Michelle Zatlyn, Matthew Prince and Rachel Gonzalez, Cloudflare

In Conversation with Michelle Zatlyn, Matthew Prince and Rachel Gonzalez, Cloudflare

Jean-Philippe Defaut
One would think supporting two busy individuals in the heart of San Francisco’s tech sector might be a challenge in today’s working lifestyles. But when it comes to calendars and company-wide meetings, Rachel (Gonzalez) Chavez has an open book for both founders of Cloudflare, Michelle Zatlyn and Matthew Prince. “Since I have access to both their schedules at all times, I’m able to synchronize them on all the relevant responsibilities without having to check in.” — Rachel (Gonzalez) Chavez

Michelle Zatlyn, Co-Founder

“This is my third business venture. It’s the biggest operation I’ve been involved with. It’s also the first time I’ve had to hire an Executive Assistant (EA). As a founder, you roll up your sleeves and dig into everything because you have to create everything from scratch. As you grow, there’s just way more things to do in one day than anyone can possibly get done. Once you’re off the ground and have traction, you have to grow your team. When Matthew and I decided to hire an EA, we realized that three of us working together would produce the output of four people. You need to be constantly keeping momentum.”

The Need and the Search

“We started looking for our first Executive Assistant when I was pregnant; I was very motivated! Not only for myself, but also for Matthew. We don’t use outside recruiters for most roles and we just went about it organically. We own recruiting in-house at Cloudflare. In the case of some senior positions we have on occasion used external recruiters, but most of the time, we keep it internal. It’s our own recruiting managers that drive process, and as a result, we have better outcomes. It’s the hiring managers’ job to build out the team, not a recruiter’s job. San Francisco is very competitive for talent and the fact that hiring managers are directly involved leads to better outcomes. Matthew and I were very involved in this search as it was directly for us. As an executive, if you’re without an EA, life can be very hard.

Our criteria was specific: we looked at candidates that had previously worked for founders. We also needed someone who was very organized and detail-oriented. There are a lot of “balls in the air” — we needed someone who wouldn’t break any of those glass balls. There’s a lot of context to be aware of, as well as a lot of context-switching. Some people love it, others find it very stressful. Additionally, whilst Rachel primarily works with both of us, she can also work with our communications team, our office team and other executives of the company. In our interview process, she met with all those other departments as well.

Life is too short to be unhappy at work and we really needed somebody fast. We wanted an EA that was going to support us for a long time. Previously there was something missing and then when Rachel arrived, we really lucked out! Matthew and I have worked together for a long time. Thankfully, Rachel has really connected with both of us. She is great at prioritizing the order of things, we don’t have to tell her, at this point, she just knows.”

The Evolution of the Role

“As you spend time here, you gain confidence in yourself. Starting a new job is so hard: you don’t know anyone, you don’t know the company, the team etc… As you learn more about the job and get things done, you create new tasks and the role grows organically. Rachel wasn’t our first EA hire so we had a little practice at delegating and staying on top of things as leaders. She also has a lot of experience and can identify places where I might need help, or where I can give up a task to free up some time. We also have to look at the things she doesn’t like doing, even when it comes with the territory to see how we can help her evolve. Tasks that as we grow over time, we can assign to others. That balance is important.”

We want people to have the career of their lives here and try out new things. — Michelle Zatlyn

“Over time, Rachel has become more involved in our company-wide meeting, known as “the beer meeting” since it happens in different time zones. We are a global company so it takes a lot to organize those on a weekly basis; she has really taken ownership of this meeting. For example, Rachel knows about many projects that are underway within the company so she can directly reach out to people and engage them in sharing their work in the meeting. It’s a great place to practice public speaking and we don’t look for a polished “keynote” type presentation. Typically we stream it live and 80% of the company are watching and participating globally. It is constantly evolving and Rachel helps the development.

Rachel owns both of our calendars. She partners with internal and external parties and maximizes my time. It sounds easy but there are conflicts all the time. We divide and conquer our time so Rachel can make trade offs between Matthew and I wherever necessary.

