Issue 11: What does a Series B Chief of Staff do?
When your company starts to with growth stage, what are you expected to do as a Chief of Staff?
Welcome back, aspiring and current Chiefs of Staff!
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What’s it like being a Chief of Staff at a Series B company?
A few weeks ago, I interviewed 4 Chiefs of Staff at Series A companies to learn more about their roles and responsibilities. That issue led to over 3️⃣ 5️⃣ 0️⃣ 0️⃣ views with the expected follow up question: “What does a Series B/C/D Chief of Staff do?”
For this issue, I interviewed 4 Series B Chiefs of Staff so you can see what some of the common threads are across the role at this stage.* Our panelists for today:
Evelyn Economy (EE) - Chief of Staff at GlossGenius
Abhi Panigrahi (AP) - Chief of Staff at Tellius
Jillian Benvenuti (JB) - Chief of Staff at Hello Alice
Evan Loh (EL) - Chief of Staff at Monograph
*Answers have been edited for length and clarity.
1. Tell me about yourself and where you are a Chief of Staff. What stage of the Series B was your company at when you joined, what employee number were you?
EE: I’m currently the Chief of Staff at GlossGenius, a Series B vertical SaaS startup. We provide business management and fintech solutions to entrepreneurs in the beauty & wellness space. I’ve been at GlossGenius for a little over three years, which is closer to ten in startup years! When I joined, we were still pre-series A and had around 45 team members. We raised our B in 2022 with joint leadership by Bessemer Venture Partners and Imaginary Ventures and participation from Left Lane Capital. We now have almost 200 team members!
AP: I’m currently the Chief of Staff at Tellius. I joined as the 70th employee and am 2 months into the role. Tellius helps companies make better decisions, faster. We have a ChatGPT-like interface where users ask questions regarding their company's data and receive visualizations, deeper analysis, and predictive models on the fly.
JB: I am Jillian Benvenuti, the Chief of Staff and Director of Investor Relations for Hello Alice. We help over one million small business owners access equitable capital. I joined Hello Alice way back in 2017 (before we were called Hello Alice and before we even thought about outside fundraising!) At the time I was on the morning production team at ABC News in San Francisco and through networks met one of Hello Alice’s co-founders. Together, both co-founders were inspired by the opportunity that not many were focused on, supporting what we call the New Majority of entrepreneurs: women, people of color, those with military connection, the LGBTQ community, and people with disabilities.
Frankly, I was awe-inspired by their passion and excited because I grew up with a mom who was a small business owner. I told them “whatever I can do to help - count me in!” What they didn’t know was that even though my early mornings were still spent at the news station helping to produce multiple morning newscasts, and my afternoons through evenings were committed to getting this new venture off the ground. The double timing didn’t last long, and eventually I gave my full focus to Hello Alice. My sweet Italian grandmother was so confused. “You’re leaving ABC for Alice? Who is this Alice, Jillian?”
EL: I joined Monograph, a project management platform for architecture and engineering firms, a few months after the Series A round, and have now been with the company for 1.5 years. Monograph had just gone through a growth spurt in engineering, which made me the 20th person to join the team, which has since more than doubled.
2. Tell me about your background and how you moved into a Chief of Staff role.
EE: Prior to GlossGenius, I worked at Bridgewater Associates for close to five years. I did a variety of roles at Bridgewater, ultimately ending up leading the talent management and operations team for the investor community. After spending several years at a hedge fund, I was ready to move to a smaller environment where I had more direct impact on a business and where I could learn a lot about how a company grows. Danielle (the CEO and founder of GlossGenius) and I connected, and the Chief of Staff role ended up being the perfect fit!
AP: I started in innovation consulting before moving to a Chief of Staff role at a Series A startup working to reduce emissions in the manufacturing sector. I moved into this role because it's like founder training. I wanted to do the things only a founder gets to do at early stages like create new functions from scratch and build the executive team. I’m now in my second Chief of Staff role.
