. HS

      Hm.

    27. AT

      And I'll, I'll speak to Gleen separately, but just to, you know, for the audience, I think everyone is being sold a, a bag of goods and, and, and a dream of this sort of AI-enabled workforce or automation, top line, bottom line. And then when it comes to implementation, it's taking six, nine, 12 months, or it comes attached with a five-million-dollar services budget next to it, which is, it's like, w- hold on. I'm paying five million dollars to f- for implement this thing for the, with one of the, you know, the big, the big companies? And, and then a- and, like, I'm paying s- like, the fees for the service? So I think what we're seeing is eve- adoption and usage is not where it needs to be. And we're seeing that even with, you look at, like, Microsoft Copilot, I mean, many customers are saying it's falling flat. (laughs) Like, it's just not delivering the value that was advertised. So what the challenge is, is not, like some of the other technologies, a, a product issue. It's more of a change management security challenge.

    28. HS

      What does everyone think they know about selling AI tools that they get totally wrong?

    29. AT

      I think that, um, that it's gonna be easy to implement is, is what they get wrong. And that, that's simply, I mean, we talked about it already. I think that lots of, lots of even our AEs that we have, like, we are educating them. Even though our product is relatively, compared to the market, easy to implement, we're, we're, we're telling them, "Set the right expectations. Make sure that you have a deployment success plan." You know, I, I took a page out of Dave Schneider's book from ser- ServiceNow, and we're implementing a system where we're not paying AEs on their deals unless they have an approved deployment success plan filled out.

    30. HS

      Hm.

  11. 30:14 – 34:02

    When Does It Make Sense to Scale Up CS?

    1. AT

      there.

    2. HS

      What size contract does it make sense to have CS as a really built-out function and really catered account?

    3. AT

      You've got to be looking at it a combo of the company size and the contract size. So I think one thing that I learned at Slack is, like, all Slack did was look at what the ARR was for the specific account and then tied it, and they would only put s- a senior CSM on the, you know, whatever, the million-dollar contracts. I think that can be a little bit of a miss, because you're, if you are closing, let's say you close a couple 100K deal with ExxonMobil.... and you're putting, like, a junior CSM on it who doesn't know how to navigate, you're gonna ha- you're not gonna g- be likely to drive an upsell. And so what I look at is a combination of employee count and are, are they over a certain dollar amount?

    4. HS

      Employee count of your company, not their company?

    5. AT

      No, it's, sorry, uh, their company.

    6. HS

      Ah. So it's an upsell potential measurement?

    7. AT

      Exactly.

    8. HS

      Yeah, yeah.

    9. AT

      TAM of the upsell.

    10. HS

      What are the biggest mistakes you think founders get wrong with building out their CSM teams?

    11. AT

      I think that a lot of them don't tie it to clear metrics. They, they don't tie it to, like, things that will go back into leading indicators for future upsells and NDR and GRR.

    12. HS

      When you say NDR, NRR, GRR, all sound wonderful. Um, you know, luckily, having done SaaS investing for nine or 10 years, I do know what they mean.

    13. AT

      (laughs)

    14. HS

      Uh, I didn't for a couple (laughs) , and then I had to ask the stupid questions. Um, which one's the most important?

    15. AT

      For me, it's, uh ... And I, I, I know I said NDR, GRR, and NRR, but let's just simplify. Uh, GRR and NRR. Most important for me, um, is GRR.

    16. HS

      Why?

    17. AT

      Churn. Like, the, the ripple effects of having an account in, especially in the enterprise space, churn. It, it's, it's the viral negative network effect that happens. And so, you know, luckily at Gleen we have like a 97, 98% GRR. The only accounts we're churning are SMBs. Like, that's what we wanna, that's what y- that's what you wanna have.

    18. HS

      Mm-hmm.

    19. AT

      Um, but to answer the question, I, I view it as GRR. But to me, what's more (laughs) , in some way more important than GRR, it's the leading indicator metrics, like time to launch. How long did it take the customer to go from signed contract value to the initial launch? And then how ... A- and measuring that, how many of the paid seats are actually active in the service.

