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Episode: 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
Author: Harry Stebbings
Duration: 01:00:40
Episode Shownotes
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?
Full Transcript
00:00:00 Speaker_00
This is 20 Sales with me, Harry Stebbings. 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.
00:00:13 Speaker_00
Today, we have one of the best in the hot seat. AJ Tennant.
00:00:17 Speaker_00
AJ Tennant is the vice president of sales and success at Glean, 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 Glean.
00:00:31 Speaker_00
Before Glean, he had incredible runs at both Slack and Facebook. At Slack, most notably, AJ helped grow revenue from six million to more than a billion in ARR. My sales enablement platform is a waste of money. Ever thought that? You're not alone.
00:00:49 Speaker_00
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00:00:55 Speaker_00
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00:01:03 Speaker_00
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00:01:11 Speaker_00
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00:01:20 Speaker_00
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00:01:32 Speaker_00
See for yourself at speckit.com slash two zero VC. You have now arrived at your destination. AJ, I am so excited for this, dude. We get to do this in person. This is so, because we were planning on doing it remote.
00:01:44 Speaker_00
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. Now, I want to start with sales leadership skills and sales skills. A lot of people suggest that they are born.
00:01:57 Speaker_00
You're a natural sales person. Do you believe that sales skills are born or they can be learned?
00:02:03 Speaker_01
I fundamentally believe they can be learned.
00:02:05 Speaker_01
I think a lot of people would say it's innate, you're born with it, it's 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.
00:02:17 Speaker_01
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.
00:02:26 Speaker_01
gregarious nature, but they were able to navigate just like figuring out how to do sales because they had the work ethic, they had the desire to learn. And ultimately, it's about inputs.
00:02:36 Speaker_01
And it's not just about being a personable, like gregarious person.
00:02:42 Speaker_00
What was the hardest sales skill to learn for you?
00:02:45 Speaker_01
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.
00:03:00 Speaker_01
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 a small business owner who was trying to make money.
00:03:12 Speaker_01
Almost the shame of interrupting their life and then that rejection of them saying, hey, look, I am not interested. Please get away. That is just a really hard thing because it's just failure, failure, failure, failure.
00:03:27 Speaker_00
When you look at young, it's super tough, and it actually just makes me think of why Mormons tend to actually be such good sellers, because they actually have to go and sell the Book of Mormon to, like, Africa.
00:03:36 Speaker_00
But my question to you is, you see this, like, generation of new young reps coming in today. Are there commonalities in what you see them struggle to pick up slash learn?
00:03:45 Speaker_01
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.
00:04:00 Speaker_01
they first think they're going to get rejected, then they find a way to like convince someone to be engaged in the conversation.
00:04:06 Speaker_01
And what happens is the customer is actually interested or the prospects interested and people go into this very specific structured prescriptive approach where I, I think that the best sellers navigate and adjust to the customer, the specific situation.
00:04:21 Speaker_01
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. tailoring it very specifically, doing the research.
00:04:48 Speaker_01
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.
00:04:58 Speaker_01
Every company I've been a part of, I want AEs to be joining expecting that they have to do outbound and they're not going to have a BDR. The reality is you're going to have a lot of help from product marketing, content marketing.
00:05:11 Speaker_01
You're going to 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.
00:05:20 Speaker_00
You mentioned the playbook there, because they obviously run the playbook with different clients and you need to be flexible with it. How do you define the sales playbook?
00:05:28 Speaker_01
The whole concept of the playbook, I'm going to be a little controversial. I'm not a huge playbook person.
00:05:34 Speaker_00
Why?
00:05:35 Speaker_01
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.
00:05:50 Speaker_01
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.
00:06:04 Speaker_01
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?
00:06:14 Speaker_01
Are you then converting those to opportunities and then working those through a funnel?
00:06:19 Speaker_00
Should the founder be the one to create that process slash plan? Or is it okay for me to say, listen, AJ, I'm a product person. I've built this beautiful product. You go create the sales playbook.
00:06:32 Speaker_01
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.
00:06:45 Speaker_01
At Slack, Stuart was very involved on figuring out how to get those first customers. and making them successful.
00:06:52 Speaker_01
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's gonna be in the trenches, in the weeds, to figure out how to get them to success.
00:07:04 Speaker_01
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.
