A Sit Down with Emma Webb

It was October 2018, my son Mikhail was 9 weeks old and I was barely hanging on. Between learning how to breastfeed, a baby that needed to be nursed every 2 hours, no sleep and generally unsure of what I was doing, I knew I needed to find some support.

Through a blurry nursing session at 3 am I got online and looked for a moms group. Three days later I pulled up outside a Barneys Burger in Berkeley, and in the adjacent building, I found my mama tribe. One of those women was Emma. In that room that afternoon six first time working mommas connected, cried, laughed, cooed at our babies and formed a bond that will be special forever.

In the last two years, Emma has become a constant in my life. She is strong, resilient and a relentless advocate for realistic expectations from women in our many roles.

Emma is the Director of Marketing at CircleC, based in Berkeley, CA with her husband Steve, daughter Whitney and son Samuel. She has just gone back to work after the birth of her son and somehow agreed to and found the time to do this interview with me. I’m excited to share her story and some great tips with you all.

What do you do? How would you explain your job to your 8-year-old self?

I’m a Director of Marketing at CircleCI. CircleCI is the leading cloud-based continuous integration and continuous delivery platform. That phrase might not ring any bells for you, and it didn’t for me before I started. At the highest level, we automate a lot of manual tasks for software developers so they can get better digital products to their customers faster.

My team focuses on content marketing and communications, so for us, that means our blog, videos, ebooks and reports, our public relations and analyst relations strategy, messaging, and all of our copy/storytelling.

I’d tell 8-year-old Emma that I’m the editor-in-chief of a newspaper that writes good news about a company and that my job is to make people excited about using our product, working at our company, and being our partners.

What’s your superpower?

My superpower is building consensus and bringing people along with me. I’m pretty good at navigating complex organizations and getting people — if not excited — then at least aware and on board with what my team or I am working on.

This isn’t something I was taught explicitly, but I think it’s pretty easy to learn. When you’re working on something, ask yourself: does this seem like something someone else is an expert in? Will this impact anyone else’s work? Is it possible someone else might get asked about this, and will they know what to say if they do?

Here’s an example — let’s say my team is working on a blog series about building a great engineering team culture, and I work with a CTO named Sarah and a CMO, Josie. I want to make sure that if an engineer Sarah is interviewing for a role on her team brings up that post, Sarah can say — “yeah, that’s what we do here!” and not, “What blog post?”

I’m always trying to avoid the situation where Sarah CTO asks Josie CMO, “what’s the deal with this blog series? None of these points are right,” and Josie says, “um, I’m not familiar I’ll get back to you.” In that scenario, I’ve really failed at my job — neither my in-house expert on the subject nor my manager is in the loop, and now I have to do damage control instead of hyping up a project.

It is much easier to bring people along with you on the journey than it is to win them back or talk them down when they’re annoyed at you.

How did you know you wanted to be in Tech?

I started my career in PR, first in internships, then at a company in Beijing, and then working at an agency where I had 4–6 clients at any time. After that, I went in-house managing comms at an e-commerce startup and then worked in partnerships and partner marketing at an ed-tech company. Now I lead corporate comms at a company in the DevOps space, focusing on developers.

Tech is a bit of a monolithic word that I don’t think captures the nuance of the kinds of environments I thrive in: fast-growth startups that are building the ship as they’re sailing it, where my challenge is to prioritize ruthlessly, make the just-in-time process, and keep a team motivated and excited amidst a lot of rapid change. Those types of companies, especially where I live in the Bay Area, happen to be in tech. As consumers, we interact with every company these days through some type of screen — I think in a few years, the word “tech” as an industry descriptor will start to become pretty meaningless.

You lived in China for some time. What prompted that move and how was that experience?

I always wanted to live outside of the U.S. for an extended period. In college, I ended up studying abroad in Shanghai for six months — I wanted to go somewhere I wouldn’t have the opportunity to go on my own. I came back halfway through my Junior year and added East Asian studies as another major on top of my public policy coursework. I had a great internship at a PR firm in New York City between my junior and senior years. At my internship, I remember asking how to get hired abroad for my first year out of college — the advice I received was that I had unrealistic expectations, and it wasn’t going to happen. In my Senior year, I applied for a program called Princeton in Asia (PiA) operated by Princeton University — I vividly remember googling “fellowships in China,” and I found it two weeks before the deadline closed.

Close to graduation, I ended up with a choice: take the job offer I’d received from the PR firm in New York or the offer to be a PiA fellow and work in a PR/marketing role at a sustainable travel company in Beijing. I chose the path that seemed more like an adventure.

I graduated from college in 2008 at the height of the financial crisis, but it wasn’t really on my radar while I was living in Beijing — I moved right before the Beijing Olympics, travelled a lot for work, and had a ton of autonomy in my role for someone so junior. I was also able to get some side gigs that I was totally underqualified for: writing a bi-weekly dining column for a magazine and blogging for a chic hotel. That experience taught me a lot about the rewards of raising your hand for an opportunity, even and especially if you’re not quite sure you can do it.

Tell us about your powerful secret cabal of other women in tech.

