Building and Selling

I've taken an extended hiatus from blogging. We all know 2020 threw a lot of plans to the wayside. The loss of routine has undoubtedly had an impact on my writing. The web site littered with blog posts saying people will write more frequently with no follow-up, but I will commit anyway to more frequent posting.

I have a very old Evernote of blog topics, and I found one titled "two CEOs: builders and sellers." The subject stood out to me because of my evolution as a CEO. The way we perceive ourselves is critical to how we go through the world. What we think of as our skills, strengths, and weaknesses affects our output and work. In that way, the idea of what we are bad at can create a self-fulfilling prophecy when our lack of self-confidence in a particular skill causes us to underperform.

For most of my life, I have struggled with identifying myself as someone good at sales. The cliched joke of a used car salesman and the environment in which I grew up, with a scientist and a librarian for parents, are both probably sources of my initial disdain for the sales profession.

Over the years, I have realized that much of life, not just work, but personal is about our ability to persuade one another to a way of thinking or action. Persuasion, which includes marketing and sales skills, are critical to life and especially important to work in the career world.

For many years, I thought that I could not sell things to people. This thought is part of the idea that there are different types of CEOs: those who can sell and those who can build. I no longer subscribe to this concept.

In 2006, I applied for a job with a now friend. It involved going to events and conferences and representing this small investment firm. I've never asked exactly how I talked myself out of the role and failed to get the offer, but I know I responded to that discussion by basically saying, "I'm not that interested in sales." I instead went to Green Dot to be a product manager.

While I was at Green Dot, I worked on our retailer implementations and interfaced directly with our retail partners like Walmart, Walgreens, CVS, Kroger, and others. After a reorganization one year in, I found myself reporting not up to the head of product, but the head of sales. I was frequently going on sales meetings with account managers and, when one left the company, found myself the interim salesperson for a mid-sized account. (Unfortunately, I didn't get any of the commissions!)

It was around this time I started to think that maybe I did have some sales skills. I realized that, earlier in my life, I had clearly sold services to people.

From 1997 to 2003, I operated a sole proprietorship making websites, managing email and web servers, and other network and systems administration tasks. Over the years, I booked more than $50,000 in revenues from this business. In retrospect, it's obvious I sold services here over the years.

At Green Dot, I had an awakening that I was capable of sales, and I learned a ton from being part of the sales team. I watched how they interacted and what they achieved. I was lucky to work with the entire sales team and, as a result, saw many very different approaches from which I could learn.

When I started Wallaby, I still didn't quite think of myself as someone who could sell. While I was successful in raising $1.6MM in funding and getting a huge waitlist started to consumers, demonstrating some real persuasion skills, I had an investor approach me a few months in and tell me to get a "real salesperson" in the door for business development. At the time, I agreed, brought in a great leader, and we thrived because of it.

At the end of that journey, I sold Wallaby. The sale was a multi-million dollar deal, with a successful outcome for founders, employees, and investors. I negotiated the deal, so I think that counts as some meaningful dealmaking.

Now with Vertical, we have put together the most unique, if not the only nationwide network of boutique wineries. We have more than 430 partners, and I have done hundreds of sales calls this year to get these wineries onboard with our unique program for the Grand Reserve World Mastercard. Now I feel like a salesperson. It's great.

I used to think of myself primarily as a product development-oriented person. I wrote code from 1997-2003 in my first two businesses. Today I write a limited number of simple scripts or programs and wouldn't claim I do much building. I had the title of product manager starting in 2006, becoming Chief Product Officer at Bankrate Credit Cards in 2015. I felt like that was who I was: the product builder CEO.

Today, I depend on my co-founder Samantha to drive our product development process, and I am the salesperson. I don't think this makes me only a seller and not a builder. You can be both, and in fact, founders must be both. Being a builder doesn't mean you write every line of code, and being a seller doesn't mean you have to close every deal. You can have a more complicated personal identity in which you are good at more than one thing.

To survive as a startup CEO, you have to engage all of your skills, grow all of your skills, and focus on the right talent for you and your team at the time. There are many types of CEOs, and you may have to be different CEO in different circumstances. What you can't do is limit yourself.