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Aaron Shapiro of Dayforward: “Flexibility can be more powerful than your vision”

Flexibility can be more powerful than your vision. You might think that you have the perfect vision to create a company, but in reality, the market tells you what business you’re in. The ability to be flexible and make adjustments as you go (even when those adjustments aren’t in line with your original intent), can […]

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Flexibility can be more powerful than your vision. You might think that you have the perfect vision to create a company, but in reality, the market tells you what business you’re in. The ability to be flexible and make adjustments as you go (even when those adjustments aren’t in line with your original intent), can be the difference between failure and success.


As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company”, I had the pleasure of interviewing Aaron Shapiro, a technology and marketing executive and serial entrepreneur. Prior to founding DayForward, Aaron was CEO of Huge, which he founded in 2005 and later sold to IPG. During his tenure, he grew the firm to a global organization spanning 1,500 employees, 12 offices worldwide and several hundred million dollars in revenue. Widely recognized as one of the leading agencies of the last decade, Huge was responsible for many groundbreaking customer experiences and marketing campaigns. This includes: the design of Apple.com, the Android operating system, HBOGo, Marcus by Goldman Sachs, and the Zelle payments platform. He first became interested in life insurance after seeing several of his insurance clients struggle to make the transition to digital.

Prior to Huge, he was founder and CEO of Silverpop, a leading marketing automation SaaS that was acquired by IBM for approximately 300M dollars.

He is a regular author, commentator and speaker about the impact of technology on business, marketing and the economy, and is the author of Users, Not Customers (Portfolio/Penguin). A graduate of Columbia Business School and Harvard College, he lives in New York City with his wife and three children.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I’ve spent my career building companies in the technology and marketing space. My first company, Silverpop, was sold to IBM in 2014. After that, I co-founded and served as the CEO of Huge, where I focused on digital consulting and helping brands innovate in the online space.

Today, I’m the founder and CEO of Dayforward, which I’ve been building for the past two years.

I first got interested in the life insurance space because we had clients in the life insurance industry at Huge, and it gave me the opportunity to see how things were being done. I learned a lot about the sector and where the opportunities were, and I thought it would be an exciting industry to found a startup that could create a very different approach to life insurance.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

I remember one meeting where I was having a conversation with a client in the insurance space, and I was talking about customers and user experience and how important it was to be customer-centric. As we were talking, I realized that when they used the term “customers,” they were talking about agents and brokers, while I was talking about their policyholders. Suddenly I could see that there was a total disconnect in life insurance companies, where they see the people selling their products as their customers over the people who are buying policies.

That moment really crystallized the problems with this industry for me, and how a truly customer-centric approach could do a better job protecting families. Then I reflected on my personal experience buying life insurance and the challenge so many families have in building financial security for their family, and I started thinking about all the things we could do to make it better.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

This is a more recent example, but we were thrown a real curveball when we started Dayforward. Just as we were gearing up for fundraising and hiring the next set of employees, the pandemic hit. Almost overnight, we went from a place of excitement and optimism to wondering just how long this was going to last. We had investors tell us “we’ll just wait to meet you next month,” but that was in mid-March, so obviously that never happened! Suddenly, we had to figure out how to pitch to investors over Zoom and build a company without being able to meet face to face.

If there was a silver lining to everything that happened, it’s that the pandemic really drove home the importance of life insurance and financial security, and that even became a rallying cry for the company.

So, how are things going today? How did your grit and resilience lead to your eventual success?

We found our footing and eventually adjusted to a fully remote model. We launched in Texas (our first market) in January, and are planning to expand nationally soon. We’ve already seen a lot of excitement and enthusiasm, especially from our target market of young families. Dayforward is actually uniquely suited for this “new normal,” with an automated purchasing process and at-home health kits to keep the process streamlined and safe, so we’re confident in our ability to really impact the lives of American families, both during the pandemic and beyond.

Honestly, every one of my companies has faced adversity, starting with the dot.com crash. I struggled in 2007 when the financial crisis hit — a lot of our competitors went out of business because they weren’t prepared for the aftermath. But I learned the importance of reacting quickly and striving to always be more prepared than you were the last time, and that’s one reason I’ve been able to keep moving forward.

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

I think that one of the most significant trends when it comes to digital businesses is that

companies are weighing on increasingly verticalizing their business, meaning they control all aspects of the value chain. From DTC’s that cut out the middleman to major brands like Nike moving away from retail and selling more of their products directly, companies are embracing the fact that controlling the full value chain allows you to produce a much better customer experience.