The boundaries can get blurry as to personal versus company. I’m a parent and if I need to get involved in school or children related activities, Rachel has my calendar and needs to know what I’m up to and when I can do those things. It can be tempting, but I have to think of what’s best for the company. Rachel works for Cloudflare and there is a line.

A lot of executives in the company share EAs. It seems to work well and it’s a great set up. When the workload gets excessive, then we will have to evolve it. Rachel has a great network outside of Cloudflare where they share and learn best practices. We are constantly looking for people who want to learn and get better. Travel is an example of something that we have evolved thanks to her initiative. She advocated for a travel agent to save time and money. She also has access to my email and that really helps me filter priority / time sensitive items to the top of my list. That’s a real time saver! As time goes on, the more tasks she gets familiar with, the more she is enabled to grow and take on additional responsibilities.

As the company grows, we really appreciate the support we get from Rachel. I don’t see that need going away. As our jobs change, so does Rachel’s. When I interviewed her, she said: “I’m happiest when I support people.” That has certainly prevailed as we’ve worked together and I hope she supports us for a long time. We are in a high-growth mode at the moment, eventually that may settle. We both spend a lot of time with Rachel, it’s a marriage or a “three-legged stool!”

“Executive Assistant” as a role still has a great positive association. There has been a transition of how roles are characterized, especially here in Silicon Valley. Rainmaker or more relevant for me — “The Enabler” is really what Rachel does!”

Prelude depicts Humans at Cloudflare: Earth 2009 — present ©2017

Rachel (Gonzalez) Chavez, Executive Assistant

Rachel started out as a receptionist in a startup company and thought that she would end up in marketing [she has a marketing degree]. As the work became increasingly administrative, she fell in love with the Executive Assistant role and organically grew into it. She has really embodied the care-taking side of the role.

I never saw myself going in there but once the opportunity came up for that role, I applied for the position. — Rachel Gonzalez

“I had the good fortune to be mentored by Maïa C. Carpenter over a few years and thanks to her, I was introduced to Cloudflare. Having seen the first tech crash, I was aware that there’s always a risk in working for a startup, but when I joined, they had a couple hundred employees, so they had stability and momentum. In bigger tech companies you can get lost in the masses, they easily move you around and it gets complicated. A lot startups want admins. with 5 plus years experience, but Cloudflare was open seeing how we could work together.”

The Bigger Picture

“Trust comes over time and over the last year, I’ve created an Executive Assistant team for Cloudflare’s executives and I managed the entire process of hiring 7 EAs for the company. I was a part of the recruiting meetings and taught the team how to work with executives and be someone who could approve things on the executive’s behalf amongst other tasks. When you start as an EA, the day-to-day tasks are an obvious requirement. As you build a relationship with people, you become an extension of the people you support. It’s a partnership role that cannot be written up in a job description. You can’t be a good EA unless you have intuition. You need to get to know the people you support on a human level and pay close attention to those you support, their moods, what they respond to and the energy they’re giving me. If I see that Matthew’s “in the zone,” rather than break his flow with dialogue, I’ll email him, even if he’s on the other side of the desk.

There is always the thought that you could fail if things don’t go well. As it was my first time supporting co-founders, there was the question: Can I really do this? Am I really good at this? Do I think I’m good at this…? I don’t have an admin team, no one trained me when I started, etc… So I designed this job as I went along, based on their needs. It was hard in the beginning, but I’m really proud of the team I’ve built and the people we’ve hired, the level of skill and good human beings I get to work with everyday — it’s AWESOME! You don’t get this opportunity often.”

