Ep. 114 – Rippling Chief Operating Officer, Matt MacInnis

Rippling is an all in one HR and IT platform that eliminates a lot of the administrative burden required to run a company. Overseeing this disruptive company’s business operations is Matt MacInnis. Formerly the CEO of the mobile learning platform Inkling for nine years, as well as an occupier of various roles at Apple for almost eight years, Matt is best described as an entrepreneurial COO who knows both sides of the CEO-COO coin. This background, combined with his long prior relationship with the company’s CEO, makes Matt very adept in handling two-way communications and debates. He shares how he does these in this interview with Cameron Herold. He also talks about identifying the fly wheel for market chair acquisition for Rippling and putting systems and processes in place to avoid corporate bureaucracy.


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Matt MacInnis is the Chief Operating Officer at Rippling where he oversees business operations. From 2009 to 2018, he was the Cofounder and CEO of Inkling, a mobile learning platform that provides on-job training for companies including McDonald’s and Whole Foods. Inkling was named as one of the fast company’s most innovative companies and raised over $100 million in funding before being acquired in 2018. Before Inkling, Matt spent eight years at Apple growing the use of products and education in the sciences. He holds an electrical and computer engineering degree from Harvard so he is one of the smart guys. Matt, welcome to the shows. 

Thanks. I learned two things by studying engineering at Harvard one, it’s studying Fine Arts at MIT. It’s not worth much and number two, I learned that I wasn’t a good engineer, which is why I went into marketing so I’m bringing up the amount of money my parents spent on that to learn those two things.

Can you give us a quick background on exactly what Rippling is? 

Rippling is an all in one HR and IT platform. The way that I would look at it is any business up to 1 or 2,000 employees has this massive hidden pain that they manually shuttle data from their HR system, their payroll system to Dropbox and Slack. There’s this original sin of all of these systems not talking to each other and Rippling is the one and only system that makes all of those systems talk. We’re eliminating the administrative burden of running a company and getting rid of all the busy work, which our customers would love not to have to do.

Why did you get involved in the company?

There are three reasons that I joined Rippling and the reason I can jump out here and say three is that I had to think pretty deeply about it. Because when I sold my previous company and after a period of time with the acquirer secured my freedom. It was a moment in time in my life where I was in my late 30s and had to figure out what I wanted to do. I thought I might invest full-time, I thought I might start another company myself, but it was low on the priority list that I would join someone else’s company.

I was pretty systematic in my thought process about what I wanted to do so I joined Rippling for three reasons. One, I know Parker well and it is not rare but effectively never that you’re presented with the opportunity to get on a rocket ship growth company and build it with one of your best friends in the world. That doesn’t happen. The fact that I was offered that opportunity was pretty special on its own. The second is that I know Parker pretty well and believe that my skills are complementary to his. It was a hand in glove fit in terms of what I know myself to be good at.

Third, as I had invested in the seed round of the company and had participated in series A and gotten to know what was special about Rippling, I came to understand that it had what I’ll call a unique structural advantage in the market. The way this company was approaching the problem of data in businesses or employee data, in particular, was the right amount of different in a way that clicked for my brain. I came to understand how this company uniquely could build a market share acquisition flywheel that no one else in this segment had ever been able to build.

If you’re going to join a company and put in fourteen hours a day and blood, sweat and tears, so far, the sweat and tears part blood is forthcoming. You better be damn sure that it’s going to work. It’s those three reasons. The uniqueness of building a company with your best friend, the confidence that your skills match precisely with what the company needs, and a conviction around the business model that was differentiated. Those three things got me to join.

On the actual product and company itself and saying you got a chance to jump on a rocket ship, what was it specifically that you saw at that early stage that made you feel it was? I told the founder of Uber one year at Burning Man, he came and he was in my camp. I told him it was a stupid idea and it was before he even hired Travis to come into the company so I didn’t see these good ideas. What did you see that makes this one good? 

I went after Parker. I have this email and it’d be printed and framed for posterity where I wrote him a pretty long screed about how he was fucking it up and doing it wrong. He was going after too many things at once. He didn’t know who his buyer was. I rolled in a wheelbarrow full of investor tropes and accused him of all of them. It was the first time of many subsequently where Parker came back with, “Respectfully I disagree with almost everything you said.” Piece by piece dismantled my argument. My initial reaction to that email was like, “Whatever.” Hands in the air. I’m going to go get another drink.

