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“Get good at hiring outside your expertise”, With Douglas Brown and Dana Levin-Robinson of Upfront

Get good at hiring outside your expertise. When I just started Upfront, I found it really challenging to assess how good a developer was since I wasn’t technical myself. Eventually, I learned that the best way to gauge skill is by asking for recommendations from fellow founders and asking for case studies during the interview […]

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Get good at hiring outside your expertise. When I just started Upfront, I found it really challenging to assess how good a developer was since I wasn’t technical myself. Eventually, I learned that the best way to gauge skill is by asking for recommendations from fellow founders and asking for case studies during the interview process.


As a part of my series about “Lessons From Inspirational Women Leaders in Tech”, I had the pleasure of interviewing Dana Levin-Robinson.

Dana is the CEO and Co-Founder of Upfront, the first site dedicated to pricing transparency in daycares. She is the former Chief of Staff at VirtualHealth, a growth-stage health tech company that was named Deloitte’s 39th Fastest Growing Company, and spent years in various advertising agencies in NYC. Dana graduated with her MBA from NYU’s Stern School of Business and BS from Boston University and lives in NYC with her husband and baby son.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

I always knew I wanted to run my own company, but it never felt like it was the right time. It took about 10 years into my career while at VirtualHealth to feel like I knew how to get started. I was really lucky at VirtualHealth- I was an early employee who got to build entire departments from scratch. Few founders get to do that in a salaried job, so it was both a learning experience and validation that this is what I wanted to do with my life.

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

We pivoted an entire industry! Upfront was originally designed to bring transparency to the wedding industry, but we realized that daycares were even more opaque as an industry. It was terrifying at first to make this change, but we realized pretty quickly that we could keep a lot of the product we already built. This decision, like all important ones, was of course done on a Saturday at 3 am.

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?

We once accidentally uploaded our directory for California twice, which is now a funny story but back then quite difficult to fix. But the effect on the site’s speed showed us that we needed a more scalable database, which allowed us to grow future cities much faster.

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?

I had wanted to start Upfront for years, and was finally ready to start when I found out I was pregnant. There was definitely a moment of “should I do both these things for the first time together?” A mentor then told me that I’ll always be busy from this moment forward, so it doesn’t really matter if I start it now or later. I decided to go for it because I knew that this company needed to exist- people needed to know how much stuff costs!

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?

Without question, my husband, David Robinson, is my support system both professionally and personally. Beyond being an incredible partner and parent to our baby son, he is a data scientist who helped architect our entire back-end when the company was just starting out.

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

“Don’t stress about things that have a solution” is something I repeat to myself. When our site breaks or a product feature isn’t performing, I remind myself that with money and time, we will solve those issues. It’s easy to get caught up in the constant fire drills of being a founder, but those fire drills are temporary.

Ok super. Thank you for all that. Let’s now shift to the main focus of our interview. We’d love to learn a bit about your company. What is the pain point that your company is helping to address?

Upfront is doing something that nobody has really tackled before- we’re making prices public and searchable in industries that intentionally hide their numbers. From our research, we saw that 62% of parents toured a daycare they couldn’t afford. That number represents so many wasted hours. We’re starting with daycares, but there’s no limit to the industries we can apply our model to.

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

Upfront is the only company focused on price. We show other details of course, but there is no company dedicated to pricing transparency the way that we have been. The idea of the company came to me when I was planning my wedding. I met with a florist who after an hour, handed me a pricing sheet that I realized was way beyond my budget. The light bulb moment of “Why didn’t I know that price before the meeting?” is the thesis of our company.

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

We are working on growing our database exponentially across the country- we’ve been able to bring down our launch timeline to seven days for each city, which means we can expand extremely fast. We launched our calculator tool in January to make the search process even easier by just entering a zip code. The more cities we are in, the more parents we help find the best daycare option for them.

Let’s zoom out a bit and talk in more broad terms. Are you currently satisfied with the status quo regarding women in Tech? What specific changes do you think are needed to change the status quo?

Of course I’m not satisfied. The numbers of female-founded companies was already atrocious (<8%), and the pandemic has only worsened the situation. To begin, I think accelerators and early-stage VCs need to institute a standard that half of their future investments will go to female-founded companies. The amount of incredible female founders that I know confirms this is not a pipeline issue, but a discovery issue.

In your opinion, what are the biggest challenges faced by women in Tech that aren’t typically faced by their male counterparts? What would you suggest to address this?

