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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

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.

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

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.

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

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.

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

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.

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

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

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

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

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

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

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

upper end of, let's call it, 5,000 to 15,000 employee-sized companies, and you are getting success and deals done, at that point, the moment that you are getting customers to value and success, and you can repeat it once, twice, three times, at that point, you just need to go fast upmarket.

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

upper end of, let's call it, 5,000 to 15,000 employee-sized companies, and you are getting success and deals done, at that point, the moment that you are getting customers to value and success, and you can repeat it once, twice, three times, at that point, you just need to go fast upmarket.

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

upper end of, let's call it, 5,000 to 15,000 employee-sized companies, and you are getting success and deals done, at that point, the moment that you are getting customers to value and success, and you can repeat it once, twice, three times, at that point, you just need to go fast upmarket.

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 it is possible to move fast upmarket from a sales segmentation. On that, sorry, let's just start on 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 think it is possible to move fast upmarket from a sales segmentation. On that, sorry, let's just start on 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 think it is possible to move fast upmarket from a sales segmentation. On that, sorry, let's just start on 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

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 1000 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,

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

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 1000 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,

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

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 1000 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,

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

At Slack, it was a lot of inbound, but even that segmentation is important to do so you at least get 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 eight of them, and we decided very quickly with the team to say, We've got to move up market.

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

At Slack, it was a lot of inbound, but even that segmentation is important to do so you at least get 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 eight of them, and we decided very quickly with the team to say, We've got to move up market.

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

At Slack, it was a lot of inbound, but even that segmentation is important to do so you at least get 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 eight of them, and we decided very quickly with the team to say, We've got to move up market.

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.