Matt Cooper sharing his keynote speech at Spero Ventures 2018 CEO Summit in Redwood City, CA.

CEO Mastery: Leadership Tips For Seed, Series A and Beyond

Skillshare CEO Matt Cooper shares insight on how to become a better leader for your company.

Great CEOs are made, not born.

Many people dream of becoming great CEO but learning what it takes to level up might surprise you. Skillshare CEO, Matt Cooper, has some pointers that should go in every chief executive’s toolkit. Cooper is on his fourth startup — two of which he’s served as CEO. Over the past 15 years his journey as a leader has taken him from highs like successful acquisitions to lows like large layoffs. At Skillshare, he recently oversaw the company’s successful $28M Series C raise and scaled the e-learning platform to over 5 million users.

At Spero’s CEO Summit in November, Cooper spoke to a curated group of promising, early-stage entrepreneurs. He detailed top takeaways over a career serving in executive roles at startups, breaking down his top tips for triaging and dealing with the biggest nightmares any chief executive could face. He also named the best accelerants for any organization, breaking down the top must-haves for every company.

Salves For A CEO’s Biggest Nightmares

Cooper has navigated gnarly challenges and difficult moments throughout his career. Here is his best advice for how to handle them with grit and grace.

Layoffs. This is probably one of the worst moments you could face as CEO, short of folding the entire operation. Cooper’s top tip for this is to rip the bandaid off. “There’s the saying, ‘If you have to eat shit, don’t nibble.’ When you have to lay off staff, think really hard about how many you need to let go. Even if it’s half the company, I exhort you to just do it. When the 2008 recession hit, Accolo was in a tough spot. We no longer had the dream market we’d been banking on. We wound up making three rounds of layoffs. It’s just catastrophic to the culture, and I wish we’d done just one big cut instead,” Cooper says.

Giving your board incredibly bad news. Once again, the “don’t nibble” advice goes here. “If you’ve got really bad news to deliver, get it all in at once. The steady stream of bad news is not how CEOs stay employed. In a difficult time, it’s not possible to over communicate to your board,” Cooper says.

Company starts tanking. Maybe a pivot isn’t paying off. Or your software springs major technical leaks. Whatever you do, resist the urge to flail. Cooper draws this analogy: he once did a rowing exercise with two athletic people and two non-athletic people. The team’s fastest time was when the strongest, most athletic two members kept their oars in the water to hold the boat steady while the two less athletic team members rowed. “Obvious lesson here: There’s an urge to grab the oar and row like crazy, particularly when things aren’t going well. But you’re going to end up making things a lot worse if you get in there and start thrashing around.”

“Sometimes the best thing you can do for your company is keep your oars in the water and let everybody else row.”

Terrible hires. “Sometimes you have culturally cancerous people. In one instance, there was a ringleader. I had a couple of conversations with this person and made clear what was OK and what wasn’t. They stuck around a few more months, then ended up leaving. To this day, I still kick myself for not saying ‘Appreciate your work, here’s a nice check — now off you go.’ This person left on their own terms, and it sent a message to everybody else that this kind of behavior was OK. As a leader, do not stand for that,” Cooper says. “When you see how you don’t want your company to be run, make the hard decision. Be magnanimous when you send them off, but send them off. Your culture is what you tolerate, not what you put on your website.

Biggest Accelerants for a CEO (and Startup)

There are several wins, that, if achieved, accelerate your company’s growth and well-being.

Clear decision-making processes. Cooper has also worked for his fair share of CEOs and seen different leadership styles. “Some CEOs are very consensus-driven — they’re about bottom-up management and getting buy-in from everybody. The challenge with that is it’s a lot of trouble to get everybody to move in the same direction. Others see it as their job to set the direction for the company. In that case, you might always have alignment but not necessarily the buy-in from the management team. Whether you choose to go with top-down or bottom-up, make sure the decision-making style aligns with what the company is going to do,” Cooper says. “If you have more time to make a change, figure out how to drive consensus and skip several levels down to do it. That’s ideal. But a lot of times you just don’t have the time, and it can be very contentious and 50–50. Make the call anyway.” For more leadership and management tips, Cooper recommends reading the book The First 90 Days.

