20Sales: Biggest Lessons Scaling Slack from $6M to $1BN in ARR | How to Build a Customer Success Machine and Where Most Go Wrong | The Framework to Hire All Sales Reps: Take-Home Assignments, Hiring Panels and more with AJ Tennant @ Glean

23 Oct 2024 · 1 h 1 min

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Podcast Summary: 20Sales with AJ Tennant @ Glean

Introduction In this episode of The Twenty Minute VC (20VC), host Harry Stebbings interviews AJ Tennant, Vice President of Sales & Success at Glean. AJ shares insights from his experience at Glean, Slack, and Facebook, focusing on scaling revenue and building customer success teams.

Key Topics Discussed

  1. Selling AI Tools in 2024
  2. Current State: Companies are in the experimental budget phase for AI tools.
  3. Differences: Selling AI differs from traditional SaaS; enterprises have unique concerns.
  4. Enterprise Buzzwords: Terms like "generative AI" resonate with enterprise customers.
  5. Churn Concerns: Anticipation of significant churn during renewal cycles for AI products.
  1. Outbound Sales Strategy
  2. Is Outbound Dead?: AJ argues that outbound is not dead; it requires creativity and flexibility.
  3. Discounting: Common misconceptions about discounting; it can be useful early on but problematic later.
  4. Creating Urgency: Strategies for sales teams to stimulate urgency in the sales cycle.
  5. Post-Mortems: Importance of deal reviews and identifying lessons learned.
  1. Mastering Customer Success
  2. Common Mistakes: Founders often mismanage CS teams and fail to create good handoff experiences.
  3. Compensation Structures: Debate on whether CS teams should be incentivized for upselling.
  4. CS Team Longevity: Recognizing how CS teams can break over time and strategies to prevent it.
  1. Hiring the Best Sales Teams
  2. Hiring Process: AJ emphasizes structured hiring processes including take-home assignments and panel interviews.
  3. Questions to Ask: Key questions to assess candidate capabilities and red flags during interviews.
  4. Identifying Outperformers: Signs of high performers in sales hiring.

Lessons from Slack and Glean

  • Collaboration: The importance of having collaborative tension between R&D and Go-To-Market (GTM) teams.
  • Market Fit: Insights on transitioning to the enterprise market and recognizing the right timing.
  • Customer Engagement: AJ’s experience with T-Mobile highlights the value of understanding customer needs deeply.

Challenges of Scaling and Moving Up Market

  • Security and Compliance: Navigating security and compliance issues when entering enterprise markets.
  • Small Contracts: Willingness to execute small contracts with enterprise customers to build relationships.
  • Implementation Challenges: High barriers in implementation of AI tools can hinder adoption despite initial sales success.

Customer Success Metrics

  • Key Metrics: AJ values Gross Retention Rate (GRR) and Net Revenue Retention (NRR) as critical indicators of success.
  • Lead Indicators: Emphasis on metrics like time to launch and active user counts as leading indicators for future success.

Conclusion AJ Tennant shares his extensive knowledge on sales strategies, customer success, and the complexities of AI tool sales. His insights provide invaluable lessons for founders and sales leaders looking to scale their businesses effectively.

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Key Takeaways

  • Learning Sales is Possible: Sales skills can be learned, not just innate.
  • Customer Success Matters: Success hinges on how well sales and customer success teams work together.
  • Be Careful with Scaling: Moving up market requires careful planning and a strategic approach to sales.
  • Hiring is Critical: A thorough hiring process with clear criteria is essential to build strong sales teams.
  • Adaptability is Key: Sales strategies should evolve as markets and technologies change.

For more insights and resources, visit [The Twenty Minute VC](http://www.20vc.com).

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Transcript

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0:00This is 20 sales with me Harry Steppings. Now 20 sales is the monthly show where we sit down with the best sales leaders to discuss their tips, tactics and strategies when it comes to scaling both sales and customer success teams. Today we have one of the best in the hot seat, AJ Tennant. AJ Tennant is the vice president of sales and success at Gleene, where he's had more than a 20X increase in revenue and a 100X increase in user base in the two and a half years he's been at Gleene. Before Gleene, he had incredible runs at both Slack and Facebook. At Slack most notably, AJ helped grow revenue from 6 million to more than a billion in error.

0:43are. My sales enablement platform is a waste of money. Ever thought that? You're not alone. Most revenue leaders feel this way watching their sales team struggle to keep up with market, product and competitive changes. Reps burn hours each day, searching, digging, slacking, desperately trying to get the answers they need out of their clunky tech stack. That's why Speckit's AI -powered enablement platform was purpose -built to cut through the noise and meet reps in their moment of need. Spekit uses AI to recommend the exact content your reps need to close deals in any tool like Gong, Salesforce or Outlook.

1:19It's that easy. If you're ready to give your reps a personalized enablement assistant at their fingertips, take five minutes and discover why leading investors like Kraft and Felicis are backing Spekit as the platform revolutionising sales enablement. See for yourself at spekit .com slash 2 -0 -VC. You have now arrived at your destination. AJ, I am so excited for this dude. We got to do this in person. This is so because we were planning on doing it remote. And then when you said you were in London, I was like, yes, this is it. Thank you so much for doing this. Thank you. I'm stoked to be here.

