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Women of The C-Suite: “Let go of trying to do it all” With Dale Sperling, CMO at STASH

Let go of trying to do it all. On the work front you’ve hopefully hired an amazing team and at some point, you need to let go and trust…


Let go of trying to do it all. On the work front you’ve hopefully hired an amazing team and at some point, you need to let go and trust that they will do a great job without you. Consider that a compliment when they succeed without you over their shoulder at every turn. On the homefront, give up trying to do it all. I’ve never met a working mom that could give 100% to work and 100% to her family. The sooner you come to terms with this fact the happier you’ll feel all around. The best you can do is to make the most of every moment. When you are home, try and turn off and have some dedicated time with the family. I try not to take my phone with me when I’m home to do the bedtime routine. I always log back on after they are asleep but I’ve learned that trying to do both at the same time isn’t sustainable or fair. I know that I don’t have the same amount of time other moms have to devote to their kids and letting go of the guilt is an ongoing effort. Coming to terms with good enough is important because I know I just can’t do it all.


I had the pleasure of interviewing Dale Sperling, Chief Marketing Officer at STASH where she is responsible for driving growth and engagement for one of the fastest growing financial platforms in the U.S.

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I’ve been very fortunate as I’ve known what I wanted to do since I was 10. I fell in love with the idea of marketing when my middle school chorus teacher taught us a whole medley of old commercial jingles. I was amazed that these companies could tell their story in a way everyone could understand and in a format that was so memorable. I can still sing every word of that medley by heart and I will forever know what kind of kids eat Armour hot dogs. Knowing I wanted to be in marketing helped me craft my ideal career path. I got a degree in business management and a minor in psychology and then went right into an internship out of college. I’ve taken roles that have given me an opportunity to learn and master all of the different disciplines within marketing, priming me for this role here at Stash where I’ve had the opportunity to build a team from just me, to three, to thirty strong.

Can you share the most interesting story that happened to you since you began leading your company?

There are so many to choose from as I encounter interesting stories all the time these days. These stories come from our customers — random people I meet on the street or in a store…. from parents at my kids’ sports games, our bus driver, ninja instructor, and more. These interesting stories are offered up when someone realizes that I work at Stash either because they see my shirt or hat or wonder why I am on the sidelines at soccer tapping away on my laptop while cheering as I watch from my peripheral vision. One very heartwarming story came from a waitress that served me at a restaurant. Upon seeing my Stash shirt she asked if I also invested with Stash and when I shared that I ran the marketing team she gushed and opened up about the financial story of her whole life. She explained that she learned to manage money from her dad who had always made her feel that it was over her head and something that her future husband would manage. Her life didn’t pan out as her father had planned, and when she found herself alone in her 30’s she downloaded Stash and decided to take things into her own hands. She shared how our service literally changed her life — not just her financial stability, but her money confidence and ultimately her feelings of personal worth. It’s such an honor to meet these people and hear these stories. To know that I’ve had a part in bringing this empowering opportunity to millions is humbling.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I can laugh about it now but at the time of this mistake I was not as forgiving (with myself). Right after we launched on iOS in October 2015 I was writing and sending all our communications, and in my haste I copied and pasted an email instead of using the merge tags. Consequently, I sent an email that said something like, “Hi <test name>” instead of “Hi Akemi,”. Right after hitting send to thousands of new investors I started to receive emails back from unforgiving investors pointing out that I failed email marketing 101. Some generously tried to explain to me where I went wrong, as if I didn’t already know. It was a painful, dumb mistake but these are the silly things that happen when you are moving fast and trying to do everything yourself. I quickly learned that I needed help and that contrary to what I tell my kids, I’m not actually perfect.

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

Stash is unique because of we bring together access, education, and intent all on one investing platform where our customers can better their financial futures. We are making a meaningful difference in the lives of our customers and in turn, they evangelize the service and our brand. The access we provide is not just fractional share investing, although that alone is a big deal for our clients. We also write in a very accessible voice and everything we design in the product is built with simplicity and accessibility in mind. But it’s not enough to just provide access. We take education very seriously and are driven to help every single customer gain financial competence. It’s a win for us if a customer can understand dollar cost averaging or explain how tariffs might affect their investments. When you bring access and education together you can finally celebrate in the magic of intent. Our investors have intent. They forego things they don’t need in their lives to Stash more. They choose investments they care about and believe in for the long run. They set up automatic features like Auto-Stash fully aware of the impact to their personal budgets. They have chosen to save and invest with intent and grow wealth. They make their own choices with our guidance and as such, have commitment and intent.

