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What’s in a role: Matt Cantatore, COO at Ollie

By: Amanda Mulay, Senior Talent Manager

When a company is in its early stages, more likely than not, its founder will serve as a one-person C-suite. But, as the company grows, so does the need for greater operational infrastructure, ensuring the right systems and processes are in place as the business scales. That’s when the COO comes in.

Formerly Director of Operations at Blue Apron, Matt Cantatore currently serves as COO for DTC healthy pet food brand Ollie. He spoke with us for our ongoing talent series “What’s in a role” to discuss his job and responsibilities as well as other insights into managing operations at high-growth startups. Below, he shares his views on topics including what founders should look for when hiring a COO, why you can’t learn ops in business school, and the skills that make operations leaders successful.

Amanda Mulay: Tell us a bit about your background and how it led to your current position as COO at Ollie.

Matt Cantatore: I received my (undergraduate) business and law degrees in Australia between 2003–2008, and during those studies spent much of my time focused on building businesses (a couple of which actually helped quite a lot with tuition expenses), and that bug to build things just never went away. That said, back then a career in the startup world was never really a prospect in Australia, as I had yet to be exposed to what then was a pretty fledgling VC community. I was committed to going into investment banking and joined Morgan Stanley because I thought the way to New York, where I wanted to be, was through a U.S. bank. I moved to the U.S. from its Australia office in 2011 and then pivoted to business school in 2012.

While at Wharton, I spent a summer renting a space in the city with a few classmates where we labored over business ideas that were doomed from the start. We didn’t really know what we were doing, but honestly that was the beauty of it. I learned more that Summer than I ever could have hoped to. I graduated with a major in Entrepreneurial Management and then started a journey to COO that was both somewhat traditional in the sense that I’m not a founder COO and untraditional at the same time. I applied for a position as an Operations Associate at Blue Apron in 2015. I then worked as an Operations Manager, Senior Manager and finally Director of Ops before joining Ollie as the VP of Ops in 2017. Serendipitously, Ollie’s cofounder, Gabby Slome, was a contact that I made back during that summer in business school and she reached out during her search. Now, I serve as her COO.

Mulay: What does your role entail and how do you typically explain it?

Cantatore: My job essentially consists of two functions. The first is heading up the business’s operations. In this role, I provide oversight of Ollie’s day-to-day operations, from upstream functions such as sourcing and supply chain management through to our complex fulfillment and logistics process, and then all the way to end-user customer support. My second role is acting in the capacity of an executive team member and leader of the company. In this aspect of the job, my focus is split across recruiting, driving cultural initiatives, goal-setting and strategic decision making, managing the P&L, fundraising with the founders, and interacting with our board.

Matt Cantatore

Mulay: When did you decide you wanted to leave investment banking and join a startup? Why choose to make the jump?

Cantatore: Working at Morgan Stanley was a fantastic opportunity for many reasons. It was a means to build a transferrable, technical skill set, and it was an accelerated way to learn as much as humanly possible about business right after college. But after several years there, finance started to become a bit monotonous. As somebody who loves solving problems and building things, I was seeking an experience where I would face different challenges on a daily basis that required me to be creative, find solutions, and drive results.

Rather than covering other companies, I wanted to work on transforming my own company’s story. I wanted to operate with a high level of accountability and see the direct, tangible impact of my work on a business’s success. So shortly after securing a transfer with Morgan Stanley to the New York office, I set my sights on taking that next step. I applied to business school at Wharton and pivoted to the world of entrepreneurship. My goal was to keep my learning curve steep and never lose the excitement.

Mulay: How did what you learned at business school impact your perspective on operating a company?

Cantatore: It helped a lot, but more from the practical skills I was able to take away than any textbook learnings. This might come as no surprise, but actual management of startup operations is extremely different to what you might read about in a dusty 500-page Operations Management textbook. What’s taught at school is still highly applicable but traditional Operations Management courses seem much more relevant for scaled businesses, where a lot of structure already exists and the wins are really at the margin. Running operations at a startup, on the other hand, is like building a plane as you’re flying it; you’re trying to distill clarity from chaos, and have new surprises thrown at you every day. It’s hard to bottle that experience and serve it in business school; you really just have to do it.

Mulay: How does your past work experience at Blue Apron and Morgan Stanley relate to what you’re doing now at Ollie?

Cantatore: Although the skills I honed at Morgan Stanley were not directly related to being an operations manager, the experience was infinitely valuable in teaching me the skills required to be an effective executive. That is, of understanding key drivers of a business and tying what we do operationally to the company’s financial objectives.

