Lessons from Matt MacInnis, COO of Rippling

In his role as COO of Rippling, and through his extensive experience as a founder and executive, Matt MacInnis has shared a wealth of knowledge on building and scaling successful companies. His insights often revolve around the critical themes of maintaining high standards, fostering a culture of urgency, and understanding the human dynamics that drive a business forward.

On Fighting Entropy and Maintaining Velocity

A central theme in MacInnis's philosophy is the concept of "organizational entropy", the natural tendency for companies to slow down and become less decisive as they grow. He offers pointed advice on how to combat this force.

On the core job of an executive: "Everything in a business is about fighting entropy. As an exec your mandate is to never lose sight of the feeling that 'If I take my eyes off of a project, it'll slow down a little bit.'" [1]
On maintaining high standards: "You have to remind yourself that there will always be constituents in your business for going just a little bit slower, or for spending just a little extra budget. Execs need to be the opposite—you need to be a constituent for the high bar." [1]
On the impact of executive intensity: "Without the intensity that executives bring to each project, MacInnis says it will drift in terms of velocity or precision." [1]
On the lethal nature of slow velocity: "Tiny markets and a poor team will kill a company. But slow velocity is the most lethal." [1]
On the importance of impatience: "Every successful outcome is led by an executive who is deeply impatient." [1][2]
On the definition of impatience: "Impatience is about accountability. It's about challenging assumptions and asking somebody why something can't be done faster, sooner, or better." [1]
On challenging deadlines: "If a team says they're going to do X by next Friday, you should reflexively be asking, 'How about this Friday?'" [2]
On the illusion of product-market fit: "If you think you might have product market fit, you don't. Because product market fit feels like getting on a roller coaster." [3]
On the feeling of true product-market fit: "When you have product market fit there is no doubt... every minute feels like that at Rippling." [3]
On the danger of premature scaling: Knowing with confidence whether you have product-market fit is crucial because "you won't scale prematurely. you won't hire too much there's all kinds of errors you can avoid as a founder." [3]

On Leadership and Executive Function

MacInnis provides a clear-eyed view of what it takes to be an effective leader, emphasizing authenticity, focus, and a willingness to engage with the details.

On the nature of the CEO role: "Every CEO succeeds for his or her own reason. The CEO job is inherently idiosyncratic. It's specific to the market you're in, it's specific to the team you have, it's specific to the moment in time, it's the scale of your company." [2]
On authentic leadership: "Show up and be yourself from day one... trying to be somebody you're not is the only Sure Fire way to get less than what you're entitled to." [2]
On the COO as a complement to the CEO: "The COO should be the yang to the CEO's yin." [4] This means if the CEO is strong in sales and marketing, the COO should likely focus on operations, and vice versa. [4]
On the importance of focus: "If there's any one secret to 'effectiveness,' it's that great executives do one thing at a time and they do the high-priority things first." [1]
On the "Go and See" principle: "It means leaders shouldn't live in the dashboard. When the anecdotes disagree with the data, you've got a problem. You have to go and see for yourself, which means getting straight down to the atomic level of the function you're interested in to gather context." [1]
On being "micro-interested": MacInnis reframes micromanagement by stating, "I'm not a micromanager, I'm micro-interested." [1]
On the burden of difficult decisions: "The hardest questions are always going to bubble up onto my plate, so if there was an easy or obvious answer, it would've been done below me. By definition, execs get all the nuclear stuff." [1]
On the mindset of a third-time founder: They've learned that many of the things they worried about the first time, like the colors on a website, don't matter as much as getting the right product to the customer and focusing on sales and win rates. [2]
On the right question to ask: Instead of the "fundamentally ego maniacal question" of "what if I look like an asshole?", the right question is "what's it going to take to win?" [2]
On the value of failure: "The experience of starting your own company and failing is an extraordinarily valuable experience... my ego was ground down to a fine powder through that process." [3]

On People and Culture

A company's success is inextricably linked to its people and culture. MacInnis advocates for a lean, high-performing environment built on respect and accountability.

