My First Year as Chief of Staff

Over the course of this first year, I was able to close more than 100 customers. I hired, trained, and managed a team of 22 contractors. I wrote blogs and launched mini products, 4Xing website traffic. I onboarded and trained several FTEs, ran 200+ interviews, designed interview loops, and ran reference checks. I launched and redesigned pages on our website, helped establish our company values, and so much more.

Before joining, I tried to read what I could about Chiefs of Staff at tech companies. Ultimately, I had no playbook and was nervous/hopeful that I would do a good job. I had to take it a day at a time, and just figure it out along the way.

Though I know the experience will be different for everyone, here’s my contribution for anyone interested in what a CoS does at a seed/Series A startup, and how my role evolved over time.

Month 1: Build Trust And Settle In

I recently read that anxiety is responsible for driving us forward to succeed. During my first month at Dover I was driving a little too fast. I grasped for things to do, feeling I had a lot I needed to prove, but soon realized there was a better way for me to approach things.

I pulled the car to the side of the road and gave myself permission to lean back. I strived to listen more than I talked, and think more than I acted, telling myself to be patient, slow down, and observe.

When I joined, our CEO (Max)’s calendar was full of sales calls and first phone screens with Dover candidates. There were also random clerical things that needed to be dealt with (cancelling bills, dealing with movers to close our SF office, scheduling meetings, etc.) Dover had also not done any marketing.

My first order of business was to shift these things onto my plate. To build trust and to free time for others, I took on the administrative work alongside some of the more exciting areas like marketing that had a lot of greenfield.

At the end of my first month, I did the marketing launch for a free tool which was a nice first win. This launch outperformed some previous ones we had done and resulted in our highest traffic website day up to that point.

Month 2: Repetition

I closed my first sale on September 13th. By this time, my calendar had become a back-to-back block of 30 minute calls all day — split between new sales conversations and candidate screens. Max’s calendar was clearing up.

Repetition is the mother of learning. I spent all day pitching Dover to both customers and candidates, answering questions and handling objections. So I had started to build enough context to contribute to strategic conversations. My goals evolved: I had abstracted tasks away from Max, but now I wanted to be equally as effective as him.

By the end of month 2, candidates I had first rounds with were progressing into late stages, and I had the opportunity to be part of their onsites and final evaluations. In preparation for their joining, I started to build out our employee handbook.

Month 3 & 4: Expanded Responsibility

Around the 3/4 month mark is where I started to see the magic of the CoS role. Our financial analyst, Frank joined in late October and took over contracts and other tasks related to sales Ops. Something that I had been a stop-gap for was now successfully handed off! That was cool.

Around the same time, Dover was experimenting with an “interviews product”: we had hired four people part-time to conduct first round candidate screens on behalf of our customers. Since we use our own product, I was able to start handing off internal first round phone screens to our Interviewers after conducting more than 100 calls myself! Again: where I was once focused on executing, I shifted to training others, and was free to think strategically about how to improve the process or product I’d just handed off.

Also in October, I launched another free marketing product with similar success to the previous one. We had another peak day for site traffic. In the time I had left, I wrote blog posts and got at some low hanging fruit to make our website, JDs, and employer brand stronger.

With my first 90 days down, I wanted to check in with myself. How had I done, and where was I going? This is when I decided to reach out to other Chiefs of Staff and interview them for an article. These conversations helped me define how I could be better, and what I should be striving for.

Month 5 & 6: Starting Workflows

Ringing in the new year, I felt I had earned trust and started to experience flow. If my goal in previous months was to absorb our CEOs tasks, and then to be equally effective, I now felt like I was adding my own signature to things. I started to establish my own playbooks and felt the imposter syndrome fade.

Sales and Management were my two biggest responsibilities at this point. My AE workload had gone from taking up 30% of my time to 70% as inbound customers continued to pound the door. The team of 4 interviewers we had experimentally hired were working out great and customers saw value in the new product offering. So we quickly hired more people — and the growing team needed a manager. I focused my remaining time on being a stand-in for this.

At this time, People Ops was suddenly becoming more necessary. This included things like facilitating team events and bonding opportunities, orchestrating the onboarding of new team members, and later reviewing and improving those processes through feedback. I responded to thoughts and ideas as they came up.

In January, Max put a daily 1:1 on my calendar. Our working relationship got better as I got more insight into what he was doing, what I should be doing, and what was coming up. Being a remote CoS can feel wobbly — you wonder whether you’re working with complete information — so at this point, the extra time was helpful.

