YouSaid · the spoken record

AJ Tennant

lines on the record
76
first
2024-10-23
most recent
2024-10-23
sittings or episodes
1
sources
podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

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

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “I call it experimental because people are still not defining it all the way back to a business issue and an ROI that is like fully defensible. 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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “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 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. We have a unique value prop, but more importantly, like 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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “I think that you can solve that by educating some of the other general SAEs 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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “I hear that argument. I still think staying generalist is important until you get to a certain scale. I think you need to be at 200 million, 250 million to go that granular because just the number of AEs that you 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 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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “I think you need to be very willing to do that. Now, the key thing that we've learned, and I learned this at Slack as well, but at Glean, you've got to have success criteria. Let's say for Fortune 100 company, we're going to do 100,000, 150,000 land deal, but you have commercial alignment and executive alignment on what are the success criteria that we need to hit to get to that seven-figure contract. So that's how we try to do it in structure. It's a very timely topic because we're like 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 seven figure contract.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “Yeah, I think people underestimate, especially R&D organizations, like how you're going to 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, hey, Jay, I've been on 20 hours of calls with this account for the same conversation about security issues. What are we doing? And I'm like, Vish, this is what it takes to figure out the playbook on how to navigate the largest companies in the world. I commit to you, we are not going to 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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “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 EchLean, 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. 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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “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. And that way, we just sort of put the resourcing, the more expensive sales resourcing on those bigger accounts. Now, at Slack, it was a lot of inbound, but even that segmentation is important to do. So you at least get your truce, like your sellers starting to think about market 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 up market. Let's cut it at 2,000 employees and above. And the below will be serviced by a smaller subset of the team. And that helped us.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “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 in 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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “I mean, my lesson was bringing those individuals onto the calls. Get R&D onto the calls to hear the feedback. We needed to get engineers and R&D and product leadership to hear and have empathy for the customer. The second biggest lesson from just the experience at Slack for context, I was there kind of employee 50. We had 6 million in revenue. I left when we were at about 1.5 billion. 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. And that's what we've done at Glean.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “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 not a research question, an RD 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 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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “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. 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 Walmart's that were some of those early enterprise customers. I think driving feedback to the product organization, challenging them, getting them on calls.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “You look at gleaned in selling the product, it was going to technology SaaS companies that were between 500 employees to two thousand, three thousand, 4,000 that weren't these true enterprise, but like on that cusp.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “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 going to fail. I think like a really good place to sell to is.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “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 kind of like how you're getting those initial customers to product market fit. You know, Slacks, Stuart was very involved on figuring out how to get those first customers and making them successful. Arvin, 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 going to 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 like 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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “The whole concept of the playbook, I'm going to be a little controversial. I'm not a huge playbook person. My view is that playbooks are fancy words 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 go around that product. And you need to go outbound, get someone interested, convert that interest into an opportunity, and then start someone through a sales funnel. Kind of building it up as more than it is. Sometimes I think I complicates it. And so I like to bring it down to just very simple things. Like, are you getting net new meetings? Are you then converting those to opportunities? And then working those through a funnel.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “Absolutely. 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. 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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “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 going to get rejected. Then they find a way to like convince someone to be engaged in the conversation. And what happens is the customer is actually interested or the prospect's interested and people go into this very specific structured prescriptive approach where I 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.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “I think rejection just this idea that man feels 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 money. Almost the shame of like interrupting their life and then the rejection of them saying, hey, look, I am not interested. Please get away. Like that is just like a really hard thing because it's just failure, failure, failure, failure.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “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 were like, oh, they're not outgoing. They don't have that gregarious nature, but they were able to navigate just like figuring out how to do sales because they had the work ethic. They had the desire to learn. And ultimately, it's about inputs and it's not just about being a personable, like gregarious person.”

    2024-10-23 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source