The Slow Track To Success

A rant about my misadventures on the "management track"

When I was growing up there was nothing more I wanted than to be part of the establishment. I saw myself wearing a suit, perhaps in a boardroom or skyscraper somewhere, leading an important meeting. It just seemed like something I was meant to do.

I made a lot of choices when I was younger in pursuit of that goal. Yes, I wanted to be a trial lawyer, but more than that, I wanted to be someone polished and articulate. Who looked and acted like a leader. The grown up I envisioned becoming was someone who wore a nice suit and knew a lot about wine.

Somewhere along the way though, I realized that wasn’t me. I’m from an underdog family from an underdog culture. We have never been part of the establishment. Which might be why when I first stepped foot in the corporate world—first at IBM, and then at Sullivan & Cromwell—I just didn’t fit in.

At first I thought it was a race thing. Which it was, partly.

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When you look at “the establishment” you can quickly see that it’s less about how capable you are, and more about how you fit in. The leaders of the establishment always find ways to jump through verbal gymnastics to justify their existence at the top.

But at the end of the day it’s obvious—they’re better at talking than doing.

Startup Sales

That’s part of the reason why I left to join the startup world. And specifically why I chose sales. I thought it might be more of a meritocracy there. After all you either closed the deal or you didn’t. And since a lot of these sales took place over the phone (ie. cold calling) my race could never be held against me.

That’s why I absolutely murdered the game my first year as a sales rep. I outproduced everyone simply because I outworked everyone. And because I found ways to adapt to my environment. I came up with my own pitch and made a hundred calls a day, and then iterated on it, while my coworkers made a dozen and left the office early.

My performance stood out to everyone. Leadership told me I’d been identified as a “rising star” and wanted to put me on the fast track to management.

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As a leader. As part of the establishment. Which is what I always dreamed of. So I agreed, and became a team lead, a manager in training. It seemed like the right decision for me.

But then that’s when I fucked up.

The Management Track

The thing they never tell you about being on the “management track” is that it’s fundamentally unfair. Promotions are based on this entire game that has nothing to do with actual impact or understanding of the market. Instead you need to have the right “sponsors” and “mentors” who themselves might not actually be good at their job. And you need to be generally liked by everyone.

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I knew I was good at sales. And yet I kept finding myself having to convince people who were bad at sales to do things. Their ideas were terribly out of touch with reality. At some point I realized it was a waste of time to debate them, so I just went along with their terrible ideas. I’m ashamed to admit that it’s because I wanted to get promoted.

At some point I also realized that no amount of people pleasing was going to get me promoted. As someone who was on the verge of receiving a promotion, I was more valuable than someone who’d actually gotten the promotion. The former was easy to control; the latter was a wildcard who could leave at any moment for another company with more money and a bigger title. So they kept me from moving up.

The realization was tough. I’d put in so much work, building so many relationships, creating so much goodwill that would go up in smoke. Because none of those assets were portable. They were all valuable so long as I stayed in the company.

In other words, everything I had of value came directly from The Organization.

Creating My Own Path

So I decided to play the game differently. Instead of generating economic value from The Organization, I decided to get it from The Market. I knew how to sell. I knew how to adapt to changing circumstances. At the time I was still early on in my social media journey, but I saw how I could access buyers directly, and without needing a huge team or resources.

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In 2019 I decided to step off the management track to become a pure individual contributor. I stopped caring about whether I’d ever find an establishment job, or an executive role. It was perfectly aligned with who I was authentically.

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An underdog with a smartphone in hand, who could make things happen just by figuring some shit out.

I stepped down and went from being a Director of Sales to becoming an account executive. It was tough on my ego but incredible for my freedom and autonomy. I no longer had to sit through meetings with mediocre managers (a common symptom of being at a venture backed “scale up”). Instead I focused on LinkedIn, and how I could use that to generate new leads in the legal market.

Uncharted Territory: Social Media

Somewhere along the way I discovered the power of Tik Toks in increasing my self generated marketing. Which is why I leaned into it hard amidst the chaos in 2020. And I was rewarded for it. Today my personal platform rivals many media companies. I created my own distribution.

The funniest thing about all this to me is that I ended joining a far more successful startup than the other ones. It’s not by accident. If your org culture is healthy, it will quickly identify those who know what they’re talking about, and find a way for them to do what they do best. That’s how Ironclad found a way to bring me into their org.

If your org culture is weak, you get hamstrung by weak managers who obscure the right path forward. Not only that, I would personally warn my friends away from those types of companies, because I don’t want them to go through what I did.

Takeaways

It’s a crazy time in the technology market right now. So here’s my message to my readers. I don’t have “advice” per se, but I feel strongly about these takeaways:

• To the individual contributors: Don’t play the game. I don’t know how it works exactly at your company but don’t play it. Instead obsess about bringing real value, whether it’s selling or building. Or whatever. The higher ups might not recognize it, but someone will. People talk. Executives talk. And if you’re legit, the word will get out—trust me on that.

• To the founders and CEOs: Create an environment for real talent to thrive. Question everything your managers tell you. Because while weak individual contributors are easy to spot, weak executives are nearly impossible to distinguish from the good ones. Once your company becomes known for supporting talented individual contributors, anyone else who’s also talented will suddenly show up at your door.

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1. I once worked at a startup full of white male executives. After attending a diversity conference, I brought back a whole bunch of leads to share with the team. The all white execs made sure those hot leads (from a conference about diversity!) went only to the white male members of the sales team. I don’t think they did any of this on purpose but it was a stark reminder of the role race and gender plays in all this.

2. Even though I was identified as a rising star, it wasn’t easy. There was one particular sales leader who kept pushing this other narrative of me being a “smart lawyer” with weak sales skills. That somehow my raw intelligence was the only reason why I ended up producing so much revenue.

3. It’s a lot of work to get everyone to like you. That’s time spent not understanding your craft or your market.

4. I have always kept myself honest by using what I call “the toothbrush sales test.” If the world falls apart and I can’t figure out a way to make money, can I just get a job selling toothbrushes (or toilet paper, or any other random product) to randoms on the street? Would I be able to move product? The answer to that question tells me everything I need to know about whether I have real skills.

5. A big part of this move was also family obligations. I’d rather have a smaller title and more variable pay, and not have to take time away from family to attend pointless meetings. I wrote about this on a LinkedIn post this week, but was less blunt about it publicly.