COO Is a Job Like No Other: My experience as the Chief Operating Officer of Talkdesk

I had the pleasure of being interviewed by Cameron Herold for his COO podcastSecond In Command a few months before I left my full-time role at Talkdesk. Cameron is the leader of the COO Alliance, an organization that focuses on the Chief Operating Officer role. This interview was less about Talkdesk and more about being a COO, a leader, and on working with a founder/CEO as a second in command. Here’s a summary of the talk.

Fun fact — In my first technology job, my office was a closet in my co-founder’s wife’s warehouse. Building that company from scratch, with limited resources, became the foundation for everything that followed in my career.

What do you run as a COO? Many people ask this question. Every COO I’ve met has a different scope based on what the CEO wants to do, and where the COO can add the most value. At Talkdesk, I lead Product, Customer Success, Professional Service, Support, Channels, Business Development, Platform, Talent and Legal. It is not the mix most COOs run, but it was a good split between Tiago and myself at the time I joined, based on my previous experience and Tiago’s focus. Leading both product and post-sales was especially beneficial since the “voice of the customer” was always in my head.

How do you grow? Most of how I learn is by doing, making mistakes and being honest about them. Even with 20+ years of experience, there is so much you don’t know, including things you thought you knew. You have to be honest about your mistakes and pay attention to them, or you will not grow. I also read and listen. It helps.

What do you do to make sure you stay up to date with technology and change? Be part of the change. When my father was 80, he sent me a Google Sheet a few days after Google launched the product with some financial data we needed to collaborate on, and he is an early adopter even at 90. I am trying to do the same and immerse myself in new technologies, try them out and learn about them. Living in San Francisco affords a great opportunity not only to read about new tech but talk with the people who built it and try everything new.

How do you stay focused on day-to-day vs. strategy? My day tends to be a mashup of different things. I spend a lot of time with customers and prospects, and a lot of my strategic inspiration comes from them. I care a lot about the founder’s vision — this is what makes startups unique, so being in sync with him is very important as well. Lastly, when you hire excellent leaders, you don’t have to spend all your time on the day to day operations. They want to run the show, and this is why you hired them.

How do you stay in sync with the CEO? There is no one way to keep in sync with your CEO. It is more about his/her personality than a repeatable process. My advice to COOs is to communicate with your CEO the way he or she prefers. You need to spend enough time in and out of the office to build trust, but the formality of communication is less important. One additional pro tip is about time, place, and manner. Not everything needs to be resolved in real time. You should be smart about what should be communicated over text, a phone call, or what could wait few weeks for face to face. Patience is essential if you want to be influential.

How do you grow your team? I give them a lot of autonomy. If you hire senior people, they don’t want to be micromanaged. They may do it for a while, but over time they will be less engaged. I also make sure that they know that I expect them to challenge me, call my BS and give me feedback. Leave an opening for people to contradict you, and hire the people that will challenge you.

How do you hire the right people? I wish I had it all figured out — I make hiring mistakes all the time. I do think that experience helps, but what helps more is including as many people as you can in the hiring process, and do as detailed reference checks as you can. Don’t outsource all reference checks to your talent team or only call the references provided to you. I always do backchannel references myself and ask many detailed questions, so I get the full picture of the candidate.

Are your decisions based on data or your gut? Your gut is a reflection of your past and experience and not the future. Most times it is very efficient to use it and not make the same mistake twice, but at other times, relying on your gut is building the past. Challenge your team to bring different opinions but ask them to support those opinions with research and data. It is hard to “outgut” your leadership if you don’t come prepared.

What do you think about titles? How flat are you? Employees and executives are interested in titles as a way to demonstrate career progression and show personal growth. Nevertheless, you can have a hierarchy but keep an organization flat. For example, at Talkdesk we don’t fuss about emailing an employee that may know the answer directly, vs. messaging her manager first to maintain the hierarchy. We also don’t care much about who goes to which meeting.

How do you win the war for talent? Winning in San Francisco is hard. For a young person, San Francisco is a Disneyland of opportunities that all look the same. You have to provide a great environment and challenging work for your employees, but also have to accept that current market conditions mean that people may only stay for a year or 18 months. You have to know to build hiring and onboarding processes that will take turnover into account.

What is your advice to someone who considers being a COO? Focus on the Number One, the CEO. He may be younger than you, and you may be more experienced than him in many aspects, but if you can’t find a few towering strengths that the founder/CEO has, don’t join. You will never really respect nor learn from him. If you don’t complement each other, it is not going to work.