Sins of the Past

Back in December, Sir Michael Moritz from the famed Silicon Valley VC firm Sequoia Capital made some waves when he bemoaned the lack of women in technology. “Oh, we look very hard. In fact we just hired a young woman from Stanford who’s every bit as good as her peers, and if there are more like her, we’ll hire them. What we’re not prepared to do is lower our standards."

The piece caught my attention because I am a male CEO who runs a technology company with a history of “women issues.” This history must also be acknowledged as my history, given I was one of the first hires at the company and have been part of the leadership team from just about the very beginning. Nonetheless, I try to distance myself from our checkered past and can almost convince myself that I am not part of the problem and instead have contributed towards a solution.

How did we get here? We were founded by a visionary, hard-charging CEO who was laser-focused on bringing a massively disruptive solution to market. Those of you who work in the tech space are correct when you parse the previous sentence and visualize this guy as a complete asshole. I would go further and diagnose him as a pathological narcissist and quite likely a clinical sociopath. He was a charmer who despite many indicators to the contrary, was quite a successful ladies’ man. My wife detested him from the instant she met him while I was being recruited. She didn’t suggest I steer clear because she understood how strongly I felt about the opportunity, but we both knew I was joining in spite of his leadership rather than because of it.

Initially it was impossible to see what the future would hold as far as our leader’s challenges with women because we didn’t have any around. Well, except for one—our admin. She had come along from his prior company and their bizarre relationship was truly fascinating. They fought like they were an old married couple even though she was a) actually married to someone else and b) twenty years his senior. She dutifully mothered him and took care of all of his personal matters as well professional ones.

During that first year, I only saw our leader’s relationship to women as a net positive for the company. Our solution targets a space where the majority of buyers are female and many of them seemed to eat his “charm" up. For a startup trying to crack a tough market, it seemed to be an advantage. I felt dirty sometimes as I watched the Cheshire Cat grin while he poured it on thick during a sales call, but the company got traction and his ability to sell was clearly a contributing factor.

A year into the company's existence a dozen men and the admin piled into a bus and headed out of town for a team-building weekend. The first night our fearless leader had sex in that same bus with a prostitute who had been acquired for him by one of our new sales reps. I don’t even know how to follow up that sentence, given how preposterous it really is when I see it in print.  This sales rep hadn’t even officially started yet and somehow he decided this would be an acceptable and welcome gift for his new boss. I knew our leader was a scumbag, but clearly I lacked whatever radar this sales rep possessed to accurately identify the depths of scumminess. Needless to say, this guy was our VP of Sales within months.

You would think it might be hard to top that story, but it was only the beginning. Fast-forward a few months and the company is diversified a little. We hired a couple of fairly young women to do customer support. They were approximately 15 years younger than the average age of our exclusively male group of sales reps. I don’t know how they stuck around working in an office that was overflowing with a toxic stew of male-dominated sales culture, but somehow they did. Most likely it was because, like all of us, they saw the enormity of the market we were chasing and didn’t want to let all of the bullshit get in the way of being part of that opportunity. This delicate equilibrium was soon thrown off kilter when our leader returned from a trip gushing about the woman he had met at a client site. “Amazing…absolutely amazing. We’ve GOT to hire her."

A few short weeks later I was shocked to meet this new hire. She was young, even younger than the two women who made up the support team. Age is not always an accurate proxy of ability and potential impact, but it was clear from the beginning this woman was both incredibly immature and inexperienced. Regardless, she was given a portfolio of influence and responsibility that radically surpassed her abilities. Why did this happen? I’ll never know for sure, but here’s a fun fact—when this woman took the job and moved to where the company was headquartered, she moved into an apartment that was directly across the street from the CEO’s. What a CRAZY coincidence. (It was not a coincidence.)

Even this does not fully represent the craziness that occurred with our leader and various women both inside and outside the company, but at some point this piece needs to move away from the actions of one deranged individual and talk about how his attitudes were inculcated into the culture of a rapidly growing enterprise. A few years into our existence, we were firing on all cylinders and growing like crazy. Our growth took a very particular form, however. The vast majority of our hiring was split between our sales organization and our support organization. Through some degree of intention and accident, these organizations were populated almost exclusively by mid-career males (sales) and much less-experienced females (support). The company leadership? Exclusively male at every level.

I knew what was happening, but was able to mentally distance myself from it by nature of working out of a satellite office. Some of this was absolutely willful ignorance, but some was a clear survival strategy. Up and down the company we each swallowed all manner of shit from our abominable leader in order to keep chasing the big potential score of this startup. I was not a complete sap and exhibited spine on more than one occasion, but by nature of my ongoing participation, I was an enabler at various times. I regret this. When I relocated to the headquarters and inherited leadership of our support team I tried to improve things, but I did it in a way that did not get to the true root of the issues around gender. I regret this even more.

On demographics alone we were an absolute failure from a gender equity perspective, but the truth on the ground was even worse than it appeared at the surface. The compensation of our team of sales bros was multiples of our support team, and they came and went as they wished while our support team was criticized for having the temerity to work remotely or take  a few hours to handle a personal matter. Yes, some of this is the nature of the jobs and market dynamics for the skill sets involved, but it was clearly not driven by merit alone. Even worse, the definition of the roles was such that our sales team could claim the glory for everything good that happened with clients, while it was always the support team that bore the blame for anything negative. It was clear from my earliest days managing support that we had bullies in our sales organization who enjoyed having our support staff at their beck and call and abused their position of power. I did my best to coach my team in how to deal with the bullies while simultaneously trying to influence the overall sales culture with their leaders, but my success here was limited. I should have pushed harder.

