EP 06: Clara Ma, from Hugging Face CoS to Ask a Chief of Staff Founder. Are Chiefs of Agents the New Chiefs of Staff?

Show Notes

About This Episode

Clara Ma joins Ceci and Bea for a conversation that picks up where most Chief of Staff conversations stop. She was Hugging Face's first Chief of Staff (employee number seven through ten, depending on the day) and watched the company go from Series A to Series B. She is now the founder of Ask a Chief of Staff, a recruiting agency and community of 500 paid members plus 16,000 substack subscribers. She also coined a term in this episode that we are almost certainly going to keep stealing: the "Chief of Agents".

The episode runs across three threads. What it was actually like building the Chief of Staff function at an AI unicorn before AI was the default backdrop. What that role looks like now that agents do a lot of the doing, and where the human still matters. And the founder turn: how a side hustle to fund a sabbatical became a business with global community events, a salary benchmarking study, and a placement record that includes the role's first cousin, the COO.

What We Cover in This Episode

The Accidental Chief of Staff

Clara had never heard the title outside of politics. She started her career in recruiting for D2C startups, fell in love with the work, and decided she should go and do it inside one. From there she moved to AngelList, where her CEO talked about hiring a Chief of Staff and kept comparing the role to The West Wing. The job description was a right hand to the executive, freeing them to focus on their zone of genius. She wanted to sit closer to the leadership table, get a crash-course MBA in how companies are actually built, and figure out whether she eventually wanted to start her own thing. That path led her to Hugging Face at Series A.

Series A to Series B at Hugging Face

Almost everyone else at the company was an engineer or a scientist. Clara was the only operations person. The better question, in her words, was "what didn't I own?" She put the hiring system in place, wrote the first parental leave policy, managed third-party accounting and legal, ran community t-shirts and the first marketing newsletter, ran the LinkedIn presence. By the time she left, the company had raised its Series B and grown to 45 people. Rather than backfill with another Chief of Staff, Hugging Face broke her role apart into a finance manager, a part-time legal hire, and so on. Clara's view on whether that decision would still hold today: probably not. With current AI tooling, a single generalist Chief of Staff with a bit more depth in one or two functions can hold more of that scope, with agents and workflows underneath.

The Thing She Most Underestimated: Access

The single biggest surprise of the role was the level of access. There was no room she couldn't be in. Her CEO eventually told her to stop asking permission and just show up: "I will rein you back in if you overstep. At this point, there's nothing you can't be a part of." Looking back, she would have taken even more advantage of that. The access is where the pattern matching happens. The pattern matching is the job.

What She'd Rebuild Today with AI

Two things, both about reclaiming time. Meeting prep was a manual scavenger hunt across email, Google Docs, LinkedIn, old agendas. Today it can be condensed into a five-minute briefing the AI builds for you. Inbox triage was the other one. Her CEO wanted to be CC'd on everything, and the cost was real cognitive load. Modern email tools can sort the urgent from the spare-time read in a way that would have saved hours every week. Clara estimates she could have cut meeting prep alone by 50%.

The Rise of the "Chief of Agents"

The new framing that came out of this conversation. As agents start owning more of the doing inside companies, somebody still has to design the workflows, gut-check the outputs, and decide what to ship versus throw out. Clara's view is that the Chief of Staff naturally inherits that work, because they already operate across every function. The first iteration of any agent or workflow is not going to be perfect, and an experienced Chief of Staff is the right human in the loop to iterate it into something usable. It is also a great career-positioning lever: you end up on the cutting edge of the tooling, which then compounds into the next role.

What Still Needs the Human Touch

Three things, in Clara's framing. Time reallocation: AI agents will agree with you. A Chief of Staff will tell you that if priority A is now the priority, here is the priority B you have to drop, and here is what that costs you in week-to-week reality. Change management: rolling out AI inside a company is not "everyone use this now". It needs the hearts and minds of the team, and the Chief of Staff is usually the person with the most trust across the organisation. Discernment: AI is black and white. Doing business is gray. The Chief of Staff brings the relational context and the macro context that lets a decision actually land.

