Issue 8: What does a Series A Chief of Staff do?
Hear it directly from 4 Series A Chiefs of Staff!
Welcome back, aspiring and current Chiefs of Staff!
🎊 Happy New Year! I hope everyone had a restful holiday season and that you were able to spend time with your loved ones and those you care about. To kick off the new year, Ask a Chief of Staff is partnering with the Founder of Hello Generalist, Shaina Anderson, to lead a resume refresh workshop. If you’re looking to spruce up your resume so that it better reflects your competencies as a Chief of Staff, you won’t want to miss this workshop!
What’s it like being a Chief of Staff at a Series A company?
One very common question I get from aspiring Chiefs of Staff is “What does the day to day look like for a Chief of Staff?” The short answer is, “It depends.” But that isn’t a great answer for someone who’s considering the role. Instead, I’ll be taking the time to interview Chiefs of Staff from different stages of companies and digging deeper into their responsibilities and projects to help provide a better picture of what the role looks like at different stages of companies.
We’re starting with Series A Chiefs of Staff - I often see this stage as the most common for startups to hire a Chief of Staff because you’re beginning to expand beyond the founding team. Having a generalist at this stage is crucial because you’ll need to hop operationally from setting up payroll to product/project management to hiring and recruiting and so much more.
For this issue, I interviewed 4 Series A Chiefs of Staff so you can see what some of the common threads are across the role at this stage.* Our panelists for today:
Aditi Bhatia (AB) - Chief of Staff at Capitalize
Saniya Surana (SS) - Chief of Staff at Rocketlane
Samantha Kanak (SK) - Former Chief of Staff at Raydiant
Maggie Zheng (MZ) - Former Chief of Staff at Doorvest
*Answers have been edited for length and clarity.
1. Tell me about yourself and where you are/were a Chief of Staff. What stage of the Series A was your company at when you joined, what employee number were you?
AB: I joined Capitalize in January of 2021 as the 8th employee and we are now approaching 40 people. I've been able to be a part of growing that team which has been pretty exciting. Our mission is to make it easier for people to save for retirement by removing some of the fees and frictions associated with that process. Our first product helps people digitally locate and rollover an old 401(k) into an IRA of their choice, and it's completely free.
SS: I’m the Chief of Staff at Rocketlane. We are a US-based, B2B SaaS company that provides collaborative, project delivery platform that accelerates B2B customer projects. We help orgs deliver delight and operationalise care and collaboration in everyday tasks with our all-in-one platform that offers project management, collaboration, documents, meeting notes, status updates, time tracking, resource management, project costing and profitability, all into a single, tightly-knit experience. I joined right after they had raised their Series A and about 7 months after product launch.
SK: I was the Chief of Staff at Raydiant, a digital experience platform: everything from digital signage to live streaming TV and there was an employee engagement platform as well. The company was around 20 people when I joined and then when I left about a year and a half later, we were well over 100 and across multiple different countries at that point.
MZ: I joined DoorVest when they were very, very early: pre-seed. There were about six full time employees and I initially started as one of the first sales hires and helped build out that team. I eventually moved into a Special Projects and Chief of Staff role when we went through our Seed and then our Series A. DoorVest is a full service turnkey real estate investing platform.
2. Tell me about your background and how you moved into a Chief of Staff role.
AB: I started out in traditional finance, which is a very structured path. I was an investment banker right out of college, moved over to an investing role, and went to business school. While I was in business school, I discovered an interest in early-stage startups through angel investing, and joined a seed-stage fintech startup as I was finishing up my MBA. That experience helped me build generalist skills, and reinforced my interest in being an early-stage operator. I came across Capitalize around the time of its seed round, and cold emailed the founders because I thought the idea and mission was really compelling. About 6 months after our initial conversation, I came on board as they were hiring for a Chief of Staff.
SS: I have a background in finance and consulting and enjoyed it thoroughly. However, I was seeking a more diverse role that would allow me to work on various aspects of building and growing an organization.
While I had initially planned to pursue an MBA, an opportunity to become a Chief of Staff presented itself through a cold email I had sent out. I saw this as a valuable opportunity to gain real-world experience and seized it. The Chief of Staff position seemed like the perfect fit for me, as it offers a hands-on and interactive experience where I can make a meaningful impact.
SK: I was at Menlo Ventures before Raydiant and I was working with a partner as well as a principal. Menlo Ventures really focused on seed, series A, and series B companies. Working with all these founders, I realized, “I want to be on the other side of it.”
