Zac Bookman, Co-founder and CEO of OpenGov, shares insights from his journey of building a GovTech powerhouse acquired for $1.8 billion. He discusses the complexities of enterprise sales and pricing strategies, stressing the importance of high gross retention in SaaS businesses. Zac reveals why founders and investors often misalign and how that can impact M&A decisions. He critiques inflated valuations in venture capital and reflects on the emotional journey of selling a company, illustrating the balance between innovation and financial health.

My guest today is Zac Bookman. Zac is the Founder and CEO of OpenGov a budgeting and financial management software for local governments. Before he founded OpenGov Zac was an Advisor to U.S. Army General H.R. McMaster in Afganistan, a law clerk on the Ninth Circuit Federal Court of Appeals, and earned a Fullbright Fellowship studying corruption in the Mexican government. This conversation is one of the most unique and wide-ranging of any I've had on the show. We cover how Zac built a world-class sales organization, the power of selling momentum, and the role capital efficiency still plays in building great companies. We also dive into the details on how local government works from mayors down to school board meetings. Please enjoy my conversation with Zac Bookman.    This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out.     This episode of Founder’s Field Guide is also brought to you by NetSuite. Netsuite allows founders to centralize their payment systems, ditch old spreadsheets and Quickbook tools, and finally gain visibility and control over their financials, HR, inventory, eCommerce - all in one place, instantly. Whether you are doing a million in revenue or hundreds of millions in revenue - see why over 22,000 companies are using NetSuite today. Schedule your free product tour at https://www.netsuite.com/invest.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes (2:56) – (First question) – His career leading up to OpenGov (5:45) – Experience in Afghanistan and lessons from his time there (8:54) – Aligning a large group on a strategy (9:56) – Aligning the team at OpenGov when getting started (11:54) – Levels of government that matter and what their systems looked like when he was getting started (15:24) – Role of budget and how money flows in in government operations (18:55) – How technology can fix the bureaucracy of government (21:40) – Can technology help the public’s relationship to government (24:20) – Defining vertical SaaS products (27:02) – Picking the right products/customers to build your product well (28:33) – Their purpose when building their first product (30:23) – Building a company in a highly regulated space (32:14) – Selling in this space and lessons learned (34:04) – Building a machine to distribute enterprise software (37:03) – Getting the technical, political, and commercial processes aligned (39:40) – Staying up to date on the market and fending off your competition (42:18) – Competency within public governments (44:03) – Metrics that he uses to understand the health of OpenGov (46:07) – The importance of charging the right price for professional services (48:36) – Hardest episode in developing OpenGov (50:17) – Valid early criticisms of the company (52:34) – Advice to new entrepreneurs entering the vertical SaaS space             (54:06) – The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers (57:04) – Engineering momentum among teams (59:00) – Personal improvement as a leader (1:01:55) – The study of death and why it’s important for him (1:04:19) – What people can get spending time in the mountains (1:06:53) – Role of capital efficiency in his work (1:09:11) – Kindest thing anyone has done for him   Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag  

Jason opens the show with a brief recap of "Noodlegate" and the end of cancel culture (2:09). Then he chats with OpenGov CEO Zac Bookman for the latest installment of our Next Unicorns series (14:10) about what makes governments ineffective (25:46), preventing corruption (30:37), the challenges selling into governments (35:54), how some states like Idaho & West Virginia have made their detailed budgets public on the cloud and more!