    20. HS

      Mm-hmm.

    21. AT

      And so because if, if you nail, in a systematic way, time to launch quickly and you get active users, GRR is just an afterthought. It's gonna be po- it's, it's not gonna be a problem, right, if you have people using the service and, and, and they're, they're using, getting deployed quickly.

    22. HS

      We haven't seen renewal cycles yet for a lot of the AI tools with a lot of revenue, uh, in terms of full-year cycles. Do you think we're gonna see a large number of churns?

    23. AT

      Oh, yeah. We're already seeing it.

    24. HS

      You are?

    25. AT

      Yeah. We're, I mean, w- we're seeing a lot of accounts kind of move off of those experimental, like, quick, knee-jerk reaction AI budgets, um, and, and shifting to our product. Uh, I also, I, I think that you're gonna see it ... For example, like, there's some of these vertical solutions that have layered on AI and sold a big story on, "Hey, you're already, uh, you know, paying X with us. We can accelerate you to go faster." Um, I, I don't think some of those solutions are actually gonna deliver enough value, that it's gonna be worth the incremental spend that they're gonna be asked to do.

  12. 34:02 – 35:24

    Should CSMs Be Compensated for Upsells?

    1. HS

      Should CSMs be comped also on upsell?

    2. AT

      I think there should be some type of kicker, an incentive, but it shouldn't be, it shouldn't be the, like, the, the number one key metric. It's kind of like right now in the sales dev world, there's a lot of, even within our organization, there's a lot of push right now for giving a kicker, like a bonus, if a sales dev rep sources a lead that not only becomes an opportunity but that it closes.

    3. HS

      Mm.

    4. AT

      Right? So it incent- incentivizes the right behavior. I think, um, I forget who, what, what company pushed that strategy, which is comp BDRs on not net new opportunities, but comp them on closed won. I think it's, it's too far and too long of a thing to do. But back to your question, I think there's a model in which you can give a bonus to ... Actually, we, we did that at Gleen, but we haven't systematically done it. So for example, you know, the companies that did these multimillion dollar expansions, we actually strategically gave a large spot bonus to the CSM that was on that because we w- we wanted to recognize the right behavior. Um, and so I, I, I think it's a good thing for us to, like, honestly take back, because we're in the middle of our planning for next year and we should find a way

  13. 35:24 – 36:01

    What Would You Change About Glean’s Sales Comp Plan?

    1. AT

      to structure it in.

    2. HS

      You've got a magic wand and you can change anything about the sales comp plan for Gleen. What would you change?

    3. AT

      More aggressive accelerators. You know, a- accelerators are essentially ways to, if someone goes over 100% of their quota, an accelerator just gives that rep the ability to move faster in terms of accelerated comp.

    4. HS

      Mm.

    5. AT

      And so what it's doing and why I say that's the number one thing, whether it's CSMs, BDRs, AEs, is you're rewarding the, the top, top performers. I think it's a good

  14. 36:01 – 40:05

    Hiring Sales Team

    1. AT

      thing to do.

    2. HS

      In funds, we call that kickers, which is like over a five X fund-

    3. AT

      Yeah.

    4. HS

      ... you get a kicker on carry, which takes it to 30%, not 20% or whatever that is.

    5. AT

      Yeah.

    6. HS

      But it's over that exceptional performance. I totally get that. That totally makes sense. Um, hiring is really fricking hard.

    7. AT

      Yeah.

    8. HS

      Like, it is the one area where I think most early stage founders get most wrong. You've hired exceptional sales teams. How do you run a process when adding to the sales team? What does that look like?