And that's when I found Raydiant on LinkedIn. I first had my interview with Bobby, who's the CEO and we just hit it off. It was a super organic conversation. We were very in line with what he was looking for and what I was looking for in terms of working styles. I think for any Chief of Staff role, it’s really important to have this genuine connection with your principal because you’re going to be working most closely with them.
MZ: I started off on the sales team and built that out for a few months. During that time, our CEO, Andrew, was quickly realizing that he had a lot of things that he wanted to do, but not a ton of bandwidth to do them. So he started exploring the idea of having a Chief of Staff. Because it was Andrew’s first time being a founder, he had never had one before and I had never been a Chief of Staff, so it was very much an experimental role for us to build together where I moved out of sales and started working on special projects, new initiatives, and building out new teams. I was excited about being able to get so much context on building a startup, just from the very beginning and working closely with the CEO on everything.
3. How would you bucket your main responsibilities as a Chief of Staff during this stage?
AB: I started off with four key areas of focus - recruiting, finance, investor management, and BD/Partnerships. My CEO and I divide and conquer because at our stage, there's so much to be done that we realized early on that doubling up on things didn't make as much sense for us. My responsibilities changed within a couple months as we began to build out the leadership teams, and I shifted focus to Biz Ops, Finance, Operations, and Legal in addition to continuing to building out the team. Over the last 6 months I've also spent a lot of time working with our growth team.
SS: There are four main buckets I would say I’m responsible for. The first is being a sounding board, a thought partner for your CEO, helping on all things strategy. The second would be operations, where one works to streamline and optimize internal processes and systems, and it can include driving new initiatives or special projects. The third would be acting as a communication channel with external and internal stakeholders. This often entails serving as a key point of contact and liaison between different departments and stakeholders. And then the last bucket is assorted “on the ground” projects.
SK: The biggest thing that I focused on my whole time there was streamlining processes and cross departmental processes. Around the Series A mark, it’s super exciting and there’s usually this big push of money. So one of the biggest things that I focused on was all of the departments really working together and following the same process. This made a huge different internally, but it also delivers such a better candidate experience.
The second thing I focused on was cross departmental goal setting: OKR organization and communication to the executive team. I also managed a lot of investor relations and how to communicate what we're doing efficiently not only on the product side, but also on the finance side. We did have a CFO and a FP&A manager, so luckily, I didn't have to be too in the weeds on the finance side, but I did have to understand it and be a sounding board.
MZ: At the Series A stage, we were really starting to scale so this is where you surpass 50 employees. It can be really difficult to scale beyond 50 and we definitely felt those pain points, especially as a remote first startup. It was really hard to make sure projects were synchronized and that there was a high level of visibility. This is really where you start getting communication breakdowns and sometimes multiple people from different departments working on the same problem. Post Series A, you're just trying to figure out how to make the things run better and also make sure that everyone clearly knows what their responsibilities and goals are. I was doing a combination of optimizing, but also rewriting a lot of the processes that used to work when we were smaller.
4. What was your favorite thing about being in the role at this stage?
AB: It's a unique opportunity to work alongside and learn from a lot of smart people, especially if you have a Principal who gives you continued opportunities to push beyond your comfort zone. I think it's the only job I've had where I've written down feedback and learnings as I go along, and they've just hit home and made so much sense to me. It’s also great having a front row seat to growing an early-stage company across a number of different phases, whether that is operationally, strategically, or from a people standpoint, and that has been incredibly valuable.
SS: One of my favorite aspects of my role is being informed about everything happening across the organization. As a consultant, I felt like a bird flying in the sky with a vast view of different industries, functions and verticals. However, as Chief of Staff, it’s like being a frog in a well but also standing on the wall and able to see everything inside the well. It allows you to have a micro and macro perspective on the specific subject and I think that’s really beautiful, unique and valuable.
SK: Watching the company grow and flourish so fast. It was so much fun and there's no shortage of opportunity. Joining right after a Series A, the team is still so small where everybody still knows everything about everybody and you really get to celebrate the small wins together. The camaraderie of the team at that size was really fun and exciting. And on the flip side, when things didn't go our way, you still had that camaraderie to ask, “How do we solve this?” and nobody was siloed at that point so it was really easy to get buy in and input from other departments.
MZ: At the Series A stage, you start to realize, “This is a real company that I have built with all of my peers and I've kind of been here since the very beginning and so many projects that I created are now up and running as fully functional departments.” That was really great to see the culmination of all your efforts. You also really feel like you have a huge impact on the stuff that’s going on. I had a lot of visibility into the problems that we'd solve each quarter and I really loved being at the table where many of the big business decisions were made.