JB: My path to becoming a chief of staff is unusual, but one I am very proud of. When we were a newly established company, we were building the plane while we were flying it and wearing more hats than a hat shop. My title when I first joined was “Intern”. I was doing everything that I could to help our founders and make sure balls weren’t dropping. What is special about just launching a company is the creativity that every member of the team can have: You have an idea? Share it! We test, iterate, fail, succeed, get knocked down, keep going! There is such camaraderie during that time. I look back on it fondly and do what I can to implement similar cultural practices into how we operate today.
With the early early days behind us, we found product market fit, set out to raise money, and ultimately began to hire experts to join our team. I became the Chief of Staff to uphold the vision of our founders, keep a positive company culture at the forefront, make teammates feel welcomed, listened to, and excited about work. I don’t take lightly the fact that I have been here from the very beginning and I use my historical knowledge of the company each and every day.
EL: My background has been heavily rooted in finance and management consulting. After some time doing M&A in the energy industry, I gravitated towards more tech-oriented companies which made up the bulk of my management consulting workload. After a few years, I left one form of consulting in order to spend even more time directly with startups by consulting as a fractional CFO to companies across the U.S., which gave me direct exposure to a lot of really interesting companies that were starting to hit their stride and looking to hire.
3. How would you bucket your main responsibilities as a Chief of Staff during this stage?
EE: The answer to this question has changed constantly over my three years at GlossGenius! But right now, there are three primary areas I’d identify:
Partner with our CEO across the company: While we ‘tag-team’ different areas of focus, we act as thought partners to each other in everything around the business. On any given week, I may be diving into a different part of the organization to help solve problems, providing input on core business decisions, and working with leaders to achieve their goals.
Strategy implementation & operations: I own our company planning motions and operating calendar and help drive accountability to our metrics. I also own transparency/internal comms functions like our regular internal town halls, and am heavily involved in the board planning/prep cadences. And of course, we’re still a quickly growing startup so I tend to be the catch-all first place to go for any new thing that doesn’t have a clear owner!
People operations, employee enablement, & talent acquisition: I manage our People Ops and IT functions and work closely with our talent acquisition function on the employee lifecycle. I spend a lot of time working through how to build a team and culture that will help us achieve our ambitious goals.
AP: I would bucket my role into three main responsibilities:
Creating + running the operating cadence: Unlike my previous company where we didn’t have an established executive team when I joined, Tellius already had a great executive team in place since it was a bit later stage. As a result, a key focus for me is ensuring we all stay aligned with weekly/monthly reporting, planning cadences, and other repeatable rhythms.
Minding the gap: This consists of stepping in and owning projects/functions where we haven't prioritized hiring a person or where additional bandwidth is needed in the short-term for a critical company need. Some examples include building the talent function, sales enablement, revenue operations, or driving cultural initiatives.
Managing investor relations and board relations: prepping for board meetings, contributing in board conversations, and following up + executing afterwards.
JB: We raised our Series-B in the summer of 2021 and prior to that we had raised our A and Series-Seed. But what was incredibly unique about this fundraising experience was that it was during a time of COVID: there was a lot unknown, little travel, and a whole lot of Zoom meetings. In many projects, especially a VC raise, I see myself as the behind the scenes “doer”: I am getting meetings organized and prepared for. I am getting data rooms in tip top shape. I am celebrating the wins and deeply feeling the nos. Raising money is a whirlwind and one where you constantly have to be available to VC firms, legal teams, and your own team - even if that means jumping out of the shower with a hair full of shampoo to answer a call! Been there, done that.
I often describe being a Chief of Staff as being the bridge: I am a resource to my employees, executive team, investors, board, and outside parties. And in no way do these day-to-day operations cease while raising capital. It’s a juggle - but one day at a time!
