Inside my first 90 days as Chief of Staff at an early-stage startup

Last August, I joined as Chief of Staff at Gather — an HR tech startup empowering those putting people first in the workplace.

In my first 90 days, I organized a week-long company retreat, overhauled our internal operating cadence, launched two strategic partnerships, and wrote content that drove thousands of new eyes to our platform.

Before becoming Gather’s Chief of Staff, I had no experience in operations or tech. I’d spent the past two years as a market research analyst, writing questionnaires and analyzing data in pivot tables.

When I landed the new role through a startup fellowship called Venture for America, I began gearing up for a lot of learning in an unfamiliar role and space.

Here’s a peek into how I approached my first 90 days as a startup Chief of Staff.

💫 Crafting my Chief of Staff mission statement

The official job description in my offer letter was: ensuring that Gather as a business is operating well. That phrase can mean a whole lot of things and at the same time, nothing at all.

As I entered the role, my first goal was to carve out a pointed objective for myself as Chief of Staff.

In our first few 1:1s, my CEO John and I talked about what success as a Chief of Staff might look like. We worked together to establish an ultimate goal that would serve as my mission statement, helping me prioritize work and narrow in on my value to the company.

We landed on becoming embedded in the core of the company.

We chose this as a north star because it had the potential to yield benefits for Gather as an organization and myself professionally. I’d gain the ability to flex into any role or project given the fluctuating needs of our early-stage company—a role that only John was filling previously. It would also open up John to work on critical strategic initiatives that needed executive attention.

To become embedded, I took on one special project for every department: creating a goal-setting framework for our leadership team, writing blogs as content for the Growth team, crafting wellness-focused workflows for our Product, and even answering customer chats for Customer Support.

My commitment to becoming embedded gave me early exposure to all parts of the business and a deep understanding of how all of the pieces of the company work together. It also fueled my strong initial relationships with everyone on the team.

Today, having reached “embedment” helps me make more informed strategic suggestions as a partner to John and our founders, and empowers me to take on any new project with confidence.

Check out another fellow Chief of Staff, Regina Gerbeaux, who wrote about establishing her ultimate goal: making her CEO feel like a superhuman.

🥇 Creating trackable, visible wins

Another challenge in my new position is measuring my success and making it visible. Working in an Opsy role, I quickly realized my CEO (and the rest of my team) might not be aware of my successes unless I explicitly talked about them.  

I like the way Paul Cohen talks about the role in his Chief of Staff Guide: “You need to find ways to ensure that others see the value you create. Don’t expect people to know the great work you’re doing unless you tell them in some way.”

To make my wins apparent, I set up a Project Tracker to log my actions as Chief of Staff. Every other week, I walk John through this tracker, give him a status update on my projects, and assess any questions or roadblocks.

The tracker includes things like:

• The project’s Notion page (helpful for if/when John wants to peek at my work on an async basis)
• The latest update on the project
• The project’s measure(s) of success
• The project’s projected end date
• The team/department I’m working on the project for

After finding a way to resurface my own work, I saw opportunities to help our other teams do the same. I introduced team-specific Sync & Shares to Gather’s bi-weekly meeting cadence we used as a platform to “show and tell” about a current project or initiative. I even took advantage of my new Strategy + Operations Sync & Share to share my work and its impact.

Doing great opsy work often looks like nothing going wrong—so when you’re doing your job right it’s easy to miss.

This made sharing my wins with John and our whole team critical for communicating my value in the first 90 days.

👯 Cultivating a community of peers

As someone who’s always worked with a team of peers in previous roles, my transition to being the sole owner of projects is a new experience. Becoming Chief of Staff, I wanted to recreate that network of peers for myself.

First, I found three other Chief of Staffs at early-stage companies and spoke to them about their experiences in the role.

I hit it off with one of the Chiefs of Staff I connected with and now we meet once a month to talk about current projects, reflect on learnings, and set one goal we’re hoping to achieve before our next meeting.

It’s been a great way to learn alongside a fellow operations leader who’s experiencing similar challenges and hold each other accountable for accomplishing our professional and organizational goals.

I also joined several communities that align to each of my special project areas — like Opsy (Operations), Demand Curve (Marketing), and Gather’s People Ops community (People Operations). I participate in meetups, workshops, and 1:1s to build up a network of folks I can lean on for anything from retreat planning advice to how to deal with New York State taxes (the worst!).

While I love that the Chief of Staff role requires me to be more independent, resourceful and self-assured in my decisions than ever before, the relationships I invested in within my first 90 days have been integral to my successful career transition.

Not only have I leaned on these peers for quick questions and project feedback, but I can connect with them for career advice, mentorship, and benchmarking my work.

🚀 What’s next

This week marks six months into my tenure as Chief of Staff at Gather.

I’m proud of the ways I’ve supported our leadership team and kept Gather on a steady upward trajectory, but there’s a lot more I hope to accomplish — for our company and for my own career as an operations professional.

In the next six months, I’m looking forward to expanding my capabilities as a generalist while also starting to hone in on a niche that compliments my skills — like strategy planning and marketing operations.

Thank you to all in the Opsy network and beyond who’ve welcomed me into the community so far. I hope this piece serves as a helpful guide for new folks breaking into the Opsy world like me! 😊