Why Today’s ‘Mentorship Programs’ Mostly Fail Women in Tech (and How to Improve Them)

Ellen DaSilva’s Journey, from Banking to Twitter to Hims and Now, Her Own NewCo!

Like many relationships these days, mine and Ellen’s began online. But we successfully converted it to an NYC IRL coffee this past summer. I really enjoyed that chat so wanted to learn a bit more about my new friend, as well as share her story with you all. Thanks Ellen for answering Five Questions.

Hunter Walk: During my childhood I went through phases where I thought I’d be a writer, or a lawyer. Were there professions you recall thinking about when you were a kid? How connected are they to what you’ve ended up doing in this first phase of your career?

Ellen DaSilva: When I was 5, we had career day in my first grade class. Each student had to say what they wanted to be when they grew up — a pretty cliche exercise given I didn’t really know much about the professional world. I thought about it, and announced to my class that I wanted to be the CEO of Coca Cola. Not a soda drinker myself, but when my teacher asked why, I said I knew I’d be the leader of an iconic American company.

In reality, I had limited visibility into the world of tech and entrepreneurship until after college. It seemed to me that the way to achieve success was to work in the financial services or in a blue-chip business. It was sheer luck that I got placed on the tech desk at Barclays and met my (now husband) at the same time. Both showed me that there was life beyond large financial services institutions, and it clicked instantly.

All of this is to say that young aspiration, while it had nothing to do with my current job, gave me the footing to be open-minded, ambitious, and strive until I reached what I wanted. It’s that kind of attitude that helps no matter what the industry.

HW: Over the last decade you worked in banking, then Twitter and Hims (which you recently left). Is there a framework you’ve used to decide when it’s time to leave a company, and how to decide what to do next? I think many new grads would be happy to mirror your early path!

EDS: My mom always told me “don’t leave a job, run toward a new opportunity.” There is a lot of truth to this. Every 3–6 months, I run a mental exercise in which I ask myself the following questions:

  1.           Am I happy with how I’m spending my time?
  2.           Am I still learning and growing?
  3.           Am I being given increasing responsibility?

If the answer is no to any of these questions, it’s a valuable moment to assess whether any of these vectors can change. If they can’t, or if something is misaligned, then it’s time to more seriously consider other jobs.

For me, it has always boiled down to honesty with my manager specifically each time I was ready for a transition. For example, I got lucky when I was an analyst at Barclays — truly a junior-level employee. My manager and I were very different, but I felt comfortable having frank conversations with him that it wasn’t the right career for me. He was supportive when I needed to take interviews at tech companies, and offered his rolodex, recommendation, and anything else I would require. That level of mutual respect when you are looking to leave a job is critical.

The world is small and we cross professional paths with people we’d least expect. So the most important thing is to leave with dignity and integrity. I try to do that every time, even if the job is no longer the right fit. I emulated that experience when I left Twitter for HBS, and when I left Hims to start my new venture. I feel grateful to have the support and blessings of my former colleagues.

HW: Both Twitter (IPO) and Hims (SPAC) went public during your tenures. Were there similarities in how it felt to live through those moments? Was there anything either company did to try and maintain focus on building & executing vs “where is the stock price today?”

EDS: It’s funny — I started my career in investment banking working on the Equity Syndicate desk taking companies public. I used to work on multiple IPOs every week, so it didn’t seem like such a big deal. It was only when I worked at Twitter that I realized how momentous a public offering was when you’re at an operating company. I had been at the company for about 2 years when we went public in November 2013, and the feeling of euphoria was palpable at 5am when we got to the office to watch the management team ring the bell on the exchange.

The differences between the two IPO experiences were fairly stark. To state the obvious, Hims went public in January 2021, before most of us had vaccines. Watching the stock exchange open with your colleagues on Zoom is a very different kind of celebration. Joyous, but more muted. We never had a proper celebration until we could all be together again.

There were plenty of similarities in these milestones: the feeling of extremely hard grind, followed by a brief moment of pause to celebrate, followed immediately by the feeling of “back to work.” These are two businesses that have an ingrained culture of working hard, so we had the sense that the IPO was the beginning of the next chapter rather than the end.

Maintaining focus became a quick post-IPO shift for both businesses: at both Twitter and Hims, we immediately prioritized ROI, cost-cutting and laser focus on the pre-approved roadmap. Inevitably, there is less room for experimentation when public scrutiny from investors increases. So we saw a bit of that happening as well.

HW: What’s one effort to support ‘women in tech’ that you think is ineffective and what’s one effort we should collectively 10x?

EDS: This is an area that’s extremely near and dear to my heart, and I’ve been passionate about spending time throughout my career working to combat gender inequality. I’ll caveat everything I say here by expressing that when I’m talking about women, I’m referring to broader women/womxn/non-binary/those who identify as female.

There are so many aspects of the system to help women that are broken. If I had to pick one, I’d say that mentorship programs are the biggest fallacy in making any real change.

For starters, mentorship has to be organic. To artificially pair individuals with someone their senior leads to a pretty mediocre experience. Both sides are looking for a spark but may lack some fundamental connection (Shared job function! Shared experience! Shared outlook and desires!). Mentorship is also a two-way street. There are plenty of people who would consider me to be their mentor, and vice versa. I also have peers who are also my mentors.

Second, women’s mentorship programs almost exclusively feature women-to-women pairings. Why is that? If anything, I’d like for a senior male to show me insight into how they got where they are. I’d like to mentor more men in their careers so that they can have a female aspirational role model to show them how to get things done. It’s not the responsibility of the minority to demonstrate their value to the majority. We shouldn’t gate it.

Finally, the whole concept of mentorship is rather blunt unless it happens naturally. What I really encourage young women to find is a sponsor. Pick someone who will say “I’m going up, and you’re coming along with me.” That’s how real mobility happens.

HW: You and I are both relatively outspoken about our personal political beliefs (even if we’re happy to work with people who disagree with us). Have you always been engaged in this area or was there a particular moment that pulled you into the conversation?

EDS: This is an area of my life in which I have been deeply consistent. Emphatically yes, I have always brought some of my politics to bear. I’ve been an active and avid Democrat my whole life. My parents instilled in me from a young age that integrity and fighting for what you believe is the best way to spend time on this earth, so I always interpreted that as supporting worthy political causes.

When I entered college in the fall of 2006, I worked for Hillary Clinton’s 2008 presidential campaign, at a time when it wasn’t exactly so popular to do so. I was very outspoken on campus campaigning for her, and it felt good to be honest about what I stood for and the belief system I possessed.

I have a distinct memory of interviewing a candidate for my team when I was at Twitter. At the time, I had my Hillary Clinton work on my LinkedIn. When he asked me about it, he started with “you’re never supposed to talk about politics or religion in an interview, but here goes…” and it was one of the best candidate conversations we’ve had. It turns out we aligned politically, but I’m all about finding discourse even among disagreement. It’s fine to disagree, as long as we keep things civil.

During the presidential election of 2020, I couldn’t hold my tongue. With thanks in large part to friends like you, Hunter, we hosted a series of fireside chat campaign events via Zoom. I was surprised to see a number of my work colleagues attending those events, and received support from all walks of life along the way. I’ll keep doing this as long as I have a perch to do so.

Thanks Ellen! You can follow Ellen on Twitter via Ellen DaSilva