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1. What is your business?

UrbanSitter helps parents and sitters connect by leveraging social connections, and it lets parents see sitters whom their friends have booked in the past. All sitting gets booked through a calendar tool much like you would use to select an exercise class or book a dinner reservation. UrbanSitter’s goal is to support the childcare needs of parents by using technology to enable trust. We use a matching algorithm to mimic word of mouth recommendations.

When I started the company in 2010, I had a vision for seeing friends’ sitters, but I couldn’t figure how to get there. I have three co-founders, and they helped me create it. Initially, when we started, Facebook was the primary means of connecting parents, but now parents can see babysitters used by their contacts on LinkedIn, from their kid’s school or their neighborhood. We use both manual and automated methods to vet our users, including some innovative technology solutions that look at identity and profile. In fact, we are constantly looking at new technologies to improve trust.


2. What made you decide to start your business and/or switch careers?

Before I started UrbanSitter, I was working at Joie de Vivre Hospitality. The company sold, and the new role at the acquirer would have required a lot more travel. At that point, I had toddler twins and my husband also had a demanding job, so I decided to leave the company and take a year-long sabbatical.

During my time off, I started thinking about the sitter problem. I had been a babysitter in college, and when I was babysitting I always wanted a better way to organize my calendar. Plus, I hated to say no to parents. As I was researching the idea, I talked to moms about how they got sitter and nanny recommendations. I started talking to sitters, asking them about whether they would get involved in a company that enabled trust. Sitters said they would love this. A bunch of the sitters I was speaking to worked for agencies and the agencies paid every two weeks. So, right from the start, we wanted to improve upon that and pay the sitters in a more timely manner for their work through direct deposit.

After all of these conversations, I ran the idea by my friend who is an engineer. He ended up being an UrbanSitter co-founder, and he built the first version of the website. In the end, what was meant to be a one-year leave of absence, ended up being two months.


3. Was there one moment that gave you the confidence that this was a good idea?

Yes, two instances gave me confidence. First, when we launched the beta product in San Francisco (where I live) and people I didn’t already know started using it. Second, nine months after launch, I was at the park with my kids, and they were being crazy. I started chatting with another mom and told her that my husband was out of town to explain away their behavior and my matching look of defeat. The mom turned to me and said that next time he was away I should book an UrbanSitter.


4. What obstacles did you face in getting started and thinking of yourself as an expert in a new setting?

The biggest obstacle to launching was stripping out ideas that I had conceived as integral to the UrbanSitter offering. Because we started the company with our own capital and elbow grease, we wanted to launch with the minimum viable product to get it up and running. This was hard for me because at launch the company was going to be different from my vision of what would make the website cool, but it was the right thing to do

And then on top of releasing my complete vision, I had trouble paring down to the most important idea. That took some time. After some work, we decided to launch the website with scheduling along with the trust and recommendations technology. Then after a year, we added the mobile phone app, and then we added payment. I would say the website had everything I originally imagined it would after four years of working on it.


5. Was there ever a particularly tough time that in retrospect was a priceless learning moment?

Early on, I had a co-founder in mind. She would have been amazing, but ultimately the time she had to give to the business didn’t match the time I needed from a partner. I knew that UrbanSitter needed to be a venture-backed business, which meant high-pressure to grow, and I had to tell her that it wasn’t going to work. Now we have the bandwidth to take someone wonderful part-time, but in those early years, we didn’t.

For me, the lesson was: be honest and have the tough conversation. As a parent, I am able to have those tough conversations more efficiently. I know that I can address this now and it will suck. But it won’t happen again. Juggling family and work, I just don’t have time to avoid problems.


6. Were there any partnerships or advice that were particularly helpful?

Laney Whitcanack, co-founder of Big Tent, was incredibly helpful to me. Our businesses were a nice match because Big Tent was a few years ahead of us and addressed a similar target audience, but didn’t compete with UrbanSitter. She gave me the lay of the land and good advice on basic things that saved me a lot of time and money.


7. What are some successes you have had with your business that make you proud?

When I founded UrbanSitter, I was more focused on the parent side, even though I had been an avid babysitter in high school and college. I am always pleasantly surprised by how much sitters like UrbanSitter too. We constantly get love letters from sitters telling us how it allowed them to grow their own sitting business, subsidize college, and move to another city with a babysitting track record that helps them find work quickly.

As our marketplace grows, we can deliver parents more and better choices. For instance, if your kid has type 1 diabetes, you can find a sitter who has nursing experience or is in nursing school and has learned best practices for treating diabetes. Unique matches like that are very cool. I have a friend who has a child with special needs, and after he posted a job, 10 qualified sitters responded.

On the corporate side, I’m proud that we are now in 40+ cities, and that the company is cash flow positive in many of our markets. And I am proud that we have retained our team and that our co-founders are still a part of the business.


8. What are some of your current challenges?

I’m not a salesperson by nature, and as a kid, I was a passive Girl Scout cookie seller. I would stand in front of our local convalescent home and wait for people to come out. As a result, venture capital fundraising is probably my biggest challenge.

We just closed our third round of funding. Raising capital is time-consuming, but obviously key for the business to grow. It is interesting to me because every time it gets less intimidating, and I enjoy pitching more. Now, I don’t take it personally anymore. I take things less personally than I did earlier in my career. When I am in the fundraising mode I spend about 20% of my time in investor meetings. But if you include preparing for the meetings and the due diligence, it is about 40% of my time.


9. Have there ever been moments when you regretted what you started or had to abandon part of the plan?

We had to abandon one of our pricing options several years ago. We had this idea that parents could pay us each time they booked a new sitter. We called it a Sitter Introduction Fee. The parent could then book that sitter over and over again without any additional fee. When they came back to book a new sitter, which we knew they would need to do based on our data, they would then pay us again to meet that sitter. While the model actually aligned well with our data on how people use the site and how often they need a new provider, it was just too difficult for customers to understand, so we abandoned this payment option.


10. What would be your biggest piece of advice you would give to yourself ten years ago?

Worry less about what other people think–both personally and professionally. When I let go of the worry about judgment, it frees me up.

Date of Conversation: July 26, 2017

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