Three lessons from scaling product teams at Zenefits and Ravelin

When you’re scaling a company, a lot can go right, but a lot can also go wrong. This post is a distillation of the lessons I learned from scaling two product teams, first at Zenefits and then at Ravelin.

I joined Zenefits when we were ~50 people doubled up on desks in the Mission in San Francisco. The next three years were a blur. The company grew from 50 to 1,000+ employees and the product team from 2 to ~40. I joined Ravelin when we were 16 employees huddled in a basement in Clerkenwell, London. We grew from 16 to 41 employees in two years and I led the product team from 1 to 5 people.

While Zenefits and Ravelin were different beasts, three principles rang true for building and scaling product teams:

1. Establish a hiring process early on

At early stage startups, adding process is counterintuitive. You’re moving fast so why add hurdles that slow you down? As the Navy Seals say, “slow is smooth, and smooth is fast.” In reality, process can help you speed up by:

  • Giving your team a clear checklist for execution, minimizing the cognitive overhead of interviewing
  • Increasing your chances of hiring the right people, avoiding costly hiring mistakes that destabilize your team… and ultimately lead to more hiring
  • Creating a better candidate experience, helping you close top talent

Each hire is an important decision, so investing time upfront to define a process is worthwhile. Once you’ve defined an initial blueprint for your process, use each candidate to validate and improve it with your team.

What should your hiring process look like? And how do you close top talent? More to come on this in future posts.

2. Balance external hires with internal hires

Hiring is hard. You need to attract top talent in a competitive market. You need to decide whether a person’s right for your company with limited information. Product hires at early stage startups are critical to the success of a company. TLDR… hiring is necessary, but easy to screw up.

So why not mitigate this risk by hiring internally? Internal hires come with several benefits:

  • Domain knowledge. Client-facing roles know the customers’ needs and pain points. Operations roles know the ins-and-outs of the business. They’ve attended countless all hands meetings and know the company’s vision, positioning in the market, and more.
  • Product knowledge. A customer success manager diagnoses bugs and product failures. An integration manager knows how to configure your product. They may not know everything about how the product works, but they have a head start.
  • Existing relationships. They’ve established a rapport with their team. They know how to communicate with other teams. They may have even gained the trust of engineers. This is gold.

So you’re probably thinking “but if an operations manager’s never been a product manager… isn’t that a risk?” Yes, it is. I’m not saying that everyone can successfully transition to product management, but people who have potential — analytical horsepower, curiosity, hustle — are worth taking a bet on.

You can also do things to help internal hires succeed:

  • Pair them with more experienced product managers
  • Center development goals on exposure to different facets of product management, such as project management, product analytics, or understanding the tech stack
  • Encourage trainings and learnings outside of work, such as attending General Assembly courses or meetups

I made the transition into product management at Zenefits because our CEO made a bet on me. I’ve since made bets on teammates at Ravelin and couldn’t have been more happy with the outcome.

3. Don’t forget “team time”

Being a product manager can be isolating. Building out a team can be chaotic. As you build your team, be sure to carve out time for your team to minimise this isolation and chaos.

“Team time” generally has three purposes: alignment, creation, and celebration.

A. Alignment

This is typically a weekly team meeting. The goal is to align on:

  • Issues. What problems are people facing? What can we do both as individuals and a team to solve these?
  • Roadmap & Strategy. What is our roadmap for the next 4–6 weeks? 1–3 months?
  • Process. What’s working? What’s not working? How can we fix it?

You can use 1:1s with individual team members to get a pulse on these questions, but the team meeting is an open forum for the team to align — both mentally and tactically.

B. Creation

Building a team is like building a company. If you don’t intentionally craft your team’s vision, values, and guiding principles, things are likely to going awry.

For example, let’s look at guiding principles. What are the principles that guide your team’s behavior? “Ship to learn” was one we stood by at Ravelin. Your team is likely already operating under these, but until you take the time to define them, they don’t exist.

If you haven’t defined them, get the team together for an hour to brainstorm. Draft a laundry list of principles. Choose your top 10. Test them out for a week or two. Refine them. Make posters. Broadcast them to the rest of the company. Live and breathe them.

They’ll inevitably evolve over time but will serve as a compass for your team’s decisions.

C. Celebration

Celebrating wins and progress are important! And yet they’re easily forgotten in the day-to-day hustle of startup life.

Celebrations come in various forms. A team lunch or dinner is a great way to reflect on accomplishments from the quarter. Cookies or cakes are always a hit for celebrating a milestone. Publicly recognizing your team’s progress at a company all hands meeting or on Slack are also ways to celebrate.

No matter how big or small, celebrations can go a long way to keep morale high.

Have you scaled a product team? What lessons have you learned? I’d love to hear from you! Feel free to share here, Twitter DM @natsandman or email me at natalie.sandman[at]

Thanks to Shannon Goggin and Jimmie Sandman for reading drafts of this post.


This post was originally published on Medium on May 13, 2018.