Startup CXO. Matt Blumberg

was not consistent—some felt we should alternate masculine and feminine pronouns, and some felt we should go with the plural. Others thought we should use female pronouns to compensate for what has historically been a male‐dominated perspective. Given the lack of an obvious standard here, for this book, we chose to use the gender‐neutral plural terms (even though it looks a little funny to a grammar stickler like me). Second, we use the words startup and scaleup in the book without precise revenue‐based or employee‐count‐based definitions, but you should assume that startups are smaller companies, whereas scaleups are ones that have already reached some meaningful level of critical mass. Third, we use terms like “executive team,” “leadership team,” and “executive committee” interchangeably to refer to a company's senior‐most group of leaders. Finally, we frequently refer to the concept of an “operating system.” I talk about this at length in Startup CEO, but basically, it means—whether for a person, a team, or a company—the collection of meeting and communication routines and operating practices that form the cadence of a team's work.

A final note about the roles we selected for this book. We tried to stick with the basics: Heads of Finance, Marketing, Sales, Customer Service, Product/Technology, HR/People, Business Development, and Privacy. Some of these don't necessarily exist in all companies, for example, a lot of B2C companies don't have a dedicated Head of Sales, and instead a lot of the responsibility for revenue generation sits within Marketing or Business Development. And not everyone has a Head of Privacy or data protection (although these days, most companies probably should). These Parts are still worth reading, as someone in your company will be fulfilling those responsibilities. There are certainly other C‐level roles you'll find in large companies, and even in smaller ones that we could have added but chose not to—mainstream ones like Chief Information Security Officer and General Counsel, and even newer niche ones like Chief Diversity Officer and Chief Sustainability Officer. And there are plenty of roles in other industries that this book skips entirely for now, like Manufacturing and Logistics. Just because we don't cover a role in this book doesn't mean we don't value it … we just had to draw the line somewhere. We also had a lengthy discussion before writing the book about what to do with the role of COO (Chief Operating Officer). Because the responsibilities associated with the COO role vary widely company by company, we landed on including a single small chapter to just talk about the different types of COO out there. Most of the functions covered by COOs are covered elsewhere in the book, or in Startup CEO.

      Because Startup CXO is a book of books, and designed as a field guide, it's not necessary to read it from front to back, although you certainly can. The choice of the words “Field Guide” in the subtitle was deliberate because a field guide is a handy resource that you quickly consult. On the continuum of written works, you have a dictionary on one end (understand the meaning of words) and a book on the other end (understand ideas and concepts). A field guide sits right in the middle. A field guide has elements of definitions, ideas, and concepts, but the main purpose is to help the reader identify something, understand it quickly, and be able to apply what they've read to their situation. If you aren't reading cover to cover, read the two general chapters up front and then pick and choose. Pick your own function if you're a CXO and start there. Then move on to the function of one of your colleagues where maybe you're having some kind of friction at the moment, so you can build empathy with that colleague. We've organized the contributions into closely related groups like corporate (Finance, HR), go‐to‐market (Marketing, Sales, Business Development, Customers), and product (Product, Privacy, Operations) to help you learn about functions that likely interact with each other extensively.

      If you're a CEO, you could start with the function you “grew up in” and then move on to whatever function you need to hire, or you're most concerned with, or even the one that's working the best so you can gain some additional insight into why—and how to replicate that success in other places. I also have a “CEO‐to‐CEO Advice” section at the end of each functional Part and in those I share my thoughts on what “great” looks like for each CXO, signs that your CXO isn't scaling, and how I engage with the CXO. CEOs, Board members, and investors can quickly get an overview and understanding of each function by reading those.

Regardless of what role you play in a company and what experience you bring to the role, I hope this book speaks to you and inspires you in some way—that it's a playbook for something meaningful to you. If you're a CEO, maybe it will help you figure out who to hire or how to more effectively manage a direct report by telling you what “great” looks like for that function. If you're a functional leader in a startup, maybe it will help you focus on some aspect of your role you hadn't thought about yet. If you're an aspiring leader, maybe it will give you some insight into the kinds of steps you need to take in order to grow your career. Whichever persona you are, on behalf of all of the book's contributors, we hope you gain some insight, and we thank you for reading Startup CXO.

Chapter 1 The Nature of a CXO's Role

      I was struck by something as I read over the nearly complete manuscript of Startup CXO for the first time: each CXO believes that their part of the business is the most important part. And they make a compelling set of arguments:

       Shawn: If you don't have a good product, you don't have a business.

       Anita: If you don't have revenues, you don't have a business.

       Ken: If you don't develop the ecosystem, you don't have a business.

       Nick: If you don't generate market opportunities, you don't have a business.

       George: If you don't create exceptional customer experiences, you don't have a business.

       Cathy: If you don't recruit, train, and develop the right people, you don't have a business.

       Jack: If you don't have the cash, you don't have a business.

       Dennis: If you don't bake privacy in at the beginning, you don't have a business.

We had a debate years ago at a Return Path Board meeting as to whether we were a sales‐driven business or a product‐driven business—and more important, whether we should be one or the other. Two of our Board members, both of whom I respect tremendously, were anchoring the different points of view, Scott Petry, on the product side, talking about how successful Apple was at getting customers to camp out overnight to be the first ones to buy the newest iThing; and Greg Sands, on the sales side, talking about how successful Oracle was at getting product into the hands of customers. I took a devil's advocate point of view in the conversation, true to our operating philosophy at Return Path, which was that HR/People was the most important function because we were a people‐driven business.

      So, who is right? Are the best companies sales‐driven, product‐driven, people‐driven, or something else? Which of the CXO's functions is the most important? My answer is—they all are important, just in different ways, at different times, and in different combinations. While it's the CEO's job to balance the functions out—to figure out which lever to pull at which time, it's the CXO's job to be at the ready when their lever is pulled. And that gets to the important question of what the nature of a CXO role is, and why those roles can be tricky. CXOs have three principal jobs that they must keep in balance at all times, although there is a clear priority in my mind of the three jobs.

      CXOs are first and foremost members of the company's Executive Team. They must, must, must put that team, understanding of the different functions, and the relationships on it at the top of their agenda. They shouldn't show up on the team only advocating for their own team. CEOs must insist on that behavior and mentality. Without it, a company simply can't function sustainably. This concept is one that we have always called the First Team concept, and it's articulated very eloquently by Patrick Lencioni in a number of his books, particularly in The Five Dysfunctions of a Team and The Advantage. As members of the Executive Team, all CXOs are accountable to each other for the success of the business as a whole and must partner with each other to achieve that success.

      CXOs are also the head of their respective functional departments. They must carry the