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Dale Sperling: “The education system has received a necessary shake up”

There is a renewed focus on local farming and sustainable living. For the past 30 years, I’ve volunteered at and supported a local organic farmer who, for the first time in his life has seen farm market sales surge and a demand for local, sustainable produce that he can’t actually fulfill. It’s amazing to see […]

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There is a renewed focus on local farming and sustainable living. For the past 30 years, I’ve volunteered at and supported a local organic farmer who, for the first time in his life has seen farm market sales surge and a demand for local, sustainable produce that he can’t actually fulfill. It’s amazing to see this new awareness in clean, sustainable food production.


I had the pleasure of interviewing Dale Sperling who serves as CMO at Stash, the all-in-one financial subscription that helps more than 5 million Americans create better lives. In this role, she drives growth, engagement, and retention for the financial platform. Dale has more than 20 years of marketing experience across Fortune 500 brands, including Time Inc., AOL and The Walt Disney Company. She lives in New Jersey with her husband and four children.


Thank you so much for doing this with us! Before we dig in, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I’ve known for a long time that marketing was where I wanted to focus my career. In middle school, we learned a medley of old commercial jingles. I was immediately impressed by the fact that these companies had found a way to tell their story in a unique and memorable way and knew I wanted to pursue that path. Once I had this certainty, I made sure my educational path supported that goal. I got a degree in business management and a minor in psychology, went right into an internship out of college, and took roles that allowed me to learn the various disciplines within marketing. This career path has culminated in my CMO role here at Stash where I’ve had the privilege to grow the marketing org from just to me to a talented team of 40.

Can you share the most interesting story that happened to you since you started at your company?

I think the most interesting part of my career at Stash and honestly, my whole working life, has been managing a team through the perils of 2020. It’s been both fascinating and challenging to have been forced into closer personal relationships with my entire team as topics of sickness, pandemic, racism, riots, anxiety, loneliness — and everything in between — were thrust into our everyday work streams and conversations, in a way we couldn’t have expected. 2020 forced us to define who we wanted to be as a brand and as a team. It’s been a unique and powerful time, and I feel fortunate to have worked at a company where everyone was given the time and space to meet their individual needs, while still driving business goals.

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

These days my main focus is driving awareness and education about our most unique feature called Stock-Back®.1 It has already, and will continue to help people understand the investing landscape. When customers use Stash for their everyday spending2, we give them little bits of stock as a reward, which can grow over time. Plus, when a customer earns Stock-Back® rewards they can learn about the companies where they shop and they can build a diversified investment portfolio automatically — just by living their life. For example, a customer can get a few cents of an ETF (fund) of their choosing when they get their car washed at a local business or when they pay for a sandwich at a local deli. And they can get Walmart stock when they shop at Walmart, Amazon stock when they buy online with the company.3 I’m so passionate about Stock-Back® — I think it can change the way we see rewards and open our eyes to the companies we support through our daily habits.

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?

Jackie Stone was one of my first bosses at AOL. I started as an executive assistant and quickly moved around in the marketing team until I landed on Jackie’s promotions team. What I admired about her, and strive to emulate myself, is her do-it-yourself attitude. Doing the work yourself first provides invaluable experience as a leader. Once someone else takes the work on, you have a better understanding of the challenges they may run into and can be more useful in providing guidance and a POV, having done the same work yourself.

The Covid-19 pandemic has affected nearly every aspect of our lives today. Can you articulate to our readers what are the biggest family related challenges you are facing as a woman business leader during this pandemic?

My biggest challenge has been the open door access the whole company now has to my home life. I literally mean, open door, as my 4 young children bust into many of my video meetings throughout the day. I’ve had to get comfortable with a new level of intimacy with my team and trust that they will honor and respect that openness and access.

Can you share what you’ve done to address those challenges?

I’ve attempted to set strict boundaries with my children but it’s a daily struggle to enforce the rules — I’ve said when my door is closed don’t come in because I’m in a meeting, but it’s very hard for 4 rowdy boys to follow. When they inevitably break the rule, I put the team on mute (if I’m lucky) and try to get them out or attempt to keep going despite the small child under my desk. My new plan for the school year is to teach them all about time management and get them proficient with Google calendar early. I’m going to share my calendar with them and encourage them to book time with me for school questions or personal 1:1 time. My hope is if they can see what I am doing, they may be more respectful.

Can you share the biggest work related challenges you are facing as a woman in business during this pandemic?

