About Sandra

Sandra Richardson Bio

I’m a serial entrepreneur and from the tech world. I love the pace of technology and the continuous learning. If you are intrigued about how I got to where I am today, I invite you to read on and learn more about Sandra Richardson.

After receiving my bachelors degree in International Relations, I went to work for several national law firms. I worked in human resources – talent acquisition, retention and people management. This led me to automation as I implemented enterprise HRIS systems. What I learned was the power of software to automate manual processes and also how HRIS systems and enterprise software are the guts of an organization – connected to everything.

I was hired by one of the top HRIS system implementers to manage their post acquisition HR M&A integration. What I learned during this was the after-effect of acquisitions and the importance of integration workstreams and management. Of course, the entrepreneurial bug had me hooked.

I married an amazing and brilliant technology leader and we opened our software company two months after being married. With a contract on the Year 2000 Census, we were off and running. I was excited to use my talent acquisition and operations skills to start building the infrastructure for our tech company, while we together built the culture and acquired funding. After 17 years in business and 5 times on the INC. 500/5000, we knew it was time to move on. We went from the first two in our industry to 250 competitors during that time. What I learned is that you have to keep your eye on the market evolution and stay ahead. Also, it’s really hard to compete with free software.

I started my freelance business and began consulting with startups and venture-funded companies in the San Francisco Bay Area. I worked with my clients on developing strategy, business plans, people management, process refinement and I helped several clients obtain funding. Shortly after starting on this track, I obtained a contract with Align Business Advisory Services, a woman-owned mergers and acquisitions firm. I helped the founder grow the company from a regional to a national brand. I also started up the technology practice in Silicon Valley and led my own deals. What I learned during this time was the gap in M&A advisory for the lower middle market. It is under served by business brokers and forgotten by investment banks. I decided to focus solely on a freelance practice integrating strategy, execution and exit. I also learned that clients want flexible M&A advisory services, so I created a business model that allows for modern, virtual delivery of a menu-based offering with commission-based, hourly and firm fixed price offerings.

I live in St. Augustine and have a passionate creative outlet with my food blog, Constrained Gourmet. My other areas of interest include being an angel investor, hobby winemaker, gardening fanatic and a dog lover.

Let’s work together!

Sassy Network

Sandra Richardson co-founded the SASSY network with esteemed, New York-based, business development colleague, Audrey Felli. SASSY is a private referral network for women deal makers to work together on making timely and strategic introductions for clients. SASSY is an invitation only network for women in M&A, venture capital, angel investing and business development. SASSY works with the leading private equity, venture capital, angel networks and strategic acquirers in the country.

Sandra Richardson Awards
  • Best Woman Run Workplace
  • Mentor of the Year; American Business Awards
  • Women in Technology Entrepreneur Leadership Award
  • Special Recognition Award for Board Leadership from Washington, D.C. Technology Council
  • Helios HR Zeus Award for HR Innovation & Employee Development
  • Judge for Stevie Awards for Women in Business
  • Nominated for the Entrepreneurial Excellence Award for Working Woman magazine
  • Named one of the Great Bosses by Washington Techway magazine
  • Rising Star Award from the Small Business Administration
  • External Role Model for the Deloitte and Touche Women’s Initiative
  • Entrepreneur Awards Final Judging Committee Chair, Stevie Awards for Women in Business, 3 years
  • PMI Distinguished Project Award
  • Hall of Fame INC. 500/5000
  • Best in Biz Most Customer Friendly Company of the Year Award
  • Stevie Award for Most Innovative Company of the Year
  • Best in Biz International Award for Enterprise Service of the Year
  • Stevie Award for Technological Innovator of the Year
  • Washingtonian “50 Great Places to Work”
  • Washington Technology Fast 50 Award
  • Winner, Emerging Business Forum
Sandra RIchardson Affiliations
  • Mindshare Alumni
  • Springboard Alumni
  • FemTech Innovation Engine
  • American Business Awards
  • Women in Technology
  • CMO Council
  • CIO Network
  • DealFlow Network
  • Women of the Vine
  • Cannabis Investors and Entrepreneurs
  • Business Transformation Management