00:07:16 Speaker_01
You need to leverage them, but they shouldn't be the one determining the strategy.
00:07:20 Speaker_00
How do you feel about verticalized sales teams?
00:07:26 Speaker_00
When you think about a relatively horizontal product like Glean, which you sell to enterprise, sure, but there's many different types of enterprise, from fintech to healthcare to consulting to financial services.
00:07:37 Speaker_00
How do you think about specialization of sales teams and advice to founders there?
00:07:42 Speaker_01
The way I look at it is when you're first going to market, you can't all of a sudden just try to sell to everyone. If you all of a sudden are trying to go to the Fortune 100 and also sell to SMBs, you're going to fail.
00:07:57 Speaker_01
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?
00:08:11 Speaker_00
What is that contract size?
00:08:13 Speaker_01
You look at Glean, 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 on that cusp. And so it's like 100k ACVs?
00:08:33 Speaker_01
A little north of that, like you could get. In 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?
00:08:45 Speaker_01
Yeah, average is about... about four and a half, five months in that segment. Wow.
00:08:50 Speaker_00
That's still quite long.
00:08:51 Speaker_01
It is, but on the sub-1,000, we're getting it down to 90 days. It's closer to the four if you blend in that below 1,000. Yeah.
00:09:00 Speaker_00
I do want to retain some sense of structure, otherwise my mind just goes everywhere. Slack was an incredible journey for you. It really shapes a lot of how one thinks when one sees such a transformational journey.
00:09:12 Speaker_00
What are one or two of the biggest takeaways for you from Slack and how did that impact how you think as a sales leader?
00:09:19 Speaker_01
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 like collaborative tension between R&D and GTM.
00:09:32 Speaker_01
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.
00:09:40 Speaker_01
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.
00:09:56 Speaker_01
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?
00:10:06 Speaker_01
In that example, there was a fundamental question of how much do we want to actually go up market to enterprise? So it was almost even a not a research question, R&D question. It was a company strategy question.
00:10:20 Speaker_01
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.
00:10:30 Speaker_01
And I was like, we got to 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.
00:10:40 Speaker_01
You got to feel for these product teams when it's like, yeah, yeah, I hear you. Now do it. Yeah. I mean, my lesson was bringing those individuals onto the calls. Get R&D onto the calls to hear the feedback.
00:10:53 Speaker_01
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 their kind of employee 50. We had 6 million in revenue.
00:11:08 Speaker_01
I left when we were at about 1.5 billion. My other biggest learning from the experience at Slack is it is important when you have like such a horizontal product like Slack that has product market fit to move up market faster and more aggressively.
00:11:26 Speaker_00
And that's what we've done at Glean. 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.
00:11:37 Speaker_01
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
00:11:48 Speaker_01
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 up market.
00:12:06 Speaker_00
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 SOC 2. It needs compliance. It needs permissioning.
00:12:18 Speaker_00
It's not like 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?
00:12:26 Speaker_01
I think it is possible to move fast upmarket from a sales segmentation... On that, sorry, let's just start on that.
00:12:34 Speaker_00
Sales segmentation, does that need to change as you move upmarket?
00:12:37 Speaker_01
Absolutely. When I joined Slack, I immediately, after we got to about 10 million in revenue, cut the team into SMB and enterprise. And I basically said enterprise is a thousand employees and above, SMB is below.
00:12:50 Speaker_01
And that way we just sort of put the resourcing, the more expensive sales resourcing on those bigger accounts.
00:12:58 Speaker_01
At Slack, it 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.
00:13:10 Speaker_01
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,
00:13:23 Speaker_01
we've got to move up market, let's cut it at 2000 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.
00:13:34 Speaker_01
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.
00:13:49 Speaker_01
T-Mobile became that account for us at Glean. Not just a sales team, as a company and leadership team, we said, we are gonna prove success at a Fortune 100, like T-Mobile, get a win, get value, get success, and that's what we did.
00:14:03 Speaker_01
And then as soon as we did that, that's when the momentum of the business started to take off, because then we said, let's move up market even more, let's go after more traditional, like Microsoft accounts, and start to build out the sales team in a more aggressive way.
00:14:17 Speaker_01
What are the biggest challenges to going up? Security. I mean, in our business, and I would- Don't hold back, mate. Yeah, I won't.