1:50Now, 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? I fundamentally believe they can be learned. I think a lot of people would say it's innate, you're born with it. It's at your personality. Some of that's outgoing. But my philosophy is that humans can learn anything if they're taught and they have the motivation to do it. I've seen in my career someone that's joined both Facebook and Slack that many people were like, oh, they're not outgoing.

2:25They 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 and ultimately, it's about inputs and it's not just about being a person in a bowl like gregarious person. What was the hardest sales skill to learn for you? I think rejection. Just this idea that man, I feel a little bit of shame. 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 guide book called the unofficial guide to life at Harvard.

3:06I felt bad interrupting like a small business owner who was trying to make like a little money. Almost the shame of like interrupting their life and then the rejection of them saying, hey look, I am not interested, you know, please get away. Like that is just like a really hard thing because it's just failure, failure, failure, failure. When you look at, yeah, I'm as super tough and actually just makes me think of why at Mormons tend to actually be such good selves because they actually have to go and sell the Book of Mormon to like, yeah, Africa. But my question is, you see this generation of new young reps coming into it.

3:41And then commonalities in what you see them struggle to pick up slash learn. Where I would say eighties are really struggling is being super creative and 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 going to get rejected, then they find a way to convince someone to be engaged in the conversation. What happens is the customer is actually interested or the prospect is interested and people go into this very specific structured, prescriptive approach where I think that the best sellers navigate and adjust to the customer the specific situation.

4:21I'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. They are always amazed by also, it's like the design for volume over depth. They want to send a thousand outbound messages versus 20 really well -crafted ones. Where I see the best outbound and ways to do messaging is tailoring it very specifically, doing the research, but more important, it's coming with a point of view and then listen to the customer and adjust from there. Do you think AES should be doing their own outbound? Absolutely. Every company I've been a part of, like, I want AE's to be joining, expecting that they have to do outbound and they're not going to have a BDR.

5:06The reality is, is you're going to have a lot of help from product marketing, content marketing. You're going to get the support you need in the field marketing, but the AE's that do the best are the ones that are also spending the time in the cycles to do the outbound themselves. You mentioned the playbooks that because they obviously run the playbook with different clients and then he's be flexible with it. How do you define the sales playbook? The whole concept of the playbook, like I'm gonna be a little controversial, I'm not a huge playbook person. Why? My view is that playbooks are fancy word for what is your strategy, what is your outbound messaging, what is your plan?

5:44Sales 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 kind of building it up as More than it is sometimes I think I 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 two opportunities and then working those through a funnel? Should the founder be the one to create that process slash plan?

6:23Or is it okay for me to say, this is an AJ, I'm a product person. I've built this beautiful product. You go create the sales playbook. I think that the founders need to be very involved and the CEO needs to be very involved in that zero to 10 million on how you're getting those initial customers to product market fit. that it's like Stuart was very involved on figuring out how to get those first customers and making them successful, are having the same thing at Gleene. And I think what it helps to do is also show your sales team that your CEO and your founder is gonna be in the trenches in the weeds to figure out how to get them to success.

7:04But I think there's a stage at which you need to have that founder and CEO not necessarily be deciding exactly what is the messaging, exactly what is the sales play that you're running. You need to leverage them, but they shouldn't be the one determining the strategy. How do you feel about verdict, I'm just completely free -winning here at this point? So how do you feel about verdict -close sales teams? When you think about like a relatively horizontal product like Clean, which is that you sell to enterprise, sure. But there's many different types of enterprise from FinTech to healthcare, to consulting, to financial services.

7:37How do you think about specialization of sales teams and advice to founders there? The way I look at it is when you're first sort of going to market, you can't all of a sudden just try to sell to everyone. Right? If you all of a sudden are trying to go to the Fortune 100 and also sell SMBs, you're going to fail. I think like 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. Can we do some patent that what is the middle market space like what is that Contrassized like it you know you look at Gleen like when we got started in selling to product It was going to technology SaaS companies that were between 500 employees to 2003 thousand 4 ,000 that you know weren't these true enterprise but like on that cusp So that's and so it's like 100k ACBs a little north of that like you could get 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 what it would be how long is the sales cycles in that yeah average is about about four and a half five months in that segment Wow, yeah, that's still quite long it is but on the sub 1000 we're getting it down to 90 days it's closer to the four if you blend in that below a thousand Yeah, I do want to retain some sense of you know strong shit otherwise my mind just gets everywhere.

9:04Slack was an incredible journey for you. It really shapes a lot of how one thinks 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 is a sales leader? Number one takeaway that I've brought to Glean, it's what I give to other founders I advise and just is how important it is to have the collaboration and collaborative tension between R &D and GTM. So when I was at Slack early days, it was interesting, I was struggling to get the organization to think about supporting the enterprise. We were so focused on just inbound in the PLG that we were starting to run into challenges with supporting and getting to customer success on the Comcast, the Wal -Mart's, that were some of those early, earlier enterprise customers.

9:55I think driving feedback to the product organization, challenging them, getting them on calls. What are the biggest points of tension between GTM and research and products? In that example, there was a fundamental question of how much do we want to actually go up market to enterprise? It was almost even a not -of -research -R &D question. It was a 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.

