Biggest Lessons Scaling Slack from $6M to $1BN in ARR

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, someone 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 are like, Oh, they’re not outgoing, they don’t have that gregarious nature, but they were able to navigate just figuring out how to do sales because they had the work ethic, they had the desire to learn, and ultimately it’s about inputs, and it’s not just about being a personable, 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 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 little money, almost a shame of like interrupting their life and then that rejection of them saying, Hey, look, I am not interested.

Please get away. That is just like a really hard thing because it’s just failure, failure, failure, failure.

Where I would say AEs 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 gonna get rejected, then they find a way to 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 think that the best sellers navigate and adjust 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. The

Where I see the best outbound and ways to do messaging 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 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 AEs to be joining expecting that they have to do outbound and they’re not gonna have a BDR. The reality is, is you’re gonna have a lot of help from product marketing, content marketing.

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 in the cycles to do the outbound themselves.

define the sales playbook? The whole concept of the playbook, like I’m gonna be a little controversial, like I’m not a huge playbook person.

My view is that playbooks are fancy word for what is your strategy, what is your outbound messaging, what is your plan? 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 good 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 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 opportunities and then working those through a funnel?

I think that the founders need to be very involved and the CEO needs to be very involved in that 0 to 10,000,000 on kind of like how you’re getting those initial customers to product market fit. Know, at Slack, Stewart was very involved on figuring out how to get those first customers and making them successful. Arvind, the same thing at Glean. 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.

But 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.

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 one hundred and also sell SMBs, you’re gonna fail. I think 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 just unpack that? What is the middle market space?

What

contract size? Like, you you look at Glean, 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 weren’t these true enterprise, but like on that cusp. And so it’s like 100 ks ACVs? A little north of that, like you could get. And that segment right now, we’re well north of that. But when we were getting going, early, early days, even before I was there, that’s what it would be. How long is the sales cycles in that?

Yeah, average is about four and a half, five months in that segment. Wow. That’s still quite long. It is, but on the sub 1,000, we’re getting it down to ninety days. It’s closer to the four if you blend in that below a thousand.

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 and 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 inbound and the PLG that we were starting to run into challenges with supporting and getting to customer success on the Comcast, the Walmarts that were some of those earlier enterprise customers.

I 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 product? In that example, there was a fundamental question of how much do we wanna actually go upmarket to enterprise? So, it was almost even not a research question, R and 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.

And bringing them on those calls, having them hear from those customers the challenges helped us push through. So that was number one. You got a feel for these product teams when it’s like, yeah, yeah, I hear you. Now do lesson was bringing those individuals onto the calls. Get R and D onto the calls to hear the feedback. We needed to get engineers and R and 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 6,000,000 in revenue. I left when we were at about 1,500,000,000. My other biggest learning from the experience at Slack is it is important when you have such a horizontal product like Slack that has product market fit to move upmarket faster and more aggressively. And that’s what we’ve done at Glean.

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, 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.

I think it is possible to move fast upmarket from a sales segmentation. On that. Sorry,

Absolutely. When I joined Slack, I immediately, after we got to about $10,000,000 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. Now, at Slack, was a lot of inbound, but even that segmentation is important to do so you at least get your true, like your sellers starting to think about upmarket inbound 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 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, because you only have eight AEs or 10 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 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. And 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.

What are the biggest challenges to going upmarket? Security. I mean, in our business and I would Don’t hold back, mate. Yeah, I won’t hold. I think people underestimate, especially R and 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 and contracting, it’s like molasses. And I remember having conversations with Vish, one of the co founders of Glean. He’s like, AJ, I’ve been on twenty 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.

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 2,000, 3,000, 4,000, 5,000, maybe even we started selling to 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 like we’re saying this is the only account you’re on. They’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 too 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, twelve months, right? Because you still gotta feed your reps while you’re slowly moving up market.

