go alone. If you want to go far, go together.
—African proverb
I haven't come this far, only to come this far.
—Unknown
Foreword
As a first‐time tech founder and CEO at ExactTarget, one phrase kept ringing through my head: “I don't know what I don't know.” Even with 10+ years of business experience and a freshly minted MBA degree, I had so many blind spots having never built software, raised venture capital or even led a multi‐functional organization. Filling in these gaps took many years and lots of trial and error.
One of my gap‐filling strategies was to learn from other CEOs going through similar highs and lows of scaling their company. On this journey, I was fortunate to meet Matt Blumberg. As CEO of Return Path, Matt was building a high growth company in the same digital marketing industry as me. I was impressed by his leadership, strategic thinking, and commitment to helping other entrepreneurs. We became fast friends and we both looked forward to learning from one another.
Matt was always gracious and willing to take my call or have dinner together. Our conversations covered every topic imaginable from leadership to board management to strategic partnerships to international expansion. My advice to entrepreneurs and leaders—build your peer network and spend time developing and nurturing these relationships. While board members and advisors are an important source of knowledge, learning from peers can be invaluable.
One of the highlights of my relationship with Matt was when we were both invited to the White House to witness President Obama signing the Jumpstart our Business Startups Act (or JOBS Act) in April of 2012. With bi‐partisan support, the law opened up crowdfunding for startups and streamlined the IPO path. ExactTarget had just gone public two weeks prior so I knew the benefits that the JOBS Act would bring to entrepreneurs. But what I didn't know in April 2012 was that the event would foreshadow my relationship with Matt and how we would work together supporting entrepreneurs and startup ecosystems.
Fast forward to 2021. We are facing unprecedented challenges in the world and the need for innovation and leadership has never been greater. CEOs and functional leaders need tools and resources to accelerate their learning curves and the learning curves of those around them. Speed of learning, thought, and action are more important now than ever. This is why I am so excited about Matt's latest book, Startup CXO.
Startup CXO provides a comprehensive field guide to starting and scaling tech companies. Really, the information is super helpful to any company. It provides a “book within a book” framework to enable and empower readers to jump into any section as needed. And it's written by practitioners who provide tons of tangible advice and actionable insights. By reading this book, I believe that leaders will be better equipped to build great companies and anticipate what's around every corner.
In my view, the best CEOs have a grasp of all functions. They can go a mile wide and a couple inches deep. They hire A+ talent and build a culture that brings out the very best in people. They understand how Sales and Marketing fit together, they value HR, Finance, and Legal and understand their interdependencies, they have a clear vision for how Product and Engineering fit together, they know how to be aggressive and how to manage risk, and so much more.
So, Startup CXO is an amazing resource for CEOs but also for functional leaders and professionals at any stage of their career. The best functional leaders and professionals understand that cross‐functional teamwork is everything. It's so important to have insight and empathy for how other areas of the organization operate. The big picture is needed to see how all of the puzzle pieces fit together.
I feel so lucky that through our venture studio, High Alpha, I have the opportunity to work with Matt and his leadership team as we build Bolster—a talent marketplace for startup and scaleup tech companies. We are living and applying the concepts and lessons contained in this very book!
My wish for you is that reading Startup CXO minimizes your “I don't know what I don't know” list; that it accelerates your development, your curiosity, your ability to ask the right questions, and helps you surround yourself with the right talent. My wish is that you dream big, lead with purpose and integrity, and master your craft. I hope—and believe—that Startup CXO will be a helpful companion for you on your company‐building journey.
Good luck!
Scott Dorsey
Managing Partner, High Alpha
April 2021
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)
