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Crafting an Effective Sales Kickoff with Jennie Drimmer, CRO of Thomas International

This week on the Revenue Insights Podcast, we are joined by Jennie Drimmer, Chief Revenue Officer at Thomas International.

In this episode, Lee and Jennie explore sales kickoffs, discussing how to make them engaging and effective as well as how to communicate business impact during them. They further dig into why sellers need to slow down during discussions with clients.

Having been in Sales leadership roles for twenty years, Jennie is a dynamic commercial leader with a track record of accelerating growth in SaaS and Consulting businesses. She has been recognized as a Top 50 UK Sales Leader by Sales Confidence three times in the last five years — 2019, 2020, and 2022 — among other awards and accolades. She currently acts as Chief Revenue Officer at Thomas International, an HR platform.

Time Stamps:

  • 01:13 – About Jennie Drimmer
  • 04:25 – Being a revenue leader in the HR space
  • 08:14 – How to make the right hiring decisions
  • 11:34 – Crafting an effective sales kickoff
  • 14:00 – Why we stopped building business impact cases
  • 16:13 – Communicating business impact during sales kickoff
  • 20:31 – Thomas International’s top-performing sellers
  • 25:36 – Using the ‘science of selling’
  • 27:03 – Thomas International’s RevOps wins
  • 27:56 – Jennie’s book recommendations: The Challenger Sale by Brent Adamson and Matthew Dixon and Dare to Lead by Brené Brown
  • 29:11 – Where to find Jennie


Selling in a Down Economy

To craft an effective sales kickoff, Jennie recommends focussing on the big themes you want to land on. These are the items that you will come back to regularly throughout the year and will drive disproportionate outcomes. You always have to be cautious to avoid getting stuck into an ‘information relay’ mode, which will just be boring for your team. You need to find an engaging format to get everyone involved and understand where you are heading. This is especially pertinent now we’re in a down economy.

Communicating Business Impact

“Growth hides many cracks,” when we’re in times of abundance, we don’t have to work as hard to get results, but in a down economy, we need to go back to focusing on business impact. To do so, you need to understand your clients. Any company cares about three things: growing, saving costs, and reducing risks. As sales reps, it is our responsibility to advise them and make connections between cost initiatives, but you will only be able to do this by truly understanding them. 

You Need to Slow Down

Thomas International’s top-performing sellers know when to slow down. Instead of rushing to a client’s immediate ask, they take the time to understand what they need and why. By taking a step back, they can appreciate the broader impact they can have for the client, appreciate where they will add value, and take time in crafting the right solution. 

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