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

The GTM Podcast

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:

1. Brought to you by Pocus. Pocus turns data into revenue. Combine all product usage and intent signals your team needs to prioritize the best opportunities and take quick action. Pocus helps you build pipeline based on real buying signals, not your team’s best guess (whether it’s landing new logos or expanding existing ones). With Pocus, go-to-market teams at Asana, Canva, Miro, and Loom save 10+ hours a week digging through data to find and close deals with confidence. Create focus for your team with Pocus – see it in action by requesting a demo Pocus dot com slash demo.
2. Brought to you by Synch. Synch is a single platform for all of your Sales & Sales Ops tooling. From using natural language to build dashboards that will make

The GTM Podcast
Features conversations with the top 1% of tech executives, VCs, and founders - the experts 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 what worked, what didn’t, and how things actually went down.
This podcast is produced by GTMnow, the media brand of VC firm GTMfund.
Visit gtmnow.com to subscribe to the newsletter and other content resources.