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

Mortgage Automator co-founder Joseph Fooks joins The Closing Call to share how he and his partners bootstrapped a niche SaaS platform for private lenders into a market-leading outcome. He discusses the early pain points that inspired the product, the pivotal moment COVID created for growth, and how partnering with Kaizen Equity shaped the process, timing, and ultimate outcome of their sale.

Follow Joe Fooks

LinkedIn – https://www.linkedin.com/in/joseph-fooks-1406754a/

Mortgage Automator – https://www.mortgageautomator.com/

Key Lessons & Insights

• How firsthand industry pain points can spark SaaS innovation.

• The impact of web-based architecture during COVID on scaling.

• Identifying an ideal customer profile (AUM $20–150M) for growth.

• Why patience and market timing are critical before a sale.

• The value of transparent, strategic bankers in achieving significant SaaS multiples.

• How to filter potential buyers and create competitive tension.

• Why emotional detachment helps founders make better financial decisions.

• The role of founder–banker alignment and trust in successful exits.

Timestamps

[00:12] Origin of Mortgage Automator and early inefficiencies

[03:46] Solving lender pain points through automation

[06:05] COVID’s unexpected boost to sales and visibility

[07:45] Defining the ideal customer and scaling to enterprise

[09:09] Deciding to explore a sale and partner with Kaizen

[13:15] Market shifts, strategic patience, and pre-sale preparation

[16:16] Achieving a market-leading outcome by following Kaizen’s guidance

[17:31] Managing 25+ term sheets and vetting potential buyers

[20:47] Advice for founders selecting the right investment banker

[23:07] Reflections and gratitude post-closing

Alex Sandkuhl, former VP of Sales at InSync Healthcare Solutions, shares how he helped grow the company from $6M to $39M in revenue and $10M in EBITDA, leading to its acquisition by Qualifacts in 2021. He explains the sales engine that fueled InSync’s growth, the importance of reverse-engineering outcomes for valuation, and how customer subscription financing became a breakthrough strategy.

Follow Alex Sandkuhl
LinkedIn – https://www.linkedin.com/in/alexsandkuhl/
Keystone Growth Advisory – https://www.keystone-growth.com/

Key Lessons & Insights
• Building a scalable outbound sales model from scratch.
• The role of BDRs, lead qualifiers, and AEs in creating a sales engine.
• How TAM/SAM segmentation drove efficient market targeting.
• Instituting accountability through compensation and culture.
• Reverse-engineering valuation metrics before going to market.
• Leveraging financing strategies to fund growth without dilution.
• Positioning as both a platform sale and strategic acquisition target.
• Lessons from post-acquisition integration with Qualifacts.
• Customer subscription financing as a source of non-dilutive capital.

Timestamps
[00:00] Episode Trailer
[01:25] Early days at InSync and building outbound sales
[03:22] First BDR hires and pipeline growth
[06:44] Scaling the sales engine through segmentation
[09:14] Lead qualifiers and demand generation inflection point
[12:20] Driving accountability with comp plans and culture
[16:27] Reverse-engineering valuation and reporting hygiene
[19:33] Managing 19 bidders and positioning the company
[20:32] Efficiency gains: reducing CAC and increasing margins
[24:17] Post-acquisition integration with Qualifacts
[27:36] Advice to founders on preparing early for a sale
[30:46] Keystone Growth Advisory and building sales engines for SaaS
[32:14] Customer subscription financing explained
[35:02] Reflections on the journey and the closing call