COO

“I would say at the end of the day, I would say the CEO is the harder role primarily because they're carrying the risk, right? It's their business. It's their company. At the end of the day, they're responsible for the growth, the scale, the vision. They own th…”

“I know there's a lot of companies out there that are trying to break that seven figure threshold and we applaud them and celebrate them, but they often say, I want a COO, but in reality, you don't really need a COO. What you really need is just to do more of w…”

“I often think COO is sort of like the set of functions that a founder knows are incredibly important and doesn't personally want to manage at this particular moment in time.”

“So to me, the ideal structure is a fifty-fifty split. So you get 50% of your bonus on top line and 50% of your bonus on bottom line. So what ends up happening is now you have founder alignment. You have an individual that's thinking about both top line growth …”

“So I regret not building a team and hiring a fractional CFO. Operations manager or a COO and a salesperson within the first year.”

“I think a lot of CEOs probably need a COO and a lot of CEOs should probably not retire, but move into the chairman role and let somebody else run the day to day of the company. And They might be surprised how much, how happy they are when they do that.”

“I suck at firing so much so that I've had my COO fire people because I don't want to do it.”

“Where you really need to institutionalize. You're going from a hero sale to more systems and processes. You probably need a CRO or a COO. Need a lot more metrics focused, and you need that machinery and that instrumentation layer to get formed.”

“Fantastic COO is just the right amount of friction and tension with forward momentum and mutual trust, because then the whole is greater than the sum of its parts, right?”

“Like start by just freeing up your calendar and do the work that a COO would do and get the business to a place where it can actually absorb that type of talent and that cost structure. Because that's not a very efficient way to spend money.”

“I've had things where I hired a COO of my company, and the day after he arrived, right, two days after he arrived, I went, oh my god, this is not going to work. I, and right, and like, I mean, literally, it was a big headline news in the business, and you know…”

“COO to me means I am here to create the absolute best Environment for product and engineering to ship everything they need to ship as quickly as possible, because we are a product and engineering led company.”

“Yeah, it's critical, right? It's critical in a couple of ways. One, it's the operations person who fulfills on the CEO's vision and dreams and goal, but it's also the right hand person to the CEO, right? So it's the counterbalance of all that enthusiasm and dr…”

“COO is one of those roles where there's not like a single COO. It's very much a custom mold to what the CEO is and what the founder is and finding someone whose strengths are the founder's weaknesses and vice versa, more so than it is just Hire a COO off the s…”

“My job as title of COO at Gusto has, in title only, remained the same. Every six months, it's an entirely different job. The expectations are higher because we have more customers. The complexity gets bigger. Our product set has expanded.”

“She was a perfect person to be a COO to, like, a, you know, crazy kind of loud mouth, visionary type person who had big ideas and big dreams. She was an executor, and that's what A lot of us founders need some time as, you know, the right person to actually ma…”

“When you're looking to hire a second in command, it really has to be a true yin and yang relationship for you. So you've got to take a look at the stuff that's on your plate that you love to do, that you get energized from, that you're really, really good at. …”

“What you're looking for in a COO is someone who is a very high second and first number. Their second number should be the highest. Their first number should be second highest. So you want someone who's a high follow through, which is putting systems in place b…”

“A true COO, you're usually three to 400,000 a year. You know, I was three 2010 years ago. It got junk.”

“The true power COO wants to make the CEO iconic.”

“Entrepreneurs have to be born with the entrepreneurial traits, and then they can be nurtured. But I don't think you can take a person and make them an entrepreneur. You're either entrepreneurial or you're not. And some of that is the craziness. It is the ADD, …”

“Your job in the first 90 days is to watch the ripples As they're getting up to speed, you have to watch for all the ripple effects that they cause. Most people miss that. They're so worried about getting the answer, the CEO up to speed that they miss all the t…”

“What does not work is two in a box where people feel like they have to ask you and this other person to decide and, you know, if you can't find both or they disagree what happens and everyone gets really confused.”

“And I'd say a million in ARRs too early. I think, you know, 40, 50 people is probably where it might become relevant.”

“The way to have a company that executes well is to execute well yourself. Everything in a startup gets modeled after the founders. Whatever the founders do becomes the culture. So if you want a culture where people work hard and pay attention to detail and foc…”