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“There was a time when we automatically looked to the “men in power” to help us get recognized and promoted; Now, there is a greater sense of unity among women” with Jason Hartman & Alyssa Schaefer

Especially in the last decade, women have built strong supportive communities to address the issues that women consistently face and often keep to themselves. I personally have observed a growing spirit of women helping other women over the last 18 years in corporate America. There was a time when we automatically looked to the “men […]

Especially in the last decade, women have built strong supportive communities to address the issues that women consistently face and often keep to themselves. I personally have observed a growing spirit of women helping other women over the last 18 years in corporate America. There was a time when we automatically looked to the “men in power” to help us get recognized and promoted. Now, there is a greater sense of unity among women: more women are sponsoring deserving women to help them reach the next level, and more women are mentoring others on how to navigate tricky situations, including the “all white boys club”.


Ihad the pleasure of interviewing Alyssa Schaefer. Alyssa is the Chief Marketing Officer at Laurel Road, a national online lender providing student loan refinancing, mortgages, and personal loans. A seasoned and passionate marketer, Alyssa has over 18 years of marketing and communications experience in the financial services and travel industries. Alyssa started her marketing journey at American Express, where after a successful 13 years she joined American Express Global Business Travel as the Head of Global Marketing. With disciplined marketing experience under an established brand, Alyssa joined Laurel Road in 2017 to completely rebrand the lending business into a credible, unique fintech brand that resonates with its customer base of highly-educated and ambitious millennials.


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

Abig part of my story is that I am an identical twin and was raised in a small town in Northern Michigan. My twin is a talented jewelry designer, while I have always gravitated towards business and social sciences. For me, marketing is a beautiful mix of these two disciplines. Without any exposure to New York City growing up, I knew I wanted to live there someday and a career in marketing was my ticket! I put plans in place as early as possible to get to New York. Where I studied in college, what I studied and what internships I took were all deliberate decisions to be able to have a career in marketing in New York. Once I made these decisions, it was about where I was going to be a marketer. American Express is such a respected brand and as I learned later, a place that values and invests in its people.

I spent 13 years in various business units at American Express — from consumer to small business on the corporate side. This is where I launched my career and truly earned a marketing discipline, diving head first into all elements of marketing, from brand to direct mail, partnerships, strategy and digital — everything across the entire marketing spectrum. My transition to American Express Global Business Travel taught me how to operate on a global scale — I learned how to centralize functions for efficiency and decentralize other functions for relevancy and local flavor. Ultimately, over the course of three years, I managed a team of 50 dynamic marketers, lead them through an ownership change and a rebrand, built a B2B2C marketing platform, and launched several new products.

I have been quite blessed to learn from some of the best and brightest during the early stages of my career, and quickly understood that my curiosity and love of challenges would take me to many different industries and verticals, which is what ultimately brought me to the fintech space. I viewed applying my marketing experience to a different type of business and brand as a great challenge and opportunity. I am not always right, but in this instance, I got what I wished for! At Laurel Road, I’ve had the opportunity to build an amazing team, launch new marketing channels and engage with customers at a deeper level — helping them consolidate, refinance and better manage their debt. My experience so far has been so rewarding and there are more exciting challenges ahead.

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?

From rebranding businesses to launching new products to delivering presentations to some of the most successful people in business, I have cherished so many experiences that lead me to where I am today. But one experience — not exactly a highlight — sticks out to me. A number of years ago I was in a demanding role as the leader of a global team, and was constantly traveling to visit my team members and business partners across the world. I mostly enjoyed this, but on one trip where I was coming off of weeks of consistent travel, I visited four countries in three days, sleeping in four different hotels due to time changes. I was completely depleted and exhausted. One night, I woke up suddenly from jetlag and for a few seconds, did not know what country or what hotel I was in. It was the most terrifying feeling I’ve ever experienced! I will always remember that feeling and it became a reminder that while demanding jobs can be exciting, we are not superheroes. Rest and taking reasonable vacations with family and friends, make us more effective in demanding roles.

