Silicon Valley is where women go to fail—unless they do these three things

Michaela Dempsey of Scout RFP says it’s time we flipped the script on tech leadership and explains that smiling is a big part of that strategy.

Despite being at the forefront of change, only 11% of executive positions in Silicon Valley are held by women. While Sheryl Sandberg, Susan Wojcicki, Ginni Rometty, and others have risen in the ranks, women’s voices are more often an afterthought in this locus of innovation.


In my early years, I likely disregarded my own voice as my manager said to me: “Why do you worry about getting promoted? You are going to get married someday.” Ten years later, at a different job, not much had changed as my manager said to me, “We really need to promote (male employee). He has a new baby and is the single earner in the family.”

Ultimately, I did pursue senior roles that often required greater achievement on my part to secure the title than that of a male counterpart. Sitting at the table as an equal among my male counterparts demands that I have a fierce sense of self, detailed data to back any decision, and to be the champion of a goal that stands on its own merits. Today, I serve as the sole female executive at my company, which forces me to be hyper-cognizant of my need to positively represent women leaders.

I attribute my success as a woman in the competitive tech field to a few key concepts I’ve kept in mind over the course of my career. Whether you are seeking an entry-level job in tech, making a career change, or working toward the C-suite, here are a few ways to flip the script on tech leadership.


Deliver seemingly inconsequential requests with a positive attitude and great diligence. We’ve all heard these pieces of advice as entry-level employees, but this must always be front and center.

As women, the principle of excelling is crucial. Going beyond basic requirements when delivering a project will only put you on the same field as a man. Crushing results by creating new value, unanticipated outcomes, or expanded insight over and over and over will start to get you noticed. That is the foot in the door, but you will need to continually keep up that level of execution and deliver such exceptional results that your presence can’t be denied, and, of course, you must wrap all of this with a smile.

Incidentally, the feedback I received even writing this article is to remove the need for women to smile or be positive. But I would be providing incomplete advice if I did not include it. What moved me from senior director to vice president was a combination that includes smiling, taking the “tiger first” personality down a notch, and dropping the reactive hammer.

Make no mistake, though, smiling is an essential component. Originally, I debated whether smiling was really a requirement. One thing my dad drilled into my head as a child was, “You must have an A for Attitude and an E for Effort on your report card.” You can be strong and smile, you can deliver tough results, and be positive, but it is 110% important to smile. Smiling is not weak, nor is apologetic, but we can get to that in another article. Smile not because you are a woman but because you are awesome and can deliver outstanding results. Smile because you are human and really enjoy what you are doing.

Most women tend to hide their authenticity because they’re concerned about how their female traits will be perceived. Change that mindset. Don’t let your own mind games damage your ability to perform because you are constantly building a work facade rather than truly focusing on the task at hand. Never withhold a smile or provide suggestions because you think it will make you look weak. Leaders with true potential don’t change to impress others—remember you are your own secret sauce. After all, consider how challenging it will be to progress if you’re constantly putting your effort into reinventing yourself to fit the crowd around you.


We’re all familiar with the “steamroller” (and honestly I have been one in the past myself). You start, they interrupt and force their opinion on you. They appear to steamroll everything anyone else is doing.

As women, we can fall victim to steamrolling because we’re afraid of being labeled bitchy. Or worse, you may become a steamroller because you don’t want to fall victim to male counterparts overstepping. Take it from one who’s been there: it never looks good on you, even when your direction is right. Being respectful is a more powerful way to lead. Remember, the quality of your team depends on its ability to work together flawlessly, so demonstrating respect will go a long way toward leading the group.

Stand your ground when a steamroller works to interrupt by asking them to hold a thought until you finish. This will allow you to take the presentation back and hit your points. After the meeting, have a real, one-on-one conversation with the steamroller about how their actions are affecting the team. These leading actions will have ripple effects across the organization, so that others will respect your time when speaking.


We can’t bring value if we aren’t true to our authentic selves. My father always said he raised me “like a boy” because that’s all he knew. Looking back, this was the best thing he could have possibly done for me. Being raised like a boy meant that I was free from gender bias, and it allowed me to remain authentic. I grew up playing on boys’ sports teams and have since taken my place as the only woman on Scout RFP’s executive team. I’ve never been suppressed by biases because I never let myself see them.

I encourage those who aren’t in the 11% of female executives in Silicon Valley to continue building a positive reputation as a team player and one who can deliver exemplary results. Think about how much more we can accomplish if we aren’t worried about lowering our voices in a meeting, wearing a power color to look important, or wearing heels to literally stand as tall as the men around us.

Michaela Dempsey, vice president of demand at Scout RFP, has led marketing at Scout for three years, including leading Scout’s SPARK customer conferences for the deep exchange of knowledge, experience, and ideas. In her new role as VP Demand, Michaela is responsible for driving global marketing demand strategy. Previously, she led marketing and demand for brands including Anaplan (PLAN) and Apteligent (acquired by VMWare).