There are five women I talk to every day who I worked with at a previous company. None of us works together anymore, but we connect about our challenges and successes. It is so invaluable to me to have this group I trust and respect deeply. They give me some gentle but constructive feedback as well; it’s my personal r/AITA.

I’ve also learned a problem-solving trick from this group. The answer to a dilemma often becomes obvious when you have to explain it to someone without your level of context. Even the process of framing your question is really helpful!

“Hey I’m having this problem with my colleague because XYZ, what should I do?”

“What did they say when you talked to them?”

“Oh yeah, I haven’t done that yet. Right.”

Every day, I’m grateful to have this group of wise women rooting for me and guiding my decisions.

You recently had your second child and have a 2-year-old. What was your experience like going on maternity leave and coming back to work? Do you feel your career has changed since having your children?

Both of my maternity leaves were great in different ways. For my first, I went completely offline for five months. With my second, I was out for about four months and stayed much more in the loop (by choice). One thing that I think made both leaves successful for me was that each time, with my CMO’s support, I was able to budget to bring in a contractor to support the team in my absence. If you can do that, I would highly recommend it: instead of thinking about how your team has to cover for you, are there things you can take off their plates so they can stretch up?

My team and company as a whole are definitely very supportive of parents. I’m both extremely grateful for this and also deeply annoyed for our country that this support is not the norm for everyone.

How do you balance work and life with two small kids?

Is balance the right word? I don’t know if I have a lot of balance at this particular moment. Work is full-on. Life with a 2-year-old and a 7-month-old is full-on. I have a super supportive partner who is equally competent or better at a lot of the parenting stuff. Finding the right split between family time — partner time — friend time — work time — solo time is a constant shuffle. I’m working on getting better at making time for myself and reminding myself that quiet downtime is the fuel that keeps the rest of the machine going.

How would you describe your leadership or management style?

I definitely practice influence over authority. I want to guide my team in making good choices instead of creating a my-way-or-the-highway-type culture. This style is more labour-intensive, but I work in an influencing role, so it works for me.

There are a couple of other reasons this style suits me. One is that I can’t possibly be the expert on everything, so practising this type of team management makes it clear that I want ideas and initiative from every part of my team. Second, it lets me reserve my authority for those rare situations I feel strongly about, so when I give a hard no or change something, my team pays attention.

If creativity is a key ingredient you need on your team, you have to create space for it with how you lead.

Do you have a nemesis, and how do you deal with them if so?

Ha! No nemesis (that I know of). I believe in tackling awkwardness head-on, as quickly as possible, and ideally face-to-face/ zoom-to-zoom.

My formula for those conversations is pretty simple:

I’ve noticed this is happening / this thing happened.

It’s making me wonder [something about how I might have contributed to the problem]. ← not admitting fault but demonstrating openness to having a reflective conversation

Is this something you’re feeling as well?

[Lots of space for their reaction]

Some other conversation starters might be:

“I’m feeling frustrated by our latest interaction because…how do you think we can be better collaborators?”

“Tell me more about your goals and priorities and how I can support them.”

“I work best when…what are your preferences?”

A willingness to have potentially uncomfortable conversations has served me very well. You can quickly air out problems, and the other person then knows they can come to you directly when they have a future issue; you’ve demonstrated you’ll dive into it with them with patience and hopefully a little bit of grace and self-awareness.

How do you create change in your workplace?

Getting any size organization to move on something — whether it’s recognizing a holiday, changing a policy, adopting a strategy — is much more of an art than a science.

You have to think about creating a scenario where everyone feels like they are winning. When you’re working within an organization, it’s really important to remember that everyone is on the same side.

I think patience, quiet persistence, and consensus-building on issues you care about are much more likely to get the outcome you want. I think the biggest mistakes I see people make are escalating tactics too quickly. I’m not saying you never want to send an org-wide email; I’m saying that would be my last tactic, not my first. It might work once, but it’s not a path to repeatable success or change.

How do you decide when to leave a job?

I’ve had some less-than-ideal job situations. At one job, I had seven different managers in 3 years. I worked at a startup that failed. In one role, I had conference calls at 11 pm, and 6 am twice a week. None of those reasons was why I eventually left those positions (well when the startup failed I didn’t really have a choice, right).

Here are some signs it’s time to leave a role:

• You’re obsessing over insignificant things or perceived slights. This is a sign you’ve lost your perspective and objectivity, and you can no longer behave rationally. You’re also probably really burnt out. Take a vacation and move on.
• If you don’t trust your manager, you have to go. Full stop.
• When you don’t trust your team is acting with the best intent. In this scenario, you’re likely going to be really unhappy: questioning everything, looking for ulterior motives, feeling defensive instead of motivated.
• When you’re skating, and no one seems to notice. There are times when you’ll be busier or less busy; most roles have some sort of ebb and flow. For me, if I find myself putting in the bare minimum and still getting praised, or no one seems to notice, it’s time to find something else. That’s a signal to me that I’m not challenged, not learning, or my work is not important/significant enough for someone to pay attention.

If you didn’t work in tech, what would you be doing?

I think I’d be a food writer, only writing about restaurants I love. Dining out is a passion — I love restaurants and food culture.