Guest Post by: Davey Friedman
Recently, I had the chance to observe a former mentee leading a sales meeting. I hired Charlotte a few years prior as an Account Executive at WeWork. (Names have been changed to protect the privacy of former colleagues). Since then, she’d risen to a Sales Director role with 10 reps reporting to her. I couldn’t have been more impressed with the leader Charlotte had become. In the meeting, she was clear, confident, inclusive, and inspirational.
But success stories like Charlotte’s are far too rare in sales organizations and commercial real estate firms. Women hold just one in five sales leadership positions in companies as a whole. They make up less than a third of upper management roles in the largest real estate development and investment organizations.
With gender discrimination so pervasive, it’s not surprising that unequal treatment exists in sales management. But I find the status quo impossible to tolerate.
Perhaps it’s because of my upbringing. My parents are equal partners in a private internal medicine practice they co-founded in Seattle 30 years ago. I grew up sandwiched between two incredible sisters. The older is a well-established corporate lawyer; the younger is an award-winning investigative reporter.
The women in my family role-modeled how to build a successful career, lead others with vision and compassion, balance work with family, and make a positive impact in the community. I grew up with zero doubt about the capacity of women to be superb leaders.
Nevertheless, women are underrepresented in all levels of sales, despite the pressing need for strong talent. Less than 12% of Silicon Valley’s top 150 companies have a woman as a top sales executive. Although sales teams led by women have higher quota attainment rates on average than male-led teams (94% vs 91%), women are paid less. Not to mention the scourge of condescension and sexual harassment women face in the workplace.
What is surprising then, given the gender imbalance, is my own experience at WeWork. In six years at the company, I reported almost entirely to senior women sales executives. Four leaders in particular deeply shaped my ability and approach as a salesperson and a leader. Here’s how:
Leading with Vision: From my first manager, Gloria, I learned to think beyond making a quick sale to the bigger picture of helping achieve an organization’s mission. Gloria was laser-focused on building the community WeWork stood for. Despite intense pressure to grow revenue, she invested a portion of her time to bring WeWork members together to help a Cambodian immigrant who, despite his background in computer science, was working as a janitor in one of our buildings. As a result of her advocacy, a member company took him on as a software engineer.
Mastering Sales Fundamentals: The coaching I received from Molly, my second manager, helped me hone my sales acumen, particularly the ability to listen and respond to customer’s needs. Those skills opened the door to opportunities to source and close multi-million-dollar deals with challenging design and technical requirements. I discovered how to navigate complex decision-maker dynamics and build creative solutions for customers who depended on WeWork to enhance many components of their operations, from financial performance to employee productivity to company culture.
Putting the Customer First: The mentorship of my third manager, Kathy, helped me develop a customer-centric approach. The comparison she drew for me between sales and medicine was an eye-opening moment, probably because it resonated so strongly with watching my parents take care of their patients. “Focus on the outcomes for the customer” she said. “Understand their pain, diagnose their needs, and prescribe the right solution.”
Hiring and Building a World-Class Team: By the time I met Helen, I was pretty accustomed to running a large sales team of my own, but my fourth and final manager’s extraordinary leadership ability helped me improve even further. I spent hours observing her interviews, taking notes on how she tested and assessed candidate’s abilities. I studied how she handled difficult situations under pressure, crafting a message to the team with just the right amount of context, transparency, and reassurance. I practiced giving candid feedback as she did: challenging the person directly while still letting them know I cared about them personally.
Because of these four leaders, I know first-hand the invaluable opportunities lost by companies that marginalize women. The fact is: gender diversity is associated with higher revenue. Companies with women making up 45% of the sales organization generate 15 times the revenue of companies with women making up less than 20%.
With a heightened awareness of the problem, I feel a personal responsibility to advocate for women in the workplace by building inclusive teams and curbing unconscious bias. At WeWork, I was fortunate to have the opportunity to hire dozens of women, many of whom have been promoted within the company to more strategic individual contributor positions or leadership roles.
Building diverse teams isn’t just a matter of fairness. It’s a matter of good business. In sales organizations and real estate companies, women leaders are as effective, if not more effective, than men. The gender discrimination that exists today must be remedied to reflect that fact.
Guest Post by: Davey Friedman. Davey is a sales leader and early-stage go-to-market expert. He was an early employee at WeWork, where he helped found the sales organization and built WeWork’s sales apparatus in the Northwest. When he’s not leading a team of awesome sellers, Davey writes reviews of sales books and advises founders on their go-to-market strategies. He’s also an avid lap-swimmer, R&B listener, and salmon BBQ-er at his cabin in La Conner.