Eventually our founding CEO left the company and his replacement brought a very different energy as it related to people and culture. At its surface it would have seemed possible for this to heal the previous damage. Unfortunately, I think the change was not deep enough. There were absolutely improvements, but at its core we were still a company where the vast majority of leadership was male. We were also still a sales culture at heart where the sales team was the beloved project of our CEO. They remained exclusively beyond reproach even while they consistently represented the weakest link in our corporate chain.

How was this ongoing male domination exhibited? In ways big and small. On the small side, it seemed that the men who ran our sales organization were given far more latitude to make demands of other organizations while those organizations, particularly one run by and dominated by women, were expected to just smile and do Sales’ bidding. On the bigger side we continued to see issues where sales (and therefore men) were catered to while other organizations got the scraps. A perfect example was a recent salary review cycle. I gave a tough message to a female direct report that she was not getting a raise in strict adherence to my CEO’s salary adjustment directives. She was in a position to learn what salary changes were happening in other areas of the organization, and she was rightfully pissed when she saw that multiple males in our sales organization were given salary adjustments that clearly violated those same directives.  I was not aware of this situation, and in fact was pissed myself when I found out about it, but the damage with my employee was done. A woman who already had her bias radar on alert by nature of having suffered through some of the worst of our historical issues now had fresh meat to bolster her concerns. I made the situation right with her, and she ultimately understood there was only ignorance behind my actions and not any form of biased intent, but still. That sucked and I will rightfully bear the burden of mending that relationship and trust for years to come.

And now the company is mine to lead. What’s different? For one thing, I have a very different team than what was in place prior to my getting the role. Whereas we previously had zero female executives and a few female managers, 40% of my executive team are women and it may actually wind up at 60%, depending on the remaining hire I need to make. These women are amazing at what they do and they are my most trusted advisors who will play critical roles in whether or not this company ultimately succeeds. Beyond my immediate team, 100% of our next level of leadership are women. I am not trying to take credit for the fact that our best people happen to be women, but I will take credit for modifying our culture to allow them to rise. One of these new female managers had previously been told she would never be able to earn a leadership role because she chose to work from home after the birth of her child. Not in my company will that be a barrier to success.

Demographics and culture are important, but even more critical in terms of what I am trying to do differently is that I am openly talking about our gender issues and talking about them repeatedly. What does this look like? I have a senior, female leader who is constantly vigilant for any signs of bias, having witnessed some of what happened in the past. I am always listening carefully to her concerns and working to be sure she feels safe to raise them. It doesn’t mean I always agree with her assessments, as I will push back and question her identification of bias where sometimes I feel it may not genuinely exist. But I believe we have established a level of trust where she sees that as healthy and not an attempt to deflect or minimize. I have another senior female leader who is new to the organization and with whom I have shared a lot of our history. I’ve asked her to be hyper-vigilant in this regard and to raise a flag if she ever gets the slightest bias blip on her radar.

More importantly, I am talking about my concerns with my male leadership. We recently went through a personnel evaluation process where a female employee was called out as being potentially problematic by the male leader who was inheriting her. “Pain in the ass” and “a handful” were some of the descriptions that had been applied to her in the past. I had recently  evaluated this employee in action and spent a chunk of time really getting to know her and came away wildly impressed. She’s extremely bright and not afraid to express her opinions—the exact profile of the people I love to work with. As I started to think about the origin of the assessments I had heard in the past, I started to worry whether there was any form of bias underlying them. I made my concerns known to her new manager and stressed how critical it was that he gave her full and fair evaluation. He came away equally impressed and raised the woman from the bottom of his original stack ranking to the top.

I feel like we’ve made progress, but there is more that still needs to be done and I know it begins with me. I kicked myself for days after  a recent group outing. A couple of us guys were being the 12-year-old geeks we are at heart and making obnoxious, double-entendre-laced jokes. It was nowhere near as vile as some of the stuff that has transpired around this company in the past, but it was gross nonetheless. Even more so given our history as a company that has not been welcoming to women. The only way my company will succeed is if it is an environment where everyone is treated fairly and can feel comfortable. Unlike Sir Moritz, I know there are top-notch women in technology because I am fortunate enough to work alongside them. I must remain vigilant about maintaining an environment that supports and nurtures them rather than devolving into the type of fraternity atmosphere that dominates many tech companies. It doesn’t mean we have to be humorless automatons, but we need to save the Cards Against Humanity quality jokes for friends rather than work.

This was a pretty terrifying piece for me to write. I have tremendous respect for the work that is being done at Graceless and the amazing voices who are being heard here. There was a lot of self-doubt as to why my story was worth being the first male voice to participate in this space. I fear this coming across as some weak-ass, trite attempt at #notallmen. I am fortunate in that I am in a professional position to make some small contribution to moving this issue forwards. Ultimately in writing this, I hope I’ve added another voice to the call for long overdue change, which can maybe move us one step closer to finally fixing this shit for good.