I came back to it a few times and read it and I thought, number one, Parker seems to have a clarity of thought and a contrarian perspective on this market that I couldn’t compete with. Number two, he might be right and I began to wrap my head around by breaking some of these rules. I know one investor uses the term The Narrative Violation. Everybody says it’s this way and this one company comes along and does it that way and that’s the winner in the category. I believe that.

When I got to know the business and got to understand, for example, that the system is architected from its first line of code to be a database for other systems to access data. Whereas everyone else in the space started with a payroll system that they then glommed a bunch of database features onto. You can’t get around ADP and Gusto. These companies are not going to be able to go back and re-architect their systems to accomplish what we were accomplishing with our system. I began to wrap my head around the fundamental difference of the infrastructure, the vision for the market, and how that translated into product insight in a way that I hadn’t been paying attention to, even as an investor. That’s what started to catalyze excitement for me about the company.

Are you still able to have those kinds of healthy debates? This was before you started the company but before you joined, are you guys still able to do that? How do you navigate that? That’s a huge lesson because the CEO needs us to be the one who tells them the truth and tells them when so often people don’t want to say it. 

There are a few things that are true about my circumstances with respect to the CEO. Parker and I would probably each lay down on the railroad tracks for the other in the sense that we have a lot of life history. Our families are close, and we trust each other. I routinely say things to Parker that he disagrees with and I would say that we’ve navigated to a point where I have a clearer sense of where I ought to defer to Parker’s instincts. He too has developed a sense of where he ought to defer to me. He has broadly delegated large areas of decision making about the company writ large to me because he knows that I have good instincts for it.

That’s all built on a foundation of preexisting trust. One thing that’s super clear to me is whether it’s about a founder looking for a cofounder, they call it founder dating. Whether it’s about a CEO who thinks he or she wants a COO, you can’t manufacture trust. It’s an inconvenient truth that if you think you need someone in one of these roles cofounder or COO. If no one in that level of trust is available to you in the world, you need to face that reality as opposed to deny it and make a decision about bringing somebody in any way. That’s true on the CEO side and it’s true on the COO side.

It’s such a yin and yang relationship. When I was the second in command for 1-800-GOT-JUNK?, I joined the company as the fourteenth employee and when I left we had 3,100. Brian was the best man at my wedding two months before I joined the company. We were similar to you and Parker. We’d known each other for years and we’re good friends already that the trust was already so completely implicit that we didn’t have to earn it. It was already deeply there. How do you think a company if you’re hiring an outside COO would go about assessing whether that level of trust can be there? Do you work hard on the interview process, give the trust to the other person, and let them throw it away if they throw it away?

I want to answer that question but I want to zoom out for a second. The first question is whether a COO is a special case of an executive or is it another executive?

It’s a special case. What do you think? 

It’s a special case in a few ways because the COO tends to be second in command. It tends to have an outsized influence over the culture and direction of the business but also, the COO gig is a special case and the cost of failure is so much higher. The success rate of executive hiring, in general, people say is roughly 50%. It depends on how you define success but it’s directionally true that 50%, 40%, or 30% of executive hires don’t work out and they don’t last a year particularly if you go through the traditional method of running a search.

A search firm has every incentive to force you to make a decision and they give you a closed set of candidates who happen to be available in the market now. They hustle you to a decision and you pick somebody from that set and you hope it works. It’s an absolute total travesty of a method for bringing executives into a business because of the odds of the seven people who happen to be looking for a CMO, VP, ENTJ or whatever job. Those people who happen to be available to you in the market that one of them must be a successful hire for you is bullshit. You pay somebody $100,000 plus some chunk of equity to run that search for you. They are going to make sure you pick someone and move on.

What system do you guys use them to make sure that you hire the executives?

It’s thoroughness, patience, and intuition. I don’t claim to have a higher success rate in executive hiring than anyone else. I’m hiring for a bunch of senior roles and I make a commitment at the outset that I’m not going to make a hire until I find the right person.

SIC 114 | Rippling COO

ippling COO: You can’t look at the reporting structure of a management team as input to your behavior. Stated differently, everybody always has to have the CEO hat on.


Have you guys ever followed any of the methodologies in Topgrading or Who

I use Topgrading. I love the definition of A player, A, B, and C potential that he uses in that book and use it as a framework. I use Topgrading more to assess the intuition of the executive. I use the framework of Topgrading even though they don’t know I’m using it to talk through how they hire and fire as opposed to applying it directly.

