Gusto Women In Engineering Roundtable Dinners

Recently Gusto’s Mango Team, our Engineering-specific diversity and belonging committee, hosted an intimate roundtable dinner for experienced women in engineering. The topic of the night was “Can I make a big impact without becoming an engineering manager?”

As part of our efforts on the Mango team and our goals for the next two quarters, we wanted to facilitate conversations that are relevant to more experienced women in engineering. While women with more years working in tech often get peppered with requests to act as role models for others (speaking, mentoring etc.), we suspected that they probably crave opportunities to learn-from and connect-with other women who are as experienced or more experienced than they are. We also wanted to share their very real stories as a source of inspiration to women starting out in this career.

Our topic
As an engineer and self-proclaimed introvert, I have been thinking about this topic for a long time. I love coding and I love my noise-cancelling headphones.

But as year 10 of a 12-year programming career rolled around, I wondered: Is staying an individual contributor software engineer your whole life a good career choice? Should I be a manager? Is there a middle-ground — what some companies call the tech lead or anchor role? What path is interesting for me? Does my company support senior individual contributors (ICs)? Not all companies can and do. Do senior ICs get paid as much as managers, directors, or vice presidents? Can I make a big impact without becoming an engineering manager?

Almost a year ago, I took on a role of technical anchor at Gusto, for a project to upgrade the frontend of our run payroll product flow. This first experience turned out to be a massive project and akin to drinking from a firehose for a first-time technical anchor. It led me to understand the depth of this topic, how the one-size-fits-all approach doesn’t work for everyone, and how much a company’s codebase can be affected by organizational approaches that we take.

The Abstract
Here’s the abstract that we sent to our roundtable dinner attendees.

What are the secrets to growing your engineering career without becoming a manager? Not all engineers are interested in becoming managers, but is it a good choice for your career? What are some ways we can enable senior engineers who are not managers to have impact within our organizations?

The logistics
Our goal for the evening was to facilitate a thoughtful, authentic conversation, and enable the guests to connect with each other. I worked closely with Steffi Wu, who co-leads Gusto’s diversity and belonging program, to produce this event.

We started out by codifying the topic and abstract. We secured a budget, date, time and location. General Catalyst Partners, one of Gusto’s investors, hosted us at their lovely office near South Park in San Francisco.

Then we compiled an amazing list of experienced women in engineering who we thought could contribute to our topic. We included past co-workers and women we admire as strong role models in the industry.

Dinner from Tacolicious at General Catalyst Partners office in South Park

The conversation
The lead up to the dinner was indescribably exciting for me. Like seeing a close friend after many years, I felt there was going to be so much to talk about. To prepare, we organized questions into three main categories:

  1. Choosing your engineering career path, including questions about being an IC vs. manager and making a career switch
  2. Coding while female, including questions about challenges faced, diversity, etc.
  3. Growing in your career

Attendees mingle before sitting down for dinner

Choosing Your Engineering Career Path
We began the evening with a question to a woman who has an almost twenty year career of being a professional software engineer. She had recently taken on a role of CTO at a small startup. Let’s call her Princess Leia.

“Princess Leia, as you've gone from being an IC for a long time to CTO of the Rebellion, how has your role changed? What are the new challenges?”

She opened up the conversation by stating that the best advice she had ever received when trying to make her decision was from a man: “The problem with you is that you are a woman.” As controversial as it sounded at first, she appreciated his point about the systematic sexism that she would have to confront. I could already tell that it was going to be a great evening.

She described being hesitant and lacking the confidence to take on this new role, and how her (male) mentor advised her that she was ready. The problem as he described was that she, as many other women do, lacked the confidence of many equally (or less) qualified male counterparts. And to add to this, research shows men are typically judged on their potential, while women are judged on their actual performance.

“If you've been both a CTO and a VP of Eng in your career, can you speak about the differences in those roles and how they functioned at your company?”

Another woman described her journey of moving from a senior IC to being the Head of Engineering at her company. She had observed a void in leadership and began taking on the leadership role without asking for permission. From then on she worked hard and the official change happened quickly. However, the increased responsibility and workload was not without side effects. She spoke about how she had to learn to take care of herself both physically and mentally, as well.


“If you've stayed an IC for a long time, what are the different ways you’ve made an impact in your company?”

A woman spoke about her experience working for a company that grew so quickly that senior ICs became highly specialized — so much that moving between management and IC tracks was difficult, especially going back to the IC track after having been in management for a while. She described her own impact, owning and executing on a system that helped the company monetize, which invariably was very valuable to the company.