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 Glean, 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 7 figure contract. So that’s how we try to do it in structure. It’s a very timely topic because 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 Glean relative to the other solution we had and 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 7 figure contract. Are we still in the experimental budget phase for AI tooling? Absolutely. I think any company that’s gonna say, Oh, we figured out what we’re doing with AI, I don’t think they figured it out.

So when you go to enterprises to say they’re like, oh, shiny, cool, 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 ways? For them. I mean, even here. I was in London meeting with a large telecommunications company and 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

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 200,000,000, $250,000,000 to go that granular because just the number of AEs that you need to hire to get to vertical, 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 financial financial services enablement, but we’re not at the point where we all of a sudden wanna just say, all we’re gonna do is have one financial services team.

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 AE who’s 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.

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 kind of 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. We 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.

I call it experimental because people are still not defining it all the way back to a business issue and an ROI that is fully defensible. My 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 gonna churn. Aren’t they willing to spend big on AI?

they need to get it now because the companies that are doing it right are actually gonna be the innovators and the accelerants in the space. And so what I think happens is the herd mentality. You’ve got a couple of these 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 $510 10,000,000 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 with inside our company.

Yeah, 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, twelve months, or it comes attached with a $5,000,000 services budget next to it, which is, it’s like, well, hold on, I’m paying $5,000,000 to implement this thing with one of the big companies, and 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 Copilot, mean, many customers are saying it’s falling flat, just not delivering the value that was advertised. So what the challenge is, is not like some of the other technologies, 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 gonna 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, 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 out of 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. I care very much about the customer success side.

I own that function at Glean, so I own the presales, 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.

I don’t think it’s a handoff. Our strategy is that in the enterprise, you as an AE are involved in the deployment. The 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 what iMetrix CS organization’s 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 CSMs not to an upsell, but it’s frankly more about are you getting users active?

And that, tied with AEs having an overlay of, Oh, I’m tied to being able to upsell incremental, makes that sort of like handoff not a handoff, it becomes a partnership. 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 turned 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 want to 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 gonna be our strategy there. What

contract

You gotta 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 miss because you’re, if you are closing, let’s say you close a couple 100 K deal with ExxonMobil and you’re putting like a junior CSM on it who doesn’t know how to navigate, you’re not gonna be likely to drive an upsell.

And so what I look at is a combination of employee count and are they over a certain dollar amount. Employee count of your company, not their company? Sorry, their company.

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,

Which one’s the most important? GRR and NRR. Most important for me is GRR. Why? Churn. The ripple effects of having an account, especially in the enterprise space, churn, the viral negative network effect that happens. Luckily at Glean, we have like a 97%, 98% GRR. The only accounts we’re churning are SMBs. That’s what you want to have. But to answer the question, I view it as GRR, but to me, what’s more, in some ways 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 measuring that? And then how long did it, not how long, but how many of the paid seats are actually active in the service? Because if you nail in a systematic way time to launch quickly and you get active users, GRR is just an afterthought. It’s going to be pot, it’s not going to be a problem, right, if you have people using the service and they’re they’re using getting deployed quickly.

We haven’t seen

Oh, yeah, we’re already 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. 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.

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, right? So it incentivizes the right behavior. I think, I forget what company pushed that strategy, which is comp BDRs on not net new opportunities, but comp them on closed won.

It’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, did that at Glean, but we haven’t systematically done it. So, for example, 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 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’ve got a magic

aggressive accelerators. Unpack that. 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. 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 top top performers. I think it’s a good thing to do.

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 Fratty taught me that at Slack, which is the who hiring method, what we call a chronological interview. I ask 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? 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 the deep motivations that people have. I’m a salesperson.

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 you didn’t like working for, and then you, in the moment, say, How do you spell their name again? You basically quiz them to say, I’m curious, if I reached out to that person, what would they give you constructive feedback on? And sometimes I even fluff it and I’m like, Oh, I think I’m connected to this person, and I might text them and call them.

