In this SaaS Buyers' Club Episode 25, your hosts, Software as a Service (SaaS) mergers and acquisitions (M&A) lawyers Omeed Tabiei and Joe Prencipe from Optimist Legal interview Sharon Gillenwater, founder of Boardroom Insiders, as she candidly shares her journey from the inception of a unique SaaS platform to its strategic $25 million sale. 

In this revealing episode, listeners will gain unparalleled insights into the crucial strategies, challenges, and decision-making processes essential for successful business growth and an eventual lucrative exit. 

Key focuses include the importance of due diligence, the differences between strategic buyers and private equity, selecting the right M&A banker, and the navigation through the emotional highs and lows of selling a business. 

Sharon also delves into the significant impact of COVID-19 on the deal, the empowerment of her team, and her post-sale transition into consulting and supporting new entrepreneurs. This episode is an invaluable guide for aspiring and current entrepreneurs looking for practical advice and inspiration for executing a successful exit strategy and embarking on new ventures.

 Tune in to learn how to navigate the complexities of the M&A landscape and harness the power of strategic decision-making for business success.

00:19 From Journalism to Tech Entrepreneur: Sharon's Journey
02:03 The Birth and Evolution of Boardroom Insiders
03:00 Navigating the Dotcom Crash and Pivoting to Success
06:25 Mastering C-Level Sales: A New Approach
08:43 The Game-Changing Software That Sold the Business
20:17 The Art of Cold Calling and Finding the Right Partners
21:54 Reflecting on Introversion and Entrepreneurial Success
28:43 The Sale of Boardroom Insiders: A Deep Dive
31:30 Leveraging Investigative Journalism in Business
38:50 The Vision of Training Consultants
39:48 The Business Journey and COVID-19 Adaptation
40:16 Diving Deep into the Deal Details
42:01 The Hiring of a VP of Operations
44:14 The Unexpected Offer and Seeking Advice
45:44 The Search for the Right M&A Banker
48:53 Setting the Sale Price and Negotiating the Deal
53:40 The Strategic Buyer and the Perfect Fit
01:07:00 Closing the Deal Amid Challenges
01:12:25 Navigating Last-Minute Challenges in Business Deals
01:12:48 The Emotional Rollercoaster of Informing Employees
01:13:52 The Surprising Outcome of Phantom Equity Agreements
01:14:33 Reflections on Gender Dynamics in M&A
01:15:33 The Power of Little Moments in Business Transactions
01:18:07 Embracing the Future After a Successful Exit
01:40:36 Exploring New Paths: Advisory Roles and Equity

#EntrepreneurJourney #StartupSuccess #TechStartupTips #WomenInTechnology #SiliconValleyStartups
#SaaSInnovations #ExitStrategyAdvice #StartupFunding #BusinessGrowthStrategies #StartupMentorship

Follow the Guest: Sharon Gillenwater

► https://www.linkedin.com/in/sharonkgillenwater/

Follow the Host: Omeed Tabiei 

► https://www.linkedin.com/in/Omeed-Tabiei

► https://www.facebook.com/omeedt

►https://www.instagram.com/saasbizlawyer

Follow the Co-Host: Joe Prencipe

► https://www.linkedin.com/in/joeprencipe

How to reach Optimist Legal about your SaaS M&A transaction to explore working with us

► https://www.optimistlegal.com

►Omeed@OptimistLegal.com

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About Optimist Legal:

Optimist Legal is a SaaS corporate and business focused law firm with extensive experience in M&A. When you work with Optimist Legal for your next SaaS M&A transaction, you can rest assured that you're working with diligent experts that are going to get you the best deal possible.