Finding Stephen Roger: One Person’s Reinvention Story

Andrea Wight, Center for Collaborative Leadership | December 01, 2016
Finding Stephen Roger: One Person’s Reinvention Story

Image by: Andrea Wight

If you are starting to struggle while going through the steps to reinvent your life, don’t give up.

How do you create the big, fabulous life you want to lead? It is a question that merits exploration. Here is a story about one Emerging Leaders Program (ELP) alum who, after a layoff, took the time to reinvent himself and pursue a career that aligned with his passions and values.

When Stephen Roger was a fellow in the Emerging Leaders Program in 2008, he was a business consultant at First Marblehead – an organization that provides private student loan solutions for lenders, credit unions, and schools. At the time, First Marblehead, which had formerly been in a high growth phase, going from 20 to 1000+ people in 8 years, was just beginning to feel the impact of the economic slowdown. By 2012, First Marblehead had shrunk to just over 100 people and continued to reduce its workforce. After spending 10 years moving up the ladder, from customer service to director of product and program management, Roger was let go.

As with any layoff, it is devastating, but Roger knew it was a great opportunity to do something different so he avoided the obvious route of taking a job at another financial services company for the sake of having a job.

“I realized I needed to be comfortable with my career and roles being fluid; if I wanted not just a job but a calling, I needed to apply my learnings from ELP and Babson, and to take risks.”

And he did just that. He took the time to reflect on what he really wanted to do. The key deciding factor was finding an organization that aligned with his values. He recalls hearing from Emerging Leaders Program Path to Leadership speaker Bob Glassman who founded Wainwright Bank.

“He was genuine and Wainwright Bank’s approach to business reflected their values – support the community, support the underserved – Bob clearly demonstrated his passion and commitment to social justice and explained how staying true to that helped Wainwright succeed in a competitive market.”

That resonated with Roger, so when the opportunity presented itself, he kept the lessons he learned from Glassman and searched out jobs that aligned with his values – Intrepid’s core values of Transparency, People, Self-Assessment and Always Add Value (to any person or company you interact with) do just that.

When asked about how he made the jump from financial services to technology startup, Roger notes that most of it was networking and building relationships. He credits ELP alumna Diane Darling. During his time in the program, he had the opportunity to hear her present on her subject matter expertise – networking.

Without the session, Roger says, “I would not be where I am now. It gave me the confidence and the skills to approach a gentleman who I heard speak at an event.” That person later became his boss at Intrepid. “I was really inspired by what I heard and I kept in touch with him over the years. When my job search began, I reached out to him for advice…and he ended up recruiting me into a company which perfectly reflects my values.”

Intrepid is a startup with expertise in creating digital products, particularly native mobile apps. In the wide-open space that is his office area, it is common to see groups of people huddled in the lounge, kitchen or around a whiteboard working, talking and eating together. Roger indicates that this is encouraged. Eating alone at your desk while working is not seen as productive, as a consultancy, sharing information and building relationships with coworkers makes the company stronger.

“People don’t hire us to have four developers, two designers, one project manager and one product strategist; they hire us because they need a fully formed team with expertise in building digital products…in order to deliver that, we need to know each other’s strengths, approaches to problem solving and have enough of a relationship to push back on things and vigorously debate the best approach without creating negative tension or resentment.”

Another plus, according to Roger, is that at Intrepid, “Being genuine is an asset. I can be who I am. I interact with clients like they are people, not sales targets. I can give them advice like I would to a friend.”   

Reinvention wasn’t easy. In fact, he did take one job that wasn’t a good fit, but it was a technology start up, so Roger acknowledges this move was a way to cut his teeth and learn about app development and the business of building and growing a digital agency.

His advice, “if you are starting to struggle while going through the steps to reinvent your life, don’t give up. If it worked for me, it can work for anybody.”

If you’d like to chat about mobile apps, digital product development or changing careers, feel free to drop Stephen a line at

A side note on Paying it Forward (the ELP Fundraising Campaign)

After the Emerging Leaders Program, Roger joined the Alumni Board. For a while, he was the development chair that raised money for the ELP Pay it Forward Campaign. Pay it Forward provides financial assistance to ELP fellows from the nonprofit sector – ensuring the valuable cross-sector networking component of the program.

When asked about why he consistently donates to Pay it Forward, he states, “On the day after the election, I saw a group of women colleagues who were all very upset about the outcome. I thought to myself, ‘I know these women…they are badasses. They will change the world.’ To me, that is what the ELP is – a group of badasses who are trained to work together to change things for the better. By donating to Pay it Forward, I am funding the future – these are the people who make me optimistic about the years ahead.”

Tags: alignment , leadership , reinvention , resilience , values

Comment on this story

Comments (2)

Posted by Linda Rossetti | December 08, 2016 - 10:16 a.m.

Great piece!  Thank you for sharing your story.

Posted by Kim | December 01, 2016 - 6:56 p.m.

Great story. Thanks for sharing.