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Lessons from the Female Titans of Wall Street: Amy Ouellette

It has been great to see more women entering finance — and more diversity across the board for that matter. My experience entering the finance industry was shaped differently from others, as I was fortunate to have the opportunity to work at smaller, family-run firms. These environments valued energy and people who wanted to learn and grow. […]


It has been great to see more women entering finance — and more diversity across the board for that matter. My experience entering the finance industry was shaped differently from others, as I was fortunate to have the opportunity to work at smaller, family-run firms. These environments valued energy and people who wanted to learn and grow. My first boss was a woman, and grew to be a close mentor. Since then, all of my bosses, both male and female, have served as mentors to me. Continued mentorship is a critical aspect of continuing and supporting the change for more diversity.

Our Betterment for Business advisory board is half male, half female. Creating diversity across leadership boards is necessary to include everyone’s voices. The women on Betterment for Business’ board are always open to sharing experiences and advice they feel can help. Finding strong people in support of your progress as an individual has been great in my travels in this industry.


I had the pleasure of interviewing Amy Ouellette, the director of retirement services at Betterment for Business, the technology-led 401(k) branch of robo-advisor Betterment. In her current role, Amy uses her extensive background and technical expertise to help shape business strategy, product build and internal processes. Prior to joining Betterment in 2015, Amy served as a principal of a national retirement services firm, managing a team of consultants. For over fifteen years, she has worked with plan sponsors on compliance issues, plan design and corrections under DOL and IRS programs. Amy is a Certified Financial Planner™, certified by the CFP Board, a Qualified Pension Administrator, awarded by the American Society of Pension Professionals and Actuaries (ASPPA) and a Certified Plan Fiduciary Advisor, awarded by the National Association of Plan Advisors (NAPA). She is a member of the IRS Subcommittee of ASPPA’s Government Affairs Committee, and previously served on the Board of the ASPPA Benefits Council of Great Northwest. Amy earned her B.S. in Economics from the Wharton School of the University of Pennsylvania.


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

Like many others in the 401(k) business, I stumbled into this field. Growing up, I thought I wanted to be an actuary. Every winter and summer break, I interned with an actuary who focused on 401(k) plans which gave me a glimpse into what 401(k) plan admin meant from the plan sponsor and compliance aspect — and overall, what it means to have a 401(k) plan and to keep one running.

Through this experience, I found that it wasn’t so much the actuarial side but the puzzle of plan admin that I found interesting. Every company looks different and figuring out how to meet various needs and keep it streamlined from an admin perspective intrigued me.

I worked at both a local firm and nationwide firm after graduation on the plan admin side which became more consultative, working closing with plan advisors. Then, I briefly stepped into a plan advisor role, providing fiduciary guidance, managing a retirement plan committee and overseeing responsibilities set by the DOL.

When Betterment called, I was already a customer for my own savings. The idea of bring that to the 401(k) arena was really exciting to me and led to my current role.

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?

My first employer had a great impact on building me into the person I am today in my career. I worked for a woman who was a small business owner and she taught me how plan admin works from the ground up, as well as what it took to run a business. Her style of teaching gave me a lot of autonomy to learn for myself. Rather than giving me the answers, she would encourage me to think for myself. By presenting this opportunity to be creative and a problem solver, my boss gave me the legs I needed to learn on my own. Beyond serving as my first boss, she was also a mentor and friend and I am lucky enough to still run into her at conferences and events to this day.

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

Across the Betterment for Business team, financial wellness is top of mind. As we look to be a holistic partner to both employees and employers, we strive to set individuals up for overall financial wellness and success. As a result, I actively stay on top of the broader range of needs — whether it be student loan repayment programs, emergency funds, etc. — to prepare for employees’ financial futures, beyond 401(k)s. The push for financial wellness looks to better prepare and help people in all life stages, as they face financial strains while also saving for years ahead.

We’re also watching regulatory changes as we’re passionate about the government increasing availability to retirement plans. There are simple designs that would be fair and reduce the levels of complexity and oversights needed. Beyond this, many companies want to offer 401(k)s but struggle with the high costs due to testing and reporting. Aware of these limiting factors and the potential for real improvement, Betterment for Business is vocal and involved with regulatory changes around retirement savings.

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

Betterment for Business is revolutionizing the 401(k), an age old product, with the goal of bringing back its original and intended goal of making saving for retirement more easily accessible. As a branch of Betterment, the leading robo advisor, Betterment for Business uses technology to deliver holistic 401(k) plans and on-demand advice to employees, at low and transparent costs.

Betterment for Business stands out as we’re truly focused on bringing employees the best options for their retirement and savings goals. We’re able to look at outside accounts and provide recommendations on an employee’s entire financial picture.

Beyond this, our offering includes automatic and on-demand features to increase employees’ participation rates in retirement savings. One of our customers, WatchGuard, began offering Betterment for Business’ 401(k) in February of 2017. By adding a more interesting userface, features like automatic enrollment and better plan design, there was a jump in participation level, employees were saving more and the risk level for investments was more in line for recommendation allocations. Specifically, there was a nearly 52% increase in the number of employees saving for retirement, an increase in the median deferral rate to 10%, and an increase from 40–91% of employees with appropriate risk levels. This highlights our work to set employees up for their best financial future after retirement.