00:14:26 Speaker_01
I think people underestimate, especially R&D organizations, like how you're gonna navigate security, deployment, POCs, pilots, like all of that nuance of getting through that, not to mention legal and contracting, it's like molasses.
00:14:45 Speaker_01
And, you know, I remember having conversations with Vish, one of the co-founders of Glean. He's like, AJ, I've been on 20 hours of calls with this account for the same conversation about security issues. What are we doing?
00:14:57 Speaker_01
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 going to do this for every account.
00:15:07 Speaker_01
But the detailed questions and how deep they're going into, like, how do we protect their data, the security, all of that.
00:15:13 Speaker_00
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 and suddenly, like, you need someone for legal, you need, like, I mean, the sales team changes dramatically, you definitely need customer success people, you probably need security people.
00:15:27 Speaker_00
We've built out a whole nother company.
00:15:29 Speaker_01
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 were starting to sell into like 10,000, 15,000 person accounts.
00:15:42 Speaker_01
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.
00:15:49 Speaker_01
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 account.
00:15:58 Speaker_01
I think the worst thing you can do early stage as a as a sales organization and a go-to company is segment too early and move way up 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
00:16:15 Speaker_01
fortune 50 or fortune 100 that would have been a nightmare because we would never get revenue for 9 12 months right because 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 yeah
00:16:34 Speaker_00
How willing are you to do small contracts, and what would your advice be to do small contracts with mega customers where they're like, hey, blend and expand? I think you need to be very willing to do that.
00:16:45 Speaker_01
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.
00:17:00 Speaker_01
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.
00:17:11 Speaker_01
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.
00:17:26 Speaker_01
It was very time-bound. It was very specific. And we were able to tie that back exactly to dollars. So that land slash paid POC, in some ways, turned into the seven-figure contract.
00:17:38 Speaker_00
Are we still in the experimental budget phase for AI tooling?
00:17:41 Speaker_01
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.
00:17:48 Speaker_00
So when you go to enterprises today, they're like, oh, shiny, cool. Yeah. Let's see what we can do.
00:17:55 Speaker_01
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 ways. For them.
00:18:08 Speaker_01
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.
00:18:24 Speaker_00
Is that even more a case for specialized sales teams though? Because it means you need to have a much clearer understanding of specific verticals. Okay, the core problems for telecoms businesses today are these three things.
00:18:36 Speaker_00
The core problems for healthcare providers, you can only get to that granular level of insight where you can show them the value if you are deep in that domain.
00:18:44 Speaker_01
I hear that argument. I still think staying generalist is important until you get to a certain scale.
00:18:50 Speaker_01
I think you need to be at 200 million, 250 million 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.
00:19:05 Speaker_01
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.
00:19:18 Speaker_00
you know i'm a podcaster and you're a very successful sales leader so this is where you push back on me but i'm like you know what we have t-mobile one of the biggest brands in telecoms in the world with real data on how they've used us effectively fuck i want one ae who is just purely focused on telecoms and they show explicitly
00:19:36 Speaker_00
with just the biggest telecoms providers, a FOMO. Do you wanna be like T-Mobile? Great, this is us. Now you need the entry point, you need that anchor into that market, but once you have it, hell, I wanna go.
00:19:48 Speaker_01
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 gonna have one AE who's
00:20:01 Speaker_01
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.
00:20:12 Speaker_00
We mentioned being in the experimental budget phase, and we mentioned showing them the value that we can provide them. Bluntly, are there buzzwords? You're a very smart and attuned sales leader.
00:20:22 Speaker_00
Are there buzzwords where you see these boardrooms light up and go, oh, that's exciting? Or buzzwords where they're, that's cynical?
00:20:31 Speaker_01
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?
00:20:44 Speaker_01
Those are like buzzwords that get people leaning in. A lot of the large accounts that we're in, like we're kind of coming to the table saying, we have a differentiated solution.
00:20:54 Speaker_01
We have a unique value prop, but more importantly, like we've got real, real customers that have gone through an AI journey. We can help you learn from those customers.
00:21:04 Speaker_01
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.
00:21:20 Speaker_00
OK, so we say this AI-enabled workforce, AI-centric employee, and they're leaning in. Why do you say they're still in the experimental budget phase? Is it because of the size of their contract, the speed of their rollout? What makes you say that?
00:21:33 Speaker_01
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.
00:21:46 Speaker_01
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 going to churn.
