Tomorrow, I start work as Head of Product at AnyPerk. This blog dissects my decision making process, so I’ll walk through this decision as well.

My first Product-related answer on Quora

It probably seemed a sudden move, but I started to push into the broader startup community a little over a year ago. I wanted to give something back of the experience I had accumulated over the years, meet other like-minded people and see what happened.*

After those many months, it was actually on AngelList that I saw AnyPerk was looking for product people (props to Naval). True to form, I emailed their CEO at 10 on a Friday night, heard back right away and met up with him the following Monday.

But that’s a lot about me, here’s what made me want to work here.
(if these compel you as well, check out our jobs page)

Product

It seems obvious, but after talking to a lot of entrepreneurs, I came to the conclusion that the products that got me most excited were those I wanted to use. I’ve met a lot people building great things, but I know my best work comes from my excitement in using the thing I build.

I joined Yammer when it was a mid-stage startup, helped it grow through the late stage and acquisition by Microsoft. Yammer had great perks, Microsoft has great perks, but finding and knowing about them isn’t easy.

More isn’t always better.

At Yammer, it was hard to know the extent of the perks and how to go collect all of your benefits. And don’t get me started on the user experience of Microsoft’s benefits site. The perks were awesome, but they were impossible to find and use.

Put simply: mature companies are spending a lot of time and money on benefits that their employees aren’t using, eliminating the positive effects of these expensive programs. The problem is solvable, but would never get proper attention from most IT organizations, which is basically the answer to “Why use SaaS?”

And in thinking about life after Yammer/Microsoft, going back to a small company without all of the perks: What had my family gotten used to when I worked at those companies? What would we need to cut back on so that I could go back to startup life?

Without knowing it, I already wanted to use AnyPerk, an app that…

  • Allows small companies to buy into a pool large enough to negotiate significant benefits for their employees
  • Maximizes the return on the investment big companies have already made in negotiating benefits for their employees

I’m betting a lot of people want to use that too.

People

Companies are people, my friend, and I have worked with people I wished I hadn’t. But Yammer built a team of hundreds of fun, frighteningly intelligent people. I knew I couldn’t go back from there.

From the first meeting with CEO Taro, AnyPerk reminded me a lot of early Yammer: the team all pulling together Sales/BD/Engineering, working hard, playing hard, very mindful of culture. This kind of excitement and cohesion can’t be faked.

Bonus point: I threw co-founder Sunny a curveball as he sat down to meet for the first time, “What’s your favorite Japanese whiskey?” Without missing a beat, he answered “Hibiki”, my favorite Japanese whiskey.

Traction

Every platform product starts out with the same chicken and egg problem. In this case, no one would pay for AnyPerk if there were no perks. And no companies would offer up quality discounts if there were no customers.

The team has dedicated a lot of time and attention on this problem and it has really paid off. The platform today is equally strong on perks and the Sales side.

And if the business side is already up and to the right, can the product make it go up-er?

Opportunity

As I was considering leaving Yammer, I had some great advice:

You get to trade on Yammer’s name once, make sure your next move continues this trajectory. If your next company’s a flop, your rep starts over.

I could say a lot about the opportunity of AnyPerk, about the ability to scale the market and adjacent markets,about publicly traded Japanese companies following this business model, but that’s pitch deck fodder.

Suffice to say, I took that advice to heart in vetting the jobs that have come up over the past year. AnyPerk stood out to me as a huge opportunity, a chance to continue that unicorn trajectory.

What’s Next

So that’s it, AnyPerk offered:

  • A product I wanted to use
  • A team I wanted to work with
  • Strong signs of product market fit
  • Huge upside

And, lastly, I saw a need to bring focus to the things I’ve learned and write about in this blog. Luckily they saw that too.

Time to get to work.

Check out the product here.
Check out our jobs here.
(I’ll be building a team of my own, but it’ll be a little while)


  • Side note: The Bay Area tech community is as humble and approachable as the hype. Every time I asked to meet, I did, for advice or an introduction, I got it. I’m proud to be part of this community and hope to live up to these examples with the companies I advise.