GTM 102: Building Trust, Embracing Old-School Tactics, and Scaling Sales Teams with David Greenberger

David Greenberger leads CHEQ’s North America sales team. CHEQ is a cybersecurity platform primarily focused on protecting the Go-to-Market organization (preventing fake leads to sales team, skewed analytics from bots/malicious users etc). David is well-versed in building and perfecting Go-To-Market processes both from $0 and at 100 y/o companies. CHEQ is David’s 5th startup. Directly before CHEQ, David was in a leadership capacity at Hitachi Vantara, in the deep-enterprise Big Data / AI space. Prior to that he’s built teams at Foursquare, Yext, Angi and Splash. 

Discussed in this Episode:

  • The importance of trust in building effective go-to-market strategies.
  • Navigating the transition from startups to large enterprises in sales roles.
  • Strategies for hiring and developing sales talent with non-traditional backgrounds.
  • The value of long-term relationships and “compound interest” in professional growth.
  • Balancing internal and external relationships in large organizations.
  • The resurgence of old-school, in-person tactics in modern sales approaches.
  • Addressing challenges of invalid traffic and bots in digital marketing.


13:35 – Insights on managing generational differences and career development in sales teams.

22:05 – David’s experience transitioning from startups to a $90 billion organization.

25:50 – The story of a successful SDR who rapidly progressed to closing multi-million dollar deals.

37:49 – One thing revenue leaders believe to be true that David thinks is bull$***

40:04 – One thing that is working for David in go-to-market right now

Guest Speaker Links (David Greenberger):

Host Speaker Links (Scott Barker):


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The GTM Podcast
Features conversations with well-known tech executive, VC, and founders – the expert operators in the trenches who have ‘been there, done that’ to build some of the fastest-growing software companies. Every week, a guest joins Scott Barker to dissect their stories, revealing expert insights around what worked, what didn’t, and how things actually went down.

This podcast is produced by GTMnow, the media brand of VC firm GTMfund – sharing insight on go-to-market from working with hundreds of portfolio companies backed by over 350 of the best go-to-market executives.

Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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