GTM 92: Unlocking $100M+ Deals, Winning in Enterprise and Chasing Customers Not Competitors with Eric Gilpin

Eric Gilpin is Chief Revenue Officer of G2, the world’s largest and most trusted software marketplace. In this role he oversees all aspects of G2’s revenue generation, including global sales and customer success, enablement, partnerships, and revenue operations. An experienced leader with 20+ years of experience building and scaling large technology businesses, Eric joined G2 from Upwork, where he oversaw a global team of 400+ and helped lead the company to a successful IPO in 2018 (NASDAQ:UPWK) where the business scaled to north of $600 million in annual revenue in 2022 while serving 50% of the Fortune 500. Prior to his tenure at Upwork, Eric held a number of leadership roles at CareerBuilder, most recently as President of Vertical Sales. Eric also serves as a limited partner at the GTMfund investor network as well as an advisory board member at Sales Assembly. He’s been recognized as one of the Industry’s top “40 under 40” by Staffing Industry Analysts in both 2017 and 2018 and as a Top 100 Global Sales Leaders in 2020 by The Modern Sale. Based in Chicago, Eric has a Masters of Business Administration from Southern Methodist University’s Cox School of Business.

Discussed in this Episode:

  • Strategies for earning the right to sell to enterprise customers
  • How to align product, marketing and sales to deliver customer outcomes
  • The importance of focus and ruthless prioritization in scaling a business
  • Tactics for engaging C-level executives to cut through the noise
  • Lessons learned from losing big deals and how to increase win rates
  • Why being effective matters more than just being efficient in revenue orgs
  • How to develop business acumen in BDRs and SDRs to set them up for success


4:15 – Eric’s lengthy tenures at CareerBuilder and Upwork.

6:31 – Upwork’s challenge of the status quo in hiring contract talent.

9:40 – How Eric chooses the right companies to work for.

14:09 – Challenges Upwork faced in breaking into the enterprise.

17:53 – An enterprise strategy is a company strategy, not just a sales strategy.

22:37 – How Eric coaches reps when pursuing sexy logos the company may not be ready for.

25:48 – Deep diving into a $13M enterprise deal at CareerBuilder that led to $100M more.

31:55 – Leadership lessons from managing a 400+ person team.

34:33 – Aligning multiple go-to-market motions across market segments.

37:00 – Listener question: Advice for improving enterprise win rates.

41:28 – One thing revenue leaders believe to be true that Eric thinks is bull$***.

46:18 – One thing that is working for Eric in go-to-market right now.

Guest Speaker Links (Eric Gilpin):

Host Speaker Links (Scott Barker):


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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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