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AJ Tennant

👤 Person
459 total appearances

Appearances Over Time

Podcast Appearances

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

And so what we did was strategically pick one or two key bets that we wanted to get to prove success in. T-Mobile became that account for us at Glean. Not just a sales team, as a company and leadership team, we said, we are gonna prove success at a Fortune 100, like T-Mobile, get a win, get value, get success. And that's what we did.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

And so what we did was strategically pick one or two key bets that we wanted to get to prove success in. T-Mobile became that account for us at Glean. Not just a sales team, as a company and leadership team, we said, we are gonna prove success at a Fortune 100, like T-Mobile, get a win, get value, get success. And that's what we did.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

And so what we did was strategically pick one or two key bets that we wanted to get to prove success in. T-Mobile became that account for us at Glean. Not just a sales team, as a company and leadership team, we said, we are gonna prove success at a Fortune 100, like T-Mobile, get a win, get value, get success. And that's what we did.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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. 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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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. 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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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. 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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

He's like, AJ, I've been on 20 hours of calls with this account for the same conversation about security issues. What are we doing? And I'm like, Vish, this is what it takes to figure out the playbook on how to navigate the largest companies in the world. I commit to you, we are not going to do this for every account.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

He's like, AJ, I've been on 20 hours of calls with this account for the same conversation about security issues. What are we doing? And I'm like, Vish, this is what it takes to figure out the playbook on how to navigate the largest companies in the world. I commit to you, we are not going to do this for every account.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

He's like, AJ, I've been on 20 hours of calls with this account for the same conversation about security issues. What are we doing? And I'm like, Vish, this is what it takes to figure out the playbook on how to navigate the largest companies in the world. I commit to you, we are not going to do this for every account.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

But the detailed questions and how deep they're going into, like, how do we protect their data, the security, all of that.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

But the detailed questions and how deep they're going into, like, how do we protect their data, the security, all of that.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

But the detailed questions and how deep they're going into, like, how do we protect their data, the security, all of that.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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 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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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 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.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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

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 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.