00:22:02 Speaker_01
Are they willing to spend big on AI?
00:22:04 Speaker_00
Absolutely. Do they have urgency when it comes to AI tools? Are they like, we need to get this in now? Or is it like part of the innovation budget of excitement? Absolutely, they need to get it now.
00:22:15 Speaker_01
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.
00:22:27 Speaker_01
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, and they're willing to spend, some of those accounts are willing to spend five, 10, $10 million annually on these type of initiatives.
00:22:45 Speaker_01
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 inside our company.
00:22:55 Speaker_00
Listen, if you're a public company CEO, you have to have an AI story. I had Vlad on from Robinhood the other day, and I said, do you have to as a public? You said I could ask anything. You can say no to answering.
00:23:07 Speaker_00
What was 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.
00:23:20 Speaker_00
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.
00:23:30 Speaker_00
To what extent are these large enterprises actually able to implement new AI technologies?
00:23:37 Speaker_01
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.
00:23:50 Speaker_01
And then when it comes to implementation, it's taking six, nine, 12 months, or comes attached with a $5 million services budget next to it, which is, it's like, well, hold on, I'm paying $5 million to implement this thing for the,
00:24:04 Speaker_01
with one of the big companies and like I'm paying like 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 like Microsoft Copilot.
00:24:17 Speaker_01
I 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, a product issue, it's more of a change management security challenge.
00:24:32 Speaker_01
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.
00:24:44 Speaker_01
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.
00:25:00 Speaker_01
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.
00:25:15 Speaker_01
I own that function at Glean, so I own the pre-sales, post-sales.
00:25:19 Speaker_01
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.
00:25:31 Speaker_00
When we think about CS, how do we bring CS in naturally without it being, thanks, AJ's closed the deal, now meet Harry? What's the right way to do that handoff from your experience?
00:25:42 Speaker_01
I don't think it's a handoff. Our strategy is that in the enterprise, you as an AE are involved in the deployment.
00:25:50 Speaker_01
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. OK, so the AE is responsible for future upsell, not CS. Not CS. Yeah.
00:26:03 Speaker_01
And I would say it's a shared responsibility. But what I metric CS organizations on is NRR, NDR, and what we call active users. We want people to get active with our service.
00:26:17 Speaker_01
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?
00:26:26 Speaker_01
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.
00:26:38 Speaker_01
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.
00:26:54 Speaker_01
They focused on deployment, they focused on success, they've tied it back to value. That's the sweet spot you want to be.
00:26:59 Speaker_01
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.
00:27:07 Speaker_00
What size contract does it make sense to have CS as a really built out function and really catered account?
00:27:13 Speaker_01
You've got to be looking at it a combo of the company size and the contract size.
00:27:20 Speaker_01
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.
00:27:32 Speaker_01
I think that can be a little bit of a miss because if you are closing, let's say you close a couple hundred K deal with ExxonMobil 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.
00:27:46 Speaker_01
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.
00:27:54 Speaker_00
Their company. Ah, so it's an upsell potential measurement. Exactly. TAM of the upsell. What are the biggest mistakes you think founders get wrong with building out their CSM teams?
00:28:04 Speaker_01
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.
00:28:17 Speaker_00
When you say NDR, NR, GR, all sound wonderful, you know, luckily, having done SaaS investing for nine or ten years, I do know what they mean. I didn't for a couple. And then I had to ask the stupid questions. Which one's the most important?
00:28:32 Speaker_01
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.
00:28:52 Speaker_01
The only accounts we're churning are SMBs. That's what you, that's what you want to have. But to answer the question, I view it as GRR.
00:29:00 Speaker_01
But to me, what's more, in some way, more important than GRR, it's the leading indicator metrics, like time to launch. How long did it take the customer to go from signed contract value to the initial launch and measuring that?
00:29:12 Speaker_01
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.
00:29:26 Speaker_01
It's not going to be a problem if you have people using the service and they're getting deployed quickly.
00:29:33 Speaker_00
We haven't seen renewal cycles yet for a lot of the AI tools with a lot of revenue in terms of full year cycles. Do you think we're going to see a large number of churns? Oh, yeah.
00:29:44 Speaker_01
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.
00:29:54 Speaker_01
I think that you're going to see it, for example, like there's some of these vertical solutions that have layered on to AI and sold a big story on hey, you're already paying x with us, we can accelerate you to go faster.