From there, Blue Apron was the perfect stepping stone and provided me with a vast array of experiences that I leverage regularly in my current role at Ollie. First, I was taught how to manage people. I had the good fortune of being able to manage both a corporate team of extremely intelligent, high energy former bankers and consultants, as well as spend meaningful time in our largest fulfillment center managing a team of close to 2,500 people.

Next, I was given real ownership of key metrics of Blue Apron’s business and was taught exactly what true accountability means (recommendation: read “The Oz Principle” and apply it daily). I was also able to build experience in scaling a complex business model through a period of hyper-growth. This translated into thinking about things like how to build the right infrastructure for growth while also staying focused on building something that was not only scalable, but also highly agile and adaptable. And perhaps most importantly, I learned a lot about contributing to the culture of an organization, and was able to spearhead a number of initiatives around professional development and culture building in our organization.

Mulay: What’s unique in an ops role at Ollie compared to other companies?

Cantatore: Coming into Ollie it didn’t seem as though our operations would be that dissimilar to what we were doing at Blue Apron. But I couldn’t have been more wrong; the truth is that when you’re doing something that no one has ever done before, the supply chain complexity that comes with it is often quite hard to understand before you jump in. There’s no one that’s “done it before” to help guide your strategy or decision making, which raises the stakes a lot. For us, the real complexities are around scaling manufacturing and building an agile fulfillment network that can serve a much more varied customer base than our human food competitors; remember, at Ollie we can’t serve a one-size-fits-all meal, our (canine) customers range in weight from 1 pound to 200 pounds, which presents a number of challenges on the supply chain side of things.

Mulay: What do you find the most challenging about your day-to-day responsibilities as COO?

Cantatore: In an under-resourced environment where everyone has to roll up their sleeves, it’s trying to strike the right balance between getting sh*t done and investing time in the company’s strategic priorities. At a startup, even leaders need to roll up their sleeves and pitch in. However, it’s always a balancing act of competing priorities, both tactical and strategic, and this is something I grapple with daily. I’m sure it’s not news to anyone that focus is critical to leadership success, but the lesson here is that focus needs to be well-directed, because paying too much attention to the wrong things can have disastrous consequences.

Mulay: What’s the most rewarding part of your role at Ollie?

Cantatore: I enjoy the process of understanding what my team wants to learn and achieve and helping them get there. There’s something really rewarding about being able to understand someone’s ambitions, to help them craft aggressive goals, and then to set out together on the road to achieving them. It’s important to me as a leader that my team members always feel that I support them in these endeavors, because I genuinely care about their success. So when I watch my team succeed and achieve the things they set their minds to, it gets me really pumped up and I feel proud and excited for them.

Mulay: When do you think a company needs to hire a COO?

Cantatore: I think it entirely depends on the nature of the business, the founding team’s skillset, and the company’s strategic objectives. COO is a role that could be filled by a CEO at many early-stage businesses. For example, if the business requires limited operational infrastructure and the CEO has operating experience, a COO may not be a critical need on Day One. Alternatively, at a company like Blue Apron or Ollie, where the business model is very ‘ops-heavy’ and building out the right infrastructure is critical to growth, having a COO early on might be imperative (again, depending on the skillset of the CEO).

Mulay: What advice would you give to anyone interested in getting into operations?

Cantatore: Leave your expectations at the door, have a good dose of self-awareness, understand what your limitations are, and how much knowledge you have (or don’t) about operations at a business. People underestimate how much you have to learn on the job versus at school or in a consulting shop. From supply chain management to labor management, it’s a very different way of operating because of the level of accountability you have in the role.

Other jobs have levels of protections or checks, but that doesn’t exist at a startup because you take ownership of something and are responsible for that success or failure. People can hit a ceiling fast if they make excuses or blame others or their circumstances.

Mulay: Any tips for founders looking to hire someone to head up operations at their company?

Cantatore: You’re looking for someone who is highly analytical because it’s so tied to the financials of the business as well as an incredibly good people manager. They should also possess strong EQ and demonstrate a high level of accountability for their decisions. Failures are important, so it’s worth understanding what those have been and how accountable the person feels for them. Having that mentality that when something goes wrong there’s no one to blame except yourself is important for top executives. Resilience, too, for when things go wrong, poise and calm, and not being emotionally-driven.

Interested in a role at Ollie? Check out current job openings here.

Read past posts in our “What’s in a role?” series:

Eric Knudsen, Manager, People Analytics at Namely

Kendall Kelleher, Internal Recruitment Manager at Vangst

Liying Wang, VP of AI Training Operations at x.ai

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Lerer Hippeau

Lerer Hippeau

Lerer Hippeau is the most active early-stage venture capital fund in New York.