What I Learned About Career Ambitions From 5 Industry Leaders

John Rodriguez
3 min readMar 22, 2021


Photo by Wes Hicks on Unsplash

As part of my professional development, I am in constant search of meaningful and tangible actions to take to further educate myself on where I want to take my career. Sometimes its learning a new skill (hard or soft), becoming more knowledgeable on a topic, or simply asking the leaders in your field what they have done.

I recently stumbled on an article from HBS on career roadmap that inspired my next action(Roadmap). It seemed like a simple yet effective way of informing how I map out my own career ambitions. I then started to ask peers on who would be best to interview. I decided to target VPs of Analytics/Business Intelligence in different major sport leagues based on recommendations. I also formulated out as part of this exercise my from/to statement. “From business analyst to managing a team of analysts and driving top line strategy for the business/certain business line.”

As part of my conversations, I have summarized my five main takeaways below.

A career path needs to be self-initiated and you need to be flexible in planning it out.

Each leader I spoke to got to their position by seizing unique opportunities and gaining exposure to different industries and positions. Many did not have plans to be in the sports industry. Career changes were accelerated by MBAs and a few took positions that were offered to them out of the blue through their own network. Life is unexpected and your career path can be too.

The generalist makes a higher quality leader than the specialist.

Each leader started in a different industry and has leveraged their previous experience to apply what they learned to their current role. The ability to again adapt and develop transferable skillsets.

Areas of opportunity often include finding the needs of the organization and delivering solutions.

Leveraging your skillset and knowledge of the organization to spot where the next big opportunity is can often lead to career advancement.

Collaboration and cross functional projects can sometimes unlock new potential, for you and your organization.

The leaders I spoke to each mentioned how devoted time for collaborative projects and working across business lines was essential to maximize one’s career.

Soft skills are equally or more important to develop than hard skills.

While each encouraged to continue to develop well rounded technical skills while I still could, what separates the highest quality strategy & analytics leaders are the soft skills. Effective communication, being self aware, amplifying and enabling others under you to excel, and making things easier for others go a far way.

In addition to these takeaways, I have pivoted my short term next steps from courses in AI and Python to reading on negotiation and design thinking.

My conversations were specific to industry leaders in my field: sports business intelligence. However, I believe anyone can take a similar approach in their field. Select five in your industry that you look up to or that others recommend and ask them selective questions on their career roadmap and gain invaluable insights along the way.



John Rodriguez

Data and business strategist who enjoys writing on technology, innovation, and strategy. Lifelong learning through books, thought leaders, and experience.