HubSync founder and CEO John McGowan joins The Closing Call to share how he transformed his Big Four experience into a leading SaaS platform that modernizes tax and audit workflows for accounting firms. McGowan discusses building HubSync from scratch, bootstrapping through consulting, raising $100M from Thoma Bravo, and the lessons learned while running one of the tightest growth processes in M&A.

Follow John McGowan & HubSync
LinkedIn – https://www.linkedin.com/in/jqmcgowan/
HubSync – https://hubsync.com/

Key Lessons & Insights
• How a Big Four CIO bootstrapped HubSync into a market leader
• Why mid-tier CPA firms (Top 5–200) are adopting unified platforms
• The importance of hiring a banker and running a formal process
• How to evaluate institutional investors beyond valuation
• Lessons from managing a high-velocity Series B process with 23 term sheets
• Building investor relationships before a capital raise
• How Thoma Bravo scaled HubSync post-investment through acquisition and AI integration
• Why founders should prioritize partnership fit over check size
• Building a product-led culture that turns clients into advocates
• The future of AI, automation, and e-sign capabilities in tax tech

Timestamps
[00:00] Episode Introduction
[01:30] Introduction: John McGowan and the HubSync story
[04:40] Leaving Deloitte to bootstrap HubSync and validate the mid-market opportunity
[06:23] Breaking through with Top 25 firms and market-leading retention
[07:42] Preparing for growth and the decision to raise capital
[08:41] Dating investors and learning early valuation lessons
[12:19] Deciding to hire a banker and structuring the Series B process
[15:25] Managing 23 term sheets and multiple investor tranches
[17:37] Handling diligence across tech, finance, and operations
[20:04] Learning from investor feedback on scaling strategy
[21:14] Post-transaction roadmap: acquisitions, AI, and payments integration
[25:05] Building a partner-led client culture inside HubSync
[27:41] The weekend that closed the Thoma Bravo deal
[30:12] Advice to founders raising institutional capital