Understaff on Purpose, Never Be Chill: Matt MacInnis on Leading Rippling Through Entropy

MacInnis credits the phrase "extraordinary results require extraordinary efforts" to Dan Gil, chief product officer at Carvana. His point is that anyone who wants outcomes in the 99th percentile should expect to be uncomfortable, and anyone who finds themselves in the comfort zone at work has probably made a mistake. Effort is not sufficient for an extraordinary outcome, he says, but it is necessary.

He says the effort shows up in a thousand small moments rather than one grand story, such as a Friday-night escalation or a pile of new bugs to triage. Those moments separate great teams from good ones. Rippling's rapid growth gives leaders air cover to ask for the last ounce of energy, he says, whereas a company growing 30% or 40% will find it harder to get people to lean in on a weekend.

Lenny adds that he saw the same drive under Brian Chesky at Airbnb, and MacInnis recalls the relentless cycle at Apple under Steve Jobs, where the next iPhone started the moment the last shipped. In a valuable market, he says, any crack you leave will be filled by a competitor. He also argues that idle teams get distracted and lose morale, so keeping people busy and fired up tends to make them happier than a long slowdown.

MacInnis shares a management heuristic: executives cannot know the right budget, headcount or deadline in advance, so they must make a best guess and decide whether to err above or below the midpoint. For staffing, he says, understaffing is clearly the lesser evil. Overstaffed projects breed politics and, most importantly, get people working on items far down the priority list before anyone knows they are needed.

He calls that wasteful, slow and a source of what he calls crust. The advice is to understaff deliberately and always, with the wisdom lying in knowing when you have gone too far. At Rippling, everyone is constantly asking for more resources, and they arrive where affordable and appropriate, but he wants the company to feel that every project is understaffed.

Lenny quotes a line that good teams get tired and that is when great teams beat them. MacInnis says it came from a colleague who found it from a women's basketball coach, and that it fits his belief in running the engine at the redline. He loves sports and military parallels for leadership, noting that the long stressful nights are the ones people remember most fondly when the company wins.

Citing Rippling CEO Parker Conrad, MacInnis calls the idea that you mainly learn from mistakes largely a feel-good trope. He spent nine years on his first company, Inkling, from 2009 until its sale to a private equity firm in 2018, and certainly learned from that. But in roughly seven years at Rippling he says he has learned far more by watching success up close.

He offers an analogy: you would rather fly on a plane maintained by someone who has seen it done right a hundred times than by someone who has seen it done wrong a hundred times. His advice is to join a winning team at any career stage, and when reviewing resumes he is drawn to candidates who were at great companies during their growth phases. Success begets success, he says, and he thinks people in the Valley do not chase it enough.

MacInnis explains his move from COO to chief product officer. He had long been the executive who fixed failing functions everywhere except R&D, and looked across the floor at what he describes as a dumpster fire. After hiring mistakes in engineering and product leadership and two years of disarray, Parker Conrad slumped at the prospect of another search, and MacInnis told him he would do the job himself. He took it on in January 2025.

He found a product organization of talented people who were understaffed and had no single leader driving consistency. In his words it was locally optimized but globally incoherent, and under Conway's law the product experience reflected that. His first work was basic: standards for test coverage, a "factory inspection" before shipping, and a definition of product quality.

He admits his view from outside, which wanted careful adoption metrics, was naive because those foundations were missing. It is a cardinal sin for an executive to sit outside the mess and think they know the answers, he says; you need to be in the boiler room and study the system bottom up. He treats every problem from first principles, and only cares about adoption metrics where the product is stable and well instrumented enough to make them useful, such as the applicant tracking system.

MacInnis borrows from finance: alpha is outperformance relative to the index, and beta is volatility. The ideal asset has high alpha and low beta, and he applies the same lens to people, products and process. A zero-to-one product should chase alpha, while a mature product such as payroll should be very low beta, with more process accepted.

The design principle he draws is that processes exist for the sole purpose of lowering beta, but they suppress alpha, so they must be applied with care. His example is the product quality list, nicknamed "the pickle" (PQL), a lightweight checklist of standards for shipping. He picked a quirky name deliberately, to create a vessel for meaning that new joiners would recognize as unique to Rippling.

He tells a story: CEO Parker Conrad, who personally runs payroll for all 5,200 employees and installs every new app, hit a blank screen on a new feedback app because of a leftover feature flag. MacInnis gave the team direct feedback, then asked why the factory inspection missed it, and added a line to the pickle allowing one feature flag governing the whole product at ship. Iterating the checklist this way, he says, lowers beta with only a modicum of cost to alpha.

MacInnis says he relies on intuition built from thousands of candidate conversations, and contrary to HR convention he thinks that is fine so long as you decode your reaction so others can use it. His tool is an acronym of traits: smart, passionate, optimistic, tenacious, adaptable and kind. When a candidate does not click, he walks down the list, for example finding someone who complained about previous managers was not optimistic.

The alpha-beta lens helps too: a strong candidate might simply be a low-beta person for a high-alpha product area. He also describes an interview tactic he found in Rippling's product organization, where every product person, from entry-level to executive, gets the same extremely difficult case study with a rubric for each seniority level. Candidates usually leave feeling they failed, while interviewers see how many corners they saw around and whether they stayed non-defensive when given new information.

He says the best joy of product is working with polymaths, since the job demands communication, project management and technical depth. Having led product, he now sees it as the highest-order bit in the business: get the product right and finance, sales, marketing and recruiting all get easier. He says he is only anti-bad product managers, comparing it to disliking Chardonnay because you have not had a good one.