Brad Smart was the author of Topgrading. His son, Geoff Smart, wrote a book called Who. He took the 800-page Topgrading book and synthesized it down to 200 pages.

It was a thick and heavy book.

Topgrading was tough, but it was good. Who was a much more entrepreneurial version of the same systems which is cool. The entrepreneurial CEOs. You were an entrepreneur so are you an entrepreneurial COO as well? 

What do you mean by entrepreneurial?

Harvard wrote a good article about years ago called The Misunderstood Role of the COO. They identified seven distinct types of seconds in command. You would be more of a partner of Parker than a hired gun. 

You could say without question that I am subordinate to Parker and the organization. At the end of the day, the CEO makes the decision and that’s absolutely crystal clear.

He controls vision. 

With that said, Parker and I, it’s fair to describe us as copilots ever. He’s the captain and on the copilot. I’ve talked to people about the way that he and I worked together before and they’ve been surprised to hear that Parker and I may spend a total of 1 or 2 together a week. Even the team within the company thinks that Parker and I are in constant contact. We’re Slacking and texting and that thing but the left hand only knows only so much about what the right hand is doing and vice versa because we’re able to execute autonomously. I have an earned sense of how to build a company and so does he. I don’t need to rely on him for insight into how to build a company from this stage. We’ve both been here before.

What areas of the business report up to him and what reports up to you? 

Even in the year that I’ve been here, it’s changed. I have responsibility formally for HR, finance, business development and product design. I have all of the post-sale services with the exception of implementation. I have customer support and customer success. My apologies to anybody who works for me who read this that I’ve forgotten, but those are the formal functions. Other than with the cadence of one-on-ones or whatever, I don’t think about it that way. The reporting structure is irrelevant. I run the executive team staff meeting. When I look at it at the management team, we have our head of sales, our CMO, general counsel, Parker. We have our VP of product and ENTJ. It doesn’t occur to me that there’s any hierarchy among those people. It’s a team and I’m on it. When I see that somebody needs feedback, I give it. If I disagree with a decision within a function, I express my disagreement.

This is something that is important for any chief operating officer, although, to be perfectly honest, it’s true of anybody who’s on a management team, you can’t look at the reporting structure of a management team as input to your behavior. Stated differently, everybody always has to have the CEO hat on. For me, the privilege of conditioning that I have from having been a CEO myself for years is that I don’t know how to operate any other way. I did struggle for a little while after I joined with having a boss.

Maybe that’s what I meant by entrepreneurial COO. It feels to me you treat the company like it’s your own completely.

It’s my own because in some literal way it is. It’s going to be an overstatement for me to say I’m as invested in the company as Parker is. It’s much more closely tied to Parker’s identity personally than it is for me but I play to win. I view business as a sport. It is my sport. Some people love tennis. Some people love football. I love business. The big question I had to answer for myself before I took this job was, “If business is my sport then what position do I want to play?”

Do I want to be the owner of a team, a partial owner of a team? Do I want to be in the bleachers? Do I want to be the coach? Do I want to be on the field? It was clear to me that I should be on the field. I should be a quarterback. I look at the management team as peers, including Parker with the exception of when it comes to tiebreaker decisions. I feel that it’s my duty and responsibility to be as much an active commander of the direction as him but also expected of everyone else on the management team.

I asked about the debate between the two of you and there’s a bit of an art in when and where you can do that as well. How often do you debate him in front of the board or in front of the other leadership team members or do you do that privately versus publicly? Does it depend? Is it more situational? 

This is an important question. Sometimes the active debate with the CEO where another member of the team is capable of representing the other position in an effective way is in its own right cathartic to the team.


If you’re a member of a management team and you’ve got a strong-minded CEO as most companies do, so many times I have seen all members of the management team wither in the face of a strong CEO opinion. In fact, by being in the position I’m in now, I recognize that I have done that to my own team as a CEO. I’ve come to the table with my strong opinion, and everyone else has gone with me. I’m like, “I did that a fair bit where the team went with me notwithstanding the fact that there was a lot of dissent in the group.” The descent wasn’t particularly strongly held so people said, “Fuck it,” and they rolled with it. Maybe sometimes that’s good because it eliminates indecision, but in this context at Rippling, Parker will come to the table and he’ll have a strong opinion.

