From Tennis Professional to Tech Executive: Career Transition Insights

Currently, I hold the position of Chief Product Officer at Planview, an advanced AI-driven portfolio management platform. Planview enables teams to optimize their workflow by providing clarity on ongoing tasks, responsibilities, and the interconnections of their work.

My journey as CPO began in June 2021, following 13 years as the Senior Vice President of Product Management and Solutions Marketing at the company.

Prior to my immersion in the tech industry, I dedicated 11 years of my life to being a professional tennis player.

Competing in all four Grand Slam events was a highlight of my career. In 1983, I secured a third-place finish at Wimbledon, achieving a global ranking of 60. Throughout my career, I trained with some of the sport's legendary figures and earned substantial prize money.

Despite the glory, my career was not without its hurdles, such as suffering consecutive ACL injuries, which pushed me into nearly two years of recovery.

With over a decade of rigorous training and competition, the time came to explore new avenues. Though hard to pinpoint, I felt an internal push toward change.

My competitive nature saw an exciting challenge in the tech domain, which allowed me to leverage skills from tennis—strategic vision, planning, adaptability, and a drive for continuous improvement. The sector's rapid innovation and problem-solving potential caught my attention.

After retiring my tennis racket, I returned to academia and completed my MBA at 34. A recommendation from Billie Jean King paved the way for my initial role in tech—a product marketing internship at a startup.

Adapting to a corporate setting required significant adjustment, particularly relinquishing personal control over my schedule. Although dedication and learning came naturally, acclimating to lower hierarchy levels and external time management was challenging.

My entry into tech came relatively late in professional contexts, akin to my late start in tennis—a factor that never hindered my progress.

Upon joining Planview in 2008, I was part of a small company with a single product line where I could contribute to their emerging product management sector.

As Planview expanded, my role evolved from tactical positions to strategic leadership. Today, our company offers a wider range of products with an evolved value proposition, resulting in more frequent engagements in C-suite discussions.

Much like a 'chief cheerleader,' I believe in motivating teams to align with our collective vision. My role involves energizing participants during interactions, ensuring they are enthusiastic about the mission.

My daily schedule includes high-level strategic meetings, product roadmap reviews, and interactions with clients, delivered both in-person and virtually. These engagements aim to steer the company towards its goals.

I've learned to protect my time more as I advanced in my career. Long workdays are not my preference, nor do I encourage my teams to adopt such excessive work hours.

We emphasize flexibility in work schedules at Planview to support work-life balance, a crucial aspect to prevent burnout and enhance productivity and innovation. I strive to exemplify this balance as a leader.

For those contemplating a late-career transition, do not be deterred by the magnitude of the leap. Businesses value age-diverse teams; older professionals bring historical insight, while younger colleagues contribute fresh perspectives and ideas.

Approach your career transition incrementally, in ways that resonate with you. This might include internships, contracting roles, joining relevant professional networks, or finding a mentor, as Billie Jean King did for me.

Focus on your transferable skills over past job titles. Diverse experiences can bring value, and while specific technical knowledge can be learned, core competencies like interpersonal skills, time management, communication, and teamwork are essential and harder to teach.

The lessons from tennis, such as risk management, strategic thinking, and resilience, are assets I utilize daily in the business environment. These soft skills can distinguish you, particularly in leadership roles.