    9. AT

      Understand the deep history of the individual over a chronological period of time. I didn't realize that that was a hiring methodology until Bob Frati taught me that at Slack, which is kind of this who hiring, the who hiring method, is what we call a chronological interview. Like, I ask people-What, what did you do in high school? Like, what were you proud of in high school? Not bec- I don't care, and then I say, "Why did you go to the college you went to? What was your proudest accomplishment in college?" And I do that through every, "Why did you leave the first job you did? Why'd you go to the next job?" And I go, really try to understand because what you can build is an understanding of, like, the deep motivations that people have.

    10. HS

      I'm a salesperson. I'm brilliant at packaging. Uh, how do you actually determine true grit, quality in my sales skills when I answer your questions beautifully?

    11. AT

      Yeah, I, I mean, o- one, one approach to this, which is in the Who Hiring method is, you ask people while you're going through that process of, "Who was your boss? Who is the hardest person you worked for? Who is someone, like, you didn't like working for?" And then you, in the moment, say, "How do you spell their name again?" And, like, you, you basically kinda quiz them to say, you know, "I'm curious, um, if I reached out to that person, what would, what would they give you constructive feedback on?"

    12. HS

      (laughs)

    13. AT

      And so w- and, you know, sometimes I even fluff it and I'm like, "Oh, I think I'm connected to this person and I might, you know, might text them and call them." But it's what you, you wanna just, you wanna get people off of their, their, whatever, their sales skill game and get real, and challenge them on that. That's one way. Um, the other is w- I think what we were talking about before I came in here was, actually have people send materials of the work that they've done, so being able to see a deck that they built, an email that they sent.

    14. HS

      Well, talk to me about that 'cause you, you, you sent me beforehand this incredible deck that you did on joining Glean. Uh, w- what deck do you r- ask people to send to you and how does that look and structure?

    15. AT

      You know, other than, like, going deep into the why and the chronological side, we move from there to a panel interview. And that panel interview is, they get an hour, they get a, a prompt. That prompt is, "Tell us your history. Uh, tell us about, like, you know, your biggest career challenge. Talk about a, a large win that you have and then walk through an example deal of selling, how you would, not sell Glean, but how you would prep for, prep for, like, going after this account." You know, you just, you don't give them much guidance after that. And you see a wide range. You see people come in that have, like, like, no slides and are just, like, going, and that's fine. I, I don't care about m- the slides or whether, whether they look beautiful. I wanna understand the deep thought that you've done in preparation, and then in that moment, the thing that I do, and I'm (laughs) I- I'm gonna, I'm gonna say it now, I, I u- used to tell candidates, like, "Please don't tell other candidates I'm gonna do this," but I'm just gonna do it because I think it's a good lesson that I'd love to just share with others. Um, and I learned this actually from Lexi Rees, who was my, one o- one of my bosses at, um, Facebook. So anyway, what I ask is, and I j- I throw off the interview, mid-interview and I say, "Hey, hey, like, let's pause here for a sec. If I give you, like, your book of business today, 100 accounts, that's an Excel spreadsheet on column, uh, column A is the name of the accounts. I want

  15. 40:05 – 50:18

    Are Sales Reps Truly "Coin Operated"?

    1. AT

      you to fire off right now 10 data points that you would use to prioritize that book of business and tell me why, and stack rank them one to 10." And what you can see, some people get to, like, employee count, you know, what industry they're in, and then they're like, "Oh, l- you know..." And I'm like, "No, no, no. I want 10." And I, you push them. And they're like, "Well, I don't think, you know, like, I think I, you know, I'm at six." And, and then you, because w- if you're on customer calls, this is what, like, you've gotta be able to, what I've described to the team, like, the competency that I'm looking for is creative problem-solving capabilities. And that is, if I, if I were to, like, you know, you, you asked me earlier on this session about, like, what is the s- what is the skillset that, uh, junior AEs struggle with? What I described to you there was almost like the, the early stages of creative problem-solving, which is like EQ creative problem-solving, which is, like, listening to a prospect and kinda morphing what you're doing based on what they're saying. What I'm looking for in that question is actually, like, higher level thinking of, like, how can you a- think not only quickly, but strategically, and then map it to what is actually gonna be your job? Like, you are gonna get 100 accounts and you are gonna need to figure out which ones you spend on.

