AMG Author Interview – Matt Blumberg, Startup CXO

Heidi Cohen interviews Matt Blumberg.

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

Heidi: Startup CXO reads like a handbook for the senior management team of a startup that intends to grow into a full fledged business. It should be required reading for anyone considering starting a business (as versus a side hustle), scaling a startup, or joining a startup in a key management role.

Unlike many books on the market, it fills a definable niche of Startup CEOs and their management team. While it’s easy-to-consume so readers can find the sections that interest them, it’s a graduate level textbook. Unlike most business books, it clocks in at 600+ pages.

To start, what inspired you to write this book and how does this relate to your new firm, Bolster?

Matt: After selling Return Path, and finishing up the second edition of Startup CEO: A Field Guide to Scaling Up Your Business, I 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?

Startup CXO is closely related to Bolster’s business, since we are in the business of helping assess and place on-demand CXO talent. The same framework we use in Startup CXO to determine what competencies there are for each role on an executive team and what “great” looks like is the same framework that underlies the Bolster profile, search and matching process.

Heidi: What is the key concept behind your book? How did you come up with it?

Matt: Startup CXO is a book of books and is not necessarily designed to be read front to back, although it certainly can work that way.

It’s a how-to manual for people who lead executive functions at startups including CFO, CTO, CRO, CMO, and more.

  • There are a ton of takeaways about how to execute different leadership jobs in a startup.
  • It is also a how-to manual for CEOs about how to hire, scale, and manage a leadership team.

startup cxo graphic

Heidi: Where did you get the idea to have each section of your book authored by an expert in that specific area? Since writing each section is a major undertaking, how did you get so many busy executives to join you in this project?

Matt: I couldn’t possibly have written this book on my own – I am not an expert in leading and scaling each individual function at a company at a granular level. The other sections of the book needed to be written by a CXO who had the depth of experience, credibility and expertise.

Most of the co-authors are my Bolster co-founders or former Return Path executives who also wanted to help executives in critical leadership functions scale.

But even though all of the authors worked together at one or two companies, all of them are 20+ year veterans of their disciplines, and all have worked at multiple companies in different industries and at different stages and sizes, so they have a broad range of experience which informs their individual sections.

Heidi: What do you want readers to take away from your book or how do you want them to be different as a result of reading it?

Matt: There are two key lessons for CXOs coming out of the book.
The first one is that you not only have to master the entirety of your role in order to excel at it, but you also have to deeply understand your “neighbor function” roles, since you are on top of all the connection points and perspectives.

So if you run Sales, you’d better understand Marketing and Customer Success and Business Development pretty thoroughly. If you’re in Marketing, you need a tight grip on what Sales is doing, but also Product.

The second key takeaway for CXOs is that there are three important things you have to do within your day to day:

  • Understand all of the details that go into making your department work:
  • Have a strategic framework or a “raison d’etre” for your department; and
  • Always be thinking about what needs to change for your department to meet the business’s needs tomorrow, not just today.

For CEOs, the key takeaway is that:

  • Every functional department can be strategic, not just tactical, but that you need a leader for that function who understands how their function can have a strategic impact on the business — and how to make that a reality while still handling the transactional components of the job well.

The key lesson for aspiring CXOs is that “your” section of the book gives you a career development roadmap. If you really want to run your department over time, don’t just be great at the job you have today. Learn and ideally do some of the adjacent jobs within the same department.

Heidi: You mention having used the services of a business coaching organization when you were the CEO of Return Path.

How did you determine you had this need and how do you recommend readers find their own business coach?

Matt: My board member Fred Wilson told me I needed a coach almost 20 years ago. I was deeply skeptical of the value of a coach, but that was in 1999 or 2000 when coaches weren’t so commonplace. I engaged a coach — I think I said something lame and arrogant to him like:

“My board is telling me to get a coach, so maybe you can coach me on how to manage my board better” — and he smiled, suggested we start with a deep 360 review, and then proceeded to work with me for almost two decades to help me learn, grow, and be the best possible version of myself every day.

Now of course, having a coach or a mentor is much more common in business. One of the foundations of Bolster’s business is placing mentors and coaches with CEOs and CXOs to help them up their games. We have thousands of those people in our network.

Heidi: Do you have a set of questions you use to qualify a coach?

Matt: To find the right [coach] you need to first figure out what you want:

  • Do you want a coach (someone to help you develop as a person and as a leader)? or
  • Do you want a mentor (someone to help teach you the craft of your specific job function)?

If you want a coach, do you want someone who is more of a therapist, or one who is more of a business consultant, or some of both?

Then you need to interview multiple candidates and find one that really fits with your personality and style.

  • Ask them what their coaching process is like and what their coaching philosophy is.
  • How do they typically start engagements? How structured or unstructured are they in their work?

Check references and ask some of their other CEO clients what it’s been like to work with them. A good CEO Coach is someone you can work with literally forever.

That may sound like a full executive interview process, but it doesn’t have to be any more than you meeting someone and then trying them out. The cost of getting one of those hires wrong is very low – maybe just a few hours’ worth of your time.

Heidi: Similarly, you mention having a peer group of other startup CEOs. I think that this is great for any professional regardless of the type of business they work for. How did you find or form your peer group?

