⚠️ WARNING Had anyone shown me this post when I was the grouchiest about titles a couple years ago I would have been so mad at them. I would have griped that the person writing this is doing so from “the other side” after they got what they wanted. I would have mocked what I assumed was faux humility. I would have been, as described, a grouch. You’ve been warned.
After enough Super Bocks some of my Portuguese friends will claim descent from aristocratic title holders. The evidence is flimsy but I love these stories. An aunt discovered a box of letters in a country house that has been in the family for generations. A grandmother’s middle name cross referenced with baptismal records in a village. Tales of squandered fortunes and scheming uncles and lurid affairs.
America lacks this kind of generational heraldry, but we are still humans and we are still status-obsessed. So we just lean on professional titles and new money instead. The system feels slightly more meritocratic but makes for mediocre dinner party conversation.
Unless we’re talking about outlaw stories. Americans love to tell tales about distant relations who were Wild West criminals. I swear to God, every woman I have ever dated seriously, including my wife, has claimed to have a prominent horse thief in their family. It is one of a few things that make me believe that this might be a simulation. Or maybe just that I have a thing for women with serious Texas roots.
Before LinkedIn became a cess pit of posts about how you can apply lessons from your divorce to B2B SaaS sales, the primary purpose of the social network was to feature your own title regalia. The first step when you signed up prompted you to create a chronology of your ascent through schools and companies.
My entries looked odd. I spent years making all the wrong decisions if you cared about titles. I just found people I liked who were doing hard things. And I am eternally grateful for it.
When I graduated from The University of Texas, I turned down a full-time offer to join Bain in order to work for this eccentric healthcare technology investor because I thought it sounded more fun. I bailed on the most prestige job someone at that stage could have in that era. It worked out.
A few years later I joined the M&A engine at ESW Capital - a firm no one had heard about (that changed slightly). Again, something that I just thought would be exciting. I didn’t think much about the brand recognition. I went to learn alongside great people and I had a blast.
That healthy habit followed me in 2018 when I joined this privately-held software company called Cloudflare that did something on the Internet. I was ready for a new challenge after ESW and the professional mentor that I trusted the most said I should do whatever it took to work with a particular leader at Cloudflare. I took his advice.
No one in my Texan life could describe what Cloudflare did much less spell the name. That was fine by me. Like the other hops, I followed the people and ideas that I wanted to spend time being around. This decision also worked out - big time.
I kept rowing the boat without thinking about titles until a little voice in the back of my head found an audience. Sometime during the pandemic I felt both a bit more accomplished and a lot more bored. Like other white collar professionals in that era, work had become my primary identity and social outlet. I started to care about that old LinkedIn page.
It snuck up on me. I had been lucky to find some success at Cloudflare but when I joined the organization we were (rightfully) stingy about titles. Everyone was just a Product Manager with a couple Directors scattered about. We were too busy building and too small to worry about levels like senior/junior prefixes.
And then someone drafted a Running Back. If you have played fantasy football, you’ll be familiar with that moment in a league draft when someone first takes a Running Back or Tight End and a scramble begins. Most leagues are configured to favor Wide Receivers and Quarterbacks, so the first pick outside of those categories changes the calculus a bit. Suddenly you are worried that you might get left behind. Do they know something that you don’t? Are you going to be left without a chair when the music stops?
A few things happened that made me (embarrassingly) green with envy. We became a more mature company and attracted more senior talent. They joined with correspondingly senior titles. The team we already had inside of the organization had also earned the right to ask for promotions after years of grinding it out. All of those are normal things in the natural lifecycle of a company, but my knee-jerk reaction was to worry that this was an arms race and I was going to lose.
So I started to care. Not in a way that changed how I worked, but enough to influence how I thought about the work in some cases. It made me feel icky. Was I the kind of person who measured myself based on my email signature? Thankfully, my fear was misguided. With some patience I wound up with a new title that reflected the growth of my team and product line - VP of Product.
I had everything my ego wanted at this stage. I was VP of Product for the most exciting product portfolio at that time. I had led that business since I was just a Product Manager and the “portfolio” was just a prototype. The company was becoming larger and more well known. People sent me DMs to talk about CPO jobs and Sales folks wanted me on more calls to impress customers.
And it didn’t matter one bit to anyone that I loved. No one at a Lisbon dinner party or 4-hour lunch in Sintra knew what it meant nor did they care. No one who knew me in the company thought differently of me. My family didn’t love me any more. People just knew Sam. When they thought about me, they thought about the way I treated them or the way I made them feel.
And all of that makes me happy. Those are the communities I want to inhabit. People who love you. And people who, when they are curious about your job, are interested in your industry or your passion for your work - not the ranking in some organizational chart. Titles are like the flashier Rolex watches - the people that are impressed by just the cost and brand (and not the stylistic choice) might not be the best crowd to aspire to join.
That’s not to say that titles have no value or you should shy away from them. They can serve a real purpose when you are job hunting or trying to recruit a candidate or demonstrating to a customer that you are, in fact, giving serious attention to a concern they have. Those are important uses of your LinkedIn display. It’s the chasing after the title that winds up making you feel hollow, at least it did in my case.
All to say, I have a new title at Cloudflare. I recently decided that the team I assembled in the Cloudflare One unit could thrive without me. So I raised my hand and asked what else the company needs most. And the answer came back that, right now, I could best help out as the Chief of Staff in our Emerging Technology and Incubation group - my old team.
I’m thrilled - especially because the leadership that made me want to join back in 2019 is still there. Not to say my old role is done, by any means, it’s just in a state that I’m proud to call it ready for a new generation to lead it to places beyond what I could.
I have always been happier over the long run by just finding ways to do hard things with people that I like. Being Chief of Staff in ETI gives me a new inning to do that. Six years after I joined Cloudflare I am once again showing up on a Monday to open a Cloudflare laptop as an individual contributor with little authority and a mountain of problems to try and tackle. Feels good to be king of that hill again.