10:32And bringing them on those calls, having them hear from those customers, the challenges helped us push through. So that was number one. You gotta feel for these product teams when it's like, yeah, yeah, hey, not do it. Yeah. I mean, 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 product leadership to hear and have empathy for the customer. The second biggest lesson from just the experience at Slack. For context, I was there, kind of employee 50. We had 6 million in revenue. I left when we were at about 1 .5 billion.

11:11My 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 up market faster and more aggressively. And that's what we've done at Gleene. How do you know when is the right time to move up market? It's a hard one. You don't want to get distracted too early, but you also don't want to leave great and big contracts on the table when you could take them. My view is that if you are delivering clear, repeatable success in that middle market segment, and you're now kind of getting experimentation into that upper end of, let's call it, 5 ,000 to 15 ,000 employee size companies, and you are getting success and deals done.

11:56At 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 up market. The trouble with going fast up market is, I don't think it's like an easy transition for the company. You do need to move whole scale, product needs sock two, 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 up market and what do you need to do to do that? I think it is possible to move fast up market from a sales segmentation.

12:32On that, sorry, let's just start on that. Sales segmentation, does that need to change as you move up market? Absolutely. When I joined Slack, I immediately, after we got to about 10 million of revenue, to cut the team into SMB and enterprise. And I basically said enterprise is a thousand 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. Now at Slack it was a lot of inbound, but even that segmentation is important to do, so you at least get your truce, like your sellers starting to think about a market inbound at a minimum.

13:10At Gleen, when I joined, we had real great success in that mid -market segment. We had strong sellers about eight of them, and we decided very quickly with the team to say, we've got to move up market. Let's cut it at 2 ,000 employees and above, and the below will be serviced by a smaller subset of the team. That helped us start to accelerate moving up, but you're right, because you only have eight eighties or 10 eighties, 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.

13:49T -Mobile became that account for us, actually. Not just a sales team as a company and leadership team, we said, we are going to prove success at a Fortune 100 like T -Mobile, 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. As we said, let's move up market even more. Let's go after more traditional Microsoft accounts and start to build out the sales team in a more aggressive way. What are the biggest challenges to going on? Security. In our business, and I don't know about me. I think people underestimate, especially our in the organizations, how you're going and navigate security, deployment, POCs, pilots, like all of that nuance of getting through that, not to mention legal and contracting, it's like molasses.

14:45And I remember having conversations with Vish, one of the co -founders of clean, he's like, AJ, I've been on 20 hours of calls 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, all of that. But that's my point, which is like, is it possible to go up market fast when you look at all of those different elements?

15:19And suddenly, 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. I hear you, but there's a way to phase it. What we did was we said, okay, this team that's going after the 2000, 3000, 4000, 5000, maybe even we were starting selling to like 10 ,000, 15 ,000 person accounts. We said, we're going to give you one or two of these key accounts that we're going to try to get into. And it's not like we're saying this is the only account you're on.

15:49They're still trying to 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 sales organization and a go -to company is segment to early and move way up market and just like 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? was you still got to feed your reps while you're slowly moving up market. Quite often, even the very large companies, they're not that confident when they sign the first land deal.

16:34How willing are you to do small contracts? What would your advice be to do small contracts with mega customers? Well, they're like, hey, land and expand. I think you need to be very willing to do that. Now, the key thing that we've learned, and I learned this at Slack as well, but at Gleene, you've got to have success criteria. Let's say for 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. So that's how we try to do it in structure.

17:11It's a very timely topic. It was we're debating it even more as a go -to -market team. We had one Fortune 100 company say, we want to test how we're lowering call resolution time with Gleen relative to the other solution we had in the competitors. It was very time bound, it was very specific, and we're able to tie that back exactly to dollars so that land slash paid POC in some ways turned into the seven figure contract. All we still in the experiment until budget phase AI tooling. Absolutely. I think any company that's going to say, oh, we figured out what we're doing with AI, I don't think they figured it out.

17:48So when you get enterprises to say that like, ooh, shiny, cool. Yeah. Let's see what we can do. Yeah, and that's what we're weary of. Our strategy is to capture that AI demand, but then turn it back into clear business value that has success criteria. And you're defining that value for them in a lot of time. For them. I mean, even here, I was in London meeting with a large telecommunications company, in, they were like, I need you to tell us and be prescriptive for us and how we should be defining success criteria because I have my board and CEO asking me to do something. Is that even more a case for specialized sales team?

18:27So 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 all deepen not domain. 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 $250 million to go that granular because just the number of eight years yet you need to hire to get to vertical and it becomes complicated to manage that.

19:03So 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 going to do is have one financial services team. 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 team 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 telecom providers, a FOMO.

19:40Do you want to be like T -Mobile? Great, this is us. Now, you need the entry point, you need the anchor into that market, but once you have it, hell, I want to go. I think that you can solve that by educating some of the other generalist AEs because the problem with it is sometimes those telecoms are all over the world. And you're not going to have one AEs based in the Bay Area, be able to service the global telecoms And so at some point you do have to scale the learnings from one account to another region. We mentioned being the experimental budget phase. We mentioned showing the values that we can provide them bluntly.

