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Lessons From the Female Titans of Finance: Dale Sperling

Time Management. For those that juggle family life, it can get messy. It’s just basic math. The more people that depend on you and need you to make decisions, the more your day is stretched thin, and the more balls you drop. I don’t have an amazing solution for this challenge. If someone could help […]


Time Management. For those that juggle family life, it can get messy. It’s just basic math. The more people that depend on you and need you to make decisions, the more your day is stretched thin, and the more balls you drop. I don’t have an amazing solution for this challenge. If someone could help extend my day 6 hours, I’ll happily keep working and spend more time cuddling my kids. But the reality is that we have to prioritize — identify the most important balls and just don’t drop them. Looking at this challenge at a more macro level, we, as a society, need to do a better job supporting women in the workplace. Better and more consistent resources for dependent care needs to be considered in policy making so that the caretakers in our society have more opportunity to share their talents and contribute to businesses and society in a meaningful way.


As a part of my series about strong female finance leaders, I had the pleasure of interviewing Dale Sperling who is CMO at STASH, one of the fastest growing investing platforms in the U.S. that has grown to over 3 million investors in under 3 years. As CMO, Dale is responsible for engagement and growth for one of the fastest growing financial platforms in the U.S. She has more than 20 years of marketing experience across Fortune 500 brands, including Time Inc., AOL, and The Walt Disney Company.


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 had spent my early career working in content, digital services and consumer products, and quite honestly I had always felt somewhat uneasy about using my marketing skills to perpetuate materialism. After I had my children I developed a deeper desire for more meaning in my work. If I wasn’t giving my time to my children, at least I could feel good having an impact on others, so I jumped at the chance when a friend and colleague introduced STASH. The business was just getting started and the super-early startup vibe combined with an honest, mission driven business was a no brainer for me. Quickly I became hooked and dedicated to marketing a service that I know can truly help millions of Americans live better lives.

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 get asked this question a lot and I always have the same answer. One of my first bosses and mentors, Jackie Stone, taught me the value of always being able to do things yourself. She gave me the knowledge and freedom to do things myself yet she always had my back when I failed. I strive to embody that work ethic and empowering managerial style.

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

This past year has been really exciting as we are branching out beyond investing and building banking services for our investors. Partnering with Green Dot Bank for our debit account has been incredibly exciting and rewarding. When you are able to approach financial services without the weight and burden of a fee driven financial model the possibilities for saving customers money is thrilling. STASH’s current 3M+ users are paying on average $75 in banking fees with their current or former institutions. We can eliminate that out of the gate with our debit account that has zero set-up, monthly, or overdraft fees plus no minimum balance requirements. $3.5B was paid by Americans on monthly maintenance fees for checking accounts at the top five U.S. banks in 2017 (Bankrate). Our business wasn’t built on charging fees so we can put that money right back into our customers pockets. It’s a small start but every little bit saved will have a positive ripple effect on our customers lives, whether it’s being able to afford more things in life, like childcare and groceries, or being able to start saving for retirement in an impactful way.

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

When Brandon and Ed (STASH’s Co-Founders) thought up STASH, they literally walked the streets of New York City and asked hundreds of people about investing and saving. Three sentiments were unanimous: 1) financial services were way too confusing, 2) everyone felt you had to be rich to start saving, 3) the “now” was too chaotic, they’d consider doing it (saving) later. It became immediately clear that there was a big opportunity to create a simple, accessible and educational investing and savings platform that truly catered to the average American. It’s pretty incredible to think that of our 3M customers, 86% of them self-identify as beginner or first time investors. While we have a ways to go, we feel so privileged to have helped millions overcome those obstacles and get started so they can afford a better future.

Ultimately, STASH’s innovative products and easy-to-use features help more Americans achieve their dreams of financial security through our commitment to education, personalized guidance and belief that everyone can learn to do it themselves. With just $5 the 99% can get off the sidelines, create positive financial habits, grow wealth, and afford more of the life they want to live.

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?

The changing face of finance is occurring due to two factors working in synchrony — enhanced technology and equality awareness. First, technology has made it impossible for the old guard to defend their castles. Technology has enabled access for all. You no longer need to wear a suit and present a polished pedigree to be a player in the game.

The only way to create a good, sustainable product for the masses, whether financial services or pure consumer, is to have the workforce, the ones building and packaging the product, represent the audience they’re trying to serve. I think that’s become even more apparent in the last decade or so. Additionally, from a recruitment perspective, it’s become one of the top things perspective employees look for: Is there enough of me? Will I be among my contemporaries? That runs across gender and race lines. It’s something that’s become a critical part of a company’s success, regardless of the sector.

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

Everyone has their own unique challenges when progressing in their career. Here’s my top 3.