There are cases where it is particularly important for me to voice the opinion I’ve heard others sheepishly share with me but not feel comfortable challenging Parker. I challenge him, maybe on their behalf in front of them so at a minimum there’s the catharsis of knowing that your perspective was effectively voiced. It was given an opportunity to be heard by the group, by Parker or whatever. I do think that that’s an important role I play. It is to debate Parker in front of the team.

How about in front of the board? 

The board is an easy one for me. Let me put this a different way. There’s no battle picking, I would say, with the board, I defer to Parker in a group setting because I don’t think there’s a catharsis needed in that setting. If I have something I disagree with Parker on at the end of the day, I can take that to him in private anytime I want and we can change course. The board is not going to tell us to do anything.

SIC 114 | Rippling COO

Rippling COO: The key to a good flywheel is when an incremental customer on the platform benefits every other customer.


I almost treated the board like parents arguing in front of their kids. The CEO and COO at a board meeting should almost be complete as a force and you never argue in front of the children, but you definitely lock yourselves in the bedroom or go for a walk and have the full-on debate.

I don’t want to be locked in a bedroom with Parker but I know the board setting is different. I will say though, that we have a pretty light touch board. We have Kleiner Perkins. They have one seat and one observer, Parker, and our Cofounder, Prasanna. It’s a pretty light touch but that dynamic is pretty straightforward. We try to be in lockstep going into that meeting and if I have disagreements I’ll take them out. I also do have a good direct relationship with the board members. I feel perfectly comfortable having a one on one with them and having a conversation about things that Parker and I disagree on. It’s never viewed as internal strife, conflict or insubordination, or whatever.

You mentioned earlier about the flywheel and identifying what the flywheel and identifying the flywheel. That’s the concept from Jim Collins in his second book, Good to Great. Walk us through what you see as your flywheel for Rippling. 

I talked about the flywheel of market share acquisition. There are a few different ways that we do this and some of its secret sauce so I’ll leave it at a pretty high altitude. The key to a good flywheel is when an incremental customer on the platform benefits every other customer. The most obvious example of this is something like Facebook, where the more of your friends signed up, the more it was useful to you. Usually, the feedback loop is not quite crazy strong the way that it was with something like a social network but that’s why Facebook got to be the size of a company that it is.

You take Salesforce as an example. Salesforce has an incredibly strong flywheel in the form of its ecosystem. Initially, when Salesforce started, they were a cloud-based CRM. It was a database where you put your customer data and they fought for years and years to get over the fear that IT people, in particular, had that putting their data into a multi-tenant cloud solution was putting their customer data at risk and there was a chance that somebody else was going to see it. Of course, we’re all over that now.

When they started, it wasn’t obvious that there was a strong flywheel there because people wanted their data segregated. What could I possibly benefit from some other company putting their customer data into but what happened over time as people started to build integrations to the Salesforce cloud? As they built integrations, more and more product capabilities came to life. To look at a big example, Marketo. You could begin to link customers’ activity before they’re ever in the line of sight of sales to the customer record and a salesperson could see the history of engagement on the website before they talk to the customer and it’s hugely useful.

The more customers join Salesforce, the more attractive it is for Marketo to be built and have deeper capabilities. That led to an entire ecosystem around Salesforce. For Rippling, we have a pretty similar dynamic. There’s never been a single system of record of employee data in all of these small and medium enterprises. In the large enterprises, the hundred thousand person companies that implement workday, the problem there is they’re implementing workday for their HRES and they’re implementing ADP for the payroll and implementing Okta for their single sign-on. It’s this giant pile of different systems that are all getting integrated by the IT department but for small and medium businesses, they can’t afford to do that. They don’t have an army of IT people and there’s no off the shelf solution.

Rippling comes in and we provide you with a place to put your employee data. Why would it be beneficial for some other company to come in and put their employee data in? I don’t want to see their employee data. I don’t want them to see my employee data. That seems a terrible idea, but the reality is that companies are beginning to build integrations to Rippling because there’s such an awesome set of APIs and interfaces for them to be able to access that data to do cool things.

Take Brex for example. You have a spending limit on your Brex card. If you and Rippling are promoted from manager to director, or if you’re moved from marketing into sales, the Brex spending limit will automatically update for you when you move over. The IT people or finance people didn’t have to do that or somebody didn’t forget to do it. It happens automatically and this is something that Brex could never do on their own in their own product. That’s one little example of the more people bring their employee data to Rippling, the more developers are going to have an incentive to build integrations to our platform. That flywheel, once it gets going, it’s unassailable and I would argue that we’ve already got it going.

