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# Lessons from Matt MacInnis, Chief Product Officer at Rippling
- URL: https://www.antoinebuteau.com/lessons-from-matt-macinnis-coo-of-rippling/
- Published: 2025-08-10T21:21:55.000Z
- Updated: 2026-09-05T03:28:31.000Z
- Description: Matt MacInnis, Chief Product Officer and former COO at Rippling, shares lessons on product leadership, high standards, urgency, organizational entropy, and scaling companies.
- Author: Antoine Buteau
- Tags: Profile, Operations, Business Leaders & Executives Profiles

In his role as Chief Product Officer—and formerly long-time 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.

![Infographic for "Lessons from Matt MacInnis, COO of Rippling".](https://www.antoinebuteau.com/content/images/2026/07/f2f532c6-1ff4-4f55-ad06-999e805c0fb5-52c7aca9-f5ad-4734-b361-6afb14f7d063-optimized.webp)

## Operating Cadence, Product Quality and Execution

1. **On Fighting Entropy:** "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.'" [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
2. **On Preserving a High Bar:** "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." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
3. **On Executive Intensity:** "Without the intensity that executives bring to each project, MacInnis says it will drift in terms of velocity or precision." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
4. **On the Danger of Slow Velocity:** "Tiny markets and a poor team will kill a company. But slow velocity is the most lethal." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
5. **On Executive Impatience:** "Every successful outcome is led by an executive who is deeply impatient." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)[\[2\]](https://www.youtube.com/watch?v=1vVvk9VwVEw&ref=antoinebuteau.com)
6. **On Impatience as Accountability:** "Impatience is about accountability. It's about challenging assumptions and asking somebody why something can't be done faster, sooner, or better." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
7. **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?'" [\[2\]](https://www.youtube.com/watch?v=1vVvk9VwVEw&ref=antoinebuteau.com)
8. **On Doing the Highest-Priority Thing First:** "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." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
9. **On Going to See for Yourself:** "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." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
10. **On Being Micro-Interested:** MacInnis reframes micromanagement by stating, "I'm not a micromanager, I'm micro-interested." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
11. **On Avoiding Overwrought Process:** "The worst bureaucracy is the overwrought process." [\[6\]](https://cooalliance.com/podcasts/ep-114-rippling-chief-operating-officer-matt-macinnis/?ref=antoinebuteau.com)
12. **On Developing Process Bottom-Up:** Processes should be developed "bottom-up" based on what is already being done efficiently, not created in a hypothetical, top-down manner. [\[6\]](https://cooalliance.com/podcasts/ep-114-rippling-chief-operating-officer-matt-macinnis/?ref=antoinebuteau.com)
13. **On Matching the Operating System to the Work:** Match people and process to the work's required upside and volatility: exploratory product areas need high-alpha experimentation, while mature and mission-critical systems need low-beta reliability. — [*Lenny's Podcast*](https://www.youtube.com/watch?v=O%5FW76LR77Vw&ref=antoinebuteau.com)
14. **On Scalable Product Quality:** Use lightweight product-quality checklists that state the minimum shipping standard and evolve continuously as failures reveal missing controls. — [*Lenny's Podcast*](https://www.youtube.com/watch?v=O%5FW76LR77Vw&ref=antoinebuteau.com)
15. **On Making Cultural Systems Memorable:** Give important internal systems distinctive language so they become shared vocabulary rather than another generic process employees ignore. — [*Lenny's Podcast*](https://www.youtube.com/watch?v=O%5FW76LR77Vw&ref=antoinebuteau.com)

## Leadership, Feedback and Executive Judgment

1. **On the Idiosyncratic 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." [\[2\]](https://www.youtube.com/watch?v=1vVvk9VwVEw&ref=antoinebuteau.com)
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." [\[2\]](https://www.youtube.com/watch?v=1vVvk9VwVEw&ref=antoinebuteau.com)
3. **On the COO as a Complement:** "The COO should be the yang to the CEO's yin." [\[4\]](https://www.youtube.com/watch?v=GcfK042VY4g&ref=antoinebuteau.com) This means if the CEO is strong in sales and marketing, the COO should likely focus on operations, and vice versa. [\[4\]](https://www.youtube.com/watch?v=GcfK042VY4g&ref=antoinebuteau.com)
4. **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." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
5. **On the Company-Specific COO Role:** The COO role is "idiosyncratic to any company and in particular to any CEO." [\[4\]](https://www.youtube.com/watch?v=GcfK042VY4g&ref=antoinebuteau.com)
6. **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." [\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
7. **On Trust Between a CEO and COO:** "You can't manufacture trust. It's an inconvenient truth." [\[6\]](https://cooalliance.com/podcasts/ep-114-rippling-chief-operating-officer-matt-macinnis/?ref=antoinebuteau.com)
8. **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." [\[6\]](https://cooalliance.com/podcasts/ep-114-rippling-chief-operating-officer-matt-macinnis/?ref=antoinebuteau.com)
9. **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." [\[6\]](https://cooalliance.com/podcasts/ep-114-rippling-chief-operating-officer-matt-macinnis/?ref=antoinebuteau.com)
10. **On Useful Discomfort:** Withholding feedback to avoid discomfort is selfish; high-performance teams make useful observations discussable even when they are hard to hear. — [*Lenny's Podcast*](https://www.youtube.com/watch?v=O%5FW76LR77Vw&ref=antoinebuteau.com)
11. **On Customer Escalations:** Treat customer escalations as gifts and study them directly, because the most painful cases expose where the product and operating system need to improve. — [*Lenny's Podcast*](https://www.youtube.com/watch?v=O%5FW76LR77Vw&ref=antoinebuteau.com)