Another two women who were coworkers, described a system that a large tech company (that we all know of) had in place for keeping careers interesting for senior ICs. They had an “open-market” system that allowed teams to advertise roles that were open and also allowed engineers to move freely within these teams. This method had helped these two women to experience, learn, and work on many different teams within the company, over their long tenures.

Another interesting phenomenon that some women described was around hiring policies. It’s a well-known fact that engineers move freely within tech companies as opportunities arise. A woman who has had many jobs in her long career described how a more established tech company took a hostile approach when she decided to leave the company after a long stint. In comparison, a newer tech company took a much more welcoming approach, saying “Feel free to to come back whenever you wish.” Ironically, the latter company has many more instances of “boomerang” employees.

“For those of you who have a deep interest in social impact, tell us your story and what your career looks like now.”

Another interesting segment of the conversation was about social impact. Some attendees had a deep interest in social impact through organizations such ACLU and Chan Zuckerberg Initiative. They described why such a path was appealing. One women described how social impact initiatives are typically bad business models — for example, putting systems in place to help find a cure for a disease will, if you’re successful, eventually lead to elimination of the disease. Another woman spoke of being moved to action through recent political events and how her day-to-day work looks a bit different from being an engineer at a technology company.


Coding While Female
Then it was time for the question I had been waiting to ask the whole night.

“For a multitude of reasons, senior women in engineering find themselves under-leveled or under-compensated. Have you ever asked for a correction? How did you find the strength to rock the boat?”

I expected an awkward silence, thinking that no one would be willing to come forth with such personal details. Instead, one woman yelled “Anger!” and launched into a story about asking for a level correction on the very first day of her new job. Her company had set the expectations about her new role incorrectly during hiring, and while her title was corrected immediately, her compensation wasn’t adjusted for another 6 months. I was at once inspired and in awe of this woman. Having been through an incorrect levelling situation myself (and taking a year to find the courage to speak about it), I was surprised to learn that the situation wasn’t as uncommon as I had thought.

Before I knew it, two more women chimed in about having to negotiate their compensation and hating it — but fighting through. They talked about pushback from recruiters who threatened that their offers would expire and employed other hostile tactics.

Another spoke of asking for a level-change from their manager and being told no. She described how she fought by providing evidence of her peers’ levels as well as benchmark compensation in the industry, and finally threatening to quit.

“Have you experienced coworkers in the workplace treating you as more junior than your experience and level should indicate, and if so, how do you manage this?”

This was a difficult question, and to be frank, I’m not sure we came up with a good answer to this question in our discussion. There was consensus that this needs to be addressed at a system-level, related to unconscious bias training and allies within companies. Attendees spoke about how it’s important for leadership to set these examples and how people from underrepresented groups should look for these traits when looking for jobs. One attendee brought up a very important point about how the burden of change should be on the majority and not the minority, in this case women in engineering. Readers, if you have any thoughts or ideas about this we would love to hear them — please leave a comment!


Growing Your Career
Finally, attendees discussed and recommended multiple resources for learning and growing in careers.


These included:

I woke up the next day feeling elated. The conversation had been riveting. There was so much to process. We were thrilled to receive thank you notes, with some attendees saying it was their favorite event of the kind that they had attended, and others who loved our gift bags (read: socks!)

One of my favorite moments of the night was reflecting with Josh, our CEO, about the burden for change. An attendee had raised the point that the effort to drive change should not be placed on the minority (in this case women in engineering), and instead should be driven by the majority. This got us thinking about more ways that we could improve within Gusto, such as Ally Skills Trainings, which we are now facilitating internally at Gusto.

Finally, though there wasn’t enough time to discuss everything we wanted, I was grateful for the feelings of connection and renewed inspiration. Moderating wasn’t as hard as I had expected and in fact, it was fun! I felt a lot of connection because a lot of people in the room had faced a lot of the same challenges that I have in my career.


Our next roundtable dinner is about “Significant Moments in Your Career” coming up in July 2018 at our new Gusto office in the Dogpatch. Please DM us on Twitter if you would like to be invited to our next dinner! We hope you will join us at a future event as we continue to host these important conversations.

About the Author
Upeka is a software engineer from San Francisco, who has worked in the cloud software industry for 11+ years. She's passionate about frontend tech, engineering excellence and diversity in engineering. She's an avid plant assassin.