Once you’re clear on what that flywheel is and stay focused on it, that’s where scale and growth happens. How do you avoid corporate hairball? How many employees do you have now at Rippling? 

About 240.

You’re there. You’re at the stage now.

We’re at the hairball stage.

The politics are coming in and the systems and you’re not even sure why. You’ve got people walking around and you’re like, “I don’t even know who you are let alone what business you are in.” How do you avoid corporate bureaucracy and waste? Do you have systems to look at that, watch for that or do you try to run fast? 

There’s this corporate bureaucracy and there are politics and these are two different things. Let’s talk about each of them. If I were to define the term bureaucracy, it’s a process that slows us down. The worst bureaucracy is the overwrought process or unnecessary process. Those things are first cousins. An overwrought process is one that’s like, “Why do I have to do this much stuff to get this task done?” There’s also a poorly designed process. There’s a lot of ways that processes can go wrong. I would say that the way that we tackle that at Rippling as we’ve grown is we have not implemented the process at all until something is clearly broken.

In other words, you have to feel the pain of the lack of process before you implement the process. That is a whole bunch of things around good process design. I will say principles of good process design and good processes are built bottom-up. Ninety percent of people who hear the word process, their first instinct is to go open up a blank Word Doc or Google Doc and begin to write down a process. It’s like, “First, we’ll do this. We’ll do that and we’ll do this. If this happens, go do it.” That’s absolutely the worst fucking way to build a process.

The way you build a process is you go to the people who’ve been doing this every day and say, “How do you do this? Can you write down the steps you typically take? What’s the fastest way you typically get this done?” They’re like, “I go, bing, bing, bing. That’s a process.” The problem is that half the time people don’t even have that much happening in their business before they decide that something needs a process. They start to develop something before it’s even been done bottom-up and that yields these terrible hypothetical processes that have no bearing on getting something done efficiently in the real world. That’s the whole I’m super interested in.

How about hiring? I’ve been batting around an idea with a couple of CEOs that I coach. I gave one the analogy that if we were going to spend $250,000 on some marketing campaign, we would spend hours debating it, looking at it, slicing the data, and looking at the different scenarios. If a VP came up to you and said, “I need to hire three more people and they’re $80,000 each,” we’d probably spend two minutes on the decision, which is terrible. Do you have any process or decision for hiring and for allowing people to hire? How do you allow those people to get hired into the organization so you don’t have people building their little factums or adding people throwing bodies out?

Is the question of how we make the decision to open a headcount? We’re parsimonious. We’re cheap. We’re frugal. It’s back to the same thing as a comment I made about the process. Don’t hire more people until the pain is intolerable.

You wait until the pain is intolerable. 

This principle holds across the board. Don’t develop processes until you need it. Don’t hire people until you need them. Don’t strategize three quarters out in a high growth company because of the amount of energy that you spend trying to get something right in advance and you take the subset of that energy that ends up generating a decision that is correct. Let’s say that there’s a unit of energy, there isn’t, but it’s time. Let’s call it 1,000 units of energy spent trying to figure out the future and make a decision. Fifty percent of those decisions were correct, 50% were incorrect and needed to be redone. Let’s say 500 of those units now were well spent and 500 were wasted.

Let’s say instead of spending those 1,000 units upfront thinking, spending, meeting, talking and building decks, and trying to get through a decision, you say, “Fuck it. We’re going to wait for this to get super difficult but in the process, I’m going to gather a ton of recon, practical data about what the hell is happening in this situation then I’m going to make a decision immediately at the moment about what I should do.” I may spend 100 units of energy on that and I get the right answer 98% of the time. It’s way better, but it’s uncomfortable because our tendency is to want to say, “Let’s sit down and think.” Because we attribute way more.

Is that a cultural norm that you set within the organization?

SIC 114 | Rippling COO

Rippling COO: The worst bureaucracy is the overwrought process.


For sure and it comes from Parker. I am predisposed to agree. Parker takes it to an extreme where he’s 99th percentile where I’m in 90th in terms of proclivity to be impulsive and reactive to the situation. I dial that back a little bit. We implemented only a quarterly planning process. We’re implementing job levels, bands, and the sorts of infrastructure that will allow us to do a little bit more in the way of financial planning. We resist the temptation to engage in deliberation for the sake of debate. You were asking me about the process, and we also talked about the related politics.