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

In just a few short weeks we are launching our new banking services, STASH Money. I’m honored and excited to help bring this product to market. I really believe that we have an opportunity to help Americans save more money so that they can invest more for their future goals. So many people are taken advantage of by bank fees and lack control over their daily balances. We believe that with technology and a transparent, customer-first business model we can make a meaningful difference.

What advice would you give to other female leaders to help their team to thrive?

I think that many women are wired to be supportive, and in a leadership role this trait can be very effective. Putting the needs of the team first and sharing power can create a happy, productive team. I always ask what I can do to unblock an obstacle or make their jobs easier. I want them to have control of their own domain and know that what they put in they also get out. It’s important to always stay close to each team members impact on the KPI’s, their career path, and their personal development.

What advice would you give to other female leaders about the best way to manage a large team?

As your team grows, clear accountability is paramount to success. You might have one employee who can do it all or who has done it all in the past, but as the team grows their role gets refined so that they can dig deeper and scale. During this process you need to over communicate to avoid duplication of effort, confusion, or general inefficiencies. Also, as the team grows it’s important make time for team building. I try and coordinate a quarterly team building event to build rapport and trust. A team that genuinely enjoys one another will be supportive and successful together.

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?

One of my first bosses, Jackie Stone, taught me so many things without even knowing it. My do-it-myself attitude came from watching her. I admired how she could fill in any role and I made sure to emulate that. I’ve never felt above any work. Give me numbers, spreadsheets, words, or an empty page that needs filling — I want to do it all. If you have done the work yourself you know how long it should take, the issues you’ll run into, and most importantly, you’ll be able to provide constructive feedback and have a helpful POV.

How have you used your success to bring goodness to the world?

Even though I always wanted to be in marketing, I did have a back up plan. That plan was to be a special ed teacher. I’ve studied for and taken the Praxis so that I could jump ship if I became disenchanted with perpetuating materialism. Luckily, my last few roles have been emotionally fulfilling and I’ve stayed the course. In my current role I do feel that we are bring goodness to the world in the form of education. We’ve tested the financial literacy of our investors and then compared that to the general population and a Stash investor with a high school diploma on average scored higher than the general population with a college degree! So, it’s working! Good will come to this world when more people are aware, empowered, and educated. Money is a big cross cultural motivator. By helping our customers learn more about money and finances, they are learning more about markets, economics, politics, and the world. And when someone understands the dynamics of our economy they are able to have an informed opinion. From that opinion, conversations are started, and from those conversations the spark for action and change is born.

What are your “5 Leadership Lessons I Learned From My Experience” and why. (Please share a story or example for each.)

1) Give up your ego. If you are doing your job well, it will be of no use to you. There are so many ideas I’ve had and shared over these past 3 years in this role — some have been executed under other names but there is no gain for anyone in chasing the glory. A win for any employee with us is a win for the company, and that is of the highest importance.

2) Give a sh*t. What’s trivial on your radar might be an issue someone deals with day in and day out. If you lose touch with issues that matter to your team or become too busy to care about the details, everyone loses.

3) Have fun. You, as a leader, set the tone for the work environment so if you’re frantic, cranky, and always the wet blanket you best be sure your team will model the same.

4) Be grateful. Everyone, regardless of level or career experience has a desire to be needed and thanked. Don’t forget to show your gratitude every day. Reward exceptional efforts and give praise generously.

5) Let go of trying to do it all. On the work front you’ve hopefully hired an amazing team and at some point, you need to let go and trust that they will do a great job without you. Consider that a compliment when they succeed without you over their shoulder at every turn. On the homefront, give up trying to do it all. I’ve never met a working mom that could give 100% to work and 100% to her family. The sooner you come to terms with this fact the happier you’ll feel all around. The best you can do is to make the most of every moment. When you are home, try and turn off and have some dedicated time with the family. I try not to take my phone with me when I’m home to do the bedtime routine. I always log back on after they are asleep but I’ve learned that trying to do both at the same time isn’t sustainable or fair. I know that I don’t have the same amount of time other moms have to devote to their kids and letting go of the guilt is an ongoing effort. Coming to terms with good enough is important because I know I just can’t do it all.

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

I’m really excited about the new custodial investing experience we are building. 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.

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

“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.” Oprah Winfrey — 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.

Thank you so much for these inspiring insights!

Originally published at medium.com

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