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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

Oct 23, 2024

AJ Tennant, Vice President of Sales & Success at Glean, has a rich history scaling sales teams at Slack and Facebook. In this conversation, he shares insights on selling AI tools, discussing the transition enterprises need to make and their adoption concerns. He addresses common mistakes in customer success management and how to create seamless handoffs between sales and CS. AJ also reveals innovative hiring strategies for sales teams, emphasizing the importance of comprehensive candidate evaluations and unique interview techniques.

01:00:40

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Episode guests

AJ Tennant

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Episode notes

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Quick takeaways

Sales skills can be cultivated through motivation and education, allowing a diverse range of individuals to succeed in sales roles.

Engaging in outbound sales activities is crucial for sales professionals, as proactive lead generation significantly enhances team effectiveness.

Integrating sales and customer success teams creates a collaborative environment, fostering customer satisfaction and opportunities for upselling post-sale.

Deep dives

Sales Skills: Learnable or Innate?

Sales skills can be learned rather than being solely innate traits. The belief that some individuals are born salespeople overlooks the potential for personal growth through motivation and education. AJ Tennant points out that even individuals perceived as less outgoing can successfully adapt to sales roles through hard work and adaptability. This opens the door for a diverse range of people to excel in sales if they are willing to learn and put in the effort.

Intro

2min

Mastering Sales Skills

7min

Scaling Sales for Enterprise Success

18min

AI Integration and Customer Success Strategies

10min

Mastering Sales Hiring Strategies

18min

Mastering Sales Strategies and Team Morale

6min

Navigating Career Challenges and Public Criticism

2min

The Power of Persistence in Achieving Success

4min

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?

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