Sales Nerds Live! Ep. 2 recap: “Leading with a Mentor Mentality”

On Sales Nerds Live! Ep. 2 , we watched QuotaPath’s Chief of Staff, and favorite in-house Sales Nerd, Graham Collins welcome Occupier Head of Sales Jacob Walker

This episode’s topic? Leading with a mentor mentality. The two friends and former coworkers explored what it means to embrace failure, how to mentor people on an individual level to ensure they’re growing professionally, and more.

Watch the 26-minute episode. Or, read on for 3 key takeaways from Graham’s and Jacob’s moving conversation.

About Jacob: Before pivoting to the wonderful world of startups, Jacob began his sales career as a sales development representative (SDR) at a little company you may have heard of: Oracle. However, just before hitting his 1-year anniversary with them, he joined TrendKite as an account executive, met Graham, and quickly moved into a sales leadership role. Today, he serves as Head of Sales at Occupier, a lease lifecycle management platform for commercial real estate. 

Jacob Fun Fact #1:  If Jacob wasn’t in sales, he would have liked to pursue a career as a veterinarian. A lover of animals, he and his wife have three dogs!

Jacob Fun Fact #2: His guilty pleasure is watching The Bachelorette. “I hate that I love it so much,” Jacob said at the end of the episode.

Connect on a human level

Sales teams… sell. That’s their core purpose. But Jacob mentioned how important it is for leaders to learn how each person on their team defines success. What are they working for? What does work mean to them? And, what are they hoping to get out of work? 

“Success is what the person you’re coaching wants it to be,” said Jacob. 

Maybe that’s becoming an expert on a sales methodology to deliver sales training with the team or holding a workshop to share effective sales tips.

Perhaps it’s developing the discovery call to beat all discovery calls or whipping up incredible cold calling scripts. Or, maybe it’s something bigger like saving up to buy a house.

No matter what it is, leaders must learn it and build a concrete plan to help them achieve it. 

Create autonomy

“My job is to provide context and autonomy, get out of their way, and help them move blockers internally,” said Jacob.

When people come to leaders with a problem, Jacob suggested rather than immediately offering the help they need, to instead give them an opportunity to solve it themselves.

“I ask ‘What do you think you should do?’” said Jacob. “More often than not, you’ll find that they’re on the right track.”

Give them autonomy to get creative, tell them they’re correct, and encourage them to take the idea through execution.

“Eventually, people start to do it instinctively,” added Graham.

Jacob mentioned that this only happens under a culture of trust and vulnerability. 

See you next month!

Thanks so much for tuning in to July’s Sales Nerds Live! LinkedIn Live. Our August episode will feature Amelia Taylor, an account executive at Carabiner Group. Follow us on LinkedIn for a date and time, and to catch up on previous episodes!

To learn more about how QuotaPath can motivate your sales teams through automated, transparent sales commissions and compensation, schedule a time with our team here.


Guide to Mastering Sales Kick Off Excellence
Guide: Mastering Sales Kickoff Excellence

With this playbook you'll, learn what it takes to strike success at your sales kickoff — including how to get your sales team hyped for the year ahead (and their new comp plans).

Download the Guide
Report: Solving the Biggest Sales Compensation Challenges

Insights from 450 RevOps, Finance and Sales leaders on how to ensure compensation plans align to business goals, motivate sales reps, and maintain simplicity in 2024.

View the Report
your guide to setting calculating and tracking sales compensation image
Your Guide to Setting, Calculating & Tracking Sales Compensation

Create sales compensation packages that reward over performance, drive productivity, and attract and retain talent.

Download the Guide