20:18Are there buzzwords? You're a very smart and attuned sales leader. Are there buzzwords where you see these boardrooms light up and go, oh, that's exciting. Or buzzwords where they're, that's cynical. Yeah. I mean, the buzzword right now is generative AI. Just saying, generative AI, how are you driving AI transformation inside your organization? How are you turning your employees into AI -centric employees? Those are buzzwords that get people leaning in. A lot of the large accounts that we're in, we're coming to the table saying, we have a differentiated solution, we have a unique value prop, but more importantly, we've got real customers that have gone through an AI journey.

21:02we can help you learn from those customers. So leaning into not like our speak of the, taking what our customers are saying, even the example of the telecom I talked about, like their CEO is talking about an AI -enabled workforce. We're taking that buzzword and bringing it to others. Okay, so we say this AI -enabled workforce, AI -centric employee, and that leaning in, why do you say that's still in the experimental budget phase? Is it because of the size of that contract, speed of that rollout. What makes you say that? 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.

21:46My view is that AI budgets that are based on just, hey, we need to 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, we're going to churn. Are they willing to spend big on AI? Absolutely. Do they have urgency when it comes to AI tools? So we need to get this in now, or is it like part of the innovation budget of excitement? Absolutely. They need to get it now, because the companies that are doing it right are actually going to be the innovators and like the accelerants in the space.

22:23And so 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, other CEOs of other companies are like, we need to move quickly. We need to drive an AI initiative within CIDA or a company. Listen, if you're a public company CEO, you have to have an AI story.

22:58I had flared on from Robinhood the other day and I said, like, do you have to? It was a public 100%. You said I could ask anything. Yeah. You can say no to answering. It could go. What's the biggest contract that Glean has? Size wise. Yeah. Well, North of 5 million. Wow. That's real money. Yeah. That's not experimental budget shit. No. 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 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?

23:37Yeah, this is where I would say the space is like falling down. Everyone is being sold a bag of goods 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 $5 million services budget next to it, which is, it's like, whoa, on. I'm paying $5 million to implement this thing with one of the big companies. And like I'm paying the fees for the service, what we're seeing is adoption and usage is not where it needs to be. And we're seeing that even with, you look at Microsoft co -pilot, I mean, many customers are saying it's falling flat, just not delivering the value that was advertised.

24:25So what the challenge is is not like some of the other technologies of a product issue, it's more of a change management security challenge. What does everyone think they know about selling AI tools that they get totally wrong? That it's going to be easy to implement is what they get wrong. That's simply, I mean, we talked about it already. I think that 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 telling them, set the right expectations, make sure that you have a deployment success plan. I took a page at a Dave Schneider's book from 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.

25:12I care very much about the customer success side. I own that function at Gleen, so I own the pre -sales, post -sales. That's for me a very important part to it, but I think going back to your question, it's a lot of companies are getting the big deals done and then assuming, okay, we can figure out the deployments later and that's what they get wrong. When we think about CS, how do we bring CS in naturally without it being thanks A .J. is closed the deal now me Harry? What's the right way to do that handle from your experience? I don't think it's a handoff. Our strategy is that in the enterprise, you as an AE are involved in the deployment.

25:50The reason you're involved is because you have an incentive to make them successful because the future upsell is dependent on your ability to drive deployment. Okay, so the AE is responsible for future upsell, not CS? Not CS. Yeah, and I would say it's a shared responsibility, But the what I metric CS organizations on is NRR, NDR, and what we call active users. We want people to get active with our service. And so we're actually tying the compensation of our CSM's not to an upsell, but it's frankly more about, are you getting users active? And that tied with AE's having an overlay of, oh, I'm tied to being able to upsell incremental, makes that sort of like handoff, not a handoff.

26:36It becomes a partnership. You're like the story I keep talking about internally is we had this healthcare company do a $60 ,000 land deal with us and over the course of nine months, the AE, the SE and the CSM, turn that account into a $500 ,000 plus contract. They focused on deployment, they focused on success, they've tied it back to value. That's the sweet spot you wanna be. Now you can't do that if you're talking about a velocity motion for like a commercial or SMB segment and that's not going to be our strategy there. What size contract does it make sense to have CS as a really built out function and really catered account?

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27:13You've got to be looking at it a combo of the company size and the contract size. 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 a senior CSM on the million dollar contracts. I think that can be a little bit of a mess because if you are closing, let's say you close a couple hundred K deal with Exxon mobile and you're putting like a junior CSM on it who doesn't know how to navigate, you're not going to be likely to drive an upsell. What I look at is a combination of employee count and are they over a certain dollar amount?

27:52Employee count of your company notes that come. Sorry, they're a company. It's an upsell potential measurement. Exactly. Tam of the upsell. What are the biggest mistakes you think founders get wrong with building out the CSM teams? I think that a lot of them don't tie it to clear metrics. They don't tie it to things that will go back into leading indicators for future upsells and NDR and GRR. When you say NDR and GR, oh, sound wonderful. You know, luckily having done such investing for nine or ten years, I do know what they mean. I didn't for a countable. And then I had to ask the stupid questions.

28:31Which one's the most important? GRR and NRR. Most important for me is GRR. Why? Turn. The ripple effects of having an account, especially in the enterprise space, turn, the viral negative network effect that happens. Luckily at Gleene, we have like a 97, 98 % GRR. The only accounts we're turning are SMBs. That's what you want to have. But to answer the question, I view it as GRR. But to me, 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 sign contract value to the initial launch and measuring that? And then how long did it, not how long, but how many of the paid seats are actually active in the service?

