GTM 90: The GTM Playbook Under Attack and Bootstrapping a Community to Multi-Million Dollar Revenue with James Kaikis

James Kaikis currently serves as the Head of Go-To-Market and Chief Solutions Officer at TestBox, an innovative company revolutionizing the way buyers interact with product demos. Before his tenure at TestBox, James co-founded the PreSales Collective with Yuji Higashi. Under their leadership, the community became a pivotal resource in the presales domain until its successful acquisition in November 2021. James also has a rich history in solution-oriented leadership roles at prominent companies including Salesforce and Showpad.

Discussed in this Episode:

  • The power of presales in driving revenue growth and customer success
  • Strategies for scaling a community-based business from zero to millions
  • The future of B2B software demos and how TestBox is leading the charge
  • Lessons learned from a successful startup exit in just 18 months
  • Insights on go-to-market strategy, product-led growth, and customer-centricity

Highlights:

6:05 – Bootstrapping a community-based business to multi-million dollar revenue.

8:35 – Secrets behind PreSales Collective’s rapid growth and successful exit.

11:05 – Transitioning from founder to Chief Solutions Officer at TestBox.

13:35 – The future of B2B software demos and TestBox’s innovative approach.

18:35 – The untapped potential of presales in driving revenue growth.

21:05 – Balancing product-led growth with customer-centricity.

23:35 – Lessons learned from building, scaling, and exiting a successful startup.

28:35 – The importance of aligning presales, sales, and customer success.

31:05 – James’ vision for the future of presales and B2B software demos.

33:35 – Advice for entrepreneurs and revenue leaders looking to drive growth.

45:05 – One thing revenue leaders believe to be true that James thinks is bull$***.

48:09 – One thing that is working for James in go-to-market right now.

Guest Speaker Links (James Kaikis):
LinkedIn: https://www.linkedin.com/in/jameskaikis/

Host Speaker Links (Scott Barker):
LinkedIn: www.linkedin.com/in/ssbarker/
Newsletter: thegtmnewsletter.substack.com/

Sponsors:

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The GTM Podcast
Don’t miss The GTM Podcast dropping every Tuesday discussing true stories and experiences including trials and tribulations in the Go-To-Market world.

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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