Startup CXO

A Field Guide to Scaling Up Your Company's Critical Functions and Teams

Matt Blumberg, Peter M. Birkeland

• Publisher: Wiley
• Year: 2021
• ISBN:
  9781119774068
• Edition: 1
• Topic: Business
• Subtopic: Business General
• Index: Business

One of the greatest challenges for startup teams is scaling because usually there's not a blueprint to follow, people are learning their function as they go, and everyone is wearing multiple hats. There can be lots of trial and error, lots of missteps, and lots of valuable time and money squandered as companies scale. Matt Blumberg and his team understand the scaling challenges—they've been there, and it took them nearly 20 years to scale and achieve a successful exit. Along the way they learned what worked and what didn't work, and they share their lessons learned in Startup CXO.

Unlike other business books, Startup CXO is designed to help each functional leader understand how their function scales, what to anticipate as they scale, and what things to avoid. Beyond providing function-specific advice, tools, and tactics, Startup CXO is a resource for each team member to learn about the other functions, understand other functional challenges, and get greater clarity on how to collaborate effectively with the other functional leads.

CEOs, Board members, and investors have a book they can consult to pinpoint areas of weakness and learn how to turn those into strengths. Startup CXO has in-depth chapters covering the nine most common functions in startups: finance, people, marketing, sales, customers, business development, product, operations, and privacy. Each functional section has a "CEO to CEO Advice" summary from Blumberg on what great looks like for that CXO, signs your CXO isn't scaling, and how to engage with your CXO.

Startup CXO also has a section on the future of executive work, fractional and interim roles. Written by leading practitioners in the newly emergent fractional executive world, each function is covered with useful tips on how to be a successful fractional executive as well as what to look for and how to manage fractional executives.

Startup CXO is an amazing resource for CEOs but also for functional leaders and professionals at any stage of their career."
—Scott Dorsey, Managing Partner, High Alpha

Part One
Introduction

Matt Blumberg

Introduction

After selling Return Path, and finishing up the second edition of Startup CEO: A Field Guide to Scaling Up Your Business, my colleagues and I at our new startup Bolster started envisioning a new book as a sequel or companion to Startup CEO.

Simply put, the first book left me with the nagging feeling that it wasn't enough to only help CEOs excel, because starting and scaling a business is a collective effort. What about the other critical leadership functions that are needed to grow a company? If you're leading HR, or Finance, or Marketing, or any key function inside a startup, what resources are available to you? What should you be thinking about? What does “great” look like for your function? What challenges lurk around the corner as you scale your function that you might not be focused on today? What are your fellow executives focused on in their own departments, and how can you best work together? If you're a CEO who has never managed all these functions before, what should you be looking for when you hire and manage all these people? If you're an aspiring executive, from entry‐level to manager to director, what do you need to think about as you grow your career and develop your skills? And if you're a board member or investor, what scorecard or metrics are you using to ensure your companies and investments are achieving greatness?

That was the origin of this new book, Startup CXO: A Field Guide to Scaling Up Your Company's Critical Functions and Teams. This book is a “book of books,” with eleven separate, detailed Parts, one for each major function inside a company, each composed of several discrete short chapters outlining the key playbooks for each functional leadership role in the company. Because it covers CFOs, CMOs, CPOs, etc.—we landed on “Startup CXO” as the name.

America's “startup revolution” continues to gather steam. There are increasing numbers of venture capital investors, seed funds, and accelerators supporting increasing numbers of entrepreneurial ventures. While there are a number of books in the marketplace about CEOs and leadership, and some about individual functional disciplines (lots of books on the topic of Sales, the topic of Product Development, and the like), there are very few books that are practical how‐to guides for any individual function, and none that wrap all these functions into a compendium that can be used by a whole startup executive team. Very simply, each Part in this book will serve as a how‐to guide for a given executive, and taken together, the book will be a good how‐to guide for startup executive teams in general. The eleven Parts are:

• Part 1 Introduction (Chapters 1 and 2)
• Part 2 Finance and Administration (Chapters 3–23)
• Part 3 People and Human Resources (Chapters 24–41)
• Part 4 Marketing (Chapters 42–53)
• Part 5 Sales (Chapters 54–69)
• Part 6 Business/Corporate Development (Chapters 70–82)
• Part 7 Customer Success and Account Management (Chapters 83–94)
• Part 8 Product and Engineering (Chapters 95–108)
• Part 9 Privacy (Chapters 109–121)
• Part 10 Operations (Chapter 122)
• Part 11 The Future of Executive Work (Chapters 123–132)

We also have a number of ancillary materials—templates and charts—that would normally be included in an Appendix. Because the book is already over 600 pages we decided to provide that material externally on our Startup Revolution website: “http://www.startuprev.com” www.startuprev.com.

This book carries my name as its principal author, and although I'm writing parts of it and editing it, I'm not THE author, I'm AN author. That's an important point. The book has a very large number of contributors and external reviewers and you'll probably notice a different “voice” for each Part. That's what you should see with multiple authors, but despite the various perspectives, we're all focused on providing a playbook for each functional area including the mistakes we made, what we would do differently, and what worked really well. Each Part has one or two principal authors who have the experience, credibility, and expertise to share something of value with others in their specific functional disciplines—most of my Bolster co‐founders are writing Parts, and the others are being written by former Return Path executive colleagues or members of Bolster's network. And that is a good lead‐in to a few caveats before you embark on the book.

First, although most of the book is being written by former Return Path executives, it is not meant to be the Return Path story. Every author here has 20–30 years of experience working at multiple companies of different sizes and at different stages and in different sectors on which he or she is drawing. It's also not the story of Bolster, the new company that a number of us started earlier this year, although Startup CXO is pretty closely related to Bolster's business of helping assess and place on‐demand CXO talent.

Related, this book is based on the experience of the contributors—as with Startup CEO, for the most part, that means U.S.‐based tech or tech‐enabled services businesses. Most of us have more B2B experience than B2C, although a number of us have both. Some of the authors write a lot about people, some write a lot about process, some are philosophical, some are more practical and tactical. They reflect the nature of those functions and the nature of the writers of those Parts. I hope the book proves to be timeless and that it spans cultural and industry boundaries but there will be some inherent limitations based on our own experience.

A few notes on language. We realize that not every leadership role in a startup is actually a “C”‐level role. Sometimes the most senior person running a functional department is an SVP, a VP, or even a Director or Manager. But Startup Functional Leader is a lousy title for a book. There are also some elements of language worth noting up front. First, we got a lot of feedback from people we trust and respect on how to handle gender pronouns, and unfortunately, the feedback 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 coll...