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
Spero Ventures


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.

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

Develop an operational cadence

Consistency of operations allows your team to relax enough so that they can generate their best work. “Your job as the manager is not to row. It’s to keep the boat steady and let everybody else pull,” Cooper explains. “If the boat’s rocking back and forth, you’re not going anywhere. And it’s super uncomfortable. Operating consistency lets people know that they can pull like hell and the boat’s going to go.”

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

Annual and semi-annual routines are essential for building a strong team. Performance reviews happen in January, when managers consider compensation and perform a full 360° peer review. A mid-year progress check-in review comes in July.

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

Skillshare blocks off half a day for each quarterly business review or “QBR.” That’s when the whole team reviews progress over the past quarter and discusses updated plans and priorities for the quarter ahead. That’s followed by a half-day of fun, splitting into a few groups — one that’s active, one for drinking and one that’s artsy. (They aim to fly each remote team member in for a QBR at least twice a year. ) Then, everyone reconvenes for happy hour.

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

On the last Friday of each month, the weekly Town Hall meeting becomes a Monthly All Hands meeting. That’s when Cooper and his team review financials and key metrics, as well as a key initiative or two. The meeting includes a quick Q & A, where anything goes, followed by lunch. “Transparency is big for us,” Cooper explains. “I can’t expect you to help me fix the engine if I don’t tell you where the problems are.“

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

Maintain connections through weekly and biweekly routines

Every team holds a departmental meeting each week or two when teams share information and address operating issues. These are big and costly (in time). That’s why teams run them with a clear objective, defined agenda, and a designated note-taker to capture decisions, questions, action items, follow-ups, and next steps.

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
Spero Ventures

Spero Ventures is an early-stage venture capital firm driven to deliver value to shareholders and society.