You wanna 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, 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. Well, talk to me about that, because you

Yeah, part of the 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 prompt. That prompt is, Tell us your history, tell us about 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 going after this account, you don’t give them much guidance after that and you see a wide range.

You see people come in that have no slides and that’s fine. I don’t care about the slides or whether they look beautiful, I want to understand the deep thought that you’ve done in preparation. And then in that moment, the thing that I do, and I’m going to say it now, I used to tell candidates like, Please don’t tell other candidates I’m going to do this, but I’m just going to do it because I think it’s 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.

So anyway, what I ask is I throw off the interview mid interview and I say, Hey, hey, let’s pause here for a sec. If I give you your book of business today, 100 accounts in Excel spreadsheet on column, column 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, 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, like the competency that I’m looking for is creative problem solving capabilities. You asked me earlier on this session about like what the skill set that junior AEs struggle with? What I described to you there was almost like the early stages of creative 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 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. I get in

Yeah. And 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? I could literally write 50. How much of a dick do you want me to be?

You wanna put

It’s tough. Sales I is fucking disagree with that. I thought you said something else. I thought you said if you’re really sharp and insightful, you’re gonna be an AE. No. 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 two thousand and eight crisis. All 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 SaaS 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.

I’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 smartest people coming out of Harvard today wanna go into sales? They will after they talk to me. Yes. So 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.

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 is 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, There is product and then there is sales. What drives technology companies and most businesses is one of those two functions.

If you are the smartest person that’s graduating from Yale, whatever, Harvard, I don’t even want to say it’s the Ivy Leagues, I actually don’t think the smartest people are always from those schools at all. You either are going to find success and 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, where you should go is sales. We had this amazing AE, I’ll give her a shout out, Rachel Sato, Northwestern grad, went to work at McKinsey, same 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. This is the career I wanted.

No, absolutely not. The sales reps that are coin operator are 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 coached and mentored. That’s what good sellers look like. You mentioned a hiring panel. Chad, Pete’s says that. Stupid, right? Stupid. Yeah. Agree to disagree. Help 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.

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 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. Give them take home 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 Pinecone who built this incredible advanced prompting methodology for how to prep for a 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.

Yeah, fun fact. So when interviewing I at 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 as much as more important, frankly, is that people are making the right decision in the company they’re gonna go to. I totally agree.

It’s all in the delivery and it’s all in the approach. Now, I had relationships with Airbnb and Uber and networked in in a warm intro way. Funny story, like the the head of procurement at Uber who I was like calling, she’s like, AJ, we’re not a customer of Glean. Sorry, like watch out for this company, they’re lying to you. And I was like, what? And she’s like, no, no, Sorry, never mind. Their company name used to be Scio and that’s what’s in our procurement system, not so, but yeah, was Your heart skips a B there.

Yeah, actually did skip a B in the moment, but what I’m saying is what we wanna see out of AEs is creative, proactive approaches to how you’re thinking and 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 Databricks who uses Glean and he did a demo of it to me. Like that shows that passion for the product. You mentioned your interview

I 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 problems that I, like 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 Arvind, 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. Can you produce something and present to me and my leadership team on how you’re gonna 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 sell to 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 hired is not very good? It depends on the segment. So if we’re talking about the enterprise segment, you’re gonna know within probably ninety days. SMB? SMB, you’re gonna know in thirty, forty five days. Do you cut them down or do you give

We have about an 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 all they’re doing is coming to you with problems, not coming with solutions and ideas. And that is a telltale sign that someone is not a creative problem solver.

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. It’s like they are coming to you and they’re saying, Oh, I can’t get my SE to do X, Y, and Z. I’m like, Cut the bullshit. What do you want them to do? Have you talked to them yet?