You’re going to burn out your EA if you keep them on edge all the time. — Rachel (Gonzalez) Chavez

Intuition and the Finer Details

“Both founders have very demanding schedules and requirements, but on the scale of executives I’ve supported, Michelle and Matthew are very low maintenance. They don’t ask for personal things, even though it’s expected by a lot of executives in most industries. The boundaries are clearly set. Being an Executive Assistant is often 24/7 support; yes my phone is on but I’m not expected to respond after hours, weekends or on vacation. They’ve said, “We don’t want to hear from you! If it’s urgent, we’ll call you!” They respect my personal time. In the past I’ve worked for people where I’ve never stopped, even on holidays I’d check my emails to avoid getting into trouble.

Michelle has a lot of email to manage so we work closely on that. Matthew is different, we work on a weekly basis and touch base periodically throughout the week. Scheduling is the major time-saving element. I work on their calendars all the time. The “to do list” is my daily time saver, I can’t start my day without it. I stay organized, everything is in folders and my email box is under control. I’m allergic to a lot of automated things. I’m a little ‘old-school’! I look at schedules and I can see where things might run over or where they might need a break, refreshments, lunch etc… Automation doesn’t do that. It doesn’t look at people as human beings. If there’s a 30 min. gap, automation wants to fill it. Sometimes people need a buffer. Not all meetings run on time; how much energy or clarity of thought can someone have after 4 hours plus of back-to-back meetings? I observe and adapt where necessary.

I get to see and work with them on a regular basis and consider that to be a huge privilege. Knowing who they are, the ups and downs, when working under pressure, I don’t take offense to things, I always see them as humans.

I think it’s the be-all and end-all of all partnerships; I like Google’s approach to referring to their EA’s as “Business Partners.” Matthew and Michelle focus on the bigger things and I’m the partner that does everything in the middle. When their lives run smoothly, they’re not aware of 90% of the things I’m doing and that’s the way it’s supposed to be. There are a lot of things I do on a daily basis and they don’t need to know what it took to get there.

I’ve maintained contact with a lot of EA’s, both internally and externally on forums, Facebook groups etc… We share a lot of information, tips/skills and always support each other. One thing I like to do for my executives is to send them a nightly email and give them a picture of what the next day looks like. Matthew is a ‘bigger picture’ person so I send him a weekly one. It’s a great way to get questions answered; I can get all the information I need and get on with all my tasks without waiting for an answer for every task.

A magic moment was when I was organizing a dinner for the founders and I had a lot of hoops to jump through to make sure all the details came through. From caterers to flowers, the details kept changing: you have to think quick and make a decision as the clock is ticking. My job is to make it happen without anyone knowing what I go through.”

“Wall of Entropy” Cloudflare lobby, San Francisco, CA

Matthew Prince, Co-Founder

“We brought someone on when we were about 70–80 employees. It was an office support role. I went longer without support so I’ve been slow at adopting any help. Left to my own devices, it would have taken longer!”

The Need and the Search

“Early on, when there were 6 of us, we set up a Google calendar and I was like, “why do we need this? Why can’t I just track all the meetings in my head…?!” I was that naïve! I’m still not to a point where Rachel has access to all my email, but she certainly controls my calendar. There’s real acumen to being a world class Executive Assistant. We had to start with help around the office, then the next person we hired we didn’t connect with personality-wise, so when Rachel arrived, we realized we had found the right person for us. When she first started, I was anxious and it took a while to get going. You need to have somebody with competence, confidence and a rapport where you can communicate things with clarity. There are many people that want to meet with me on a daily basis. It’s an education for both of us to figure out who the priorities are and how to schedule those people. Michelle and I are very different people and we need different things from Rachel. We went from an organization with one EA to a team of EAs. For now, it works and makes sense for us. As our lives become more complicated, we will probably end up each with our own EAs. We are low-key people and you need to find a good personality match. I need someone who has basic confidence and common sense.”