00:30:07 Speaker_01
I don't think some of those solutions are actually going to deliver enough value that it's going to be worth the incremental spend that they're going to be asked to do. Should CSMs be comped also on upsell? Great question.
00:30:19 Speaker_01
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.
00:30:33 Speaker_01
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.
00:30:42 Speaker_01
I forget what company pushed that strategy, which is comp BDRs on not net new opportunities, but comp them on closed one. 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.
00:30:57 Speaker_01
Actually, we did that at Glean, but we haven't systematically done it.
00:31:01 Speaker_01
So, for example, 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 wanted to recognize the right behavior.
00:31:15 Speaker_01
I think it's a good thing for us to 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.
00:31:22 Speaker_00
You've got a magic wand and you can change anything about the sales comp plan for Glean. What would you change? More aggressive accelerators.
00:31:32 Speaker_01
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.
00:31:47 Speaker_01
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.
00:31:56 Speaker_00
I think it's a good thing to do. In funds we call that kickers, which is like over a five X fund. You'll get a kicker on carry, which takes it to 30%, not 20% or whatever that is, but it's over that exceptional performance. I totally get that.
00:32:08 Speaker_00
That totally makes sense. Hiring is really fricking hard. It is the one area where I think most early stage founders get most wrong. You've hired exceptional sales teams. How do you run a process when adding to the sales team? What does that look like?
00:32:25 Speaker_01
My process is understand the deep history of the individual over a chronological period of time.
00:32:33 Speaker_01
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?
00:32:45 Speaker_01
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 did you go to the next job?
00:32:54 Speaker_01
And I go really try to understand because what you can build is an understanding of like the deep motivations that people have.
00:33:01 Speaker_00
I'm a salesperson. I'm brilliant at packaging. How do you actually determine true grit quality in my sales skills when I answer your questions beautifully?
00:33:11 Speaker_01
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?
00:33:24 Speaker_01
You 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.
00:33:36 Speaker_01
And I might, you know, my text them and 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.
00:33:45 Speaker_01
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.
00:33:57 Speaker_00
Well talk to me about that because you sent me beforehand this incredible deck that you did on joining Glean. What deck do you ask people to send you and how does that look in structure?
00:34:07 Speaker_01
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.
00:34:20 Speaker_01
Tell us about like, you know, 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.
00:34:33 Speaker_01
You don't give them much guidance after that. And you see a wide range. You see people come in that have like no slides and that's fine. I don't care about the slides or whether they look beautiful.
00:34:45 Speaker_01
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,
00:34:53 Speaker_01
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 a good lesson that I'd love to just share with others.
00:35:01 Speaker_01
And I learned this actually from Lexi Reese, 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, like, let's pause here for a sec.
00:35:12 Speaker_01
If I give you like your book of business today, 100 accounts, an Excel spreadsheet on column, column A is the name of the accounts.
00:35:20 Speaker_01
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.
00:35:29 Speaker_01
Some people get to like employee count, what industry they're in, and then they're like, oh, you know, and I'm like, no, no, no, I want 10. And you push them.
00:35:37 Speaker_01
Because if you're on customer calls, this is what like, you got to be able to, what I've described to the team, like the competency that I'm looking for is creative problem solving capabilities.
00:35:49 Speaker_01
You asked me earlier on this session about like, what is this, what is the skill set that junior AE struggle with? What I described to you there was almost like the early stages of creative problem solving, which is like,
00:36:00 Speaker_01
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.
00:36:08 Speaker_01
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 going to be your job.
00:36:19 Speaker_01
Like you are going to get 100 accounts and you are going to need to figure out which ones you spend on.
00:36:23 Speaker_00
I get in trouble. I think it's iQIYI. I think people are just not that smart. And then they also just don't have great energy.
00:36:30 Speaker_00
And you need both the razor-sharp intellect combined with high energy to really be able to map out a vision and articulate it well to that customer. And I just find that there's not that many insightful people.
00:36:40 Speaker_01
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.
00:36:51 Speaker_00
How much of a dick do you want me to be? Really? You want to put me on the spot? If you're a really sharp, insightful person, you're not going to be an AE. I'm going to get killed by our whole AE audience.
00:37:03 Speaker_00
But if you're really sharp, I can make money in so many better industries.