Balancing your professional and personal lives can be tough, especially in a demanding industry like tech. One of the reasons I always knew I wanted to start my own company was having schedule flexibility. In no way does it mean I work fewer hours (quite the opposite), but I control my day and it’s really freeing to spend the time I want with my baby son on my terms. All employers should commit to a minimum of 12 weeks, preferably 16, of parental leave to all employees. More than just supporting women in the workplace, several companies have shown that it reduces employee turnover, which is a win for everyone.

What would you advise to another tech leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth or sales and “restart their engines”?

Go back to why you started the company- the users. Start asking “what could we do better” by reviewing your data. Are users leaving at a certain point of their journey? Is one marketing channel carrying the others? Once you have some theories, approach the question qualitatively with more in-depth user interviews to learn exactly where your gaps are.

Do you have any advice about how companies can create very high performing sales teams?

My advice for building any team, not just sales, is to hire people who truly care about your company mission and are proactive, collaborative individuals. Someone inexperienced but driven will always win over someone with years of experience who is unmotivated.

In your specific industry what methods have you found to be most effective in order to find and attract the right customers? Can you share any stories or examples?

From the beginning of Upfront, we targeted our users where they were already spending time: Facebook parenting forums and reading blogs about parenting topics. We have presence in every marketing channel possible, but we’re always astounded when one reply on a large Facebook parenting group outperforms every campaign we’ve done.

Based on your experience, can you share 3 or 4 strategies to give your customers the best possible user experience and customer service?

A few strategies come to mind when trying to make your product the best it can be. First, design your product for the users, not for yourself. It’s not a coincidence the Upfront homepage reflects two search pathways: by business name or location and price. Those are the two user search behaviors we identified in our early research. Second, do a lot of market research, both qualitative and quantitative, but don’t think that process is ever done. Plan to go back to users every six months to get feedback on new features. Lastly, respond to your users if they email. It sounds simple, but I always make sure to personally respond to any users who reach out via our main [email protected] email.

As you likely know, this HBR article demonstrates that studies have shown that retaining customers can be far more lucrative than finding new ones. Do you use any specific initiatives to limit customer attrition or customer churn? Can you share some of your advice from your experience about how to limit customer churn?

Our blog is very popular with parents and is often the gateway to our site. Our site data shows that users are also returning each , which not only strengthens our relationship with parents but also maintains our authority in the daycare space.

Here is the main question of our discussion. Based on your experience and success, what are the five most important things one should know in order to create a very successful tech company? Please share a story or an example for each.

There are so many factors that go into a successful tech company, but I found these five to be critical:

  1. Find a co-founder or business partner. This isn’t just about bandwidth, but about adding a new perspective to the company. It was really difficult running the company as a solo founder, which is why I’m so grateful for my amazing cofounder Shefali Shah. The company just wouldn’t have been the same without her.
  2. Get good at hiring outside your expertise. When I just started Upfront, I found it really challenging to assess how good a developer was since I wasn’t technical myself. Eventually, I learned that the best way to gauge skill is by asking for recommendations from fellow founders and asking for case studies during the interview process.
  3. Building is hard. There are no shortcuts when it comes to building a company- doing something for the first time is difficult work. For example, doing a proper QA of our site took a long time in the beginning as we wrote out the process from scratch. Now that we’ve done it hundreds of times, we know what tools to use and the fastest way to communicate changes within our team.
  4. Follow your own schedule. I’ve never been a morning person, and my best work is always done at 11pm. Early in the company’s history I learned that I have the ability to set my own schedule as long as I accomplish what I need to. It’s easy to feel like you have to work the 9am-6pm daily, but the freedom of building your own company also means building it the way you want.
  5. Keep talking to users. Don’t forget why you started the company- it’s about making a solution for someone’s real pain point. At Upfront, we’re planning on running user interviews every six months to make sure we keep our finger on the user’s pulse.

Wonderful. We are nearly done. Here are the final “meaty” questions of our discussion. You are a person of enormous 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 want to see people, especially women, talk about money. The more we talk about money, the more we can a) find out how much we should be making and b) whether we are overspending. I saw an incredible statistic that 61% of women would rather talk about their own death than money, which just confirms how uncomfortable this topic is. I’d love to see more women share their finances with each other, and I’m happy to go first.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

Rich Barton is the patron saint of Upfront- he just doesn’t know that yet! All his companies are dedicated to bringing transparency to their industries and empowering consumers to make the best choices for themselves. We try to do exactly that with prices at Upfront.

Thank you so much for this. This was very inspirational, and we wish you only continued success!

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