Episode 154: Breaking the Boardroom Barrier with Tommy Richardson, Chief Product and Technology Officer at Litmos

In this episode of Product Thinking, Tommy Richardson, Chief Product and Technology Officer at Litmos, joins Melissa Perri to unveil what it’s like to move from an operating role as a C-Suite executive to a board role and how to position yourself to work with Private Equity and VC firms.

With a rich background spanning more than two decades in executive and general management roles, Tommy has developed a passion for fostering value creation in customer satisfaction, employee engagement, and investor returns. His professional history includes key experience in 3 Fortune 500 companies, 3 private equity-backed firms, and 2 startups.

A key highlight of Tommy's career has been his active involvement in the strategic aspects of corporate growth, especially in M&As. Moreover, he facilitated five successful companies and has played an important role in over 25 major deals. Some of Tommy's previous roles include Chief Technology Officer at FinThrive, President, CPO, and CTO at BARBRI Global, and Operating Partner at Francisco Partners.

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You’ll hear them talk about:

[08:17] - While private equity businesses (PEs) are frequently portrayed negatively in the media, many, especially in the software and technology sector, are mainly focused on business growth and expansion. This approach contrasts with VC companies, which may focus on early-stage or high-growth ventures. Leaders navigating a transition to PE ownership have to embrace the opportunity with optimism, prepare innovative ideas, and communicate in terms that resonate with the investment-focused mindset of PE businesses.
[17:59] - Regardless of the role you currently have, stepping out of your comfort zone to seek knowledge and mentorship from other leaders within your organization is essential for career advancement. Remember, most leaders, including CFOs and CEOs, were once in earlier stages of their careers and likely received guidance along their path. Moreover, leaders are generally supportive, especially when someone shows a readiness to take on more responsibilities. Another key ingredient is the need to be prepared and delivered when given an opportunity. Last but not least, use modern tools and techs to gain basic knowledge in sales, management, and forecasting before approaching leaders.
[22:32] - Thriving as an executive requires three critical skills: communication, practice, and expertise. Effective communication bridges the gap between technical language and investor-savvy dialogue, allowing leaders to articulate strategies and mission-driven work in a way that resonates with diverse audiences. Alongside communication, having meaningful expertise is essential. This involves a deep understanding of the subject matter, ensuring credibility and the ability to engage in meaningful discussions about complex topics like AI or software development.
[40:37] - For executives aspiring to join a board or work with a private equity business, you must achieve multiple successes in your career, as success is relatively rare in the business world and tends to attract attention. Be open about career ambitions with colleagues and networks, as this can lead to unexpected opportunities through connection. However, career advancements might not happen as quickly as you might hope. That's where patience comes into play.

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Previous guests include: Shruti Patel of US Bank, Steve Wilson of Contrast Security, Bethany Lyons of KAWA Analytics, Tanya Johnson Chief Product Officer at Auror, Tom Eisenmann of Harvard Business School, Stephanie Leue of Doodle, Jason Fried of 37signals, Hubert Palan of Productboard, Blake Samic of Stripe and Uber, Quincy Hunte of Amazon Web Services

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