Birth of a Salesman

Last year, I left the law world and joined a legal technology startup as a sales rep. My original hypothesis was that it’d be a great fit for me because I enjoyed sales (when I ran my own law practice) and because there was a great opportunity at the bleeding edge of an industry I was familiar with. (I never wrote about this specifically but alluded to it in my post Get Lucky By Knowing Your Industry and Knowing Yourself).

It’s now been eight months since I’ve entered the world of tech sales. Things haven’t gone exactly as I planned, but for the most part, things have gone well. Last month, I was promoted from being a Sales Development Rep (SDR) to Account Executive (AE) position on an accelerated timeline in part due to my performance. Sales has come to me much more naturally than law ever did.

Before I move on, a quick explanation: In software sales, you frequently see specialization in roles of sales reps. It’s like an assembly line for sales. SDRs are responsible for cold calling and setting appointments for AEs, who are then responsible for closing the deal. I joined my company as a SDR (a position typically held by someone with little to no experience right out of college).

My experience as a SDR (and in sales generally) has been pretty good. Cold calling may seem like a nightmare to most people, but I find it kind of fun. Certainly it’s no worse than doc review or cite checking. When I talk to my friends, they’re often incredulous that I enjoy calling strangers and getting rejected again and again. But it’s true. I don’t mind the rejection, and I love it when I’m successful and able to set that appointment.

My conversations with my law friends also got me thinking. The skills and talents that make for a great lawyer are often very different than those required to be a successful salesperson. I’ve done well because I have some natural competitive advantages in my role, such as having legal industry knowledge. But more importantly, the sales industry has certain values that mesh well with my personality. A few that come to mind:

Mistakes are encouraged. Sales skill development requires that you go out there and make lots of mistakes. You grow by having bad conversations, pitching people the wrong way, and just messing up in general. It’s very much a trial and error process. In law, mistakes aren’t just discouraged, they’re not even tolerated. Perfection is expected. In my former life, I was always criticized for making careless mistakes. Now I’m praised for thinking quickly and acting decisively. They’re really just flip sides of the same coin.

Your credentials and past matter less. Law is very pedigree-conscious. You’re assumed to be a good lawyer if you went to School X or Firm Y. We live in the past. (That’s also why litigators always worked off old forms and briefs; “precedents”). Not so in sales. As long as you have a college degree, you don’t really have an advantage if you went to a good school or previously worked for a big company. Sales pitches are also constantly evolving.

Asking open ended questions. As a SDR, I was constantly told to make sure I ask open ended questions that allow my prospect to talk about themselves and their processes. You never know what they might bring up, and if they raise an unexpected but important point, you have to run with that. On the flip side, in law you’re always trying to build a record. So you’re trying to get people to say certain things by framing your questions in a specific way. The most obvious example is through the use of leading questions during cross examinations. I’m not gonna lie-there were times I found myself doing a mini cross X when I was trying to pitch someone on the phone. It usually did not turn out well.

Results matter more than hours worked. As a lawyer, I’m rewarded more if I spend 100 hours on a matter but lose the case, than I am if I spend 50 hours and win a case. This creates all sorts of perverse incentives and just feels wrong. In sales, you are measured by what you generate. Whether that’s appointments or closed business, nobody really cares how long it takes you to get it done. As long as you produce results, you are rewarded.

Optimists win, pessimists lose. Being a great lawyer requires you to be prepared for all possibilities, so it’s super helpful to imagine everything going wrong. If you have a knack for this, you’re probably a pessimist. Being a great salesperson requires enormous persistence and resilience which means it helps if you can be sustained by a tiny glimmer of hope. If you’re good at this, you’re probably an optimist.

It hasn’t been all that long but so far sales has been a great fit for me. Hopefully things continue to go well. Stay tuned for more!

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