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Women In Finance: “Women think asking questions is a sign of weakness when, in fact this is the best way to learn”, With Capital One’s Jennifer M. Flynn

Ask the top-of-mind question. I think there is still a stigma out there where women think asking questions is a sign of weakness when, in fact, this is the best way to learn. Approaching your career, and financial acumen, as a continuous spectrum will accelerate your learning curve. As a part of my series about strong […]

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Ask the top-of-mind question. I think there is still a stigma out there where women think asking questions is a sign of weakness when, in fact, this is the best way to learn. Approaching your career, and financial acumen, as a continuous spectrum will accelerate your learning curve.


As a part of my series about strong female finance leaders, I had the pleasure of interviewing Jennifer M. Flynn. Jenn is the business leader for Capital One Small Business Bank. She is a highly respected corporate finance executive with 20+ years of experience leading high-performing diverse teams in an inclusive environment. She joined Capital One in 2015 as the CFO for Capital One Healthcare, which was acquired from GE Capital, and played a key leadership role in the integration. She later became CFO for Capital One’s International and Small Business division before assuming her current role leading Small Business Bank in June 2018. Jenn spent 12 years in finance leadership positions at GE Capital prior to joining Capital One, and has an extensive background in finance, credit and accounting. While at GE, Jenn was named one of Working Mother Magazine’s Working Mothers of the Year. Jenn started her career at PricewaterhouseCoopers where she spent seven years in financial audit. She holds a BA in Accounting from Bryant University and is a Certified Public Accountant. She serves on the Executive Steering Committee for Capital One’s Women’s Business Resource Group in McLean. Jenn also serves on the Board of Directors for 1863 Ventures.


Thank you so much for doing this with us! Can you tell us the “backstory” about what brought you to the Banking/Finance field?

I’ve always loved math and business, which led to an accounting major in college. My plan was to follow the partner path in public accounting, and after seven years, I realized a life in client service wasn’t for me. At the time, I was looking to move to Connecticut and went to work for the best employer in the state — General Electric. My first role was with GE Capital, the financial services arm of the company. I had no previous experience in financial services; I had spent the majority of my career in the technology, entertainment and media sectors. It was definitely a learning curve but, at the end of the day, math was the common denominator — a big help! I spent 12 years at GE Capital and held 10 different positions as I progressed in the organization. I never felt like I worked in banking at GE, I felt like I worked for a financial services arm of an industrial conglomerate. It wasn’t until I joined Capital One that I realized I had become a “banker” and since then, I have truly enjoyed the path I have taken thus far in my career.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

One of the most impactful experiences of my career was a two-week trip to the Middle East. Along with 45 colleagues across GE, I was selected to participate in one of its premiere leadership programs, which provided me with the opportunity to spend two weeks in Dubai and Abu Dhabi. It was an amazing opportunity to experience another culture, quite different from the westernized cultures I have been accustomed to — especially as a woman. I engaged in business discussions with UAE government officials; networked with resilient, amazing local professional women; partnered with 45 of GE’s best and brightest on an expansion project; experienced a 7-star hotel; rode a camel in the desert under the night sky; and shopped in the spice markets. It was a once in a lifetime experience, and my biggest takeaway was gratitude. I came home feeling incredibly grateful for the experience and for the bold trailblazers that came before me in our country. The 19th Amendment had new meaning, and my respect for the women who continue to push the Women’s rights agenda forward only deepened.

Are you working on any exciting new projects now? How do you think that will help people?

I sit on the Board of Directors for 1863 Ventures, an amazing nonprofit led by an inspirational leader, Melissa Bradley. 1863 Ventures bridges entrepreneurship and racial equity to accelerate new majority entrepreneurs from high potential to high growth. I’m really excited about the work that they do and we’re exploring how we can leverage the talent and skills of Capital One Small Business Bank associates to assist a subset of these entrepreneurs who have made it past the critical 5 year mark for small business — a point where more than 50% of small businesses fail according to the SBA.

What do you think makes your company stand out? Can you share a story?

Capital One is truly invested in the communities that we serve, and we have a number of initiatives that help budding entrepreneurs start their businesses, or support business owners as they grow their companies to the next level. For example, our partnership with Future Founders supports a national residency program that helps entrepreneurs (between 18–30 years old) start and scale businesses. Danielle Tubbs, founder of Tubby’s Taste, credits Future Founders with helping her to nearly quadruple her sales and turn her side hustle of making Jamaican-American baked goods into a full-time business that does catering, corporate gifts and more. We have dozens of stories like these, and they are incredibly inspirational to me and my team.

Ok. Thank you for all that. Let’s now jump to the main core of our interview. Wall Street and Finance used to be an “all white boys club”. This has changed a lot recently. In your opinion, what caused this change?

I think people caught on to the fact that the world doesn’t look like that. Today, four out of every 10 businesses in the U.S. are now owned by women — a remarkable growing trend. Even better, the changing demographics of small businesses doesn’t just touch women. New data compiled by The Business Journals show there are more than 11 million minority-owned businesses in operation nationwide, nearly double the number 10 years ago. As the business world becomes more diverse and more leaders learn to speak up and share their ideas, people are uncovering some unique and exciting truths — namely, that diversity breeds success.