Month 7–9: Role Evolution

By February, I’d already seen my role and responsibilities evolve several times, and I could see another big change on the horizon with the possible addition of several new employees. Wanting to take stock of things, I did a sort of “audit” on my role, reviewing all I had accomplished in my core areas (Sales, Marketing, Hiring). I learned a lot about the impact of my work that had previously gone over my head.

Other Chiefs of Staff called out to me in our interviews “if you’re doing the role well, no one will know.” Chiefs of Staff therefore need to be proactive about making sure the right people know what they’re doing. So in March, I had a conversation with Max to share what I’d learned.

By April, Dover was 23 FTEs (triple since I had joined), and by May, it was time to establish our company values. I worked with our CTO to create a process for uncovering and solidifying them, then lead the workshops with our broader team. We were starting to feel like a ‘big’ company!

The contract interviewers team was growing, too. We were 12 people and counting by this point, so I appointed three Team Leads to assist with some of the ‘people’ aspects, and focused on being a liaison between the interviewers feedback and the product team building workflows for them.

In the spring, Dover supported me in going through the Coho Chief of Staff Fellowship and I was able to represent Dover at the YC GTM Expo. By this time, daily syncs with Max were no longer necessary, so we paired down to meeting once a week.

Month 10–12: Continuous Growth

In June, we hired our first growth lead, Harry, to take over Sales. Our second growth lead, Bryant, came shortly after. This was a big deal as it meant I’d be stepping back from the day to day work of the department I’d been most focused on.

I had done short, simple trainings with other new employees as I handed off small things here and there. But this would be different. I worked closely with Harry, investing myself in ensuring he was set up for success, being an ongoing thought partner. By the time Bryant joined, Harry and I were able to share some of the onboarding responsibilities. With new sales officially off my calendar — I turned myself toward Account Management and Strategy.

In July, Mario joined as our first operations manager. Our contract interviewer team had grown to 22, and where I was previously a make-shift stop gap for managing them, Mario would be a dedicated leader for that team.

The majority of my time early Summer was spent on onboardings for Mario, Harry and Bryant. I saw my role start to transform again as in my free time, I was able to jump into what I call “strategic projects” — the random one-off side projects that are high potential for Dover and need to be proven out. I saw myself becoming the end of escalation paths, and striving to be a true stand in for our CEO on various issues/a final decider.

Over the summer, we opened an office in New York City, and announced the close of our 20M Series A.

Looking Back

This month marks one year at Dover, and I am very happy with how things turned out. My goal coming in was to observe and understand how a company scales from point A to point B, and to be a core part of that growth with the ability to point to things and say “I did that!”

I’m excited to see where we go from here and see what else I am able to accomplish in this role.

My Advice / What I Did To Be Successful

I mentioned early on that I did not have a playbook for being a CoS at a seed stage co. So here are a few of the things I did that I think made the difference for me.

• I asked for what I needed. I tried not to be passive about what I wanted from others. I asked Max to keep a standing weekly meeting with me even after he suggested we no longer needed to meet in a structured way. I didn’t wait for other people to bring up problems, I proactively scheduled time on calendars and initiated conversations. I reminded Max and George (our COO) of what I wanted out of my job: the things I wanted to learn or areas I wanted to focus on. When I spoke up to ask for what I needed, I almost always got it.

• I was patient. You can’t come into a startup expecting the world on day one. I was fine with learning and listening during my first few months. I was fine with doing admin work. I was fine with earning my stripes. Sure enough over the course of the year, I proved myself and got to see my scope of work change several times.

• I leaned on my peers. I reached out to other CoS to learn from them. I thought writing an article was a great excuse to get a ton of different perspectives. This was so I could get a better idea of how I could structure my own role. I did the Coho Chief of Staff Fellowship to expand on this.

• I shared my work. I was told that if a CoS is doing a good job, most people don’t know it. ~6 months in, I had a meeting with our CEO to tell him about everything I’d accomplished. It’s easy to procrastinate on this, but I try to think of it as something healthy, like ‘eating vegetables’. It’s interesting to see where you can go when you are proactive. I would put “writing Medium articles” under this umbrella, too.

• I got to know people individually. Dover is remote first. As much as I could, when new people joined in my city, I asked to meet them in person outside of work. This eventually became unscalable, but I really tried to extend myself when I could.

• I was flexible. I was comfortable taking on new things that were intimidating, believing I would be able to figure out the MVP version and go from there. Eventually, I had to be comfortable hading things off to others without being territorial.