What To Do If You’re a Startup CEO & You Don’t Know How To Sell

You’ve heard the expression “All sizzle, no steak?” Or the Texan equivalent of “All hat, no cattle?” [sidenote: it’s weird that cows feature prominently in both of these]. Basically these sayings are referring to people who talk a big game but then can’t back it up with action. Sparkly but no quality behind it.

While it’s readily agreed among investors that these types of leaders eventually get seen for what they are over the long haul (although distressingly they usually get funded initially), what I wanted to discuss today is whether a founding team that’s the complete opposite (a TON of steak, very little sizzle) can also be problematic when it comes to building a successful company. This topic matters to me not just intellectually but because it’s a combination I find full of potential and often want to support. Especially since VC pattern matching may inappropriately label people this way (can’t sell) who are merely nervous or new to their environment.

What I’ve concluded is that if you’re an “all steak, no sizzle” CEO you’re gonna harm your company if you don’t address this weakness (but good news, you can address it). You may end up decreasing the quality of outcomes by a standard deviation or more. How does this harm occur? If things are going great, you still may get a lower valuation or smaller round. A hire or two that you should have been able to close won’t join. You’ll wonder why “inferior competitor X” got to headline the conference or was chosen for the big partnership with a major distributor. It’s a bunch of incremental frictions that slow you down and cause more entropy than is otherwise optimal.

The first thing to confront is that as a CEO you’re the company’s primary salesperson. It doesn’t matter what industry, what product, what revenue model, what stage of development. You’re spending much of your time selling: the vision to employees, the opportunity to investors, the story to the press, the offering to the customers, the relationship to partners. Sales is just storytelling with a desired outcome at the end of the story. Figure that you will *always* be spending at least 50% of your time selling in this manner. Some weeks you’ll be selling more than you’re sleeping!!!

Photo by Teresa Vega on Unsplash

Can your lack of interest or skill in “selling” be counter-balanced by a cofounder or team that’s great at it? Yes and No. Of course you’ll have lots of functional partners who basically sell as a job responsibility. And a non-CEO cofounder who can sell the heck out of your company is just about the next best thing to being skilled yourself. But I’d make the case that if, as CEO, you’re not embracing the unique responsibility -and opportunity- you have, you will eventually not be CEO. And I want you to be CEO for a really really long time. So let’s talk about what to do if you’re a startup CEO who doesn’t know how to sell:

  1. Watch videos of great salespeople and storytellers: This doesn’t necessarily mean literally sales technique videos, although I’m sure there are some solid ones out there. I’m thinking people who are amazing at telling stories, who take different approaches to making you believe. For example, I adore JJ Abrams’ Mystery Box TED talk. Or the Union Square veggie cutter salesman.
  2. Work with a coach: Whether it’s a sales advisor, a communications/public speaking expert or a true CEO coach depends a lot on what you think is holding you back from being effective. And what type of ‘sales’ you’ll mostly be doing. At Homebrew, we keep a list of coaches that work well with startups and then try to help match against need and personality type. The best recommendations are going to come from your community as this is a true ‘word of mouth’ network.
  3. Practice in low stakes environments: For some people it’s Toastmasters. For others it’s signing up to do phonebanking/fundraising for a nonprofit they care about. Or go to a flea market and haggle. Cross-training muscles for discussions that usually make you uncomfortable.
  4. Be the best version of you, not anyone else: Often, the best, most sustainable sales personalities are real — they’re you, just turned up to 11. So know that you are merely drawing out, and drawing on, abilities and characteristics you already have, not trying to become a different person. You can even draw your inexperience or nervousness into the story — “you know, it was always really hard for me when I worked at BigCoX to try and convince folks to join us because I wasn’t always sure myself. But now at OurStartupY I believe in our mission so strongly.”

Are you a founder who trained themselves to become a better salesperson? I’d love to hear your story on Twitter where I’m @hunterwalk.

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Notes and More

My heart goes out to Tony Hsieh’s close friends and family, a smart and generous tech entrepreneur who passed away this week at 46. His book, Delivering Happiness, is wonderful.

📦 Things I’m Enjoying

COVID’s second wave rattling the US means that small businesses are going to have a really challenging holiday season. Here are three of my Bay Area favorites that ship: Ritual Coffee Roasters, 3 Fish Studios (art), and Bitters & Bottles (alcohol, can be shipped within CA).

🏗 Highlighted Homebrew Portfolio Jobs

Boom is building a supersonic aircraft. No, seriously, they are. Quite credibly and quickly too. It’s a well-funded, A+ team that is growing across a number of functions. Look here for jobs and you can tell your grandchildren you helped build this plane!

You’ll find me @homebrew , Seed Stage Venture Fund w @satyap . Previously made products at YouTube, Google & SecondLife. Married to @cbarlerin .

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