Of course, despite the progress, we still have a lot more work to do to achieve parity. According to this report in CNBC, less than 17 percent of senior positions in investment banks are held by women. In your opinion or experience, what 3 things can be done by a)individuals b)companies and/or c) society to support this movement going forward?

There are many reasons this is still the case and we all (female executives, companies and society) have the ability to elevate women further and enable more seats at the executive table in finance.

As women continue to rise to leadership positions in the business world, it is important for them to:

  1. Lean into discussions involving the financial health of their businesses and companies at which they work. Understanding the finances of a business is a huge factor to success.
  2. Build relationships. Relationship building comes naturally to many women and this superpower can pay dividends in the business world.
  3. Be aware of their own knowledge gaps and surround themselves with expert resources who can help connect the dots. Don’t be afraid to ask questions.

Companies should also focus on:

  1. Creating and fostering an inclusive and flexible work environment that attract, retain and develop talent. In other words, invest in leaders who “walk the talk.”
  2. Harnessing the power of technology to promote flexibility. With a computer, an iPhone and a strong work ethic, many jobs can be done from anywhere these days.
  3. Adopting best practices. A good place to start would be for companies to look into their benefits packages and ensure they accommodate the needs of women today. Capital One has earned spots on Best Companies for working women, executive women and for multicultural women and offers generous maternity leave packages, emergency childcare services, and financial help for those using surrogates, fostering or adopting a child.

Society should:

  1. Pay it forward — model the behaviors they want to see adopted by businesses and leaders.
  2. Embrace varying perspectives and see differences as opportunities to grow.
  3. Continue to push for gender equity and equal rights.

Let’s now turn to a slightly new topic. According to this report in Fortune, nearly two-thirds of Americans can’t pass a basic test of financial literacy. In your opinion or experience what is the cause of these unfortunate numbers? If you had the power to make a change, what 3 things would you recommend to improve these numbers?

The ability to comprehend, manage and discuss finances is critical. My recommendations to improve financial literacy include:

  1. Be aware of knowledge gaps and surround yourself with expert resources. Seek out additional information sources for investing, insuring and saving to ensure you are making sound decisions. Banks, like Capital One, are a great place to start when seeking financial counsel, and offer programs designed to educate and support consumers through all life stages.
  2. Build relationships. Seek out mentorships and the expert advice of others. This can pay dividends to your financial success.
  3. Learn your options. Take the time to compare investment opportunities, loan offers and even checking and saving account options. This is time well spent and can greatly help your financial situation.

You are a “finance insider”. If you had to advise your adult child about 5 non intuitive things one should do to become more financially literate, what would you say? Can you please give a story or example for each.

1. Ask the top-of-mind question. I think there is still a stigma out there where women think asking questions is a sign of weakness when, in fact, this is the best way to learn. Approaching your career, and financial acumen, as a continuous spectrum will accelerate your learning curve.

2. Learn by doing. I find the best way to learn is to actually do it. Raise your hand for the project with a financial flair; volunteer for the treasury roles at your child’s school; take an active role in managing your own personal finances.

3. Surround yourself with experts. Learn from those who have spent their life in the field. I find that passion can be contagious — who knows, you may end up liking finance after spending some time with a financial advisor or business banker. I always leave a discussion with our Capital One Business Bankers feeling energized and financially savvy.

4. Make small talk on the ball field or in the waiting room at dance class. So much in life is trial and error, and the same holds true for learning about personal and business finances. I learn so much from other women and their experiences — what to do and what not to do. It just takes some courage to start up the conversation.

5. Don’t underestimate the power of social media. Follow a few financial institutions and financial social influencers. There is a lot of content out there, and different content formats (podcasts, blogs) make learning easy and fun.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

It took a village, and a few people who placed a bet on me. I am incredibly grateful for the coaches, mentors, and leaders who have supported me on my journey. The biggest question I am asked is — are those coaches, mentors, and leaders women? My answer is no. As I was coming up in my career, there were very few women in leadership positions, and candidly, I couldn’t see myself in the few that existed. Fortunately, I think this is changing and every day, I meet another amazing female leader that inspires me and propels me forward. In the past, however, this was not the case. I did and still do have the opportunity to work for several amazing men during my time at Capital One, General Electric and PwC. I learned something different from each of them — whether it be technical skills; change management; inclusive leadership; strategic execution; or how to build a team, etc. I am incredibly grateful for the investment these leaders have made and continue to make in me.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

If you want to go fast, go alone. If you want to go far, go together.

This quote reminds me of the power of the village, and the potential that comes when you bring a diverse group of people together chasing the same goal. This is especially true for professional women, who often face bias and stereotypes that can make the road to success more challenging. When women are up against these challenges, having a network of allies cheering you on can make such a difference; lifting you up during challenges, building confidence and offering inspiration for the future.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

I find inspiration through movements like 1863 Ventures. This group’s mission to bridge the gap between entrepreneurship and equality not only improves the lives of the small business owners they serve but also gives hope and provides economic benefits to their communities. These kinds of movements drive me to find unique ways to further and encourage their mission — coming alongside them in whatever way I can. I make it a priority to leverage my position and influence so I can support causes that focus on the human aspect of small business ownership. When people feel cared for and heard, it opens the doors to endless possibilities for growth.

Thank you for all of these great insights!

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