Cindy Whitehead has been selling stuff since high school. It started with convincing Fijians to start a cheerleading squad and evolved to selling cosmetics, pharmaceuticals, retail products on QVC and most recently, the Food & Drug Administration.
The Raleigh entrepreneur and investor made a name for herself for lobbying the FDA to approve the first female-libido enhancing drug, her company’s brainchild Addyi. Just after the historic event happened in 2015, Whitehead sold her company Sprout Pharmaceuticals for $1 billion.
She’s selling a different sort of product now—the experience and insights that came from 20 years building businesses. The Pink Ceiling is part-consulting business, part-venture capital firm, part-incubator (it runs the Pinkubator at North Hills in Raleigh) and its mission is to support women-led and women-focused startups and technologies.
Whitehead will share some of her story, along with the six choices she’s made every day of her sales career, with attendees at SalesJam 2.0, Friday February 10. As a teaser, we asked her to share some stories from her career and some insights about sales she’s learned along the way.
When did you decide on sales as a career?
I started in retail sales to make money in high school and then worked for cosmetic companies. I’m attracted to great stories and I love telling stories—that was part of the attraction to sales.
How did you separate yourself from others in your career?
I invited people into my fun. As I hired sales people ultimately into my companies, part of what was so important to me was people who could bring others into their experience. That was really a deciding factor for who fit in my cultures and who didn’t.
What’s an example of inviting people into your fun?
When I worked in Seattle, I took my whole sales team to Pike Place Market. What could be less attractive than fishmonger clothing? But the fishmongers made the decision to be world class and let people be part of their fun. We learned to be the fishmonger wherever we’re at, at trade show or in an office. When you walk in and have no context, it’s your responsibility to bring your customer into a positive experience.
What do you like most about sales?
The joy of the interaction. What better job is there than to be able to wake up every day and your job is going to be a little different. You’ll be introduced to characters who will shape your thinking in one way or other, offer challenges to problem solve. A lot of jobs are very task-oriented and repetitive. Sales is not. It’s a job in which every day you’re going to learn something new.
Is there a common misconception about sales?
That it’s easy and 10-2. That is the common misconception. Lots of perks, not long hours. But the best sales people I know get there before everyone else and leave later than anyone else.
Highlight of your career so far?
The FDA was the ultimate lesson in perseverance pays off. For any persistent-with-sales type personality, it’s those things that were the hardest to win that you remember the most.
What do you or have you done to stay motivated when it was hard to sell?
Sales can feel pretty defeating any given day. Reminding yourself why you’re doing it in the first place is crucial to keeping the passion. I went to my inbox and read all the emails that women were sending in to me—they were opening their lives up to me and cheering me on. It becomes a responsibility and duty to do right by them.
I like to nickname everybody. That’s my odd fact. A sales rep is Biggie Smalls and one is Back Draft. He hates his the most. (A full wall in her office is dedicated to caricatures of her staff, family and portfolio companies, all with nicknames)
Purple Cow, by Seth Godin. I look for who is the purple cow in the room (now the pink cow). I think the pink cow is defined by choices they make. I hire the purple cow, who stands out in the sea of sameness.
Why The Pink Ceiling as your next venture?
I had an extraordinary exit and how do you pay it forward? To me, my privilege had been witnessing women advocating for themselves and each other. The gap in talking with other female entrepreneurs was they still are looking for a mentor. A lot has changed—I started my businesses before Shark Tank—it was a different startup climate in terms of resources and conversation. But the only thing emerging now is coursework. And it’s typically one size fits all, entrepreneurship in a box. Mentorship remains a glaring gap.
Will you start another company?
Never say never. I would like to think that as opposed to me going and running it again, I can walk a mile next to somebody and get them there. The joy of all this is how it was transformative in the lives of people that worked for me, what they’ve gone on to do and the businesses they’ve created. I want to open that beyond my proteges. My employees were my tribe who I loved to see succeed and now Pinkubator members get to do that.