Matt: I started my own group that consisted of local CEOs that I either knew well or at least a little bit. At the beginning, our companies all had a number of things in common such as size/stage, and even (very broadly speaking) sector.

I have had a few groups over the years but my current group has been my longest group to-date. We have all sold, started or joined new companies throughout its tenure but our group has stayed together since we have so much context on each other at this point.

Our group meets over dinner (real or virtual) for about three hours about six times per year. We are only semi-structured in our approach.

Heidi: How do you recommend that readers go about finding or forming their own peer group?

Matt: There are a number of ways of finding or joining a group if you don’t want to make your own. The most common professional, moderated, and structured ones are Young Presidents Organization, Entrepreneurs Organization, Vistage or the CEO Forum. These Groups cost real money to join and have a time commitment.

It is my belief that it is less important what kind of peer group you join or form than it is that you form or join one. Having a group to lean on and learn from is the most important thing.

Heidi: In terms of the section related to Marketing and the CMO, I have a few specific questions since our audience is generally marketers.

As a marketer who has worked with a variety of different businesses from Top Global Corporations to Startups, I follow Peter Drucker’s view that marketing should be integrated across an organization.

Because a business exists to create and fulfill a customer need.

When viewed from this perspective, marketing takes a bigger role at the management table. And this is important, not just for the marketing department, but also, for the business. Because without being integrated across the organization, it’s difficult to show the full financial impact of its profitable revenue generation activities.

This integration helps to reduce costs by removing redundant activities such as salespeople creating their own materials or onboarding creating different materials from the marketing acquisition team. As businesses increase their investment in AI-driven technology, quality data across the business will also become more important.

What do you think of this perspective?

Matt: I totally agree and always told our head of marketing at Return Path that there were two kinds of marketing departments:

  1. Service centers who fulfill requests from across the organization, and
  2. Strategic groups that proactively drive everything from the brand to the customer experience through the rest of the organization.

If you’re a CMO, which do you want to be – the tail of the dog, or the nose? Marketing starts with brand and strategy and really clear math around customer acquisition and retention costs (and tactics) and can inform a massive percentage of the activities across the company, if done correctly.

Heidi: In the pandemic and post-pandemic period, customers and employees expect businesses and their brands to serve a higher purpose. This is documented in the Edelman Trust Barometer.

Employer media is most believable

Given the need for businesses to support their broader audience including employees and society in general, more businesses including DTC (aka: direct-to-consumer) often build their brand and audience first, for example Glossier. So marketing no longer has to choose between branding and driving sales. Memorability and consistency are what matters.

What do you think of this perspective and how should the CEO approach it?

Matt: I like to think that Marketing has always been about driving brand through sales and sales through brand – it can’t be a tradeoff!

I do think that CEOs should approach these issues pragmatically, not ideologically. Your shareholders are not likely going to hold you accountable for being a good citizen. They are going to hold you accountable for building a good business for the long haul.

The good news today is that because so many consumers care so deeply about issues like environmental sustainability, or fair wage labor, that companies who have the best business practices can let those drive their brand development and stakeholder perception to the benefit of the business’s bottom line.

Heidi: What books inspired your work/career? How did they influence you?

Matt: I’ll read anything Patrick Lencioni writes. He has incredibly practical frameworks and a great storytelling capability. But his book The Advantage is in my view his seminal work in that it combines multiple great management frameworks from across his books in one place. A lot of the basis of my company’s “operating system” can be found in this book.


Similarly, a lot of the basis of my personal “operating system” can be found in David Allen’s Getting Things Done. His simple approach to how you process work—what you do when, in what order, and how you keep track of both things and tasks—has been deeply influential to the way I work.


Finally, when I think about influences on my philosophy of corporate culture, there are many books that come to mind, but the shortest and simplest one is a book called Whale Done by Ken Blanchard, which is all about positive reinforcement and helping your people be the best versions of themselves.

Heidi: What is the biggest challenge that you’ve had to overcome in your life or career?

Matt: Starting an internet business in December 1999 seemed like a great idea until the massive dot-com crash only a few months later. The whole world we were operating in collapsed before we even had a chance to get a product in the market, and all of a sudden, no customer would take our calls — and most had gone out of business.

Fortunately, we were able to persevere by conserving resources, being smart about which customers we were going after and making sure we were solving a real pain point for them, and ultimately also by merging with a competitor so that when the market rebounded, we were ready to meet its needs.

Heidi: What’s something unusual or fun that most people don’t know about you?

Matt: I love reading American presidential history and biographies. My current count is well over 100 books, two biographies on all presidents other than the most recent few, plus many other thematically related books. I love studying American history through the lens of executive leadership.

Oh, and I have traveled to all 50 states and (if you count Antarctica), 50 countries.

Matt Blumberg

Contact Information:

Name: Matt Blumberg

Company: Bolster

Other book(s): Startup CEO, soon to be Startup Boards

Twitter: @mattblumberg

LinkedIn: blumbergmatt


Happy Marketing,
Heidi Cohen

Heidi CohenHeidi Cohen is the President of Riverside Marketing Strategies.
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