    2. HS

      I get in trouble, I think it's IQ. I think people are just not that smart.

    3. AT

      Yeah, th-

    4. HS

      And then they also just don't have great energy, and you need both the razor-sharp intellect combined with high energy to really be able to map out a vision and articulate it well to that customer. And I find, like, there's not that many insightful people.

    5. AT

      It's shocking to me how many AEs I ask this question to and they just get stumped at five. I'm like, "Are you kidding me?" (laughs) Like, I could r- I could literally write 50.

    6. HS

      How much of a dick do you want me to be?

    7. AT

      Uh, really? You wanna put me on the spot?

    8. HS

      Okay, if you, if you're a really sharp, insightful person, you're not gonna be an AE.

    9. AT

      (laughs)

    10. HS

      I, I, (laughs) I'm gonna get killed by our whole AE audience.

    11. AT

      No. No, I-

    12. HS

      But, like, if you're really sharp, I can make money in so many better industries.

    13. AT

      I-

    14. HS

      It's tough. Sales is fucking hard.

    15. AT

      No, no, I disagree with that. I, I, I, I thought you said something else. I thought you said if you're really sharp and insightful, you're gonna be an AE.

    16. HS

      No.

    17. AT

      I think that, a- this is, this is very top of, like, very top of mind for me because I think I, I was very lucky and shouldn't have gotten into Harvard. My dad went there. I had a chip on my shoulder, worked all four years throughout college. My parents went bankrupt so I graduated with $100,000 in debt. And I-

    18. HS

      (laughs)

    19. AT

      They got caught up in the 2008, you know, crisis. But, um, all my friends went into investment banking, consulting, and I, and I n- I know you're, uh, like, I think that technology sales, it has the potential to, like, capture some of the smartest minds because when you, when you really peel back the layers of what technology and AI sales is, it is-It is taking what's happening in investment banking, consulting, but actually putting it to work on driving transformations within companies. Why I love sales, and why I love enterprise SaaS sales, like, I- I went from ad sales at Facebook to, uh, B2B at Slack, and I'm never going, never going back, is, like, the level of learning and depth you get to do, like, figuring out how to make T-Mobile successful. Like, I've- I've been working with T-Mobile for almost eight years. (laughs) Like, because I worked with them at Slack, I helped them learn about Gleen. Like, you can drive, like, drive true business transformation if you choose the right product technology and you believe in it. And-

    20. HS

      Do you think the smartest people coming out of Harvard today want to go into sales?

    21. AT

      They will after they talk to me.

    22. HS

      (laughs)

    23. AT

      I mean, we're honestly, we're, uh, uh, so, h- yes. So, uh, I- I wouldn't say sales, I would say that they wanna go into... I think the smartest people coming out of the top universities wanna go work for the best technology companies.

    24. HS

      I agree with, I agree with that, but I think they, and this (laughs) I'm, I'm really-

    25. AT

      No, it's fine.

    26. HS

      ... Maggie is gonna listen and go, "You prick." Uh-

    27. AT

      I love it.

    28. HS

      Yeah, she thinks that with most shows, don't worry. Uh, but it's like, I think they wanna go into product. I think they wanna go into strategy. I think they even might want- go into consulting because they think it's a way into venture or another thing. I don't think the smartest minds are like sales.