However, this is still a relatively new concept in the insurance space. Here, you still have brokers, you have agents, and you have customers who are not being well served. Everybody in this industry sells the same exact products. The fact is, this is a commoditized space where the whole industry relies on brokers price shopping on behalf of their clients. And we’re saying that’s the wrong model because we can make a better product and nobody’s doing that in this space.

The fact that we’re a fully verticalized provider means we can create a truly great experience for our customers and build rewarding relationships with them. It also means that we can create better products that are really custom designed to our consumer’s needs.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

I don’t know if it’s a mistake, per se, but my first company Silverpop was actually focused on creating electronic greeting cards. It was the early days of the internet, when people were sending Happy Birthday emails with dancing pineapples or whatever animation they liked. At one point, Silverpop became one of the top 500 sites on the internet — that shows you how small the web was back then! Eventually we started to see that people were using our greeting cards as regular communications, but with animations (similar to how we use emojis today). At that point, we pivoted to working with companies and building out the marketing animation capabilities, the technology for which was eventually sold to IBM and became the building blocks to Watson AI. So it became something really serious, but it started out as a completely lighthearted way to entertain people.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

That’s such a hard question to answer, because I generally think that making mistakes is the best way to learn. Good things can even come from bad advice, so I don’t think of it as things I wish I’d done, I just think of the things I’ve learned.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

I think a certain curiosity about the world and how things work, as well as the ability to really listen have been important in my career. It helps me understand that the market tells you the answers, and not the other way around.

I can also admit when I’m wrong, and not get entrenched in an idea just because it was my original vision. I mean, building a greeting card company that became a serious marketing SaaS solution is a pretty good example of that!

There seems to be this myth of the “visionary entrepreneur” who just has all the answers. I don’t think that’s entrepreneurship in real life. I think it’s really about deeply observing things and learning and understanding and being open-minded enough to change course when it’s time. If you’re not able to be agile and learn from what’s happening around you and what the market is really looking for, it becomes much easier to fail.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Stay curious! Try to do things that are intellectually stimulating to keep your mind active. If you’re ever having doubts or feel stuck, don’t be afraid to try new things, new approaches, new angles, or try to think about a problem differently.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

I think one of the most common mistakes is trying to do too much in either direction. Sometimes I see entrepreneurs trying to do too many things, and they all end up half-baked. Other companies are so stubborn that they don’t want to change, and that CEO just goes down with the ship. It’s a tricky balance of finding your focus, yet being able to pivot thoughtfully.

For me, the key to building a strong company is doing one thing really well, having the discipline to figure out what exactly that is, and then being willing to learn as you grow.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

Hiring the right people! I think the ability to delegate is one of the most underestimated skills, and something a lot of CEO’s miss the mark on when they’re launching a company. The role of a CEO is to direct the company and facilitate the opportunity for good things to happen. When you hire the right team, you give the company, and yourself, the best chance to be truly successful.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading My Company”? Please share a story or an example for each.

  • Failure is your friend. There’s a saying that some people are “an overnight success ten years in the making,” and this is especially true for entrepreneurs. Most ideas will fail, but it’s your ability to learn from those failures and persevere that will determine how successful you are.
  • Your relationship with money might need to change. Before you raise money, funding is the limiting factor to growing the business. But once you have the capital, talent and hiring great people becomes the limiting factor.
  • Know your role, and don’t micromanage. Your company will outgrow you if you can’t learn to let go and trust your team. The job of a CEO is to hire the right people and create the tools for them to succeed, so don’t get caught up trying to do everything yourself.
  • Embrace constraints. If you had told me a year ago I would have been pitching investors and launching a startup without the ability to meet anyone in person, I would have thought you were crazy. But our team has been able to thrive virtually in ways we never could have expected.
  • Flexibility can be more powerful than your vision. You might think that you have the perfect vision to create a company, but in reality, the market tells you what business you’re in. The ability to be flexible and make adjustments as you go (even when those adjustments aren’t in line with your original intent), can be the difference between failure and success.

You are a person of great influence. If you could start 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 believe that climate change is the most important issue we have today. Of all the problems we’re facing, it’s the one that fundamentally threatens our existence. Climate change affects not just our future, but our health, our security, and our economic equality. Because I don’t personally have the tools to fix climate change (I wish!) I tried to tackle one piece of that puzzle by making protecting families and helping them feel more secure about the future my personal mission.

How can our readers further follow you online?

You can visit us at Dayforward.com to learn more about Dayforward life insurance, and follow us @dayfwrd on Instagram, Facebook, and Twitter.

This was very inspiring. Thank you so much for the time you spent with this!

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