EL: As I joined partway between the A and B round, I had some fixed responsibilities and others that were more project oriented. As Monograph grew to a Series B company, I took on fewer bespoke projects for our CEO and spent more time enabling other departments as a cross-functional executive. From a department perspective, I lead the operations and finance teams with HR which means my time is geared towards strategic planning (annually, quarterly), budgeting, and performance management. I will then typically lead a single big project for my principal at a time, which can involve standing up a new business line, exploring new partnership opportunities, or doing a deep-dive on specific product enhancements.
4. What was your favorite thing about being in the role at this stage?
EE: The experience of building a rocketship while it’s taking off is difficult to describe. It’s exhilarating to feel like we have a clear vision and momentum toward that vision but that we need to execute quickly to really get it right. We have a lot of excitement from customers and other key stakeholders about the direction we’re going, and it feels like we control our destiny. I don’t just have a front-row seat, I’m an active participant in shaping our success. That’s really exciting!
AP: At a Series B startup, my favorite thing is having a larger team that you can get input from and get to know. And while there are always resource constraints, more people = more firepower, if you’re able to leverage it the right way.
JB: To see ourselves go from a new startup to a Series-B backed company was incredibly rewarding. I am proud of my team and the tangible impact we have been able to make on the New Majority community of entrepreneurs. With now over a million using helloalice.com, I often run into our Owners (we call our users, owners) when I am doing my everyday local shopping. I will never forget this one encounter I had with an Owner. During COVID when we were all shopping outdoors, I wanted to give my team a little boost - we call these “surprise and delights”. I went to my favorite chocolate company to purchase bars to send to my team. The woman at the booth was taken aback by the number of bars I was buying. “They’re for my hardworking team at Hello Alice”, I told her! She was quickly in tears telling me what the resources we provide meant to her and her business. Interactions like that fuel us and we make sure to share in the excitement. We have a Slack channel called “It’s a Small World” where our team can share Owner highlights, interactions, and wins so we can all celebrate them.
EL: At this stage it is certainly a training ground for everything you need if you want to step into an executive role, but with the flexibility to still be hands on in spinning up new parts of the business.
5. What was the hardest thing about being in the role at this stage?
EE: Navigating the transition from being a small, scrappy startup to a company that, while still growing quickly, is a little more established. We are still a lean team and I’m cognizant of the nature of larger organizations to become bureaucratic. I never want that for us, so navigating implementing the right level of process that will enable our team to move faster without holding us back is a constant challenge.
AP: The goals just keep getting bigger which is always fun, but this is also often the stage where the strategies, products, or skillsets that got the company to the current stage may not take it to the next stage.
The other hard thing is that now you're considered a “growth” company which means that venture markets expect predictability. You need a lot more rigor about your metrics in a way that you likely didn't need to before. This means creating discipline around definitions, measurement, regular reporting, goal setting, etc. This is especially true of SaaS companies where there are very clear benchmarks in the marketplace.
JB: I am very proud of the way we listened to our employees during the pandemic, as well as, once areas started opening, deciding that remote work really worked for our team! It gave people flexibility, autonomy, and comfort at work. What is challenging is that many on our team have yet to meet in person. We are working hard to change this with regional meet-ups and offsites. But it has taken us being creative - trying, failing, iterating, and succeeding - to find what is best for us.
EL: If you step into an organization that is growing through stages (A to B), be prepared for the cultural and managerial shifts that it brings. The company will start to develop more structure and your principal’s focus can shift to scaling or hiring leaders for the next stage of growth. As the Chief of Staff, I need to break the habits I developed at a smaller scale as well as those of my principal; prioritizing different/new relationships and driving more accountability for results with other executives/teams is a lot of change to manage for young startups.
6. How have you seen yourself change or grow during your time as a Chief of Staff?
EE: I’ve become more of a long-term thinker, more decisive and opinionated about the direction we should go, and more comfortable with the ambiguity of my own path. I’ve never been drawn to a standard career progression; instead, I am energized by solving challenging problems with fantastic people. When I started as a Chief of Staff, I assumed I would find one area of the business I gravitate toward and would specialize there. Three years later, I recognize there’s immense value in being able to dive into any almost area of the company and am very excited about the opportunities ahead of us!