29:19Because if you nail in a systematic way time to launch quickly and you get active users, GRR is just and after thought it's going to be put. It's not going to be a problem, right? If you have people using the service and they're using getting deployed quickly. We haven't seen renewal cycles yet for a lot of the AI tools with a lot of revenue in terms of fully -hicicles. Do you think we're going to see a large number of trends? Oh, yeah. We're seeing it. We're seeing a lot of accounts move off of those experimental, like quick knee jerk reaction AI budgets and shifting to our product. 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 paying X with us, we can accelerate you to go faster.

30:07I 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. Should CSMs be comped also on upsell? Great question. I think there should be some type of kicker and incentive. It shouldn't be the number one key metric. Right now, in the sales dev world, 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. So it incentivizes the right behavior. I think I forget what company pushed that strategy, which is Comp BDRs are not net new opportunities, but comp them on closed one.

30:50It's too far and too long of a thing to do, but I think there's a model in which you can give a bonus Actually, we did that at Glean, but we haven't systematically done it. So for example, you know the companies that did these multi -million dollar expansions we actually strategically gave a large spot bonus to the CSM that was on that because we we wanted to recognize the right behavior. 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 to structure it in. You go to magic wand and you can change anything about the sales comp plan for Glean.

31:29What would you change? More aggressive accelerators. I'm Pac -Man. Accelerators are essentially ways to, if someone goes over a hundred percent of their quota, an accelerator just gives that that wrap the ability to move faster in terms of accelerated comp. And so what it's doing, and why I say that's the number one thing, whether it's CSM's, BDR's, AES's, you're rewarding the top top performers, I think it's a good thing to do. And funs we call that kickers, which is like over a five X fund. Yeah. You get a kicker on carry, which takes it to 30%, not 20%, or whatever that is, but it's over that exceptional performance.

32:08I totally get that totally made sense. Hiring is really frickin' hard. Like it is the one area where I think most of the stage founders get most wrong. You've had exceptional sales teams. How do you run a process when adding to the sales team? What does that look like? My process is 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 Frattie taught me that at Slack, which is the who hiring method, what we call a chronological interview. I asked people, what did you do in high school? Why did you go to the college you went to, what was your proudest accomplishment in college?

32:49And I do that through every, why did you leave the first job you did, why did you go to the next job? And I go really try to understand, because what you can build is an understanding of the deep motivations that people have. I'm a salesperson, I'm burdened up packaging. How do you actually determine true, great quality in my style skills when I answer your questions beautifully. You ask people while you're going through that process of who is 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?

33:24You basically quiz them to say, you know, I'm curious if I reached out to that person, what would they give you constructive feedback on? 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, my text and then call them. You want to get people off of their, whatever, their sales skill game and get real and challenge them on that. That's one way. The other is what 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.

33:57Well, talk to me about that because you sent me beforehand. It's incredible that you did on joining Glean. What deck do you we've asked people to send you, and how does that look in the structure? Yeah, part of the going deep into the Y and the chronological side, we move from there to a panel interview. And that panel interview is, they get an hour, they get a prompt, that prompt is, tell us your history, tell us about like your biggest career challenge, talk about 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 like going after this account.

34:33You don't give a much guidance after that. And you see a wide range. You see people come in that have like no slides. And that's fun. I don't care about the slides or 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 gonna say it now, I used to tell candidates, like please don't tell their candidates, I'm gonna do this, but I'm just gonna do it is I think it's a good lesson that I'd love to just share with others. And I learned this actually from Lexi Rees, who is one of my bosses at Facebook.

35:05So anyway, what I ask is I throw off the interview and mid interview and I say, hey, hey, let's pause here for a sec. If I give you like your book of business today, 100 accounts in Excel spreadsheet on column, I'll call them A is the name of the accounts. I want 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. Some people get to employee count, what industry they're in, and then they're like, oh, and I'm like, no, no, no, I want 10. And you push them. Because if you're on customer calls, this is what you gotta be able to what I've described to the team, the competency that I'm looking for is creative problem solving capabilities.

35:49You asked me earlier in this session about what is this skill set that Junior AE struggle with? What I described to you there was almost like the early stages of creating problem solving, which is like EQ, creative problem solving, which is like listening to a prospect and kind of 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 at think not only quickly but strategically and then map it to what is actually going to be your job. Like you are going to get a hundred accounts and you are going to need to figure out which ones you spend on.

36:23I get in trouble. I think it's Ikea. I think people are just not that smart. Yeah. And then they also just don't have great energy. And you need both the razor shop intellect combined with high energy to really be able to map out a vision or articulate it well to that customer. And I just find like, there's not that many insightful people. Yeah. And it's shocking to me how many AEs I asked this question to and they just get stumped at five. I'm like, like, are you kidding me? I could literally write 50. How much for a date do you want me to be? I really, you want to put me on the spot? If you're a really sharp insightful person, you're not going to be an A.

