Jen Randall on Pivoting, Scaling, and the Importance of Culture and Mentorship

[caption id="attachment_64880" align="alignright" width="300"]Jen Randall - Maestro Jen Randall - Maestro[/caption]

Participating in Google’s 40Forward initiative to support women in tech, Startup Grind Kalamazoo had the honor of hosting Jen Randall, Co-Founder and CEO of Maestro; an Inc 5000 mobile app development company. Jen spent an evening with us sharing her story, and answering the audience's questions.

As a former middle school math teacher, Jen joined Josh Little who was founding Maestro as an e-learning company from a room over his garage in Michigan. Jen started working with Josh from her basement in South Carolina. As the company grew they consolidated in Kalamazoo and eventually took a different path toward a new opportunity in building mobile applications.

They initially started by targeting medical technology companies, such as Zimmer, Stryker, and Johnson & Johnson. Jen chose to focus on this industry at the beginning because of her previous sales career in the medical technology space. The company later grew its portfolio to more than 75 companies, including Facebook, Twitter, and Netfilx.

Maestro’s pivot into a new industry was a bittersweet decision, as the company had to let talented Maestronauts go. Although it was a hard decision to make, the Maestro team helped those let go find jobs by writing recommendation letters, reviewing their resumes, and more. This situation represented a great example of the strong net community and culture at Maestro; a culture represented by passion, collaboration, humility, honesty, and excellence.

The growth of the company also had an interesting effect on the CEO’s role. From being the heroic ambassador who would make sales and bring new projects to the company’s weekly meetings, Jen took on the role of the visionary how would lead the company and ensure its success.

Jen highlighted the importance of mentorship, and how she is still surrounding herself with great mentors. This is a remarkable note that young entrepreneurs should take into consideration in starting and building their own companies.

As a business leader in the Kalamazoo community, Jen continues to contribute through fostering the startup ecosystem. She provides mentorship to local entrepreneurs, participated in judging panels such as WMU Pitch and WMU’s Business Accelerator, Starting Gate, and welcomes events to be hosted at her company’s office space, such as Startup Grind, Pitch Zoo, and The National Day of Civic Hacking.

In summary, here are the lessons learned from Jen:


  • If you can pivot your business to take advantage of new and bigger opportunity, do it.

  • Start by focusing on a customer segment (industry) you are comfortable with, and then scale your business.

  • Founders should be ready to let go some of the responsibilities as companies grow, and take on different responsibilities to lead the company to success.

  • Seek mentorship and other resources for self-improvement, such as books, talented people (including employees), and local events and organizations.

  • Give back by helping other individuals and the community.