On the importance of kindness: "Every day, almost 3,000 people choose to get out of bed and put their limited energy into our company... if you don't treat people with respect, they can go somewhere else. The long and short of it: It's bad business to be unkind to people." [1]
On being tough but respectful: "You can be tough on people, and you should be tough on people. You should demand the very best of them. You should make them uncomfortable. You should hold them accountable." [1]
On the dangers of overstaffing: "One of the most sinister side effects of overstaffing is politics. When you have too many people, they won't have enough ultra-high-priority work to do." [1][5]
On the performance of lean teams: "A team of five that ought to be seven performs much better than a team of nine or 10 that ought to be seven." [1]
On hiring former founders: Rippling is known for hiring former founders, with MacInnis being one of over 150 on the team. [1][3]
On identifying top talent: "When it comes to holding people to a standard or finding rare talent who's hungry to win and terrified of losing, those are two sides of the same coin. They have to go together." [1]
On empowering star players: When you find people who love their work, "load them up with responsibility in excess of what you think they would be capable of on paper." [1]
On the reality of startup life: "If they wanted in on the startup adventure, then that's what they're in for. As a leader, that's something you have to be comfortable with saying out loud." [1]
On the source of politics: "Politics to me, emerges from an environment where people don't have enough work to do, to put it simply." [5]
On the cure for politics: "The cure for politics is not to lecture people about being apolitical; it's to make sure the team has too much to do." [2]

On Building a Company

From product strategy to the role of the COO, MacInnis offers practical advice on the mechanics of building a lasting enterprise.

On the "compound startup" model: This approach involves building multiple products at once, which is contrary to the common wisdom of focusing on one thing. [4]
On earning the right to be a compound startup: "You are in a market where your product has the right to be a compound... or it's not. The market's going to give you the right to do that or it's not." [4]
On the power of integrated data: Rippling's advantage comes from starting with the design assumption that they would have access to every piece of data about an employee, enabling them to build features other systems can't. [4]
On the flywheel effect: "The key to a good flywheel is when an incremental customer on the platform benefits every other customer." [6]
On avoiding bureaucracy: "The worst bureaucracy is the overwrought process." [6]
On developing processes: Processes should be developed "bottom-up" based on what is already being done efficiently, not created in a hypothetical, top-down manner. [6]
On the role of a COO: The COO role is "idiosyncratic to any company and in particular to any CEO." [4]
On the psychological difference between CEO and COO: "It's an order of magnitude less stressful because I don't own everything... I could quit... Parker can't quit." [3]
On trust in co-founder/COO relationships: "You can't manufacture trust. It's an inconvenient truth." [6]
On the importance of storytelling: "It's a missed opportunity to not engage in these channels like it's really important Otherwise other people tell your story for you. and that's not cool because they're not going to tell the right one." [3]

On Personal Learnings and Mindset

MacInnis's journey as a founder and COO has forged a distinct and often contrarian perspective on what it takes to succeed.

On the futility of pleasing your younger self: "I spent my 20s trying to please my 18-year-old self which in hindsight was not a great use of my life energy." [3]
On the ego grind of a struggling company: "If the motive behind your company is ego and your company doesn't do well then almost by definition... the business sucks therefore you suck. and like that was a voice in my head for a lot of that experience." [3]
On the fatalistic view of startups: "The outcome of your company is predetermined by the universe You're just showing up to run the experiment and find out what the answer is." [2][5]
On the value of early-career experience: He advises those not starting a company to first "go work at a company that has some traction and like has product market fit so you get a dose of that... you can be inoculated against product market fit confusion." [3]
On the two types of "hard" in startups: "One was hard because it wasn't going well and one is hard because it is going well." [3]
On the importance of being your authentic self: "Anything other than your authentic self is a less good version, so stick with what's authentic." [6]
On the COO's relationship with the board: In a group setting with the board, he defers to the CEO, Parker Conrad, to avoid the appearance of "parents arguing in front of their kids." [6]
On one-on-ones: "If your one on one is not the space that offers an employee the opportunity to talk about themselves or their relationship with you or others, you're guaranteed they have no other place for it." [6]
On learning from feedback: When launching new and potentially controversial products like an AI performance management tool, he stresses, "we're really committed to learning from them and making sure that we make this a tool that works for everybody." [7]
On the non-founder's role: "One of the most important things a non-founder can do... is to learn how to operate in the context of the company they're joining... An executive coming in to fly your airplane better learn the engine." [3][8]

Learn more:

Lessons from Matt MacInnis, COO of Rippling

On Fighting Entropy and Maintaining Velocity

On Leadership and Executive Function

On People and Culture

On Building a Company

On Personal Learnings and Mindset

Written by Antoine Buteau

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