00:37:07 Speaker_01
It's tough. Sales is 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 AE. No.
00:37:15 Speaker_01
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.
00:37:29 Speaker_01
They got caught up in the 2008 crisis. All my friends went into investment banking, consulting.
00:37:36 Speaker_01
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.
00:37:56 Speaker_01
Why I love sales is because, and why I love enterprise SaaS sales, I went from ad sales at Facebook to B2B at Slack, and I'm never going back. The level of learning and depth you get to do, figuring out how to make T-Mobile successful.
00:38:15 Speaker_01
I've been working with T-Mobile for almost eight years because I worked with them at Slack. I helped them learn about Glean.
00:38:21 Speaker_01
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 want to go into sales? They will after they talk to me. Yes.
00:38:35 Speaker_01
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.
00:38:46 Speaker_00
I agree. I agree with that. But I think they, and this I'm pretty, you know, it's fine. Maggie's going to listen to you prick. But it's like, I think they want to go into product. I think they want to go into strategy.
00:38:56 Speaker_00
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.
00:39:04 Speaker_01
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.
00:39:17 Speaker_01
I learned this from David Han, 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.
00:39:32 Speaker_01
What drives technology companies and most businesses is one of those two functions.
00:39:37 Speaker_01
If you are the smartest person that's graduating from Yale, whatever, Harvard, I don't even wanna say it's Ivy Leagues, but I actually don't think the smartest people are always from those schools at all.
00:39:47 Speaker_01
You either are gonna 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 wanna do product management. If you are smart, where you should go is sales.
00:40:01 Speaker_01
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.
00:40:13 Speaker_01
We convinced her to be a sales development representative, to do outbound cold calling, and she was like, thank you AJ, this has changed my life, this is the career I wanted.
00:40:23 Speaker_00
Are sales reps coin operators?
00:40:25 Speaker_01
No, absolutely not. The sales reps that are coin operators 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.
00:40:39 Speaker_01
They want to figure out how to get like coached and mentored. That's what good sellers look like. You mentioned a hiring panel. Chad, Pete's. Yeah. Says it's stupid, right?
00:40:50 Speaker_00
Stupid.
00:40:51 Speaker_01
Yeah. Agree to disagree. 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.
00:41:06 Speaker_01
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.
00:41:17 Speaker_01
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. We don't, we're debating this.
00:41:33 Speaker_01
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.
00:41:41 Speaker_01
The take home that we sort of do at Glean is more about asking them to follow up with a artifact that they've done.
00:41:50 Speaker_01
Like we had this one great AE that's coming over from Pinecone who built this incredible advanced prompting methodology for how to like prep for a customer call. It was amazing.
00:42:01 Speaker_01
He used enterprise chat GPT and now he's using Glean to do it and we're implementing it. And like he he shared that artifact with us and it wasn't like IP for the company that shows like that's a that's an artifact that has depth.
00:42:15 Speaker_00
Oh yeah. You come into a hiring process with that and how you've used it before you're like fucking job.
00:42:20 Speaker_01
Yeah, fun fact. So when I was interviewed, when I was interviewing 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.
00:42:33 Speaker_01
I think as much as more important, frankly, is that people are making the right decision on the company they're going to go to.
00:42:39 Speaker_00
I totally agree. It's a bit of a risky strategy. Some companies could be pissed that you called up their main buyer and was like interviewing them ahead of time.
00:42:47 Speaker_01
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.
00:42:56 Speaker_01
Funny story, like 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?
00:43:08 Speaker_01
And she's like, no, no, no, no, no, sorry, nevermind. Their company name used to be SCIO, and that's what's in our procurement system. So, but yeah, it was- Your halt skips a beat there. Yeah, it actually did skip a beat in the moment.
00:43:20 Speaker_01
But what I'm saying is what we want to 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.
00:43:35 Speaker_01
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 how they were more efficient in the work they did.
00:43:47 Speaker_01
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. That shows that passion for the product.
00:44:01 Speaker_00
You mentioned your interview process with Glean. With the benefit of hindsight now, what could be done to have made that process better?
00:44:08 Speaker_01
I think that the, and this would be more feedback for Arvind, right? My CEO and what he could have done better.
00:44:13 Speaker_01
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.
00:44:36 Speaker_01
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.
00:44:50 Speaker_01
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.