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

In January of 2019 Laurel Road was acquired by KeyBank, with the goal of enabling growth of Key’s digital offerings and deepening customer relationships. Now, as an integrated company, we combine KeyBank’s credibility and scale with Laurel Road’s tech-driven agility and digital lending capabilities. The acquisition and integration has been a huge priority for me for the past six months, and while we will share our technology, some products and center office operations with KeyBank, Laurel Road will remain a distinct brand and business. The initial integration has been successful, and we are now focused on working together to better support our customers on their financial journey.

At Laurel Road, we are continuously improving our user experience to provide customers with a seamless, simple and flexible experience through all of their life milestones — from paying off student debt to purchasing a home. Because all of our technology was developed and engineered in-house, we are able to make product updates quite nimbly based on customer feedback, so we’re always identifying ways to improve and getting those up and running.

Refinancing is one key way to save on student debt, but because it’s become such a heavy burden for young people, more creative ways to lower student debt are emerging. For example, progressive employers are starting to offer student loan repayment to help their employees, and this is an area we are very passionate about. We are already working with employers to offer a student loan refinancing product to their employees, including some special rates and resources. Currently, we are looking to expand this part of our business to provide more options for employers to support their employees and relieve the baggage of student debt.

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

Millennials today face the uphill battle of paying off their student debt at the same time they enter their adult lives — a time when financial freedom and ambition is top of mind. Laurel Road has been originating student loans since 2013, and today we have refinanced over $4 billion in loans. Our products stand out because they offer a truly digital experience that’s personalized for each borrower, and low rates that help our customers save over the life of their loan. I’m consistently impressed by our ever-evolving platform and proud of the positive feedback we get from customers about how we helped them achieve their financial goals. The words “easy” and “pain-free” often come up in our testimonials.

We understand that student debt is a crippling issue for many, and while we can help them save through our low rates, we also support our customer base in other ways. In 2018, we executed a sweepstakes that would land three lucky winners across the country with $25,000 towards their student loans. With the country’s student debt at $1.6 trillion, Laurel Road chose to put a positive spin on the problem, receiving 10,000 applicants to the sweepstakes. We ultimately helped several people including Heather Durbin, a licensed nurse who is raising a family in Spokane, Washington while working on her Masters at Grand Canyon University. The sweepstakes funds will help her meet her $50,000 loan debt much faster than anticipated.

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?

Women today have more opportunity and are more empowered than ever before. We don’t shy away from building their knowledge on financial matters and filling positions that were traditionally male dominated such as lawyers, doctors, bankers, etc.

Especially in the last decade, women have built strong supportive communities to address the issues that women consistently face and often keep to themselves. I personally have observed a growing spirit of women helping other women over the last 18 years in corporate America. There was a time when we automatically looked to the “men in power” to help us get recognized and promoted. Now, there is a greater sense of unity among women: more women are sponsoring deserving women to help them reach the next level, and more women are mentoring others on how to navigate tricky situations, including the “all white boys club”.

I have been mentored and promoted by both men and women leaders — again, I’ve been so blessed! But it is the women who have gone out of their way for me that remind me to do the same for others.

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?

Agreed! Both individuals and companies are responsible for creating a diverse workplace and making employees and colleagues feel comfortable, welcomed and equal in their environment. There are various female-led communities that bring women together to discuss ways to improve workplace equality and boost confidence for women who work in traditionally male-dominated industries, such as finance. It is important for companies to also foster relationships with these communities to show support for female professionals and encourage them to pursue their careers. For example, Laurel Road has partnered with IVY, the social university, to present a discussion around women and personal finance, and how we can close the gender gap through fiscal confidence.