The other thing to remember about politics is in a business if you give people a ton of free space to worry about, “How I’m doing? Am I going to be important? What’s that other guy doing? Is he going to be more important than me?” There’s room to put yourself above the team or the team above the company, you inevitably get politics, but the antidote to that is if you don’t overhire and in fact, if you barely under hire and everyone’s like go, go, go all the time on what needs to get done, you don’t have much in the way of politics because people don’t have time for that shit. They’re too busy trying to deliver the result. I know that that sounds almost glib in its simplicity, but if you’ve ever been in a high growth company that politics tends to fall by the wayside because it’s about results. If you’ve never been in a high growth company, you’re not allowed to argue with me.

You are right, politics do tend to creep in when growth slows down at a time. 

When growth slows down, there’s more room to worry about yourself.

This is a back question about the exit that you had. Any lessons from that exit that you could refer to that or that you can share with us? That’s an open-ended question.

I learned a lot of lessons all along the journey. I would say that the single largest existential learning from the entire journey from starting a company, getting funded by Sequoia, and feeling like we were a predestined success to pivoting multiple times, doing multiple rounds of layoffs, disappointing many people. Ultimately building a business to profitability with tens of billions in revenue but having an exit where you returned a fraction of every dollar invested in the business.

As a founder and CEO having gone through that whole experience coming out the other end, I got a check and I’m grateful for that but didn’t get rich. It wasn’t the giant multibillion-dollar outcome that you assume is your only option when you’re a twenty-something starting a company in Silicon Valley. It tore my ego apart. It completely stripped me of this armor that I had built up around myself as a predestined success. If anything you go through high school, you get good grades, you graduate valedictorian, you go to Harvard, you study engineering, and realize you’re not a good engineer.

You didn’t have those failures. 

I had other failures. I’m a gay man and I had to go through the challenge of being a gay kid in high school in the “90s. I was in Canada, which is a better place to be than Alabama, for sure. I had my challenges, but as an individual contributor in my own life, I was able to achieve an outcome that would reinforce the notion that I am the master of my own destiny. What I had to learn the hardest way is that number one, no amount of energy on my part can guarantee an outcome. Number two, life is a team sport.

In the academic world, we’re trained or conditioned to believe that the grade that you get of your own effort at the end of the semester is under your control and that conditions you with that pattern in life. Your effort is correlated with your results but it’s bullshit. There are way too many externalities and too much dependence on other people. For me, when I got to the end of that experience, I had been beaten to a pulp and I’m so much better for it. I’m so much better of a human being and I’m so much more at ease with who I am. I’m so much more at ease with the pursuit of the sport of business now than I was for the vast majority of the time that I was the CEO of my own company.

Where in Canada did you grow up? 

I grew up in Nova Scotia.

My dad went to school in Antigonish, St. FX.

My mother also went to St. FX.

I was a big disappointment because my dad, my grandfather, and my great grandfather went to St. FX when it was still in New York State. 

My brother and sister both went there. My mom went there and I was a great disappointment too because only I went to Harvard.

I went to Carleton because they accepted me. The great disappointment is going to Harvard. I grew up in Sudbury up in Northern Ontario. Last two quick questions before we wrap. How do you do the big rounds of layoffs right? They’re tough.

For a period there maybe still I am a go-to guy on layoffs. I know that Sequoia tends to have the person to whom they send their founders when layoffs are necessary and I’ve been on the receiving end of that email a few times. For layoffs, there are a few rules. I have a rule about rules. It’s advice about advice. My advice about advice is if you hear someone you trust, give you a piece of advice and you get roughly the same advice from two other people, 100% of the time, take the advice. On layoffs, if you go and talk to people who have conducted them successfully in the past, you’re guaranteed to get the same advice over and over again.

Number one, the minute you make a decision to do layoffs, execute them aggressively. What I mean is go quickly because people are going to know you’re going to do them. Make sure you cut more than you think you need to cut otherwise, you’re going to regret it, because you’re going to be back to the trough for a second round later, which is ten times as demoralizing as the first. Two, when you do layoffs, you have to execute with absolute precision.

There is no margin for error. You can’t fuck up the paperwork and the messaging. You can’t outsource the problem. I heard about a CEO who hired a PR firm to advise him on the employee messaging and it was terrible. The PR firm was advising him in such a way as to minimize what it would look like to the media. The media is not your audience in a layoff. It’s your employees, in particular, the employees who are remaining.

