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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 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.

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 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.

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 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.

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

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.

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

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.

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

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.

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 rejection. Just this idea that, man, I feel a little bit of shame. I started my sales career doing outbound, almost in-person sales, doing print ad sales in Cambridge, Massachusetts. I was selling to mom and pop shops on buying ads in this guidebook called The Unofficial Guide to Life at Harvard. I felt bad interrupting a small business owner who was trying to make money.

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 rejection. Just this idea that, man, I feel a little bit of shame. I started my sales career doing outbound, almost in-person sales, doing print ad sales in Cambridge, Massachusetts. I was selling to mom and pop shops on buying ads in this guidebook called The Unofficial Guide to Life at Harvard. I felt bad interrupting a small business owner who was trying to make money.

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 rejection. Just this idea that, man, I feel a little bit of shame. I started my sales career doing outbound, almost in-person sales, doing print ad sales in Cambridge, Massachusetts. I was selling to mom and pop shops on buying ads in this guidebook called The Unofficial Guide to Life at Harvard. I felt bad interrupting a small business owner who was trying to make money.

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

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.

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

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.

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

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.

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

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 convince someone to be engaged in the conversation.

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

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 convince someone to be engaged in the conversation.

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

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 convince someone to be engaged in the conversation.

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 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

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 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

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 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

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

actively listening and morphing and changing to the conversation.

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

actively listening and morphing and changing to the conversation.

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