Slow Down To Speed Up

Why getting overlooked for a promotion at my first sales job helped put me in the right place at the right time to succeed

This week I posted on LinkedIn about my first year after leaving the law and moving into legal tech. The post describes being overlooked for a promotion, why I decided to not quit for a higher paying job, and how it was all worth it. Today I’ll expand on my thoughts about some of the details I shared in that post.

Not having the right credentials

"I know you used to be a lawyer, but you're just not ready to be an account executive yet," they said. And then they went back to reviewing resumes from gym salesmen and 23-year old tech bros for the job of selling software to law firms.

It really sucked when I learned that my new employer didn’t care about my legal background. Well. They pretended to. Gave me lots of compliments about being smart even though they really had no evidence for that. It was just how I was perceived. And yet my tangible skills and knowledge were overlooked.

I had lots of experience using, buying, and working with e-discovery. Which was exactly what my employer focused on! They just didn’t want to promote me to a senior sales position.

Instead they hired all sorts of random people to sell the technology. There’s a belief that if you can sell something, you can sell anything. So sales leaders hire based on “years of sales experience” even if that experience is in something completely different, like gym memberships or HR technology. Of course, how these hires perform is a different question entirely.

As a lawyer with 0 years of sales experience, I certainly wasn’t gonna get promoted.

This belief, by the way, is not uncommon in the tech startup space. I recently advised a late stage legal technology company, and found the same pattern. The main go-to-market executive, who had deep functional experience with no background in the legal industry, was placed in charge of sales & marketing. No one could figure out why the team was struggling to create compelling sales pitches to these lawyers.

Why I didn’t quit

I wanted to quit. But I didn't. Because even though being overlooked sucked, the sales game was just starting to get interesting. I was so efficient at my job that I had the time to experiment with advanced techniques, like how to leverage LinkedIn for social selling.

It was super tempting to leave. At the time, SDRs (entry level sales reps) like myself with just a few months of experience were a hot commodity on the market. It was very strange—I was far more marketable with just a few months of experience as a SDR, than I was as a regular old lawyer.

¹

A few months wasn’t anywhere near enough time to really learn anything. So it kind of didn’t make sense.

But if you look at it from a signaling perspective, it did. Companies care about what other companies are doing, especially if they’re competitors. If you’re good enough to get picked, then the perception of your value changes. So tech wasn’t all that different from law—they just viewed your resume as a proxy for how good you are.

²

Which is why today I always tell people, if you want to make a career pivot, just get your foot in the door somewhere. Because you become more marketable afterwards.

I’ve been in legal tech for almost 6 years now, and I’ve worked for three different companies. At every single one, the pattern was inevitably the same: If you want more money or a promotion, it makes sense to change jobs. I’ve seen several friends go from $50k a year to $150k+ in just three or so years, all by changing jobs. This is particularly true at the junior levels (as you get more senior, the picture gets more complex and nuanced.)

As a junior, you should be constantly on the lookout for new jobs. The only exception I’d make (which I did for myself) is if you are getting something intangible but valuable from the job.

If you’re growing, don’t interrupt it unnecessarily

But it was far more valuable for me to stay. I was learning so much and developing so quickly, and I didn't want to interrupt that growth.

The decision to stay was surprising to some because I would’ve doubled my compensation by leaving. However, as I said above, staying had its advantages too. I was just really good at cold calling, which I knew going in. The great thing about not being on a billable hour model for work is that if you’re really fast and efficient, you benefit from them. I got really good at my job which gave me a lot of free time.

So that’s how I started experimenting with different things. The example I used here was using LinkedIn to do social selling, but in truth, I experimented with lots of things that ended up not working out. Like cold calling people who had just been quoted in e-discovery news articles. Or using PACER and court dockets to identify law firms that might have a case with e-discovery needs.

What I love about sales is that if you’re really good at your job, no one will bother you. So you can actually be a great employee by working far less than your peers. Which frees you up to work on other projects, or spend more time with your family. I wasn’t a dad yet so I invested that time into figuring out problems.

Getting promoted

I did eventually get promoted. The tech bros they hired didn't work out, so management decided to change things up, and try a different type of salesperson. Someone like me. That's when they decided to promote me to account executive. The timing couldn't have been more perfect.

There were several reasons why the timing was perfect. When I first got overlooked for the promotion, I was angry because I thought I was just as good at as the existing account executives, from a skills and knowledge perspective. By the time I actually got the promotion, I was better than average. Like, I knew the product (and its limitations) really well, and I had all of the sales pitches down cold. So by the time I moved up, I was almost overqualified for the position.

Second, there were market issues, that were unrelated to my own capabilities as a salesperson, that took some time to resolve. Specifically, we were selling fixed subscriptions while the market wanted variable per-usage pricing. Making that switch made the product far more easily sold, so when I stepped up to an account executive role, it was easier to win deals.

Third, and perhaps most importantly for me long term, all that time spent experimenting gave me a clearer idea of what my secret sauce would be. Social selling on LinkedIn emerged as the most high ROI initiative, so I decided to double down on posting. I’d started to get inbound leads without making a single cold call or email, which was unheard of at the time.

Takeaways

If you’re on a new career journey I highly recommend that you get your foot in the door. Once you do, slow things down. Don’t chase money and promotions. Instead, find the right environment and then develop valuable skills and contacts, and grow your reputation.

I’ve been giving this advice for years but most people don’t follow it. I’ve seen this cycle play out and have witnessed several lawyers stall out a few years after the transition, because they never became great at what they do. Law taught us that your credentials are all that matter, and that couldn’t be farther from the truth. At least in the rest of the world.

So to succeed in your next act, you’ll have to unlearn some of the lessons you learned from your past life.

1. Which I’ve written about before, in the article describing my job search to find my first legal tech job.

2. And pre-laws look at law school rankings obsessively to decide where to attend. I made a joke about this in a Tik Tok this week, after U.S. News released its new rankings and Harvard Law fell behind The University of Chicago. It also inspired this tweet (that received 400+ likes) about hypocritical schools are when it comes to being measured by a single number.