The ones that are going to have the survivor guilt.

There are tons of good resources out there on layoffs. It’s like a hook line. Layoffs are one of those cases where there is a right answer and deviation from the answer is worse. There are relatively few times in business where that’s true where there’s a right answer to something. If it’s available to you, don’t be an idiot.

Are you part of The C100 at all?

SIC 114 | Rippling COO

Rippling COO: 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.


I’m familiar with The C100. I’ve done events with them. I don’t spend a lot of time on it but I’m loosely affiliated.

It’s a great group. There are more VCs from Canada living in the Bay Area than there are VCs in Canada. 

Canadians run Silicon Valley as far as I can tell. Every time you turn around, there’s another Canadian.

It’s funny you mentioned Kleiner. I was a reference for Elon in his first round of funding in January of “95 when hidden Kimbal had one employee. I had to call Kleiner and I didn’t know what the internet was. It was a crazy phone call. 

I hope you got shares in the company.

I did not. It was for Zip2. I wish I had. They did a huge exit. Last question on one-on-one meetings. I’ve got an idea that you probably have a great way that you run your one-on-ones for your team. How do you run your one-on-one meetings? 

First of all, I have a user manual which is a document that’s based on an essay from Elad Gil and he captured it in his book the High Growth Handbook. I highly recommend that to all executives but in particular, COOs in any growth company. Take the time to articulate your user manual because every time a new employee joins, a new executive, or anybody’s going to have to work with you, you can hand them the user manual and say, “Here’s a cheat sheet on how to work effectively with me.”

A user manual for you. 

It’s User Manual for Matt MacInnis. It’s like, “Here are my strengths, foibles, the things that bugged me, and here are the things I appreciate.” One of the things I put in there is how I like to run on-on-ones. I stick with it and I don’t. I have to be perfectly honest. What I like to do with one-on-ones is I like to have a document where I keep a running backlog of what I want to discuss with somebody. People with whom I have one-on-ones regularly are usually a bunch of items that have come up over the course of the week that aren’t urgent, but we should talk about what I toss in there. It serves as the agenda when we do get together and we keep notes in those documents and I’ll say that I’m not militaristic about its use so most of my employees use it.

For some, it doesn’t work for us and we do it a different way so I would say I’m pretty flexible with it. One thing that’s important to me as a leader is that I have to check in on the individual and how they’re doing which serves as the foundation of our relationship. I like to check in on us and how our relationship is going and on top of that we can talk about the tasks that have to get done. You can’t run into a one on one and say, “How’s this project going? Where’s the project?” If you’re one on one is not the space that offers an employee the opportunity to talk about themselves or to talk about their relationship with you or others, you’re guaranteed they have no other place for it.

Could you share your manual, your Matt MacInnis Manual?

Of course, I’d be happy too.

I would love to read that. Do we have your permission to share it with our readers? 

I’ll have to read it one more time. Make sure there’s nothing too revealing in there.

It could be one of your legacy moves. It’s a powerful idea that I haven’t heard and I’ve heard a lot of stuff in business.

I’m happy to share it.

If we were to go back to the 20, 23, or whatever year old self graduated from Harvard and you wanted to give yourself some advice, what would you tell yourself back then? 

There’s a lot but I’ll say the highest order of it for me at least and it is true for every human. I would try to convince myself that the authentic version of me is the best available version. I should accept whatever comes from that with grace. I shouldn’t try to be someone else. I shouldn’t look to outside benchmarks to frame up what I need to become. I should look within for the answer. If I’m good at this and not good at that, I’ll spend all my time on this and let that go. Even if I’m supposed to be good at that.

I like that you’re saying it’s the best available version of you.

It is because anything other than your authentic self is a less good version, so stick with what’s authentic.

Matt MacInnis, the Chief Operating Officer from Rippling, thank you sharing with us.

It’s my pleasure, Cameron. Thanks for having me.

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About Matt MacInnis

SIC 114 | Rippling COOMatt MacInnis is the Chief Operating Officer at Rippling where he oversees business operations. From 2009 to 2018, he was the co-founder and CEO of Inkling, a mobile learning platform that provides on-the-job training for companies including MacDonald’s and Whole Foods. Inkling was named one of Fast Company’s most innovative companies and raised over $100 million in funding before being acquired in 2018. 

Before Inkling, Matt spent eight years at Apple, growing the use of its products in education and the sciences. He holds an Electrical and Computer Engineering degree from Harvard.




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