And you have to do this annoying coaching to them, which is something that at this point in the senior AE careers, 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. 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. 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. It’s about collaborating in a very prescriptive, direct way that is gonna have tension. And if you can’t do that effectively, then you can’t be a part of these hyper growth companies because that’s what they need to make progress.

what was the biggest? Moving too fast. At 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 gotta move super fast to fill in AE, and I didn’t take the time to actually do the full chrono, to listen to some of the flags I had, to do back channeling. I think when you move too fast through the process, you make mistakes. Someone said to me the other

Totally. I mean, I ended up having to like 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 two weeks, three weeks, four weeks, month to get the right people. What is

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, I used to not believe in therapy, I used to not believe in medicine in terms of for mental health, there’s a long history of stuff in my family that I hardened, but then I realized as I got married, as I had kids, wow, I gotta soften that approach a little bit. And related to that, and this is how work life all come together, during my time at Facebook, was like, Fuck enablement.

I don’t think enablement’s ever gonna help anyone. I was like, If you’re a good rep, you’re gonna fucking figure it out. You don’t need enablement ever. The best reps will figure it out. And that was like the hard AJ back then. And what I 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. It’s going to 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 a 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 fully embraced it with Glean.

I approach it early days, do it, get the deals But once you get past like $10.15, 20,000,000 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. Do logos really help subsequent logos? Absolutely. 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.

What do you advise them? Get your hands dirty on doing deals. The three things I would say to them are do the deals and learn it, and the reason I say that is my framework for decision making on going to companies and for how I coach my AEs that set up time with me is focus on the product. That’s number one. Learn the product, sell the product, figure it out. Number two, know the people. Get to know the people in your organization. Figure out how to build the relationships, and three is learn the position that you have, and it’s the three Ps.

It’s kinda like how I have always kinda simplified both my career making decision framework, focus on good products, good people, good position. Can I ask you, 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, how they differentiate both with customer experience in the retail stores and online. And so what I did is went into a retail store, became friends with one of the retail people, recorded him on the technical challenges he was having, how he works, where he thought Slack could play a role.

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 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 on-site, that night before, I just stayed in that W Bar, like just hanging out. And John Leisure 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. And Cody Sanford at the time was like, How do you know John?

Get back to the vision, get back to the why, focus on the small wins. Is effective goals ones where you can only ever achieve 80% of it? No, no. Effective goals are goals that you can achieve and you can outperform. Effective stretch goals are ones that you can only get to 80%. What 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 wanna be a CEO of a company. 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. 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 CROs turned into a great CEO? Frank Frank Slootman, right?

Wasn’t he like a CRO to start at some point? No. I don’t think so.

So, Wiz, what they’ve done with their partner and channel strategy is just phenomenal. They 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’re gonna go all in. And what that does is essentially turned Wizz’s sales team of whatever, when it was, like a year or two ago, 100 AEs into 5,000, 10,000 AEs. Why I view that as the most effective is it’s because sales and GTM is a distribution strategy.

We lost the distribution war at Slack. I think part of why we lost that war was yes, monopolistic behavior by Microsoft, but because we didn’t lean into other effective fast distribution strategies other than PLG. It’s a really fucking

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, can I flip it and do a little question to you?

Oh, it’s the hardest part there.

That can hurt. I was thinking about it because I was looking at obviously your LinkedIn followers, your Twitter followers. Like my organization now is like two thirty people. I feel bad when I look at our GKO reviews and someone’s like, Oh, I didn’t think AJ’s Prizo was that great, like, whatever. I get some negative feedback from just a small group of people, and I can only imagine being sort of a public figure now that it just becomes, yeah, it becomes more heightened. Where did the chip on your shoulder come from to be able to even going back to, like, didn’t even know you didn’t go to college or I started when I was 17.

This? What got you to the point that you were like, I guess where did that come from even going earlier? I didn’t have a choice.

Yeah.

So you’re probably like me. Do you agree that sales can be

Yeah, and at like top 5%, I’m with you, there’s that echelon that’s kind of like professional sports. It’s innate that LeBron James is where he is. But there’s players that have made it to the NBA that like they were you know, 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. Listen, I love this. Thank you. Dude, you’re a star. Well done, my man.