Stop Running Mad Libs: What the Top 10% of Outbound Teams Do Differently

Stop Running Mad Libs: What the Top 10% of Outbound Teams Do Differently

From Go To Masters Show by Conversations with GTM experts by Everstage

May 30, 2026 · 27 min · Season 3 · Episode 82

About this episode

Kris Rudeegraap discusses the differences between high-performing outbound teams and others, focusing on personalization and the evolving BDR role.

Kris Rudeegraap co-founded Sendoso after a decade in software sales, when he watched email go from effective to noise and started looking for a better way to build relationships with prospects. Today Sendoso is the leading direct mail and gifting automation platform, and Kris has spent years watching what separates high-performing outbound teams from everyone else. On this episode of GoToMasters, he and host Mike Groeneveld get into the "Mad Libs problem" — why 75% of teams are still running templated sequences that look identical — and what the top 10% are doing with AI and multi-channel to fix it. They also cover how the BDR role is splitting into two distinct profiles in 2026, what it takes for AEs to win longer enterprise sales cycles, and why personalization is what determines whether a direct mail gift lands or backfires.

People in this episode

Host: Mike Groeneveld

Guest: Kris Rudeegraap

Topics covered

  • outbound sales
  • AI in sales
  • personalization
  • direct mail
  • sales strategies
  • BDR roles

Keywords

  • outbound teams
  • sales cycles
  • templated sequences
  • relationship building
  • direct mail automation

Mentioned in this episode

Organizations: Sendoso

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