The GTM Podcast

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


Listen Later

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 your RevOps lead jealous, to getting forecasting, pipeline management, and lead routing from a single vendor, Synch allows you to spend more time dr

The GTM Podcast
The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content.

...more
View all episodesView all episodes
Download on the App Store

The GTM PodcastBy GTMnow by GTMfund

  • 4.6
  • 4.6
  • 4.6
  • 4.6
  • 4.6

4.6

142 ratings


More shows like The GTM Podcast

View all
This Week in Startups by Jason Calacanis

This Week in Startups

1,270 Listeners

a16z Podcast by Andreessen Horowitz

a16z Podcast

1,027 Listeners

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch by Harry Stebbings

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

514 Listeners

The Official SaaStr Podcast: SaaS | Founders | Investors by SaaStr

The Official SaaStr Podcast: SaaS | Founders | Investors

173 Listeners

Founders by David Senra

Founders

1,873 Listeners

Invest Like the Best with Patrick O'Shaughnessy by Colossus | Investing & Business Podcasts

Invest Like the Best with Patrick O'Shaughnessy

2,299 Listeners

Masters of Scale by WaitWhat

Masters of Scale

3,985 Listeners

Y Combinator Startup Podcast by Y Combinator

Y Combinator Startup Podcast

213 Listeners

All-In with Chamath, Jason, Sacks & Friedberg by All-In Podcast, LLC

All-In with Chamath, Jason, Sacks & Friedberg

8,922 Listeners

30 Minutes to President's Club | No-Nonsense Sales by Armand Farrokh & Nick Cegelski

30 Minutes to President's Club | No-Nonsense Sales

389 Listeners

Grit by Kleiner Perkins

Grit

190 Listeners

The Exit Five CMO Podcast (Hosted by Dave Gerhardt) by Dave Gerhardt

The Exit Five CMO Podcast (Hosted by Dave Gerhardt)

41 Listeners

The Logan Bartlett Show by by Redpoint Ventures

The Logan Bartlett Show

187 Listeners

Revenue Builders by Force Management

Revenue Builders

147 Listeners

Lenny's Podcast: Product | Growth | Career by Lenny Rachitsky

Lenny's Podcast: Product | Growth | Career

1,332 Listeners