37:00Oh, I'm going to get killed by a whole A audience. No, but like if you're really sharp, I can make money in so many better industries. It's tough. So, you know, it's fucking hard. I disagree with that. I thought you said something else. I thought you said if you're really sharp and insightful, you're going to be an A. I think that this is very top of mind for me because I was very lucky and shouldn't have gotten into Harvard. 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. They got caught up in the 2008 crisis.

37:32All my friends went into investment banking, consulting. I think that technology sales has the potential to capture some of the smartest minds because when you really peel back the layers of what technology and AI sales is, it is taking what's happening in investment banking, consulting, actually putting it to work on driving transformations within companies. Why I love sales is because, and why I love enterprise -ass sales, like I went from ad sales at Facebook to B2B at Slack, and I'm never going back, like the level of learning and depth you get to do, like figuring out how to make T -Mobile successful.

38:15I've been working with T -Mobile for almost eight years. Because I worked with them at Slack, I helped them learn about Glean. You can drive true business transformation if you choose the right product technology and you believe in it and you have, do you think the smallest people coming out of Harvard today want to go into sales? They will after they talk to me. Yes, so I wouldn't say sales. I would say that they want to go into I think the smartest people coming out of the top universities want to go work for the best Technology companies. I agree. I agree with that But I think they and this I'm pretty you know, it's fun.

38:51Maggie's gonna listen to you prick But it's I think they want to go to product. I think they want to go to strategy I think they even might want to 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 I agree with you that the smartest minds aren't, but I think the smartest minds will get there with time because when they realize there's two paths to making a big impact inside a technology company. I learned this from David Hahn, who was a VP of product at LinkedIn in technology companies, and this might be controversial because this is putting aside all the other things that make these companies go.

39:29There is product and then there is sales. What drives technology companies in most businesses is one of those two functions. If you are the smartest, smartest person that's graduating from Yale, whatever, Harvard, I don't even want to say it's Ivy League, but I actually don't think the smartest people are always from those schools at all. You either are going to find success in a path through product, but if you realize, you know what, I'm not an engineer, I don't like that, I don't want to do product management. If you are smart, that where you should go is sales. We had this amazing AE, I'll give her shout out, Rachel Sado, a Northwestern grad went to work at McKinsey.

40:09Same thing had this thought that she wanted to go work in product management at Lyft. 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. All sales reps, coin operation. No, absolutely not. The sales reps that are coin operator, the ones you don't want to hire. The sales reps that have that insightful IQ that you talked about, want career development, they want challenges, they want to figure out how to get like coached and mentored. That's what good sellers look like.

40:45You mentioned the hiring panel. Chad, Pete says that stupid, right? Yeah. Agreed to disagree. You know, that helped me. I'm naive. Yeah, I think that a hiring panel is equivalent to you showing up to a customer meeting and there's three or four people that are in the room that you are presenting to. Like a panel presentation is for me an opportunity to see how someone is going to have the IQ and EQ to read a room and present. I think that's a it's a miss to bring someone into your company that their core job is to get on Exactly a call like that every week multiple times a day and you don't see them in action I think it's important.

41:29It gives them take time assignments We don't we're debating this so at Slack Anyone that was coming in as an AE had to do a writing exercise and it wasn't a take -home like I think you just had to write something The take home that we sort of do at Glean is more about asking them to follow up with an artifact that they've done. Like we had this one great AE that's coming over from Pinecon who built this incredible advanced prompting methodology for how to prep for customer call. It was amazing. He used Enterprise Chat GPT and now he's using Glean to do it and we're implementing it. and he shared that artifact with us, and it wasn't like IP for the company, that shows like, that's an artifact that has depth.

42:15Oh yeah, you come into a hiring process with that and how you used it before you like fucking job. Yeah, fun fact. So when I was interviewing a Glean, and I like when reps do this, I found out who the customers of Glean were and interviewed the buyers about their experience with Glean. I think it's much more important, frankly, is that people are making the right decision and the company that they're gonna go to. Totally agree. It's a bit of a risky strategy. Some companies could be pissed that you cooled up their main buyer and was interviewing them ahead of time. It's all in the delivery and it's all in the approach.

42:49Now I had relationships with Airbnb and Uber and networked in in a warm intro way. Funny story, the head of procurement at Uber who I was calling, she's like, AJ, we're not a customer of Gleene. sorry, like watch out for this company that are lying to you. And I was like, what? And she's like, no, no, no, no, no. I'm sorry, never mind. Their company name used to be SIO, and that's what it's in our procurement system. No. So, but yeah, it actually did skip it being the moment, but what I'm saying is what we want to see out of eight years is creative, proactive, approaches to how you're thinking.

43:30And that can come in the form of, okay, Let's get an example of an artifact that you built. I want to see how you creatively problem solved on a business case And it can come in the form of hey an AE shares an artifact that's not about an account But it's about like how they were more efficient in the work they did or I love like I said when reps are saying Oh, I talked to x y and z customer I interviewed my friend who's at data bricks who uses Glean and he did a demo of it to me like that shows the that passion for the product. You mentioned your interview process was clean. With the benefit of hindsight now, what could be done to have made that process better?

44:08I think that the, and this would be more feedback for Arvind, 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 of problems that I think senior leader interviews that CEOs are doing. 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. And so, Arvin, he could have spent all this time with me and it not really lead to anything. I think that having him ask me, hey AJ, here are the three problems that we're dealing with as a company right now.

