3 CEOs Offer Advice on Becoming a Salesperson

When a startup’s CEO is not its chief salesperson, it always raises a red flag for me. In the early days, a company is still testing product/market fit, and should be listening closely to potential customers during sales meetings. A CEO needs to be central to that activity, even if she is not yet experienced or confident in her sales abilities.

In my journey to interview 100 entrepreneurs in 2016, I have asked each one how a CEO can become the chief salesperson when she has no sales experience. These three CEOs — who all overcame a lack of sales experience to become successful salespeople for their companies — shared their strategies for success.

Employ the Scientific Method
Find your best sales approach through trial and error, advises Tanya Van Court, CEO of Sow — a financial technology startup that provides children with a new way to source and save money. Van Court began viewing sales as “an art form and a skill” while working alongside excellent salespeople at ESPN and Nickelodeon, and realized she needed to hone her own skills in this area when she started Sow.

As an engineer with a bachelor’s degree and a master’s degree from Stanford, Van Court was familiar with using the scientific method for testing. She created a process and experiments, and carefully mapped out Sow’s audience, message, and message distribution plan. Through this, she created both a B2B and a B2C strategy for acquiring customers, and she built her sales process around customer acquisition goals. “It does take a lot of trial and error and staying close to your customer,” she says.

Keep Your Ears Open
In her early days as an auditor, Mary Juetten was always taught to keep her ears open — even as the most junior person in the meeting. Now, as CEO of Traklight — a SaaS (software as a service) product in the legal technology industry — she uses this same strategy for customer sales and fundraising from investors. (Note: Barbara Clarke is an investor in Traklight.)

Juetten focuses mostly on consultative sales, which aim to provide customers with products and services that will solve an issue they face, or increase the value of their own business. To maximize these consultative sales, she listens carefully to her customers’ needs, developing leads into long-term strategic partnerships and large-scale B2B sales.

Be a Subject Matter Expert
Although sales initially “terrified” her, Ashley Reid tapped into her management consulting background to work on funding and business development when she founded Wellist — a marketplace platform for caregivers and patients. This background helped her identify and solve complex problems, particularly those focused on patient outcomes.

Reid leveraged her deep knowledge of the problems facing hospitals and honed in on a particular area of pain points. She knew that hospitals were increasingly accountable for patient outcomes, and often non-hospital issues like transportation and food delivery were real problems for patients. This allowed her to reach out to the head of the cancer center at a prestigious hospital, and they delved into the problems and how Wellist could solve them. Reid was seen as a partner in solving these important problems and put herself at the center of the solution. This strategy helped Reid build success through word-of-mouth referrals amongst cancer centers.

These three approaches to sales are all different, but they share two common through lines: Design a sales process that is authentic to your personal business style, and maximize your existing professional skill set. When thinking about your startup, spend time considering your own personal style and experience, and what kind of sales process that implies. Your success will depend on it.

This article is not investment advice, nor is it a solicitation to buy or sell any shares. Read more about Clarke’s angel investments, including DailyWorth, here.

Barbara Clarke is a member of the DailyWorth Connect Program. Read more about the program here.