BC Startup Sales Podcast – How To Have Tough Sales Conversations with Trenton Truitt (Apollo GraphQL)

This week on the Bowery Capital Startup Sales Podcast we welcomed back Trenton Truitt, Chief Sales Officer at Apollo GraphQL, to discuss a wide range of topics around how to have tough sales conversations. What do we mean by tough sales conversations? Whether discussing performance improvement plans with reps you manage, establishing a foundation of sales ethics for your company, or striking a work-life balance with your manager and team, you ultimately are going to have to deliver difficult feedback and advice. For those that do not know Trenton, he is a phenomenal sales executive and manager of teams having worked his was up as an individual contributor, manager, and executive at major SaaS companies like PTC, Documentum, EMC, PagerDuty, and Wizeline. We’ve had Trenton on the podcast before talking through coaching sales employees through their career. Trenton did not hold back in today’s episode as he graciously shared his wisdom on the good, the bad, and the ugly when it comes to tough sales conversations. He has been around the block and we appreciated him sharing so openly.

Trenton Truitt is the Chief Sales Officer at Apollo GraphQL based in San Francisco. He has over 20 years of experience across all aspects of sales, and especially enjoys coaching and teaching folks who are up-and-coming in their sales careers. Prior to Apollo GraphQL, Trenton was the SVP of Sales at Wizeline and prior was the VP of Worldwide Sales at PagerDuty. Prior to PagerDuty he was SVP of Worldwide Sales at Appcelerator, and Regional VP of the Informational Intelligence group at EMC. He started his career as an Account Manager at Parametric Technology Corporation. Trenton graduated from California Maritime Academy with a degree in Business Administration. Outside of his professional life Trenton is Heavybit’s Sales Faculty Chair where he spend his days coaching and advising the next generation of revenue leaders.

In this episode, we covered a wide range of tricky conversations that we all have to have in sales. We started our chat by discussing how to pick the right job in sales, and some of the questions to ask or consider when interviewing. They’re not always easy, but they are necessary. Trenton took us through his own journey in why he chose to work at Apollo GraphQL. We also spent some time on his PagerDuty, Wizeline, and EMC experiences. We then dug in to topics like discussing performance issues with reps, coaching them through challenges they face, and how to have tough sales conversations when dealing with firing someone. We headed even deeper into this topic and discussed working amicably with your board members and founders to set realistic sales numbers. We talked about how reps can own their sales metrics and destiny while discussing their own challenging numbers with managers too. No topic was off the table for this session, as we also delved into establishing a culture of sales ethics and integrity, how sales reps can achieve work-life balance, and build a healthy mindset while trekking through the rigors of carrying a quota. Today’s episode was packed with wisdom, great one-liners, and memorable advice, and we hope you enjoy it!

If you liked “How To Have Tough Sales Conversations” and want to read more content from the Bowery Capital Team, check out other relevant posts from the Bowery Capital Blog. If you haven’t already, subscribe to the podcast to get all our new content each week!