As a society, we can support and advocate for women to be educated about finances earlier, and even consider making it a requirement for graduation. We have seen that while women are more likely than men to learn about basic money management, such as budgeting and managing bank accounts, men were more likely to understand common finance terminology — hence the reason why more women (85%) are significantly more likely than men (67%) to believe that earlier financial education is necessary and are advocates for a personal finance graduation requirement in high school.

I have learned from experience that meaningful education doesn’t just happen in the classroom — it happens in conversations with mentors, peers and like-minded communities. It is our collective responsibility to encourage women to set professional goals — within and outside of the finance industry — and accomplish them.

You are a “finance insider”. If you had to advise your adult child about five 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.

I cannot stress enough the importance of financial literacy as young adults enter the workforce. In our survey on personal finance, we found that respondents believe they’ll be paying off student loans until age 49. However, there are signals that millennials are taking their personal finances more seriously — for example 87% of millennials (and 75% of all respondents) have spent more time managing their personal finances compared to the previous year. However, women were less likely versus men to do so.

First and foremost, I am an advocate for everyone to enroll in a personal finance management course that teaches at least the basics of finances such as budgeting, credit scores and how to navigate them, investments and their purposes.

Once in the workforce and earning an income, it is important to take a few minutes to write out monthly expenses, and do the math — how much can you afford to save, and how much “fun money” do you have every month?

  • Make sure to account for savings and an emergency fund
  • Automate payments whenever possible so it doesn’t slip your mind
  • Enroll in reward programs to save incrementally
  • Make a holiday budget! Around busy holiday gifting times of the year, set a budget to keep expenses in check

A piece of advice that has really helped me is to save nearly 100% of every bonus and 50% of every raise you make. It’s a win-win situation where you can move money towards an emergency fund account, save up for a down payment on a home, pay off debt, or put towards savings while also enjoying some additional cash.

From there, it’s a great idea to start looking into additional ways to save, such as refinancing or consolidating debt which can significantly lower your interest rate, reduce your total debt and essentially help you pay it off faster. Look for special offers or discounts such as tax deductions or credits.

For example, at Laurel Road we offer a special program for medical students in residency.

I have also learned a lot from personal finance podcasts like Financial Grown-Up, select episodes of Life Kit from NPR and Millennial Money. These are great because you can listen on your commute or in transit and build in the learnings and tips into your daily life.

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?

I could share stories about so many people here! But one person sticks out to me in particular because she invested time and energy in me when I hadn’t even given her anything “in return” — I had never worked for her directly, I never signed a big deal for her, promoted her or made her business more successful in any way. She was a successful CMO of a major brand who I had worked with years before. I reached out to her casually on LinkedIn to connect as I was looking for my next opportunity. Because I had impressed her years before — but mostly because she strongly practices in “paying it forward”, especially for women — she took the time to introduce me to the right people, provide feedback on my resume and coach me on how to go about a job hunt like an executive. Though I landed in my later roles through other means, that experience was invaluable. I think about it often and strive to “pay it forward” in the same way with others.

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.

If I could inspire a movement, it would be about financial equality for all — both from a knowledge and pay standpoint.

As I mentioned previously, I believe financial literacy is so important to preparing women and all young adults for a successful financial future, where they’re able to capably and independently manage their personal finances. When I started working in 2001, I didn’t really know anything about financial matters. I didn’t want to spend every penny I made — but I did — because I didn’t understand that small changes can make a big difference and that making sound choices early on puts you in a better position for your entire life. I finally “smarted up” about personal finances in my 30s and this is way too late!

I think this is very common for women. For example, our survey found that 37% of women versus only 20% of men did not understand the basics of student loans — timelines, monthly payments, interest rates, etc., before they borrowed. Unfortunately, women are already facing an uphill battle with the pay gap. One year after graduation, female college graduates that are full-time workers are still paid 18% less than their male colleagues. So while financial literacy and education is crucial for all, it’s especially important for women who are already disadvantaged by the pay gap and by holding majority of the country’s student debt.

Thank you for all of these great insights!

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