Why I Enrolled in Sales School
-- by Jessie Gabriel
If you are a founder, you are in sales. You are SO in sales. You are actually more in sales than your average salesperson. This is because founders have to sell to everyone. You’re selling to your customers, you’re selling to your investors, you’re selling to the manufacturing partners who think you’re too small to take on, you’re selling to prospective hires who you need to convince to take a job with more work and less pay, you’re selling your current team on why they should stay with you for the aforementioned more work and less pay, you’re selling to your family and friends who wonder why you continue on in this position (with WAY more work and WAY less pay).
The same is true for lawyers. If you are a lawyer, you are in sales. You’re selling to clients, to counterparties, and to judges. But as lawyers, not only are we not taught to sell, but we are effectively told that sales is beneath us. Lawyers don’t sell. This is a profession. Even our antiquated rules of professional responsibility require lawyers to write “Attorney Advertising” at the bottom of their websites and other “marketing” materials. We are just so precious.
Then when you become a partner, that changes. Congratulations! You’ve been promoted to partner because of your excellent lawyering (sort of—post for another day on how most lawyers really make partner). Now as a partner you have a new job—go out and build a book of business! How do you do it? We don’t know and we’re not going to train you. Just go do it. You know, take people out to lunch. Call your buddy from law school who’s now GC at company blah blah blah. It’s not sales (ew), it’s “building your book.” We’re professionals, not used car salesmen!
The truth is that part of me does not want to write this post because part of me still feels shame over the fact that I’m in sales school. If we were really so great, we shouldn’t have to “sell,” right? Clients—and the right clients—should just be running through the doors. If Jessie is in sales school does that mean All Places isn’t doing very well? They basically have to pound the pavement to get more clients to come through the doors? These are all real thoughts that are running though my head right now as I write this. But I’m writing it anyway because this is something I am genuinely excited about and that I hope many of you will relate to. Plus, I’m proud that I have taken this step for our business. There, I said it.
Late last year I realized that I needed some help. Since launching All Places in October 2020, the person who had been creating our marketing strategy was someone without any training or expertise: yours truly. In some ways, I was the only person who could do it because I was the only person who truly understood what All Places was about (i.e., our brand). Unfortunately, that alone is not the same as understanding sales and marketing strategy. So in late summer 2024, I started looking. By the end of the year, through an incredible organization I’m part of called The What Alliance, I found my way to Special Projects and Nina Willdorf.
Nina and I worked together for two months. She spoke to our clients, our top referral sources, and our team. She waded into our newsletters, LinkedIn, and other marketing data. She reviewed our website and analyzed how we were speaking about All Places. Then she and I worked together to come up with a clear overview of what we do uniquely well, who we want to work with, and how we communicate what we do to those businesses. It was exhausting. Thinking this way about your business takes a huge amount of mental energy, even when you’re being guided through it by an expert. You have to do the work. They can’t do it for you, even someone as amazing as Nina.
At one point in this process Nina recommended I check out a podcast about sales. That may sound dull to some people, but even then some part of me knew this was what I needed. Plus, I’m a sucker for a long walk and work-related podcast. Thus began my relationship with Leah Neaderthal and the Smart Gets Paid podcast. From the first episode, I felt like Leah was speaking to me. She was talking about sales in a way that I understood and that helped me quickly identify what was missing from our sales strategy. It was obvious Leah had spent so much time thinking through her approach. Each time she recommended something, it was clear why she recommended it and why it was effective. There was nothing about manipulating people or trying to get people to buy something they didn’t need. It was about partnership—being clear on what a client needs and what we provide and how we provide it, so we can figure out if we’re the right fit.
By the time Nina suggested I check out Leah‘s sales training program, The Academy, I was already hooked. I didn’t care that it was targeted to consulting businesses—I knew this was for me. It’s been a little over a month now of me diving into pre-recorded modules on big-picture things like how to speak clearly about what you do, the components of a great conversation, fostering genuine relationships, providing value to the people you serve—and more brass tacks items like writing proposals, how to show up on LinkedIn, and managing a CRM effectively. I participate in group coaching calls where we, the students, get feedback from the experts. I’ve transformed from just a lurker to an active participant in The Academy’s Slack channel, where other students and coaches provide incredibly thoughtful and helpful advice. I am in it.
Now, going back to those nasty little questions running through my head. Being “great” doesn’t mean you don’t have to sell. Apple has billboards—hardcopy, up on Sunset Boulevard, right above a massive trash bin, billboards—all over town. Great companies know that being a great company requires regularly going out and speaking to your current and future customers. They need to know what you do and who you’re about, they need to know about the products, and they need the information to figure out if the products are for them. Why does everyone at your local coffee shop have a MacBook? Because Apple has done an exceptional job of communicating the value of its products to its target consumers and then delivering that value.
If you’ve seen me during the last couple of months and asked me what I’m excited about, this is probably what you heard me talk about. If you had come over to our house during this period, chances are you would have walked in on a conversation between Bik and me about sales strategy, with regular references back to my husband’s time in college selling books door-to-door. Numerous people have mentioned that I light up when talking about sales. And it’s true. I’m obsessed with learning about sales. That’s because I’m obsessed with my business and someone has just presented me with a step-by-step solution that I strongly believe will take my business to the next level. That is a great f’ing feeling. So yeah, sales school. Obsessed.
