How You Run Your Startup Will (And Should) Change

Skillshare CEO Matt Cooper likens his company’s operating model to their product. It’s constantly improving.

Spero Ventures
Mar 5, 2020 · 5 min read
Matt Cooper presents to founders at CEO’s at Spero Ventures Founder Summit in October 2019.

Founding a tech startup is sexy. Running one, often, is not. That’s why tested and trusted tactical advice is gold. At the 2019 Spero Ventures Founder Summit, Skillshare CEO Matt Cooper shared the routine processes he and his team have built to manage and grow their business over the past three years. If it sounds routine, it is. But Cooper swears that good process promotes great work.

To build it, you have to start somewhere.

Keep in mind, every startup’s process will evolve over time. “What works today won’t work in a year and wouldn’t have worked a year ago,” Cooper explains. Take the time to step back and ask, ‘What’s working and what’s not?’ Then give new changes time to take root, so they can help you grow.

Skillshare is a global learning community for creative and curious people, offering online classes in illustration, photography, design, technology and other disciplines. The company’s 90-some team members work in New York, Colombia, and sites throughout the Midwest, Canada, the UK, Romania, and Costa Rica. Cooper recently oversaw Skillshare’s $28M Series C raise and scaled the e-learning platform to upwards of 5 million users.

But this isn’t his first rodeo. It’s his fourth startup. Experience has taught him that consistent operations, solid performance reviews, and quarterly, monthly and weekly strategies, help Skillshare achieve its annual goals. That known rhythm also supports meaningful engagement for every member of a growing team. Structure breeds creativity.

Scaling up? Here’s how.

“Put some space between your big, strategic decisions. Then give them time to play out.”

Develop an operational cadence

Next, create a consistency of strategy. Smaller companies often suffer from the whipsaw effect: When something isn’t working this week, they decide to go the other direction and try something new next week. Instead, put some space between your big, strategic decisions. Then give them time to play out.

Balance short- and long-term strategic decisions. Cooper and his team work to balance their three-, five-, and 10-year vision with the stuff they need to tackle this week, this month, and this quarter.

Yearly routines keep the train on the tracks

Skillshare starts annual planning for the following year in Q4. The company’s approach combines bottom-up input from the entire team and top-down structure and guidelines from management.

This starts with a company-wide engagement survey. “We try to get as many ideas, concerns, and things they’re excited about trying all on the table,” Cooper says. Leaders then consolidate the contributions and come up with a high-level strategy, including three primary goals for the year.

OKRs (shorthand for Objectives and Key Results) are a method for tracking progress toward goals. Some leaders use them as a way to measure personal performance, but Cooper considers them a key alignment tool, instead. That way, OKRs become realistic but aggressive — and team members stretch themselves, Cooper says. “We want people thinking bigger.”

Quarterly routines fuel your teams

The company’s product and engineering teams update their product roadmaps and priorities during a quarterly roadmap refresh. These offer a deeper dive into what they’re building and how projects are shaping up, Cooper says.

“I can’t expect you to help me fix the engine if I don’t tell you where the problems are.”

Simple monthly routines build momentum

With these financials and metrics in mind, every team member then updates their OKRs. Every month.

Maintain connections through weekly and biweekly routines

Each Monday, the executive team and directors meet to discuss weekly metrics and progress toward OKRs. This business operations or ‘BizOps’ meeting is a chance to share progress and identify new opportunities or problems early. “Having a strong, well-informed, super-engaged director level is where a lot of the successes come from,” Cooper says.

The management team holds two other weekly meetings. The ‘flex agenda’ is as it sounds: a free-for-all to share information and talk about issues that need more attention. The second is strategy, when they focus on bigger topics, including decision making and innovation.

Each manager holds a 1:1 meeting with his or her direct reports once every two weeks. The direct report sets the agenda, and the manager aims to serve. Cooper likes the model of the “4Ps,” which cover:

  • Plans (quarterly goals)
  • Progress (how you moved things forward)
  • Problems (where you’re stuck) and
  • Priorities (where you are focused).

The Friday Town Hall is Skillshare’s weekly all-hands meeting. Leaders briefly cover business metrics, management thinking, spotlights on new features and general housekeeping.

“Aim for structure that’s consistent, not dogmatic.”

Structure supports healthy growth

You want every member of your team to know how they’re contributing — at every stage. That’s especially important, and increasingly challenging, as your startup ramps up.

When you’ve got 10 people in the same room, and everyone can hear every phone call, disseminating information and aligning around your big goals is simpler, Cooper explains. “As your company grows, alignment will scatter if you don’t have the right structure in place.” Aim for structure that’s consistent, not dogmatic.

At Skillshare, what worked with 30 employees doesn’t work with 90. And operations will continue to evolve as the company grows. Their process may be messy, but it’s deliberate — and constantly improving. “Things always look cleaner on paper. And that’s okay,” Cooper says. “An imperfect, inconsistent process still beats no process.”

Matt Cooper’s presentation was given Spero Ventures Founder Summit in October 2019. Watch the full talk below.

Spero Ventures

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