Wall Street used to be an “all white boys club”. This has changed a lot recently. In your opinion, what caused this change? What lessons can be learned from that to support this change going forward?

It has been great to see more women entering finance — and more diversity across the board for that matter. My experience entering the finance industry was shaped differently from others, as I was fortunate to have the opportunity to work at smaller, family-run firms. These environments valued energy and people who wanted to learn and grow. My first boss was a woman, and grew to be a close mentor. Since then, all of my bosses, both male and female, have served as mentors to me. Continued mentorship is a critical aspect of continuing and supporting the change for more diversity.

Our Betterment for Business advisory board is half male, half female. Creating diversity across leadership boards is necessary to include everyone’s voices. The women on Betterment for Business’ board are always open to sharing experiences and advice they feel can help. Finding strong people in support of your progress as an individual has been great in my travels in this industry.

Can you tell us 3 top challenges that many women face when they step from a from mid-level position to a senior board?

As women become more senior, there is a more pressing need to be strategic. While everyone wants to be able to do everything, senior leaders must delegate to others on their team in order to manage bandwidth. This requires thinking about how much is on your team’s plate, giving your team support and trusting them. Beyond overcoming these challenges, senior leaders must elevate thinking and decision making to a holistic perspective and approach.

I know women who tell themselves that they will not try to take up senior executive roles because they want to prioritize being a “good mother”. In your experience, are the two really in conflict? What suggestions would you give to balance both?

While I am not a mother, I’ve seen colleagues around me work hard to find the balance between work and life outside of work. As with any part of life, it is necessary to build up a great team around you that you can trust and lean on and to learn how to prioritize.

As leaders, we can do our best to share information readily, create processes and provide guidance so others around us can step in when needed. While we often want to, no one can do everything. Sometimes, you’ll need to step away from work and lean on others.

Another aspect is being comfortable with the idea that you won’t always find the perfect balance all the time. Sometimes, being a bit off balance allows you to reset and come back with more energy. Overall, building up strong partnerships and communities both at work and in your personal life gives you the support system to succeed.

Boards are more effective when there is diversity in its members. What are 3 benefits that bank boards will see if they seek to be more inclusive of women?

As mentioned above, the inclusion of women among Betterment for Business’ advisory board is incredibly valuable. However, I think the benefits have less to do with gender and more to do with overall diversity. For example, women on the board not only represent the voices of female employees and potential employees, but also the voices of female consumers. This goes for different backgrounds too.

Additionally, diversity brings more viewpoints to the table. As everyone has had different life experiences, it allows for conversations and decisions to be informed with all of these considerations in mind

Finally, a diverse board creates a holistic environment where all opinions and experiences are heard, respected and valued. In this environment, there is an effort to make members feel comfortable speaking up, to give credit for ideas and to empower diverse thinking moving forward.This creates a domino effect on the way the board functions.

Sadly there is a gender stereotype that men are “more strategic” than women. This perception may be one of the reasons why boards have a smaller female representation. What should be done for women to position themselves as strategic leaders?

Women, and rising leaders across genders, can be effectively strategic in a few ways. First, it is important to remember that everyone you work with has a different style of learning and taking in information. You can be more effective and strategic by offering multiple forms of communication on the same information that is tailored and adjusted to the audiences in front of you. For example, some people are visual learners while others prefer written documents.

When delivering messages, strategic leaders hit on their top points early on, explain why and then dive into the other considerations. This allows points to be made while you still have your audience’s attention. And finally — the key to success — is being able to then say what you’re not doing and why that is the case. No individual or organization is able to do everything, so it is important to draw clear lines.

Which organization would you encourage a woman aspiring to be on a bank board to join?

As women encourage other women to join boards, there is a great deal of information shared in terms of the ways to accumulate experiences to make you an effective board member but also about the struggles faced. There is a willingness and desire among women to help others earn their board spots as well. Beyond this, there are several small company and non-profit efforts to put women on boards. Some resources a female board member of Betterment for Business shared with me for corporate boards are Women Serve on Boards, BoardList, Board Options Inc., 2020 Women on Boards and more. In terms of the non-profit space, she directed me to resources like Board Source and Board Match.

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

“Remember that this day will never dawn again” and “this too shall pass” often cross my mind. While there are many meanings and applications of these quotes, in my personal and work life they serve as a reminder that not only will you get through anything, but that you only get one shot. These quotes encourage me to make the most of what I’ve got, and to keep trudging through when situations are tough.

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?

I’d encourage a movement to take stock of your finances. While everyone has different goals and no one’s financial pictures look alike, making the most of your money and thinking about your lifestyle choices (paying off debt, taking out loans, etc.), gives you more freedom and flexibility to do what makes you happiest in life. Rather than feeling beholden to decisions you made years before, individuals can take hold of their financials, identify what is important, determine a balanced plan and approach and create more financial freedom for the future.

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