Resetting goals: realistic exit strategy

Shailesh Hegde is the CEO of Hubilo, a Bangalore-based webinar software company that initially started during COVID as virtual events tech and raised $150M in VC funding before the market shifted. Originally joining as head of product, he stepped into the CEO role during a chaotic downturn and led the company through a full strategic reset after returning all the remaining capital to investors.

When the virtual events boom collapsed, Shailesh and the team rebuilt Hubilo into a mid-market webinar platform serving B2B marketing teams. They shifted from large in-person event organizers to marketers running frequent webinars, emphasizing differentiated AI-driven content repurposing. Hubilo stabilized revenue, rebuilt its GTM motion, and reached a 50/50 split between new webinar revenue and legacy customers.

Earlier this year, Hubilo was acquired by BrandLive, a U.S. enterprise video platform seeking a complementary webinar product. About 80% of Hubilo's team moved over, and Shailesh now leads product integration and customer continuity during the transition. He shares hard lessons on pivots, returning capital, leading through uncertainty, and executing a practical exit when the original VC-scale vision is no longer realistic.

Key Takeaways

• Refounder Mindset – Shailesh stepped into the CEO role and reframed the mission from hypergrowth to survival, focus, and a practical exit.
• New ICP Reality – Moving from event organizers to B2B marketers required a complete repositioning and GTM rebuild that took longer than expected.
• AI as Differentiator – Hubilo used AI-generated content and repurposing tools to stand out in a crowded webinar category with entrenched incumbents.
• Practical GTM – LinkedIn thought leadership, SEO content, and product-led demos outperformed outbound or expensive Google ads in this competitive space.
• Strategic Fit Wins – BrandLive acquired Hubilo for complementary capabilities, product acceleration, and access to a strong India-based engineering team.

Quote from Shailesh Hegde, CEO of Hubilo

"Now that I just sold our company, I'm thinking about what's next for me. It comes down to, Will I be able to find a viable problem that people are willing to pay for and will I be able to use sort of all of this experience that I have in order to solve it really well and kick off a company off the ground?

"Now is probably the best time to start a company where there's so much action, there's so much happening in AI, and it's super exciting to be in this space. It's also a great time to not have like revenue pressure on your shoulders and just think out loud, have open conversations and just be free, before you really dive in and choose a focus.

"The same types of business pressures will come back as you start a company. But now is a great time to just help with transition, make sure the team is good, but at the same time, start thinking about the types of problems I want to solve in the future with a new startup."

Links

• Shailesh Hegde on LinkedIn
• Hubilo on LinkedIn
• Hubilo website
• Brandlive website

This podcast is sponsored by Fraction. Fraction gives you access to senior US-based engineers and CTOs — without full-time costs or hiring risks. Get 10 to 30 hours per week from vetted and experienced US-based talent.

Find your next fractional senior engineer or CTO at fraction.work. You can start with a one-week, risk-free trial to test it out.

The Practical Founders Podcast

Tune into the Practical Founders Podcast for weekly in-depth interviews with founders who have built valuable software companies without big funding. Subscribe to the Practical Founders Podcast using your favorite podcast app or view on our YouTube channel.

Get the weekly Practical Founders newsletter and podcast updates at practicalfounders.com.

Practical Founders CEO Peer Groups

Be part of a committed and confidential group of practical founders creating valuable software companies without big VC funding. A Practical Founders Peer Group is a committed and confidential group of founders/CEOs who want to help you succeed on your terms. Each Practical Founders Peer Group is personally curated and moderated by Greg Head.