5. What was the hardest thing about being in the role at this stage?
AB: At the end of the day, this is a role that operates in service of the company's goals and needs more so than others. If you're the type of person who is used to that high level of very specific ownership, and sticking with that for a long period of time, I think that can be a bit challenging. You have to reframe your perspective of impact to being what is most impactful to the company as opposed to, “What do I individually think is most impactful for me to work on?”
SS: For me, it’s being able to effectively communicate with a diverse group of people. In consulting, everybody understands where you’re coming from because they all speak the same language. At a startup, people are diverse. They come from very different backgrounds and they have different priorities, different interests. So I’m learning how to speak to different people with different goals and being able to bring all of them together to align on one core objective or goal. It’s challenging and it’s very exciting because I’m learning so much about human psychology and nature, everyday.
SK: The most difficult thing for me was navigating the priority list from all the different stakeholders and then communicating that information. For those of us who were EAs shifting into the Chief of Staff role, we inherently like to take care of people and we like to be the problem solver. And when you have every single problem, either coming your way or in your line of sight, it can get really hard to prioritize - especially if you have the added challenge of multiple department priorities all within your purview.
MZ: Being a Chief of Staff, you're always a jack of all trades and master of none. In the beginning, when the company is still early stage, it's easy because you're the person building everything out so you have the most context. But then once you pass the Series A stage, many of the things are already built and you’re going in to try and fix things. Sometimes that can be difficult because you're no longer the person who knows the most about a certain subject and to really dive deep and fully understand something isn't the best use of your time anymore. You have to be very deliberate about what you choose to spend your time on and realize, “Where can I make the most impact?” and making that call can be difficult.
6. What advice would you give to someone considering a Series A Chief of Staff role?
SS: I would say be open minded because you never know what you are going to be working on next. Startups are challenging and exciting at the same time, and at such an early stage, even more so. The other thing is you need to really know is how to prioritize and manage your time well, because sometimes it can get really overwhelming just with the sheer number of things that you have to do. As a startup employee, you may not have as much access to coaching and mentorship, so it’s important to be a quick and self-motivated learner. Finally, be curious and seek out opportunities to learn as much as you can.
SK: I think my biggest piece of advice is to have the confidence in the position that you're in, especially if you're new to the company. Have confidence in using your voice to better the company and speak up to bring things to the table that maybe everybody's not aware because you have that high level view. You are the dot connector and glue of the company.
MZ: Be very clear with yourself on what you want to get out of this role and make sure that you communicate that clearly with whoever you're interviewing with to make sure that it's a good fit. I think a Chief of Staff role is very much shaped by the person in it. Communicating what you can do and where you can help out, but also what you're trying to grow into or learn is very important. And also make sure that the principal is someone that you respect and want to work with because you'll be spending a lot of time together.
💜 Huge thank you to Aditi Bhatia, Saniya Surana, Samantha Kanak, and Maggie Zheng for participating in this interview! We so appreciate them sharing their insights as Series A Chiefs of Staff and hope that this newsletter has helped inform you
Open Chief of Staff Roles:
I’ll be sharing a few of the roles that I’m working on each issue. If you’re interested in any of these positions, reply to this newsletter with a copy of your resume and I’ll follow up!
Complete - Chief of Staff to the CEO
Industry: Startups, Future of Work, Pay Equity
$4M Seed, 5 person team
Location: San Francisco
Preferred Qualifications:
Operations experience with a strong lean to execution
Strong organization and communication skills
Experience with SQL (or a penchant to learn)
Prior experience at a high growth startup
Trinsic - Chief of Staff to the CEO
Industry: IDTech, FinTech, SecureTech
$8.5M Seed, 13 person team
Location: Remote, US time zones only
Preferred Qualifications:
5+ years experience, including time in an ‘operating’ role such as Chief of Staff or Bizops
Experience at venture-backed, early-stage startups
Experience or interest in security, identity, infrastructure, dev tools, or web3
Strong financial acumen with ability to: prepare for board meetings, own financial model and forecast, help raise a Series A in the future
Additional Chief of Staff Related Reads:
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👋🏼 Until the next issue,
Clara
PS: I’m going to work hard to keep all the content in my newsletter free so that it’s accessible for everyone, but if you want to help support my writing endeavors, you can buy me a matcha 🍵 Special shoutouts to RD, Marissa, Jennifer, Liv, Daphne, Charissa, Alyssa, Mindy, Shani, and Danny for supporting the last issue!