Sales & Startups: Jessica Cunningham’s Path to Bloomberg

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Jessica Cunningham, Director of Business Development at Bloomberg Second Measure, is building out the leading provider of data analytics.

After spending over a decade as a sales leader at startups and large corporations, Jessica joined Second Measure. Recently acquired by Bloomberg, Second Measure analyzes billions of credit card transactions to provide valuable insights into company performance and consumer behavior.

We asked Jessica about the lessons she’s learned throughout her journey and the advice she has for others looking to join the startup world.


Q: What, in the earlier parts of your career, best prepared you for this particular role? 

A: Way before I was in sales, I embarked on a career in acting. Let’s just say I got very accustomed to rejection and not taking it personally. I think this is an essential trait to be successful in sales and particularly at a startup.

Q: What was the best piece of advice you received before joining the startup world? 

A: “Get comfortable being uncomfortable” was one of the best pieces of advice I received when I entered the startup world. Things change moment to moment in startups and you have to adjust accordingly. There’s often no playbook to follow; you’re creating the playbook as you go along. To me, that’s the fun part.

Q: Looking back, is there anything that you would change or do differently within your career journey? 

A: I would have spent a lot less time second-guessing decisions, fixating on mistakes, and worrying about how other people perceive me. It’s something I’m still working on, but luckily, the older I get, the more I realize that most people are focused on themselves, so no one is paying attention to my mistakes.

Q: What do you most look forward to every day? 

A: Knowing that I will learn something new every single day and that no two days at work will be the same. 

Q: Which books, podcasts, educational programs, or other resources have been most helpful to you? 

A: I have a bit of a podcast obsession, so I won’t name them all. Some of my favorites are Pivot, a16z, Ten Percent Happier, How to Be Awesome at Your Job, and HBR’s Women at Work. I’ve also recently been immersing myself in Bloomberg’s content, resource, and training library (called Bloomberg University) since their acquisition of Second Measure late last year. There’s no end to the amount of in-depth educational opportunities they have across all facets of a business, whether that’s data, technology, leadership training, financial markets, personal growth, etc. I could spend days in that library.

Q: What advice would you give someone starting out on the journey you’re on? 

A: Don’t get hung up on needing your career to be linear. The best careers, in my opinion, zigzag. I’ve gone back and forth in roles, from being an individual sales contributor to leading a sales team and back, and from working at big companies to startups and back. If you only focus on one path and one way of doing things, you’ll likely miss out on many great opportunities and experiences along the way.


Jessica Cunningham is a member of Dreamers & Doers, a private collective that amplifies the entrepreneurial pursuits of extraordinary women and non-binary individuals through thought leadership opportunities, authentic connection, and access. Learn more about Dreamers & Doers and subscribe to their monthly The Digest for top entrepreneurial and career resources.