    29. AT

      I agree with you that the smartest minds aren't, but I think, (laughs) I think the smartest minds will get there with time, because when they realize... There's two path- there's two paths to making a big impact inside a technology company. I learned this from Da- uh, David Han, who was a VP of product at, at LinkedIn. In technology companies, and this, this might be controversial, because, uh, like, you know, this is, like, putting aside, like, all the other things that make these companies go, there is product, and then there is sales. Like, what drives technology companies and most businesses is one of those two functions. If you are the smartest, smartest person that's graduating from, you know, Yale, whatever, Harvard, uh, n- I don't even c-, I don't even wanna say it's the Ivy Leagues, but I actually don't think the smartest people are always from those schools at all. You either are gonna find success and a path through product, but if you realize, "You know what? I'm, I'm not an engineer, I don't like that, I don't wanna do product management," if you are smart, the, where you should go is sales. And I've seen that, like we, we, we had this amazing AE, I'll, you know, I'll give her a shout-out, Rachel Sato, who, Northwestern grad, went to work at McKinsey, same thing, had this thought that she wanted to go work in product management at Lyft, and we convinced her to be a sales development representative, to do outbound cold calling, and she's like, "Thank you, AJ, this has changed my life. Like, this is the career I wanted."

    30. HS

      Are sales reps coin operated?

  16. 50:18 – 54:32

    How To Improve Glean’s Interview Process

    1. AT

    2. HS

      You mentioned your interview process with Glean. With the benefit of hindsight now, what could be done to have made that process better?

    3. AT

      I think that the, um... And this would be more feedback for Arvind, (laughs) right? My CEO, on what he could have done better. I think that Arvind should have been challenging me to put together a point of view on a couple problems that I... Like, I think senior leader interviews that CEOs are doing, and, and, and this is another reason we do the panel the way we do, I'll explain in a second, is interviews are very precious in terms of the time that your leadership team is spending on them.

    4. HS

      Mm-hmm.

    5. AT

      Right? And so, Arvind, it could- he could have spent all this time with me and n- it not really lead to anything. I think that having him ask me, "Hey, A.J., here are the three problems that we're dealing with as a company right now. Can you produce something and present to me and my leadership team on how you're going to solve it?" It has two benefits. Even if I don't turn out to be the right guy, it's giving him ideas.

    6. HS

      Mm-hmm.

    7. AT

      And that's what we- so that, the other, one of the strategies we have in our panel interview is, I always ask my managers, it's a double- like, choose the account that this person is prepping for their sell to on a new prospect (laughs) that we are trying to get into. I hate wasted effort. It's money. I like to kill as many birds with one stone as I can.

    8. HS

      How fast do you know when someone you've hired is not very good?

    9. AT

      It depends on the segment. So if we're talking about the enterprise segment, you're gonna know within six- probably 90 days.

    10. HS

      Wow.

    11. AT

      And-

    12. HS

      And SMB?

    13. AT

      SMB you're gonna know in, like, 30, 45 days.

    14. HS

      Do you cut them down or do you give them a bit of time?

    15. AT

      We have about a, all-time, like a 20% turnover rate of AEs.

    16. HS

      Which is pretty good.

    17. AT

      Yeah, it's pretty, it's pretty good. Some, some might argue we need to be more aggressive.

    18. HS

      What are the biggest commonalities in why they fail?

    19. AT

      Number one is, uh, th- this, the, the topic I, I, I want to bring up is like, a lack of two things: creative problem-solving (laughs) and collaborative tension. And collaborative tension is a new word I coined at our big company kickoff called GKO. Um, the creative problem-solving, it's, it's not just... You can very quickly know when you've got an AE that's all they're doing is coming to you with problems and not coming with solutions and ideas. And that is a telltale sign that someone is not a creative problem-solver. So, like, the best, the best employees are the ones that, when they meet with their boss or a stakeholder, they say, "Here's the problem. Here's what I've thought about for it, and here's one or two ideas I'm thinking about. What's your feedback?" Whereas the AEs that fall into that bucket of, like, that I'm like, "Damn," like, it's like, they are coming to you, and they're saying, "Oh, like, I can't get my SE to do X, Y, and Z." I'm like, "Cut the bullshit. Like, what do you want them to do? Have you talked to them yet?" Like, and you have to do this, like, annoying coaching to them, which is, which is something that, at this point in their senior AE careers, like, you need to be going to try to solve that problem or coming to me with how you're thinking about solving it. The second one is the collaborative tension, um, just on why we get rid of people is if you do not have the ability to collaborate effectively in a way that's driving your point of view, that, that does require some tension, and you are steamrolling people, people don't want to work with you, you're, you're gone. Like, it does just- it just doesn't work. And I, I, I like to use the word collaborative tension because I don't want to have this soft culture where everyone is just like, "Oh, we're collaborating and find it," like, we're gonna be all, you know. It- it's about collaborating in a very prescriptive, direct way that is going to have tension. And if you can't do that effectively, then you need- you, you can't be a part of these hypergrowth companies because that's what they need to

  17. 54:32 – 57:52

    Hiring Mistakes

    1. AT

      make progress.

