New Helpshift CEO Takes Gender Bias Head-On

Helpshift CEO Linda Crawford weighs in on why she felt compelled to come out of retirement to lead her company and the lack of women in decision-making positions in business.
Helpshift CEO Linda Crawford

I am encouraged by the brave women who have recently stood up for women and for themselves at Uber, Google and elsewhere. Being in tech for 30 years, I have personally experienced some overt harassment and gender bias. I deeply regret that I didn’t stand up more assertively at the time it was occurring.

I recently became the CEO of Helpshift, a Silicon Valley startup revolutionizing the customer support industry through messaging-first and AI-powered consumer service. I am thrilled to be with a company that appreciates my experience and embraces my perspective as a woman in a male-dominated industry.

Earlier in the year, I decided to retire from full-time corporate life and sit on a few boards.  I felt good about bringing diversity to the board room. But something was nagging at me. I kept thinking that I needed to do more to advance the representation of women in tech. It was time to be a CEO. Becoming a CEO allows me to make diversity a top priority at our company. More importantly, as a CEO, I have a “megaphone” and the opportunity to influence other executives to do their part.

“I urge my former colleagues to come back into the workforce as CEOs.”

As I was networking and interviewing for the CEO role, I quickly realized that the overwhelming majority of people sourcing and hiring CEOs are men. I tallied up the people I met along the way—recruiters, corporate executives, board members and venture capitalists. Of the 80 people with whom I met, only seven were women. How do we change the course if we don’t have more women in decision-making positions? I urge my former colleagues to come back into the workforce as CEOs. I also encourage my fellow female senior executives to step out of the number two and three positions and become a CEO.

As CEO, we can mandate an initiative for fair pay. Let’s pay fairly for those in our organizations making the largest contributions. Often women are poor negotiators on the way into a company, so from the very beginning they are behind in pay. We can stop penalizing people for being poor negotiators. When a candidate has the experience and skills to join your organization, pay them fairly from day one.

Additionally, we need more coaching and performance management training for men and women. I recently sat through a performance calibration session. I noticed a pattern of women being categorized as high performer/moderate potential. When I probed, the feedback was shockingly consistent—these women were the star performers on the team. They volunteered for the tough projects, mentored new teammates, were innovative, were the proxy for their managers, and on and on. So why weren’t they considered high potential? It was their lack of confidence, their inability to brag, and their willingness to give others too much credit. They never took the stage. We need to teach women how to say “I” more often, to take the microphone in an all-hands meeting, and to celebrate their accomplishments in public. Let’s help these high-achieving women execute a personal marketing plan.

As CEOs, we can reshape the board and demand diversity. I have an extensive network of female executives that would be incredible board members. Most of these women need sponsorship to get into the right circles and encouragement to go for it. I’ve started making it a practice to bring up two to three names of “diverse” candidates every time I speak to an executive recruiter, venture capitalist or fellow executive. Working together, we can change our industry—for the better.


  • Get the CEO Briefing

    Sign up today to get weekly access to the latest issues affecting CEOs in every industry
  • upcoming events