MacInnis recalls a line that you know product-market fit when you see it, so if you are unsure you do not have it. During his years at Inkling he says they repeatedly believed they had it, but looking back after Rippling it was obvious they did not. Having invested in 60 or 70 companies, he says reading updates from founders years into the struggle is like reading his own investor updates from 2011 and 2012, and it breaks his heart.

He calls the Silicon Valley "never quit" mantra venture capital propaganda, because investors cannot get their money back and so are incentivized to have you keep trying against long odds. Wild pivots that work, like Slack, are exceedingly rare. He stresses it is not anti-VC, since people follow their incentives, but young founders should know them. He tells founders to quit, reset the clock and cap table, and says good seed investors expect zeros and will back your second company.

Asked when to quit, he says his relevant experience, and he urges people to ask for experience rather than advice, is that Inkling could have called it after the second or third pivot, around year four. If year four or five is not obviously a screaming growth story, he says, it is extraordinarily difficult. Timing matters enormously, and when fit arrives it is super clear.

MacInnis dismisses launch posts as a thimble of water in an ocean of noise, because nobody cares about your launch. Marketing can raise awareness but not change whether the market wants the product. He uses drug discovery as the analogy: no one at Genentech thinks they can market their way to receptor binding, and software is the same. Fate has already decided whether the receptors exist, so you should find the right drug rather than convince the body to grow them.

Asked about Notion, where he was an early investor and which took years to find its footing, he says it cannot be replicated. He cites investor Jeff Lewis's idea of narrative violations, that outsized winners violate conventional wisdom in some important way. Notion's was persistence, driven by founder Ivan's insistence on craftsmanship, while Rippling succeeds for almost opposite reasons. In both, he says, the company succeeds on the idiosyncrasies of its founder.

Asked for other investments, he refuses to list only the winners, calling it survivorship bias. He names a few hits, then lists several that went to zero and says roughly 70 investments, most of which failed, have left him with enduring relationships. Lenny agrees that logos on a website hide how many at-bats an investor has had.

MacInnis ties together three ideas: power laws, entropy and effort. Power-law distributions are everywhere, he says, so at 80% or 90% of the way there the reward has barely moved, while people in the top 5% or 10% get ten or a hundred times the reward. Entropy, the tendency toward disorder, means every line of code added to a codebase demands more energy to maintain it, and the only antidote to decay is energy.

Teams will always optimize for local comfort over company outcomes, he says, and a leader's job is to fight that daily. That means dropping every bug at the feet of the responsible manager, ideally in public, and insisting on a back-channel before any hire. He told Rippling's top 75 managers that the founder CEO is the purest source of intensity, that each concentric circle can lose an order of magnitude, and that they should mirror that intensity rather than buffer people from it.

To model it, he sits in each product team's public feedback channels, reporting what he does not like or understand, and personally reviews a recorded walkthrough of every major flow against the pickle, giving feedback publicly. He says the team's reaction was relief, not exhaustion, because nobody in leadership wants to be chill. Being intense, good and respectful beats being a "chill boss", and a drop in effort does not cost 10% of results but collapses them.

MacInnis says the most selfish thing you can do is withhold feedback, because you are optimizing for your own comfort over someone's improvement. He demands feedback and gives it, though it is open to discussion. High-performance teams, he argues, do not operate any other way.

He wants customers to escalate too. Even founders he has invested in hesitate to bother him, yet finding problems is literally his job, and an escalation is the greatest gift to a product executive. Rippling has a dedicated escalations team that digs for true root causes, not just fixing a data error but tracing the software and the system that produced it.

He tells Rippling customers listening not to hold back because he might already know. He keeps a queue of minor issues from recent days and takes them straight to product teams to understand what happened, not in a negative way. Nobody inconveniences him by escalating, he says.

MacInnis describes Rippling as more than payroll and HR: it aims to be the most successful business software platform in history, built on the people record as a core primitive. He says Workday, despite its success, has not built a broad platform on that foundation. Rippling covers payroll, HCM, IT and spend, is about to launch business intelligence and data management, and has tens of thousands of customers while being under 1% of the market.

He argues this is a period of bundling. Point solutions lack the data AI needs for joins and correlations, and integrations leave even the best "drinking their data through a straw". He uses a shovels-and-mines metaphor: model providers sell shovels and Rippling owns a mine, while AI startups in between face unit economics crushed by both. He expects that to kill 80% or 90% of standalone AI businesses he sees.

He says SaaS applications are all bit flippers changing values in a database, and AI is just a new way to flip bits. He declines to give AI-startup advice, saying he lacks the relevant experience. His own AI use is as a thought partner for wording ideas such as the pickle: roughly 80% of the output is trash, but the other 20% sometimes hits the nail on the head.

To balance the emphasis on intensity, MacInnis says life is amazing: we are brief instances of consciousness on a blue marble, and that perspective brings levity to the work. He describes Silicon Valley in 2025 as Florence in the Renaissance, with an unparalleled pace of invention. So you work on Friday night and compete in the arena of business, but you never forget two things: none of this matters, and it is a beautiful thing to be alive doing it now.

In the lightning round he recommends Conscious Business by Fred Kofman, which Rippling's product leadership team is reading as a club, Thinking in Systems by Donella Meadows, and the 1960s classic The Effective Executive. His life motto, from his father, is that nothing is ever so bad that it could not get worse. He asks Rippling customers to tell him when they have problems, and he can be reached by DM on Twitter or by email at his last name at rippling.com.