AP: I can't answer quite yet since I'm only at day 60, but I’m excited to find out!
JB: My confidence in who I am as a young professional has grown leaps and bounds. Owning that I know what I am doing, I have experiences to share, and I have learnings that have led me to where I am today. It is unique to find someone like me that has had 5+ years as a Chief of Staff, so I now use what I have learned to mentor others in the field or hoping to step into it.
7. What advice would you give to someone considering a Series A Chief of Staff role?
EE: To really understand what kind of Series B company it is, and whether the company’s spikes align with your interest. At this stage, I think most companies are further along in some ways but further behind in others. Find out the shape of the company. For example, are they pretty advanced on people management but further behind on metrics-based goal setting? Are they relatively developed on product but light on marketing, or the other way around? Where do they really need someone to go build? Then make sure the mix of challenges excites you and aligns with what you can bring to the table.
My other general advice for any Chief of Staff role, no matter what stage, is that your relationship with your principal is the most critical component of the role. You can love the company, but if you don’t mesh with the person you’re working most directly with, the role isn’t for you and you should keep looking. I feel very fortunate that my CEO and I built a strong foundation of shared trust and respect from the beginning. It’s made me much more effective in my role, and has also made the job a lot more fun!
AP: Do your due diligence! At Series B, there should be a lot more data about the business. Throughout the interview process, gather that data whenever you get the opportunity to ask questions. After you get an offer, ask to sign an NDA if you haven't already and ask for access to more data. For example, if the company raised recently, you can ask for access to their recent fundraising data room.
First, you should ensure there aren't any big red flags like liquidation preference above 1x or revenue that doesn't align with ARR. Beyond those things, this is a great opportunity to learn about the company just like an investor would. Every company will have weaknesses - the important thing is that you get some transparency into the challenges before you join. Doing this kind of due diligence should be seen as a good thing and if you get a lot of pushback, treat it as a yellow flag and proceed carefully.
Finally, conduct references on the company and the principal, just like they should conduct references on you. References are a great opportunity to ensure your personality will work well with that of your principal.
Feel free to reach out to me on LinkedIn if I can be helpful!
JB: Industry, who you report to, the size of the company, etc all change what it looks like to be Chief of Staff. I’d love to connect 1:1 to understand your unique experience and give advice. Find me on Linkedin!
This position is not for the faint of heart, get ready for early mornings and late nights. But if you find a company you are passionate about, founders you report to that have your best interest in mind, and a team you can rally for - it is so rewarding!
EL: I do think Series B is a level where a generalist can step in and execute exceptionally. I would recommend having a good idea of what you want as your “next step” following a Chief of Staff role before going into it, as it can be harder to find opportunities to fully explore different functions of your company when you are so focused on scaling.
💜 Huge thank you to Evelyn Economy, Abhi Panigrahi, Jillian Benvenuti, and Evan Loh for participating in this interview! We so appreciate them sharing their insights as Series B Chiefs of Staff and hope that this newsletter has helped inform you about the role at this stage of company. Stay tuned for an issue on Series C Chiefs of Staff coming up in the future.
🎥 Upcoming Workshops:
The Ask a Chief of Staff workshop calendar is starting to fill up with workshops led by Chief of Staff experts and industry leaders. Make sure to register for a chance to ask your questions live and learn from some of the top names in the Chief of Staff world!
February 22nd: One Objective to Rule Them All - How to use OKRs to Get Remote Teams Hyper-Focused and Reduce Management Overhead
March 8th: Discovering Your WHY as a Chief of Staff
March 13th: Establishing Trust with Your Principal
April 12th: Deciding What Comes After Your Chief of Staff Role
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Additional Chief of Staff Related Reads:
10,000 Hours with Reid Hoffman: What I Learned
“T-shaped” vs. “V-shaped” Employees
How not to over engineer your OKRs!
How to Run an Employee Listening Session
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👋🏼 Until the next issue,
Clara
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