There’s a lot of acumen to being a good Executive Assistant. — Matthew Prince

On Job Titles

“We are really “title-light” here at Cloudflare. We look for people that are competent, good team members and able to do their jobs. Someone who wants to work here for a specific title may not be a good fit for us. For example, the Chief of Staff (CoS) role needs to be clearly defined. Often, there is too much ambiguity around it. You don’t want all your executives to have a CoS. I am somewhat skeptical. You can’t have a CoS for every Executive. We have a CoS, but they play a very different role than that of an EA. We are interested in people who care about the mission, that are confident, smart and able to do the job. We don’t spend time worrying about people’s titles. When you have an organization that is growing as fast as we are, there’s an infinite amount of things to get done. Those who thrive here are those who address what needs to be done, not focus on the title.”

The Partnership

“If you think of the best founding teams, you don’t want two people that are the same, you want them to be different so you can cover a wider range of responsibilities. Michelle and I have very different styles so Rachel has to adapt to each of us. Michelle is more internally focused, I’m more externally focused.

One of the consequences of giving up your calendar to someone else is you don’t have a sense of how it looks, so once a week she sends me the whole week up ahead so I see all the activities, those that require context and those that don’t. Rachel gives me the notes and I can run through them on my phone. She also is the defender of my time. She puts in blocks of buffer to allow me time to recharge or refocus. She’s not omniscient, but she’s very good at reading how enthusiastic or un-enthusiastic I am about meetings. Things don’t make it on my calendar unless Rachel signs off on it.

Automation is more likely to expand the team rather than replace employees. I’m unlikely to use automation, but Rachel might use it to assist her daily tasks. For example, recruiting is a complex process and there are many calendars involved. Automation in this process is a very useful tool. Technology will help assist administrative tasks but not replace administrative staff.

It’s an EQ (emotional intelligence) puzzle most of the time. You need a human being to piece it all together. We’ve not drawn hard and fast lines and Rachel doesn’t do anything personal. But if I’m running late, she might arrange lunch. It’s more of a “know it when you see it” and occasionally there is something that she volunteers that can be hugely helpful.”

What you really want from an EA is someone who can be on top of anything and never let it get to the point of a crisis. — Matthew Prince

“One of Rachel’s super powers is to keep everything under control and look effortless. I recently thought that if I knew everything that’s going on across the entire company, I would not sleep! What’s comforting is that we’ve hired a great team and we’ve given them independence and responsibility to solve those problems. Things tend to just work and Rachel stays on top of that. Ask Rachel about the stressful things that I don’t know about and I’m sure there are a million things! I know what Rachel does is incredibly hard and my life is more straightforward because she’s out there as my “guardian angel” being the gatekeeper. That’s the mark of a great Executive Assistant.

Some things are predictable and sometimes things come out of nowhere: you have to solve a personal problem first to address a professional problem. I was in Europe on vacation and we had a global bug. I had to drop everything and once it got fixed, I had to give a hundred 15-minute interviews. Because of the volume of roaming calls, AT&T cut off my mobile phone service! Rachel was instrumental in sorting out one problem after another.”

You really want to hire people that want to do this as a career. It’s not a cheap position and in some cases a very well-paid role. — Matthew Prince

In Summary

As our conversations with Executives and their support roles deepen, it’s evident that there is no “one size fits all” to how people work together in this capacity. Businesses are progressively moving closer to automation through the constant evolution of technology. It’s clear that these are very welcome tools in a fast-paced and demanding work environment. That said, as long as we are hiring and working with people, there is still a requirement of human interaction. More specifically, human interaction requires being present and, in most cases, intuition. This is not something we can measure on a job application or a CV. References can shed some light in vetting candidates, but human connectivity is only apparent when you try working together. In a data-focused world, Cloudflare prioritize the notion of EQ over IQ when it comes to employees, but are others following suit? To be continued…

Mission statements from Cloudflare, San Francisco, CA

If you are a Founder, C-Suite Executive or other leader who has a great working relationship with your support personnel, an Executive Operations Director, Executive Assistant, Business Partner or Chief of Staff, we’d love to feature you in our interview series. Connect with us: hello@ccpartners.co

Jean-Philippe Defaut

Storyteller, Hybrid Creative & Photographer

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