Startup Interview with Henry Shapiro, Co-founder at Reclaim.ai

Please tell us briefly about your background.

My name is Henry Shapiro, and I’m the co-founder of Reclaim. I’ve worn a lot of hats over the years, but my core focus has been on product management, most recently at New Relic before my cofounder and I departed to work on Reclaim full-time!

I was born and raised on the east coast, but fled to Portland, OR for college 14 years ago and never looked back 🤪

What's your startup called? And in a sentence or two, what does it do?

We’re called Reclaim (or Reclaim-dot-ai if that’s more your cup of tea), which is an intelligent calendar assistant that blocks adaptive time for anything you care about. Think of your calendar, and now think of what it might look like if it knew what mattered to you -- that’s Reclaim in a nutshell.

What is the origin story?

My cofounder and I were product leaders at New Relic, a hypergrowth company that went from dozens to hundreds to thousands of employees in a matter of several years. We learned firsthand that as companies grow, calendars get hectic. Too many meetings, not enough time to focus on your most important work, and lots of after-hours and weekend work. Yuck.

We also noticed that as companies grew, they had a really hard time answering “simple” questions, like “What the hell is everyone working on?” or even “How many people are working on our top priorities?”

We started building Reclaim with the intention of basically addressing two major problems across individuals and organizations:

1. Giving people an easier way to protect their schedules and manage their time week-to-week
2. Helping teams and organizations to get a better handle on where their time is going, where teams are overstretched, and what distractions are in the way

We fundamentally believe that enterprises don’t buy software, people do. So we’ve focused all of our efforts on problem #1, which we believe leads us to a big opportunity around problem #2.

What do you love about your team, and why are you the ones to solve this problem?

What I love about our team (and we’re a small one!) is that we all possess a tremendous amount of ownership and autonomy. Everyone is a bus driver, and in a small company you sort of have to be. I love how scrappy everyone is, and how much stuff we are able to accomplish with a small number of people in the mix. I also love our culture as a group: we try not to take ourselves too seriously, and at the same time we have an immense amount of empathy and urgency to solve the key problems that face our users.

I believe we’re the right people to solve this problem because we’ve lived it, and we deeply understand that this isn’t just a “software problem” -- it’s human, it’s emotional, there are power dynamics at play, and the calendar is a really sensitive space where people can win or lose lots of social capital. We’ve built Reclaim with these values in mind.

If you weren’t building your startup, what would you be doing?

Great question. Riding dirt bikes? Teaching middle school history? Climbing the corporate ladder? Hard to say, but I’m glad I chose this path.

At the moment, how do you measure success? What are your core metrics?

We have a few key metrics that we track aggressively, and most of them have to do with customer love, adoption, and engagement:

1. PMF ranking: we have a survey that gets sent to any user who has used Reclaim for >2 weeks, asking them how disappointed they’d be if they couldn’t use Reclaim. We want the “Very Disappointed” set to make up >40% of our userbase.
2. Retention: we have extremely positive retention rates among our userbase, but we track them aggressively to ensure that people stay with us once they convert and sign up.
3. Signup → Conversion Rate: we track our conversion rate from the moment someone clicks the signup button to the moment they finish onboarding, and we’ve had some pretty world-class results over the past year.
4. Smile Curve: we track what % of users use Reclaim 30d in a row, which tells us if we’re really becoming a daily habit for people.

We also think about qualitative and anecdotal signals (e.g., positive tweets, Intercom love letters from users) but the metrics give you confidence in the anecdotal stuff.

What’s most exciting about your traction to date?

I’d say the biggest thing is that we’re being used across over 5,000 organizations, and we’ve barely been in market for ~1 year. It’s clear we’ve tapped into a very real pain for people, and we haven’t even launched the team edition of Reclaim yet.

The runner-up would be the spread we’re seeing organically in organizations. Hundreds of companies are using Reclaim across massive swaths of their employee base, even without us doing any kind of targeted outreach. Again…we’re floored by that.

What technologies are you currently most excited about, and most worried about? And why?

I think the fact that we’ve proven remote work can actually be successful (we didn’t intend to start a remote company pre-COVID, but we’ve been doing it for 2Y now) is validation that the technologies are really there to support it. That side of the technology equation is super exciting and I think if there’s a silver lining from the shitshow of the past couple years, it’s that we’ve enabled a whole set of businesses to hire and build teams without having to stand up big, expensive physical plants.

I’m most worried about technologies that pollute our environment and contribute to the accelerating emergency that is climate change.

What drew you to get published on HackerNoon? What do you like most about our platform?

The thing I love the most about HackerNoon is the immense amount of practical knowledge y’all distribute to the startup ecosystem. In fact, when we launched our first feature on ProductHunt, we used this HackerNoon article as our reference architecture.

What advice would you give to the 21-year-old version of yourself?

Another great question. I graduated college a bit early at age 20, which was back in 2010 when we were still reeling from the recession. Jobs were hard to come by, and having majored in something that was -- from my perspective -- pretty impractical (history), I was pretty down on my ability to forge my own path.

I think the advice I would have given myself is to just keep pushing, and to not let what you studied or majored in define your career path. If you say yes to enough things, and take the opportunities that present themselves, some pretty bananas stuff can come from it.

What is something surprising you've learned this year that your contemporaries would benefit from knowing?

There are actually far fewer productive hours in a workday than any of us are willing to admit.

Anyways…vote for us here!