    2. HS

      When you look back over your mistakes as a hiring leader, what was the biggest?

    3. AT

      Moving too fast. You know, I, I, at Slack, we, we got this sort of like, when, when the acquisition happened, and even maybe before the acquisition, I got this sort of like, "I've got to move super fast to fill an AE." And I didn't take the time to actually do the full chrono to like, listen to some of the, like, the flags I had, to do back channeling. Like, I think when you move too fast through the process, um, you, you make mistakes.

    4. HS

      Someone said to me the other day, "You have to sometimes let fires burn and actually just..."... be okay letting-

    5. AT

      Yeah.

    6. HS

      ... a fire burn if it means you've got to wait another month. As painful as it is, it's better to wait the month.

    7. AT

      It's totally. I mean, I, I ended up having to like, you know, I moved super fast with this one AE, ended up having to let them go, and then it became this drama, and it was like a nightmare to deal with. And so, I think you just... It's so much more important to take like an extra week, two weeks, three weeks, four weeks, month to get the right people.

    8. HS

      What is the biggest mistake that founders or sales leaders make in new rep onboarding?

    9. AT

      Not doing it. (laughs) Uh, and- and I'm- I'm- I'm definitely, uh, guilty of this.

    10. HS

      It's hard. That you're fricking busy and you are closing big contracts, you're trying to get new contract, you're... There's a lot. And then it's like, "Onboard."

    11. AT

      Yeah. I guess my mi- like, the mistake is, um, not investing in enablement early enough. So when I was at Facebook, and this is like probably like also my development as a human being, like I used to not believe in, like, therapy. I used to not believe in, like, medicine in terms of like for mental health. Like, you know, there's a long history of, like, stuff in my family that's like I hardened, but then I realized as I got married, as I had kids, like, "Wow, like, I gotta soften that approach a little bit." And I think related to that, and this is how like work life all come together, during my time at Facebook, I was like, "Fuck enablement. I don't think enablement's ever gonna help anyone." Like, and- and I tru- truly, like, did not think it was... I was like, "If you're a good rep, you're gonna fucking figure it out. You don't need enablement ever. Like, the best reps will figure it out." And that was like the hard AJ back then. And what I've realized more in my middle point of Slack and 100% at Glean is founders and sales leaders that have the mentality that I have, like had back then, who are just like, "Let's hire the best reps, they can figure it out." I- it's gonna, it's gonna hurt you in the long run. And hiring, we hired a world-class, um, enablement leader who used to be a salesperson, who used to be a sales dev manager, like was a- a chief of staff to the Pure Storage, like CEO, like someone that's a ex- M- Molly Golden, who's amazing and like that has changed the trajectory of what I think good enablement looks like. And it started at Slack with- with some of the folks there, but n- I've like fully embraced it, uh,

  18. 57:52 – 1:08:41

    Quick-Fire Round

    1. AT

      with- with Glean.

    2. HS

      Listen, I wanna do a quick fire.

    3. AT

      Yeah.

    4. HS

      So I'm gonna say a short statement, you're gonna hit me with your immediate thoughts, okay?

    5. AT

      Yes.

    6. HS

      Discounting, is it always bad? Do you sometimes do it? How do you approach it?

    7. AT

      I approach it, early days, do it, get the deals done. But once you get past like 10, 15, 20 million of revenue, you really need to have a very tight discount matrix and don't- don't give away just horrible deals, because it's gonna impact the- the- the market discount rate.