1) Time Management. For those that juggle family life, it can get messy. It’s just basic math. The more people that depend on you and need you to make decisions, the more your day is stretched thin, and the more balls you drop. I don’t have an amazing solution for this challenge. If someone could help extend my day 6 hours, I’ll happily keep working and spend more time cuddling my kids. But the reality is that we have to prioritize — identify the most important balls and just don’t drop them. Looking at this challenge at a more macro level, we, as a society, need to do a better job supporting women in the workplace. Better and more consistent resources for dependent care needs to be considered in policy making so that the caretakers in our society have more opportunity to share their talents and contribute to businesses and society in a meaningful way.

2) Overcoming labels. Specifically for women it can be hard to make your voice heard — literally and figuratively. The age-old stereotype is that if a woman is outspoken or strong-willed she’s perceived to be a “B”. To that, I say, bring it on. The same playground rules apply. The kids that label and bully are generally just less confident and or jealous so we should flip that word right around and take it as a compliment. (Disclaimer: sometimes woman (and men) are just simply mean people and then the label is likely applicable.)

3) Taking Risks. No guts, no glory right? Decisions made in a senior role have more impact on the business and directly on more people (both customers and employees). It’s a lot of responsibility and the decisions can sometimes feel paralyzing. It’s important to make sound, thoughtful decisions based out of hard data and modeling but sometimes you also have to give yourself the credit of your tenure and trust your gut. Hopefully you’ve made it to your senior role for good reason so continue to take calculated risks — even when the ante doubles.

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?

These two roles — “good mother” and “working mother” are only in conflict if you set that expectation. Instead, I choose to embrace all the great, “good mothering” values I bring to the table because I am a working mother. For instance, my children have a clear handle on the concept of work ethic. They know I wake up while they are still sleeping and go to the gym. They know I stay up late after they are in bed and cook dinners for the following nights. And they know that they get to enjoy fun family time together on the slopes because mommy works for the money to help pay for these experiences. They know what it’s like for mommy to be gone and so our daily reunions are that much more valued and joyous (at least for like 10 minutes). All of this good doesn’t come without tradeoffs. Guilt is inevitable because you can’t do it all. This was summed up for me this past weekend when I was playing with my kids in the basement before bedtime. It was time to get ready for bed but my 9 year old didn’t want the fun to end. He proclaimed that we never spend time together anymore, that I’m always at work or on my computer, and that he misses me. These statements were accompanied by waterworks and sobs which were quite effective in pushing on all my guilt buttons. I know he was being dramatic and strategic to stay up later but there was some basic truth in his argument — I am around less than other moms.

Ultimately, any working parent just needs to come to terms with the fact that they can’t ever do it all. There are trade-offs to every scenario. All we can do it try to make the most of every moment (work or home).

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

I flat out disagree that women aren’t strategic in their business decisions but I do think that the stereotype is a spillover from lack of strategy climbing the corporate ladder. I just don’t believe that most women come pre-wired to play the corporate game. Often, this is something that must be learned. Women should to use their relationship building skills to better position themselves in meetings, on projects, and as experts in their fields so that they can shine as the strategic leaders they truly are.

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

I have so many favorite quotes and they are all usually all about the concept of gratitude. Here’s one… “Nothing is more honorable than a grateful heart.” — Seneca

Unfortunately, we all live in a media driven society of excess. It’s filled with “not enough” and “more”. You can take that statement and apply it to almost any person, anywhere. Americans are in debt because they want it all, and they want it all yesterday. We’ve become so materialistic… social media drives us to constantly look at what everyone else has, pushing us to get what everyone else has. We compare ourselves to our friends and peers. How do we measure up to their strengths and weaknesses? This game we play with ourselves feeds into these negative habits. To combat this I’m always trying to remind myself to count my blessings every day and focus on what I do have.To be truly happy and fulfilled — in both your personal and professional life, take stock of what you have and how you can make it more meaningful. Don’t look at your weaknesses as negative. Instead, look at them as an opportunity to grow and learn. Someone is always going to have “more” than you, but if you can find sincere gratitude in what you do have, and the confidence to own it, your cup will always be full.

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. 🙂

As I’ve said before, I’m really excited about the custodial investing experience we’ve built and continue to iterate on. I am a big believer that change, real change, has to start with our children — the next generation. If we can reach more children and teach them the basics about money, budgeting, and the the real value of a dollar. If we could show them the opportunities that are afforded to everyone in our amazing, free, country. If we could give them all a STASH custodial account they could learn while doing it themselves and participate in the world economy by putting their money into companies and investment themes they believe in for our shared futures. Giving children this gift, this power, this real-world education can change the world.

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