00:45:02 Speaker_01
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.
00:45:17 Speaker_01
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 90 days. SMB?
00:45:31 Speaker_01
SMB you're gonna know in 30-45 days.
00:45:33 Speaker_00
Do you cut them down or do you give them a bit of time?
00:45:36 Speaker_01
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.
00:45:50 Speaker_01
The creative problem-solving 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.
00:46:02 Speaker_01
And that is a telltale sign that someone is not a creative problem solver.
00:46:07 Speaker_01
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?
00:46:19 Speaker_01
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?
00:46:33 Speaker_01
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 their senior AE careers, like,
00:46:43 Speaker_01
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.
00:46:50 Speaker_01
If you do not have the ability to collaborate effectively in a way that's driving your point of view, that does require some tension, and you are steamrolling people, people don't want to work with you, you're gone. It just doesn't work.
00:47:03 Speaker_01
And I like to use the word collaborative tension because I don't want to have this soft culture where everyone is just like, Oh, we're collaborating. And it's about collaborating in a very prescriptive, direct way that is going to have tension.
00:47:18 Speaker_01
And if you can't do that effectively, then you need you can't be a part of these hyper growth companies because that's what they need to make progress.
00:47:26 Speaker_00
When you look back over your mistakes as a hiring leader, what's the biggest? Moving too fast.
00:47:32 Speaker_01
I 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 got to move super fast to fill in AE.
00:47:45 Speaker_01
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.
00:47:58 Speaker_00
Someone said to me the other day, you have to sometimes let fires burn and actually just be okay letting a fire burn if it means you've got to wait another month. As painful as it is, it's better to wait the month. It's totally.
00:48:08 Speaker_01
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.
00:48:18 Speaker_01
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.
00:48:26 Speaker_00
What is the biggest mistake that founders or sales leaders make in new rep onboarding? Not doing it.
00:48:33 Speaker_01
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 like also my development as a human being, like I used to not believe in like therapy.
00:48:48 Speaker_01
I used to not believe in like medicine in terms of like for mental health.
00:48:52 Speaker_01
Like, you know, it's a long history of like stuff in my family that's like I hardened, but then I realized as I got married, as I had kids, like, wow, like I got to soften that approach a little bit and related to that.
00:49:04 Speaker_01
And this is how like work life all come together. During my time at Facebook, I was like, fuck enablement. I don't think enablement's ever going to help anyone. I was like, if you're a good rep, you're going to fucking figure it out.
00:49:16 Speaker_01
You don't need enablement ever. The best reps will figure it out. And that was the hard AJ back then. And what I realized more in my middle point of Slack and 100% at Glean is founders are
00:49:28 Speaker_01
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.
00:49:37 Speaker_01
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
00:49:54 Speaker_01
Slack with some of the folks there, but I've fully embraced it with Glean.
00:49:59 Speaker_00
Listen, I want to do a quick fire. I'm going to say a short statement. You're going to hit me with your immediate thoughts, okay? Yes. Discounting. Is it always bad? Do you sometimes do it? How do you approach it?
00:50:11 Speaker_01
I approach it early days, do it, get the deals done.
00:50:15 Speaker_01
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 going to impact the market discount rate. Do logos really help subsequent logos?
00:50:31 Speaker_01
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.
00:50:41 Speaker_01
So I think it's less about the logo and it's more about that customer becoming successful to then do reference calls.
00:50:50 Speaker_00
has just got a job as head of sales at a new company, at a series A stage company. You call them up the night before. What do you advise them?
00:50:58 Speaker_01
Get your hands dirty on doing deals. The three things I would say to them are do the deals and learn it.
00:51:05 Speaker_01
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. Learn the product, sell the product, figure it out.
00:51:19 Speaker_01
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.
00:51:30 Speaker_01
It's how I have always simplified both my career making decision framework, focus on good products, good people, and a good position. Can I ask you, what's the most creative thing you've done to win a deal?
00:51:41 Speaker_01
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.
00:51:51 Speaker_01
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.
00:52:05 Speaker_01
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. Get in the day of the life. And then the cherry on top was I knew the CEO at the time, John Ledger.
00:52:21 Speaker_01
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. And then the next day I saw him in the lobby.
00:52:38 Speaker_01
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?
00:52:48 Speaker_00
Like the CEO of our company. How do you maintain morale when goals are missed in a sales team?
