Stephen Clifford (Cliff), Managing Director of East Coast Client Partnerships at Infillion, thinks a lot of sales professionals spend too much time behind a screen — and not enough of it getting in front of their clients.
Cliff shares how creative outreach (like a game of pickleball) and empathy-driven approaches can help sellers connect with even the toughest decision-makers. He also discusses the importance of asking tough questions, managing rejection, and balancing healthy paranoia, grace, and humility in a high-stakes career.
Tune in for practical advice and powerful anecdotes from a sales veteran who knows how to turn connections into long-term partnerships.
Join us as we discuss:
[4:00] Building a long-term relationship by getting whipped in pickleball
[14:37] How being too nice can backfire in sales meetings
[19:24] Approaching sales relationships with a pizza delivery mindset
[26:40] Why Cliff does hard activities to make sales feel easier
Check out these resources we mentioned during the podcast:
For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player.
Hosted by Ausha. See ausha.co/privacy-policy for more information.
Popular Podcasts
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
New Heights with Jason & Travis Kelce
Football’s funniest family duo — Jason Kelce of the Philadelphia Eagles and Travis Kelce of the Kansas City Chiefs — team up to provide next-level access to life in the league as it unfolds. The two brothers and Super Bowl champions drop weekly insights about the weekly slate of games and share their INSIDE perspectives on trending NFL news and sports headlines. They also endlessly rag on each other as brothers do, chat the latest in pop culture and welcome some very popular and well-known friends to chat with them. Check out new episodes every Wednesday. Follow New Heights on the Wondery App, YouTube or wherever you get your podcasts. You can listen to new episodes early and ad-free, and get exclusive content on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. And join our new membership for a unique fan experience by going to the New Heights YouTube channel now!