Randy Wootton is a SaaS executive, board member, and advisor with over two decades of experience leading high-growth companies through strategic inflection points and technology shifts.
Most recently, Randy was brought in as CEO of Maxio (a billing, RevRec, and reporting platform) to lead the merger of SaaSOptics and Chargify. Earlier, he led RocketFuel (NASDAQ: FUEL), one of the first AI-driven marketplaces, and Percolate (a Content Orchestration Platform acquired by Seismic), where he drove successful turnarounds and exits.
Randy currently serves on the board of Opal, a content strategy platform, and has been advising CEOs on growth, go-to-market, and AI adoption. Specifically, he helps SaaS companies develop and operationalize AI and data strategies, leveraging his experience leading both first-generation AI companies and advising today’s AI-first & Agentic-AI innovators.
Professional Highlights:
- As CEO of Maxio, led the integration of two companies, rebranded the business, and expanded its leadership in financial operations for over 2,200 B2B SaaS customers.
- As Chief Strategy Officer at Seismic, deployed $300M in capital across two acquisitions and a strategic investment.
- At Microsoft and Salesforce, helped deliver triple-digit growth by focusing on customer-centric innovation.
- Co-founder of Vetforce.org (now Salesforce Military), which had a mission to train and employ 10,000+ veterans. He is also a long-time advisor to Rally Point Networks, dedicated to preventing veteran suicides.
Randy was recently selected to join First Wave, a private network of Service Academy graduates fostering business and civic leadership through annual gatherings, professional development, and philanthropy.
He has also been passionate about children’s education throughout his career, serving on the boards of the YMCA (Embarcadero Branch, SF) and Boyer’s Children’s Clinic in Seattle.
Finally, when not advising founders or writing about SaaS growth and AI, Randy can be found biking, skiing, and hiking with his family in California and Idaho.