## People, Culture and Hiring

1. **On Kindness as Good Business:** "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." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
2. **On Being Tough and 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." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
3. **On the Politics 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." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)[\[5\]](https://review.firstround.com/podcast/how-to-be-effective-up-and-down-the-org-chart-matt-macinnis-rippling-inkling-apple/?ref=antoinebuteau.com)
4. **On Lean-Team Performance:** "A team of five that ought to be seven performs much better than a team of nine or 10 that ought to be seven." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
5. **On Hiring Former Founders:** Rippling is known for hiring former founders, with MacInnis being one of over 150 on the team. [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)[\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
6. **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." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
7. **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." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
8. **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." [\[1\]](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
9. **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." [\[5\]](https://review.firstround.com/podcast/how-to-be-effective-up-and-down-the-org-chart-matt-macinnis-rippling-inkling-apple/?ref=antoinebuteau.com)
10. **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." [\[2\]](https://www.youtube.com/watch?v=1vVvk9VwVEw&ref=antoinebuteau.com)
11. **On Comparable Hiring Signals:** Give candidates across seniority levels the same deliberately difficult, multidimensional case and evaluate how far and how thoughtfully each person gets rather than expecting completion. — [*Lenny's Podcast*](https://www.youtube.com/watch?v=O%5FW76LR77Vw&ref=antoinebuteau.com)

## Company Building, Strategy and Founder Judgment

1. **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." [\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
2. **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." [\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
3. **On Avoiding 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." [\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
4. **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. [\[4\]](https://www.youtube.com/watch?v=GcfK042VY4g&ref=antoinebuteau.com)
5. **On Earning the Right to Build 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." [\[4\]](https://www.youtube.com/watch?v=GcfK042VY4g&ref=antoinebuteau.com)
6. **On Platform Flywheels:** "The key to a good flywheel is when an incremental customer on the platform benefits every other customer." [\[6\]](https://cooalliance.com/podcasts/ep-114-rippling-chief-operating-officer-matt-macinnis/?ref=antoinebuteau.com)
7. **On Telling Your Own Story:** "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." [\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
8. **On Knowing When to Stop:** When repeated pivots still fail to produce unmistakable product-market fit, quit, reset the clock and cap table, and start again instead of letting venture incentives turn persistence into self-deception. — [*Lenny's Podcast*](https://www.youtube.com/watch?v=O%5FW76LR77Vw&ref=antoinebuteau.com)
9. **On Narrative Violations:** Look for the specific way a company violates conventional wisdom, because every outsized success needs an idiosyncratic reason the consensus is wrong. — [*Lenny's Podcast*](https://www.youtube.com/watch?v=O%5FW76LR77Vw&ref=antoinebuteau.com)