44:50Can 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. One of the strategies we have in our panel interview is I always ask my managers choose the account that this person is prepping for their cell 2 on a new prospect 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. How fast do you know when someone you've had is not very good? It depends on the segment. So if we're talking about the enterprise segment, you're gonna know within probably 90 days.

45:30SMB. SMB. SMB you're gonna know in 30, 45 days. Do you cut them down? Don't you give them a bit of time? We have about a all -time like a 20 % turnover rate. Some might argue we need to be more aggressive. What are the biggest commonalities in why they fail? Number one is a lack of two things. Creative problem solving and collaborative tension. The creative problem solving, 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, not coming with solutions and ideas. And that is a tell -tale sign that someone is not a creative problem solver.

46:07The 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, 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 something that at this point in the senior AEC careers, like, you need to be going to try to solve that problem or coming to me with how you're thinking about solving.

46:48The second one is the collaborative tension. 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 wanna work with you, you're gone. Like it does, it just doesn't work. And I like to use the word collaborative tension because I don't wanna have this soft culture where everyone is just like, oh, we're collaborating and 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 can't be a part of these hypergrowth companies because that's what they need to make progress.

47:26When you look back over your mistakes as a hiring media, what's the biggest? Moving too fast, I slack, we got this sort of like 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 in 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, you make mistakes. Someone said to me the other day, you have to sometimes let fires burn and actually just be okay letting it burn. If it means you go to wait another month as pain flizz it is.

48:06It's better to wait the month. It's totally. I mean I ended up having to like, I move super fast with this one AE, ended up having I'm 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 two weeks, three weeks, four weeks month to get the right people. What is the biggest mistake that founders will say I'll sleep is make a new rap on boarding, not doing it. I'm definitely guilty of this. It's hard. The mistake is not investing in enablement early enough. So when I was at Facebook And this is also my development as a human being.

48:45Like I used to not believe in therapy. I used to not believe in medicine in terms of for mental health, like long history of 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 got a soft and that approach a little bit. And related to that, and this is how work life all come together. During my time at Facebook, I was like, fuck enablement. I don't think enablements ever gonna help anyone, like 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.

49:22And what I realized more in my middle point of slack and a hundred percent of green 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. It's gonna hurt you in the long run. We hired a world class enablement leader who used to be a salesperson, who used to be a sales dev manager, was it with chief of staff to the pure storage, like CEO, that has changed the trajectory of what I think good enablement looks like, and it started at Slack with some of the folks there, but I've like fully embraced it with clean.

49:59Yeah, listen, I wanna do a quick fire. So I'm gonna say a short statement, you're gonna hit me with your immediate thoughts, okay? Yes. Discounting. Is it always bad? Do you sometimes do it? How do you approach it? I approach it early days do it get the deals done But once you get past like 10 15 20 million in revenue You really need to have a very tight discount matrix and don't give away just horrible deals because it's gonna impact the market Discount rate the logos really help subsequent logos Absolutely if you get a the marquee customer and get them successful. It's more important than the logo.

50:37It's actually they will do reference calls. They will do intro. So I think it's less about the logo and it's more about that customer becoming successful to then do reference calls. Your friend has just go to a job who's had a sales at a new company at a series A stage company. You cool them up the night before. What do you advise them? Get your hands dirty on doing deals. The three things I would say to them, 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.

51:17Learn 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 P's. 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 good position. Can I see what's the most creative thing you've done to win a deal? With T -Mobile at Slack, one of T -Mobile's key differentiators is the team of teams. They're how they differentiate both with customer experience and the retail stores and online.

51:51And so what I did is went into a retail store, became friends with one of the retail pre -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 became friends with this guy, did the same thing with a support agent where I just called in, pretend to be a T -Mobile customer and like just chatted up with a T -Mobile customer care, like get in the day of the life. And then the cherry on top was, I knew the CEO at the time, John Leisure, used to hang out at the W -Bar in Seattle before an onsite that night before, I just stayed in that W bar, like just hanging out and John Ledger came in and I went up to him and we spent time chatting.

52:36And then the next day I saw him in the lobby, I'm like, hey, John, he's like, hey, Jay, good to see you again. And that was like as I was walking into a CIO meeting and Cody Sanford at the time was like, how do you know John, like the CEO of our company? How do you maintain morale when goals are missed in the sales team? Get back to the vision, get back to the why, focus on the small wins. Is effective goals one's way you can only ever achieve 80 % of it? No, no. Effective goals are goals that you can achieve and you can help perform. Effective stretch goals are ones that you can only get to 80%.

53:10What would you most like to change about the world of sales? Kind of what you said. I want the world to see that this is a career path that enables you to become a CEO of another company. Career -wise, at some point I want to be a CEO of a company. 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. I want that next grad that regardless of whether you go to college or you're at an Ivy League or at a state school to realize that you can have a massive career by investing in tech sales. Which CRS turned into a great CEO?

53:53Frank Slutman, right? Wasn't he like a CRO to start at some point? No. Because we can take that, but there have been quite a few examples. And I've been quite a few examples of CRS, moved to CROs. Hasn't one. Yeah. Well, give me a shot. That is the best answer. But it is true. I'm trying to remember there's quite a famous one. Anyway, I shouldn't say even if I could remember it. I want to finish on one, though, which is like, when you look at company sales strategies or GDM motions, which one have you been most impressed by recently, other than Gween, and why? So, with what they've done with their partner and channel strategy is just phenomenal.