    8. HS

      Do logos really help subsequent logos? Have-

    9. AT

      Absolutely. I, I mean, if you get a marquee customer and get them successful, it's more important than the logo. It's actually they will do reference calls, they will do intros. So, I think it's less about the logo and it's more about that customer becoming successful to then do reference calls.

    10. HS

      Your friend has just got a job as head of sales at a new company, at a series A stage company.

    11. AT

      Yeah.

    12. HS

      You call him up the night before. What do you advise them?

    13. AT

      Get your hands dirty on doing, doing- uh, doing deals. Like, the- the three things I would say to them are do the deals and learn it. And the reason I say that is like my framework for decision-making, on going to companies, and for how I coach my AEs that like set up time with me is focus on the product, that's number one. Like, learn the product, sell the product, figure it out. Number two, know the people. Get to know the people in your organization, figure out like how to build the relationships. And three is like learn the position that you have, and it's the three Ps. It's kind of like how I have always kind of simplified both my career-making decision framework, focus on good products, good people, and a good position.

    14. HS

      Can I ask you, what's the most creative thing you've done to win a deal?

    15. AT

      With T-Mobile at s- at Slack, um, there's a couple things. Like one is I- I knew that if I could... One of T-Mobile's key differentiators is, um, the c- team of teams, their- how they differentiate both with customer experience in the retail stores and online. And so what I did is went into a retail store, made- became friends with one of the retail p- people, recorded him on the technical challenges he was having, how he works, where he thought like Slack could play a role. Like, I went, I- I became friends with this guy. I did, like, we were texting. We're still texting. Did the same thing with a support agent where I just called in, pretend to be a T-Mobile customer, and like just chatted it up with a T-Mobile, uh, customer care, like getting the day in the life. And then the- the- the cherry on top was I kno- I knew the CEO at the time, John Legere, used to hang out at the W Bar in Seattle. And so, before an onsite, that night before, I just stayed in that W Bar, like just hanging out, and John Legere came in and I went up to him and we spent time chatting. And then the next day, I saw him in the lobby, I'm like, "Hey, John." He's like, "AJ, good to see you again." And that was like as I was walking into a CIO meeting. (laughs)

    16. HS

      (laughs)

    17. AT

      And Cody Sanford at the time was like, "How do you know John? (laughs) Like, the CEO of our company?"

    18. HS

      That is amazing. I absolutely love that. (laughs) How do you maintain morale when goals are missed in a sales team?

    19. AT

      Get back to the vision, get back to the why, and like focus on the small wins.

    20. HS

      Is effective goals ones where you can only ever achieve 80% of it?

    21. AT

      No. Effective goals are goals that you can achieve and you can outperform. Uh, I think that effective stretch goals are ones that you can only get to 80%.

    22. HS

      What would you most like to change about the world of sales?

    23. AT

      Uh, kind of what you said. Like, I want the world to see that this is a career path that enables you to become a CEO of another company. Me- meaning, like, I, uh, like, career-wise, like, at some point I wanna be a CEO of a company. Like, and I think I am uniquely positioned to do that because I am on one pillar of what makes companies great, which is go-to-market and sales. And so, I want that next grad that, regardless of whether you go to college or you're, you know, uh, at, at an Ivy League or at a state school, to realize that you can have a massive, like, career by investing in tech sales.

    24. HS

      Which CROs turned into a great CEO?

    25. AT

      Frank Slootman? Right, wasn't he, like, a CRO to start at some point?

    26. HS

      Mm.

    27. AT

      Hmm.

    28. HS

      No, I don't think so. 'Cause there, I mean, we can take this up, but there've been quite a few exam- and I would take this up, there's been quite a few examples of CROs who've moved to CEO roles. How's that one?

    29. AT

      Yeah. Well, give me a shot. (laughs)

    30. HS

      (laughs) I, I, yeah. That is the best answer. (laughs)

Episode duration: 1:08:51

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