The Rise of the COO Role, Part 2

Envisioning Your Career as COO

Following my fireside chat with Tomasz at Redpoint, I published a post on the Rise of the COO Role, discussing why founders are increasingly recruiting COOs, and offering advice to founders on how to find the right COO for them. In this post I'll address the other side of the "dynamic duo": the COOs themselves. If you're currently a COO, or if you're aspiring to be one, this post is intended for you!

So you want to be a COO…

As Gainsight CEO Nick Mehta and I discussed during a conversation with a few SaaS leaders on Clubhouse recently, sometimes there's something a bit "off" about declaring "COO" as your ultimate career goal. Here are a few reasons why:

(1) Desire to be internal-facing

Some people who say they want to be COO actually mean that they don't want to be external-facing like a CEO. They primarily want to focus on keeping the internal operations in order. But the reality is that many (even most?) COO roles that are opening up nowadays -- often concentrated in the CRO/"Chief Journey Officer" (Type #3) and President/"Runs the Biz" (Type #4) categories of COOs -- have major external-facing responsibilities. In fact, the entire purpose of the role is often to be more external-facing so that the founder, typically with a technical background, can focus on the product. 

If you want to be internal-facing, you may want to instead set your career goal to be CFO and focus on developing your finance skill set. This expertise can form the cornerstone of you becoming a "CFO-plus" (COO Type #2).

(2) Actual desire to be a CEO

Some people secretly want to be CEO but aren't confident they can do it. So instead they say they want to be a COO, as the #2 role within a company. I say, if you want to be a CEO, make that your aspiration, and figure out the best path, which may or may not require you to become a COO. Be bold! 

(3) Vagueness in what "COO" means

As I mentioned in my earlier post, COO is one of the vaguest titles. Make it clear what type of COO you want to become -- for example, by identifying with one of the four types outlined here.

(4) The element of opportunism

Because the definition of any particular COO role is so specific to what the CEO needs, many COOs come from internal promotions. Because of the rise of technical founders and the increasing need for COOs, many more companies are recruiting externally than before. But even then, unless you're on the radar of the company, their board, or their (sometimes secretive) search firm, it may be hard to hear about COO roles when they come up. (Btw, I have plenty of thoughts on the ethics of how recruiting searches are run...starting here.) In other words, it's very hard to "apply" for a COO role. 

What can you do to get the job?

All that said, there are definitely a few things you can do to position yourself for COO roles that come up. 

(1) Be opportunistic

  • Get to know COOs who may get a lot of recruiter calls but aren’t interested in taking another COO role. They may pass those opportunities to you.

  • Get to know investors. VCs build exec networks and can place you in COO roles at their portfolio companies. Many firms have talent partners that run those exec networks and assist in exec searches for the portfolio.

  • Get to know headhunters who recruit for COOs.

  • Get to know founders. They're looking for their "other half," so see this as a matchmaking process.

(2) Build the background and skills

  • Type 1 (Chief of Staff): Learn how to build frameworks from scratch and coordinate cross-functionally without much guidance. 

  • Type 2 (CFO+): Learn finance. Build processes. Form healthy relationships with the business line leaders.

  • Type 3 (CRO/Chief Journey Officer): Run different go-to-market functions over time. Own revenue numbers and prove that you can consistently exceed your targets. Hone your leadership abilities; read a lot (biographies, books on communication and EQ) so you can absorb past leaders' intuition; and develop strengths in change management.

  • Type 4 (President/Runs the Biz): Everything in Type 3 above, plus put on "your CEO hat" as much as you can. Feel ownership over the strategic direction and success of the company as a whole.

(3) Don’t be afraid to be a “generalist.”

The typical career path at tech companies involves specializing in a function and rising through the ranks. A number of folks who don’t fit that mold have asked me, “Am I hurting myself by being a generalist / jack-of-all-trades?” If you want to be a COO, the answer is generally “No.”

Given the cross-functional nature of their role, COOs can be more effective when they have previously been in the shoes of multiple functional leaders. Moreover, if you’ve worked in multiple functions, you’re probably the kind of person that will enjoy the varied work activities of a COO.

I do think it’s a good idea to be deliberate about your career choices. Know why you’re switching functions when you do. Make sure you’re taking on more responsibility over time and not solely hopping across functional lines. But it’s okay to be unconventional: being a generalist is a good signal of (although not a prerequisite for) your effectiveness as a potential COO and could accelerate your career progression.

You got the job! Now how do you work with the CEO?

I'll avoid discussing tactics for collaboration in this section -- although this could be an interesting topic for a future post -- and instead focus on a beneficial mindset that COOs can bring to their relationship with their CEO.

The best CEO-COO pairs feel a great deal of mutual respect, even admiration. This sentiment is in contrast with a belief among some COO candidates that they'll be taking on the role to be the "gray hair" or "adult supervision" for a young founder. A COO with a healthy mindset believes that their founder CEO has tremendous talents, e.g. product instinct or fundraising ability. And that COO is always thinking: "How can I bring out the best in this CEO?"

This respect can lay the foundation for deep trust, which is obviously an underpinning of a high-functioning CEO-COO relationship. One COO I know refers to her relationship with her CEO as a "work marriage," an indicator of the degree of closeness that the best pairs demonstrate. The importance of trust is one reason why COOs are sometimes promoted from other roles at the company: trust has already been established.

How should you evaluate yourself?

In the case of many roles, there is a primary metric that defines success. Sales quota attainment, renewal rate, and pipeline generation are a few examples. Certainly the COO will be accountable for certain metrics like these, particularly if they are a Type 3 or Type 4 COO.

However, the measure of a COO's success can't be defined so narrowly. One reason is that they should pay more attention to the long-term than the typical C-level executive, in addition to ensuring the achievement of near-term targets. Ask yourself:

  • Are you meeting your objectives today, with all relevant stakeholders — investors, customers, and employees?

  • Are you laying the groundwork to meet your targets next year?

  • Are you laying the foundation to fulfill the company’s ultimate purpose / mission

Another reason why a COO can't be evaluated using a narrow set of universal benchmarks is that the context matters. What's most important is that you as COO effectively complement your particular CEO, with the success of the overall company in mind. To figure out whether you're complementing your CEO well, ask yourself: 

  • Are you dividing and conquering appropriately with your CEO, or are you overlapping too much?

  • Are you aligned on near- and long-term priorities?

  • Do you resolve disagreements constructively?

  • Do you make each other better (1+1=3)?

P.S. One way to evaluate yourself regardless of your role is to ask: "Am I the best person that this company could possibly hire for my particular role?" If you’re at a hot company, they can always recruit your replacement. So figure out, who are those people who could possibly replace you? Get to know other COOs with similar roles and at companies with similar stages, and learn what gaps exist between their abilities and your abilities, then strive to learn everything you can from those people.


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