54:37They have a direct sales motion, but what they did is they went to the sort of channel, whether it was the hyperscalers and the cloud service providers, but more importantly, like the resellers and the channel players and said, we are going to go all in. And what that does is essentially turned Wiz's sales team of whatever, when it was like a year or two ago, a hundred AEs into 5 ,000, 10 ,000 AEs. Why I view that as like the most effective is it's because sales in GTM is a distribution strategy. We lost the distribution war at Slack. I think part of why we lost that war was yes like monopolistic behavior by Microsoft, but because we didn't lean into other effective fast distribution strategies other than PLG.

55:25It's really fucking good answer. Normally people don't have shit answers to that question. I always say I wondered about scrapping it because people never have any good ones. I just go open AI in a moment. Yeah, fantastic. Hey, I love this. Thank you so much for being so willing to free wheel with my open -ended questions. You've been amazing, and I so appreciate it, dude. Yeah, amazing. Can I ask you a question? Yeah. What's been the hardest part of your career in this world that you're in now? Yeah, I flip it and do a little question. Sure. It was the hardest part of that. At every stage of my career, people have told me that I will not be able to do the next thing.

56:02Oh, well, you're a podcast that will find that you won't be able to make the move into being an investor. Oh, you're an investor, but you won't be able to make the move into being a lead investor. Oh, you're a lead investor. You won't be able to make the move into having your own fund. You won't be able to make the move into having your own big fund at every stage. It's how you can't do it. And at every stage, you have to be like the one solitary person in the crowd as well as my mother who claps and says, like, you can do it. And that is hard. And then And also now as we, you know, we get bigger and bigger, which is great in many ways.

56:33You get a lot of hate. Yeah. And it's not very nice. That can, I was thinking about it because I was looking at obviously your LinkedIn followers, your Twitter followers. Like my organization now is like 230 people. I feel bad when I like look at our GKO reviews and someone's like, oh, I didn't think AJ's Priso, like was that great? Like whatever, like I get some negative feedback from just a small group of people. And I can only imagine like being sort of a public figure now that it just becomes, yeah, it's becomes more heightened. Where did the chip on your shoulder come from to be able to like even going back to like I didn't even know you didn't go to college or like I started when I was 17.

57:14This? What got you to the point that you were like, oh, I guess where did that come from even going earlier? I didn't have a choice. I didn't go to university. I didn't do that well in school. My life was set out to be pretty mediocre to shit if I followed any conventional rules. And so I think it's this realization that there's only one way to win, which is to work hard on everyone else. And I haven't had a weekend in 10 years since I started. I haven't been on hold for 10 years. There's very few people that are willing to do that. The grind. Yeah, but it's actually great companies are built on solving grind problems, whereas not actually sometimes that difficult technically, But it's just a lot of fricking work.

57:55I think it's like planned as a great example. It is a company built on a grind problem, intense amounts of integrations, data challenges. It's not technically hard, but the man hours to do that was insane. This was a grind problem. I did five shows a week, one a day, for five years. By the way, we didn't have a thousand players per show for the first 18 months. Everyone would have stopped. Everyone. 90 % of podcasts don't make it to episode 10. The other 10%, 8 % more don't make it to episode 50. If you just keep going for 50 shows, you'll top 2%. Like this is a game of who survives the longest.

58:35Also, there's another big problem is I everyone's like, you know what, I'm not good at content. I'm not, I don't think like in tweets like you do Harry. I was terrible. Like if you listened to my number one, like first episode, who was it again? Guy Cowar Sackie. But I was like question number two, question number three. It was the worst and it's just like the gym. No one goes into the gym and is like, I feel great on the treadmill. What a natural habitat for me. It sucks, but 50 times in, you're like, okay, I got this. So you're probably like me, do you agree that sales can be tight and it's not innate?

59:09I think it is innate for the top 1%. And I think that's the same with most things. Roger Federer is an innately brilliant tennis player. It's in his bones. And at like top 5%, I'm with you. There's that echelon that's kind of like professional sports. It's a Nate that LeBron James is where he is. Yeah. But there's players that have made it to the NBA that like, they were Steve Nash. I don't know that like Steve had an innate ability to play in the NBA when you looked at him early, early on in his life. But he just grinded at it. I love this. Thank you. Dude, you're still. Oh, well done my man.

59:47My sales enablement platform is a waste of money. Ever thought that? You're not alone. Most revenue leaders feel this way watching their sales team struggle to keep up with market product and competitive changes. Reps burn hours each day, searching, digging, slacking, desperately trying to get the answers they need out of their clunky tech stack. That's why Specki's AI powered enablement platform was purpose -built to cut through the noise and meet reps in their moment of need. Speckit uses AI to recommend the exact content your reps need to close deals in any tool like Gong, Salesforce or Outlook.

1:00:23It's that easy. If you're ready to give your reps a personalized enablement assistant at their fingertips, take five minutes and discover why leading investors like Kraft and Felicis are backing Speckit as the platform revolutionising sales enablement. cvacelf at speckit .com -20VC

From the publisher

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. 

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?

 

 

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