Jun 9 2021

Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams

Matt Blumberg has a new book out titled Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams. It’s a follow-up to his previous book, Startup CEO: A Field Guide to Scaling Up Your Business.

I’ve been working with Matt since 2000. That year, we merged two companies: Return Path and Veripost. Matt was the co-founder/CEO of Return Path. Fred Wilson was his lead investor. I was the lead investor for Veripost. The two companies did the same thing and were the only two competitors in a nascent category called “email change of address” (Veripost’s original name was IECOA which stood for “Internet Email Change of Address”). They were bashing each other over the head in a non-existent market as the Internet bubble began collapsing.

The founders of each company talked and, in between efforts to decimate the other, agreed it might be worth merging to survive. This guy named Greg Sands at a firm called Sutter Hill had met with both and was interested in the category and encouraged them to merge, at which point he’d fund the combined company. Fred called me and said, “Let’s figure out a deal.” I said, “They are both worthless right now – how about 50/50?” Fred responded with, “I have more money invested in Return Path than you do in Veripost – how about 55/45.” I answered, “Deal.” So for the deal, investors on both sides converted to common, we split the combined company 55/45, Matt became CEO, and Greg led a new Series A financing into the combined company. Twenty years later, we sold the business, a $100 million, profitable company, to Validity. Matt was still CEO. Fred, Greg, and I were still on the board.

Last year, Matt started a new company called Bolster. He co-founded it in partnership with High Alpha (we are LPs) and SVB. Soon thereafter, USV (Fred’s firm – we are LPs) and Costanoa (Greg’s firm – we are LPs) invested. It’s off to a great start. If you are looking to expand your leadership team or board, are looking for a part-time executive role or board role, or are an investor looking for fractional executives to join your portfolio companies, you should become part of the Bolster network right now.

I’ve worked with Matt for over 20 years and have experienced many ups and downs. His hard-won lessons from Return Path show up in Startup CEO: A Field Guide to Scaling Up Your Business.

For lessons from Matt and his Return Path management team, many of who are now execs at Bolster, you want to read Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams. When I saw the outline for Startup CXO, I grinned a wry smile. The book is 132 chapters broken into 11 sections. After the intro, the following sections are written by each exec.

  • Finance – Chief Financial Officer – Jack Sinclair
  • People – Chief People Officer – Cathy Hawley
  • Marketing – Chief Marketing Officer – Nick Badgett and Holly Ennerking
  • Sales – Chief Revenue Officer – Anita Absey
  • Business Development – Chief Business Development Officer – Ken Takahashi
  • Customers – Chief Customer Officer – George Bilbrey
  • Product – Chief Technology Officer and Chief Product Officer – Shawn Nussbaum
  • Privacy – Chief Privacy Officer – Dennis Dayman
  • Operations – Chief Operating Officer – Jack Sinclair

There’s a final part on The Future of Fractional Executive Work with a chapter by a different leader for each area above. Matt’s writing shows up regularly throughout, including an ending chapter for each section titled CEO-to-CEO Advice.

Each chapter is two to five pages long. It’s tons of information, organized well, in tight, bite-sized chunks. For example, here are the chapters in Part Five: Sales by Anita Absey (p. 247-302)

  • Ch 54: In the Beginning: From Prospect to Customer
  • Ch 55: Hiring the Right People
  • Ch 56: Profile of Successful Salespeople
  • Ch 57: Some Myth Busting
  • Ch 58: Compensating Sales Team Members
  • Ch 59: Pipeline
  • Ch 60: Scaling the Sales Organization
  • Ch 61: Scaling Your Team Through Culture
  • Ch 62: Scaling Sales Process and Methodologies
  • Ch 63: Scaling the Operating System
  • Ch 64: Marketing Alignment
  • Ch 65: Market Assessment and Alignment
  • Ch 66: Expanding Distribution Channels
  • Ch 67: Geographic Expansion
  • Ch 68: Pricing and Packaging
  • Ch 69: CEO-to-CEO Advice

The brilliance of this book is that everyone on your leadership team, including the CEO, should read it and then discuss it. Pick one section each week. At the end of a quarter, the entire team will have discussed all the functional roles, have a deeper understanding of expectations and responsibilities, use a common language for talking about what people are doing, and be able to adapt things to your own company. Also, if you aspire to be a CXO – you can figure out your career path by understanding the whole functioning of the relevant and adjacent departments.

I’m going to encourage every leadership team I work with to take this approach with Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams.

Matt and team, thanks for writing this!