00:52:53 Speaker_01
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.
00:53:06 Speaker_01
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.
00:53:25 Speaker_01
Career-wise, at some point I want to 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.
00:53:38 Speaker_01
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 Slootman, right?
00:53:55 Speaker_01
Wasn't he like a CRO to start at some point?
00:53:58 Speaker_00
Because I mean we can take that but they've been quite a few example and I would take that there's been quite a few examples of CROs have moved to CEO roles. Yeah, well, give me a shot. That is the best answer.
00:54:15 Speaker_00
But it is true, I'm trying to remember though, there's quite a famous one. Anyway, I shouldn't say it even if I could remember it.
00:54:21 Speaker_00
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 Glean, and why?
00:54:31 Speaker_01
So Wiz, what they've done with their partner and channel strategy is just phenomenal.
00:54:37 Speaker_01
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 are going to go all in.
00:54:52 Speaker_01
And what that does is essentially turned Wiz's sales team of whatever when it was, I don't know, a year or two ago, 100 AEs into 5,000, 10,000 AEs. Why I view that as the most effective is because sales and GTM is a distribution strategy.
00:55:10 Speaker_01
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.
00:55:25 Speaker_00
It's a really fucking good answer. Normally people have shit answers to that question. Honestly, I wondered about scrapping it because people never have any good ones. They just go open AI and I'm like... Fantastic. AJ, I've loved this.
00:55:37 Speaker_00
Thank you so much for being so willing to freewheel with my open-ended questions. You've been amazing and I so appreciate it, dude. Yeah, amazing.
00:55:46 Speaker_01
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?
00:55:55 Speaker_00
Sure.
00:55:56 Speaker_00
What's the hardest part that at every stage of my career people have told me that I will not be able to do the next thing Oh, well, you're a podcast that will find but you won't be able to make the move into being an ambassador Oh, well, you're an investor, but you welcome and you won't be able to make the move into being a lead investor Oh, well, you're a lead ambassador.
00:56:11 Speaker_00
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
00:56:16 Speaker_00
at every stage they tell you 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 also now as we you know we get bigger and bigger which is great in many ways you get a lot of hate yeah it's not very nice yeah that can hurt i was thinking about it because i was looking at obviously your linkedin followers your twitter followers like
00:56:41 Speaker_01
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 prezo like was that great, like whatever.
00:56:52 Speaker_01
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
00:57:04 Speaker_01
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... I started when I was 17. This?
00:57:15 Speaker_01
What got you to the point that you were like, oh, I guess where did that come from even going earlier?
00:57:21 Speaker_00
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.
00:57:32 Speaker_00
And so I think it's this realization that there's only one way to win, which is to work harder than everyone else. And like, I haven't had a weekend in 10 years since I started. I haven't been on holidays for 10 years.
00:57:41 Speaker_00
Like, there's very few people that are willing to do that. The grind.
00:57:44 Speaker_00
Yeah, but it's like, actually, great companies are built on solving grind problems, where it's not actually sometimes that difficult, technically, but it's just a lot of freaking work. I think to, like, Plaid is a great example.
00:57:58 Speaker_00
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.
00:58:15 Speaker_00
By the way, we didn't have 1,000 plays per show for the first 18 months. Everyone would have stopped. Everyone. 90% of podcasts don't make it to episode 10.
00:58:26 Speaker_00
The other 10% 8% more don't make it at episode 50 if you just keep going for 50 shows your top 2% Like this is a game of who survives the longest Yeah, also the another big problem is that 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.
00:58:42 Speaker_00
I was terrible Yeah, if you listen to my number one like first episode who was it again guy Kawasaki? Yeah, but I was like question number two I
00:58:51 Speaker_00
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 you do you agree that sales can be taught and it's not innate
00:59:09 Speaker_00
I think it is innate for the top 1%. And I think that's the same with most things. Like Roger Federer is an innately brilliant tennis player. It's in his bones.
00:59:18 Speaker_01
Yeah, and like top 5%. I'm with you. Like there's that like echelon that it's kind of like professional sports. It's innate that LeBron James, you know, is where he is. Yeah.
00:59:28 Speaker_01
You know, and 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.
00:59:40 Speaker_01
But he just grinded at it. Listen, I love this. Thank you. Dude, you're a star.
00:59:45 Speaker_00
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