## AI, Integrated Systems and the Future of Software

1. **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. [\[4\]](https://www.youtube.com/watch?v=GcfK042VY4g&ref=antoinebuteau.com)
2. **On Foundations for Action-Taking AI:** Build action-taking AI on an integrated data model and integrated services; a conversational layer alone cannot safely orchestrate real business work across fragmented products. — [*AI Is Broken: Rippling CPO Matt MacInnis*](https://www.youtube.com/watch?v=TwoUB7pxb8c&ref=antoinebuteau.com)
3. **On Permissions Below the Agent:** Enforce permissions in the underlying system rather than asking the model to reason about access, so the agent automatically sees only what the user is allowed to see. — [*AI Is Broken: Rippling CPO Matt MacInnis*](https://www.youtube.com/watch?v=TwoUB7pxb8c&ref=antoinebuteau.com)
4. **On Earning Trust with Every AI Interaction:** Make agents cite their underlying data and preview consequential actions for human confirmation before execution, building trust through visible evidence and control. — [*AI Is Broken: Rippling CPO Matt MacInnis*](https://www.youtube.com/watch?v=TwoUB7pxb8c&ref=antoinebuteau.com)
5. **On AI and Engineering Leverage:** Treat coding agents as leverage that raises the return on each engineer and expands what teams can build, not as a simple rationale for reducing engineering headcount. — [*AI Is Broken: Rippling CPO Matt MacInnis*](https://www.youtube.com/watch?v=TwoUB7pxb8c&ref=antoinebuteau.com)
6. **On the Post-GUI Software Model:** Expect software interaction to shift from navigating graphical interfaces toward conversational agents that can answer, analyze, and execute work. — [*AI Is Broken: Rippling CPO Matt MacInnis*](https://www.youtube.com/watch?v=TwoUB7pxb8c&ref=antoinebuteau.com)

## Personal Growth, Career and Mindset

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. [\[2\]](https://www.youtube.com/watch?v=1vVvk9VwVEw&ref=antoinebuteau.com)
2. **On Asking What It Takes to Win:** 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?" [\[2\]](https://www.youtube.com/watch?v=1vVvk9VwVEw&ref=antoinebuteau.com)
3. **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." [\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
4. **On Outgrowing 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." [\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
5. **On Ego and 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." [\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
6. **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." [\[2\]](https://www.youtube.com/watch?v=1vVvk9VwVEw&ref=antoinebuteau.com)[\[5\]](https://review.firstround.com/podcast/how-to-be-effective-up-and-down-the-org-chart-matt-macinnis-rippling-inkling-apple/?ref=antoinebuteau.com)
7. **On Learning Product-Market Fit Early:** 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." [\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
8. **On Two Kinds of Hard:** "One was hard because it wasn't going well and one is hard because it is going well." [\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
9. **On Being Your Authentic Self:** "Anything other than your authentic self is a less good version, so stick with what's authentic." [\[6\]](https://cooalliance.com/podcasts/ep-114-rippling-chief-operating-officer-matt-macinnis/?ref=antoinebuteau.com)
10. **On Learning from Product 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." [\[7\]](https://www.youtube.com/watch?v=hoShhKmK8so&ref=antoinebuteau.com)
11. **On Learning the Engine as a Non-Founder:** "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." [\[3\]](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)[\[8\]](https://podcasts.apple.com/us/podcast/215-coo-rippling-matt-macinnis-learn-the-engine/id1510985491?i=1000675583900&ref=antoinebuteau.com)

---

Learn more:

1. [Everything in Business is About Fighting Entropy — Here's How Rippling Does It](https://review.firstround.com/everything-in-business-is-about-fighting-entropy-heres-how-rippling-does-it/?ref=antoinebuteau.com)
2. [How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)](https://www.youtube.com/watch?v=1vVvk9VwVEw&ref=antoinebuteau.com)
3. [#215 Matt MacInnis: COO Rippling on Flying the Growth Engine - YouTube](https://www.youtube.com/watch?v=NJQU9LCOutI&ref=antoinebuteau.com)
4. [From 0 to 11.25 Billion at Breakneck Speed with Matt MacInnis, COO, Rippling - YouTube](https://www.youtube.com/watch?v=GcfK042VY4g&ref=antoinebuteau.com)
5. [How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)](https://review.firstround.com/podcast/how-to-be-effective-up-and-down-the-org-chart-matt-macinnis-rippling-inkling-apple/?ref=antoinebuteau.com)
6. [Ep. 114 - Rippling Chief Operating Officer, Matt MacInnis - COO Alliance](https://cooalliance.com/podcasts/ep-114-rippling-chief-operating-officer-matt-macinnis/?ref=antoinebuteau.com)
7. [No Priors Ep. 83 | With Rippling COO Matt MacInnis - YouTube](https://www.youtube.com/watch?v=hoShhKmK8so&ref=antoinebuteau.com)
8. [215 COO Rippling Matt MacInnis: Learn the Engine - Apple Podcasts](https://podcasts.apple.com/us/podcast/215-coo-rippling-matt-macinnis-learn-the-engine/id1510985491?i=1000675583900&ref=antoinebuteau.com)
9. [10 Contrarian Leadership Truths](https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths?ref=antoinebuteau.com)
10. [Matt MacInnis on Lenny’s Podcast](https://www.youtube.com/watch?v=O%5FW76LR77Vw&ref=antoinebuteau.com)
11. [AI Is Broken: Rippling CPO Matt MacInnis](https://www.youtube.com/watch?v=TwoUB7pxb8c&ref=antoinebuteau.com)