Choosing the right nail to strike for your business. “You can kill your company searching for a silver bullet but consistent incremental improvement works every time. There’s a saying that smart people have a tendency to want to solve the hard problem that’s out of reach, rather than the easy problem that’s right in front of them,” Cooper says. One small tweak on the checkout page at Skillshare boosted conversion 10%. They’d previously spent six months on a difficult long-term project that wasn’t nearly as fruitful. Another time, the company was mired in figuring out its six-month plan, and took their eyes off the tech debt. It resulted in performance issues that slowed the whole site down; Cooper had to make the call to pause everything and focus on fixing the bugs.

Pivoting until you hit your A+ model. “B-players in an A+ business model will beat an A+ player in a B business model every time. In one of his earlier startups, Matt had a great team that worked super hard, but it was just a tough business. At a more successful startup, they were more in the mode of ‘letting everything run’ amid a hot market. “You can’t polish a turd. There are just certain businesses that have good bones and when you find it, you’ll know it.”

Getting the whole company to row in the same direction. Cooper breaks this down into a balance between these key ideas:

  1. Communicate your company’s most critical messages over and over and over… “You have a channel meeting, then you send an email. Then write a blog post. Then another town hall. Then another email and write another blog post. The next day, people still don’t remember what you said,” Cooper says. “Go overboard on your most important messages. If people aren’t actively making fun of you behind your back, you haven’t said it enough.”
  2. …But know when to shut up. “Beware of adding too much value. There’s a tendency of smart managers and executives to do this thing where they latch onto another person’s idea and start adding a bunch of suggestions. Suddenly it becomes your idea that you have to execute on, as opposed to their idea that they had to execute on,” Cooper says. “When are you actually making it better enough to offset the degradation of execution from being their idea versus your idea? Consider shutting up and saying, ‘Sounds great. Go get ’em. Look forward to seeing the results.”

Masterful listening is also selective listening. It’s not just about how you listen, but who you’re listening to. A CEO’s success hinges on her ability to stay in constant contact with the truth. “Find your truth-tellers. There’s a big difference in how you’re treated as CEO versus VP, and when you have 15 employees versus 75. When you’re a CEO, people respond very differently to you. They start to lie to you. I haven’t been CEO long enough to believe my own bullshit yet. I encourage people to feel free to tell me what they think.”

“When a CEO can find employees who will tell the truth and say it like it is, that is extraordinarily valuable.”

Hires who knock it out of the park. This comes down to two components: planning and vision. “Build a team from the top down. Ask if they’ve been where your company is going in two years. You need people who have muscle memory and knows where you’re going when you’re figuring things out on the fly,” Cooper says. “If I fly a plane and it’s my first time, that’s pretty scary. I want people with hands on the wheel experience who know things I don’t.”

A strong vision and mission is a critical recruiting tool. “You will not be able to outspend Google or Facebook. You need another draw. Finding people who want to help other people learn keeps Skillshare’s retention high,” Cooper says. “Everyone has something to contribute, that others can learn from. Our platform facilitates that connection and really gives people learning tools that they would never have otherwise had access to. Having a strong mission and vision if you’re trying to recruit in New York and San Francisco — there’s got to be some other draw besides salary.”

Building a strong support network. “You should have a great board, a network of advisors, mentors, people you can bounce ideas off. My executive team is my team. I don’t have to know everything. I shouldn’t know everything,” Cooper says. “I need people to push back and to have as sounding boards. You shouldn’t be doing this alone. I never want to be the smartest guy in the room. I want to be the dumbest. Your job is to surround yourself with the right people so that it’s never lonely and you’ve always got the backup you need.”

“As a CEO, the highs are higher and the lows are lower. But when things are working, there’s nothing better.”

In Conclusion

Cooper has seen a lot in his years as a startup executive. Critical components to being a good CEO include communication — both strong communication to the board and to employees. It’s also about decision-making: Taking decisive action and being clear with your support team how decisions will be made. Execution: Pursuing both the right business model and incremental improvements to the existing product. It’s also a mental game, understanding when to butt in and when to stay out, as well as cultivating a support network so that you’re not toiling alone.

Finally, remember to have fun! Being a chief executive isn’t for the faint of heart, but it will be an incredibly rewarding journey, especially if you arm yourself with the right tools to be successful. “As a CEO, the highs are higher and the lows are lower. But when things are working, there’s nothing better,” Cooper says.


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Matt Cooper presents at Spero Ventures CEO Summit, 2018.