Startup CXO: A Field Guide to Growing Your Business' Critical Functions and Teams

Matt Blumberg has released a new book titled Startup CXO: A Field Guide to Scaling Up Your Company's Critical Functions and Teams. It follows his previous book, Startup CEO: A Field Guide to Scaling Up Your Business.

I've worked 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 its main investor. I was the lead investor in Veripost. The two companies did the same and were the only two competitors in a nascent category called "change of email address" (Veripost's original name was IECOA, which stood for "Internet Email Change of Address"). They were battling each other in a non-existent market as the dotcom bubble began to collapse.

The founders of each company chatted and, in between attempts to decimate the other, agreed that it might be worth merging to survive. This guy named Greg Sands at a company called Sutter Hill had met the two and was interested in the category and encouraged them to merge, at which point he would fund the merged company. Fred called me and said, “Let's find a deal. I said, "They're both worthless right now - how about 50/50?" Fred replied, "I have more money invested in Return Path than you have in Veripost - how about 55/45." I replied: "Deal". So for the deal, investors on both sides converted to joint stock, we split the combined company 55/45, Matt became CEO, and Greg led a new series A funding into the combined company. Twenty years later, we sold the company, a profitable $100 million business, to Validity. Matt was still CEO. Fred, Greg and I were still on the board.

Last year, Matt launched a new company called Bolster. He co-founded it in partnership with High Alpha (we are LPs) and SVB. Soon after, USV (Fred's company - we're LPs) and Costanoa (Greg's company - we're LPs) invested. It's a good start. If you are looking to expand your executive team or board, are looking for a part-time executive position or board role, or are an investor looking for split executives to join your portfolio companies, you should be part of the Bolster network now.

I have worked with Matt for over 20 years and have had many ups and downs. His hard-earned lessons from Return Path appear in Startup CEO: A Field Guide to Scaling Up Your Business.

For lessons from Matt and his Return Path leadership team, many of whom are now executives at Bolster, you want to read Startup CXO: A Field Guide to Developing Your Business's Critical Functions and Teams. When I saw the outline of Startup CXO, I smiled with a wry smile. The book is 132 chapters divided into 11 sections. After the intro, the following sections are written by each executable.

Finance – Chief Financial Officer – Jack Sinclair People – Director of Human Resources – Cathy Hawley Marketing - Marketing Director - Nick Badgett and Holly Ennerking Sales – Revenue Manager – Anita Absey Business Development - Business Development Manager - Ken Takahashi Clients – Client Director – George Bilbrey Product – Chief Technology Officer and Chief Product Officer – Shawn Nussbaum Privacy – Privacy Officer – Dennis Dayman Operations - Chief Operating Officer - Jack Sinclair

There is a final section on the future of fractional executive work with a chapter by a different leader for each area above. Matt's writing appears regularly throughout, including an ending chapter for each section titled CEO-to-CEO Advice.

Each chapter has between two and five pages. It's tons of information, neatly organized, in tight, bite-sized chunks. For example, here are the chapters of Part Five: Sales by Anita Absey (pp. 247-302)

Ch 54: In the beginning: from prospect to customer Ch 55: Hire the right people Ch 56: Profile of Successful Salespeople Ch 57: Some Myths Shattered Ch 58: Pay Sales Team Members Chapter 59: Channeling Ch 60: Scaling up the business organization Ch 61: Developing your team through culture Ch 62: Scaling sales process and methodologies Ch 63: OS Scaling Ch 64: Marketing alignment Ch 65: Market assessment and alignment Ch 66: Expand distribution channels Ch 67: Geographical expansion Ch 68: Price and packaging Ch 69: Advice from CEO to CEO

The genius of this book is that everyone...