My personal challenges as a woman in business have lessened during this pandemic. I know that might seem surprising but my challenges are interwoven with my responsibilities of being the household manager, grocery shopper, money manager, bill payer, school day coordinator, sports team manager, wife, mom, and family social calendar coordinator. Since we are currently working remote, I now have more time back in my life to better manage my home life. I’m not missing meetings to pick sick kids up at school. Instead, I’m multitasking and being more productive at work because home life management is happening in parallel.

Can you share your advice about how to best work from home, while balancing the needs of homeschooling or the needs of a family?

Keeping a strict schedule with the kids is essential. It’s hard but it’s helped to write out a daily schedule with the children and review it every morning together. When they know they get 30 minutes of screen time at 4:30pm if they behave throughout the day, they are more likely to embrace and enjoy their scheduled work sessions and whine less about what they’d rather be doing. What else has worked is scheduling a quick 10 minutes with each child early in the morning to talk through their individual concerns or hopes about the day. This gives them the “mommy” time they want and they are more likely to work independently for longer.

Can you share your strategies about how to stay sane and serene while sheltering in place, or simply staying inside, for long periods with your family?

I’ve taken this opportunity to teach my children how to play my own favorite games. They are finally old enough to hold their own in strategy games and so we’ve dumped the mind numbing “kids” games in exchange for games like Setback, Cribbage, Michigan Rummy, and Rummikub. We still have a lot to learn, but reinvesting in family game time has been a saving grace during this trying time at home.

Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the coronavirus pandemic have understandably heightened a sense of uncertainty, fear, and loneliness. From your perspective can you help our readers to see the “Light at the End of the Tunnel”? Can you share your “5 Reasons To Be Hopeful During this Corona Crisis”? If you can, please share a story or example for each.

1. There is a renewed focus on local farming and sustainable living. For the past 30 years, I’ve volunteered at and supported a local organic farmer who, for the first time in his life has seen farm market sales surge and a demand for local, sustainable produce that he can’t actually fulfill. It’s amazing to see this new awareness in clean, sustainable food production.

2. We got a sneak peak into the dramatic changes that are possible when we collectively lower carbon emissions. One simple change we saw in my area of NJ was an increase in the deer population as fewer cars on the road meant fewer deer being hit. There also seems to be a consensus in my area that the lower carbon emissions allowed the insect population to thrive more this spring than in years past. Neither of these examples are world changing but just imagine what could happen at scale if we could coordinate a sustainable effort to lower emissions around the world.

3. Remote work is mainstream, accepted, and now preferred for many workforces. This fact has changed so many things for businesses including the ability to source and secure the best talent from all over the world.

4. We’ve reconnected to our neighborhood and local communities. When you have to stay in your COVID safe bubble, you are focused to talk to and interact with your neighbors. Before COVID, I barely knew half the neighbors on my street. As we’ve been walking around the neighborhood as a family and chatting up more people, we’ve made new connections and have a renewed sense of local community and support that didn’t exist before.

5. The education system has received a necessary shake up. The outcome of this shake up is still to be determined but I’m excited that our system has been challenged to think out of the box, address the gaps in access to technology, and redefine how we approach learning across populations. I fully expect this school year to be a struggle for both students and teachers but this new challenge and all the constraints of distance learning should breed innovation and drive better access for all American school-aged children.

From your experience, what are a few ideas that one can use to effectively offer support to their family and loved ones who are feeling anxious? Can you explain?

I’ve had a lot of success in curtailing feelings of angst by digging deeper into the issues causing the concern. When we can break things down and talk about what we personally can do to combat or fix the issue, we can gain a sense of empowerment. A lot of the anxiety comes from feeling helpless and vulnerable. Finding ways to turn that around into ways we can drive change or feel powerful can quickly turn the focus to more positive thoughts.

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

I’ve shared this quote before, and it’s become even more relevant given our circumstances through COVID. Oprah Winfrey said, “Be thankful for what you have; you’ll end up having more. If you concentrate on what you don’t have, you will never, ever have enough.” It’s easy to focus on what material things other people have and feel a desire for more. Through the pandemic, I’ve found a renewed appreciation for my health, access to care for myself and my family, support from others, and a flexible work environment.

How can our readers follow you online? I’d love to say that I have invested time in my online presence but I haven’t. My work and family get all of my time. The best way to stay up to date with me and see what I’m working on is by following Stash online, where you’ll see many of my team’s efforts come to life.


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