From Chief of Staff to Founder: Ask a Chief of Staff

After Hugging Face, Clara went to OnDeck to lead the Chief of Staff fellowship, scaling it from 80 to over 400 people over two and a half years. When OnDeck downsized she took three months off, told herself she would explore community manager roles, then realised on a tapas-fuelled trip through Spain that she could not stop thinking about Chief of Staff problems. Ask a Chief of Staff started as a placeholder LLC for some fractional recruiting work to fund the rest of her sabbatical. She set herself a personal target: one placement by end of December 2022 and she would do it full-time. She made three. By March 2023 the placed Chiefs of Staff were coming back to her overwhelmed, asking how to actually do the job. That feedback turned into the community platform now sitting at 500 paid Slack members and 16,000 substack subscribers.

The 30-60-90 Day Playbook for a New Chief of Staff

Clara's three-point starter pack for any new Chief of Staff:

Do a listening tour. Not just leadership. The ICs and managers actually shipping the work will surface culture signals, blockers, and pattern-match material you cannot get from the top. It is also the one window in your tenure when you can ask anyone anything.
Agree with your principal how the role gets introduced. Clara's CEO told the whole company on day one to come to her first for anything people, payroll, or finance related. Public credibility from your principal compresses the trust-building timeline dramatically. This applies double if you are an internal transfer: be explicit about what you used to do and what you do now.
Start thinking ahead from day one. Most Chiefs of Staff are in the seat for under two years. If you do not have a thesis on what this role is setting you up for, you risk ending it with a wide CV and no narrative. Clara told her CEO early she was on a COO track, and that shaped what she was given to own.

What's Changed in Chief of Staff Job Descriptions Since 2023

Two non-obvious shifts based on the Ask a Chief of Staff hiring data. AI literacy is now a non-starter. Whether you've built it at work or in personal projects, you need to be able to talk through how you'd systematise a workflow with AI. Go-to-market is the new surprise entrant. With capital scarcer for non-AI companies, founders increasingly need a right hand who can stretch into product launches, growth motions, and revenue. Clara is seeing it more often in 2026 than she did even a year ago.

On Compensation

Clara is the first to admit the bandings are wide because the work is so context-dependent. Her rule of thumb: sit between the executive layer and the management layer, with stage and experience pulling the number up or down. Ask a Chief of Staff runs an annual compensation survey, and Clara shared a story of a community member who used that data in Chicago last week to negotiate tens of thousands of dollars more in their starting offer. Two practical tips: benchmark off the survey, and never anchor below your previous role's salary, because Chief of Staff scope is always larger than it looks on paper.

Why the Role is So Lonely

Bea and Ceci both call this one out, and Clara built her whole business around it. A Chief of Staff usually has no team, has soft authority across the whole company, holds confidential context that cannot leak (including, often, layoff information), and is constantly making judgement calls about which conversations to surface and which to hold. Founder communities exist everywhere. Until Ask a Chief of Staff, equivalent communities for the role that sits next to the founder did not. The thing that brings people in for the templates is what keeps them subscribed for the belonging.

Rapid Fire

AI tool she pays for and won't give up: Granola. Best AI note-taker she's used, and the ability to group meetings into a single context view is the killer feature.
Most overhyped AI tool: Anything calling itself an "AI Chief of Staff". Build systems for Chiefs of Staff, automate the manual parts, but the role itself is not replaceable. If yours is, you weren't doing it well.
Substack every Chief of Staff should read: Molly Graham's. She also recently took over as host of WorkLife. Strong philosophies on scaling teams and building systems that don't break.
Best advice she was given: "Give time to time." Her principal blocked two-hour thinking windows on his calendar every other day and pushed her to do the same. Being booked nine-to-five is not the same as being productive. She still protects Wednesdays and Fridays for it now as a founder.

Frequently Asked Questions

Who is Clara Ma?

Clara Ma is the founder of Ask a Chief of Staff, a community and recruiting agency for Chiefs of Staff and adjacent operations roles. She was previously Hugging Face's first Chief of Staff (Series A to Series B) and the program director of the Chief of Staff fellowship at OnDeck.

What is a "Chief of Agents"?

A term Clara uses for the emerging shape of the Chief of Staff role in an AI-native company. A Chief of Agents owns the design, iteration, and quality control of the workflows and agents running across the business. The Chief of Staff is the natural fit because they already operate cross-functionally and bring the discernment AI lacks.

What did Clara do at Hugging Face?

Everything that wasn't engineering or science. She built the hiring system, wrote the first parental leave policy, managed third-party finance and legal, handled community marketing including merch and the first newsletter, and ran the company's LinkedIn presence. She was there from Series A through Series B.

What does Ask a Chief of Staff do?

Two things. The recruiting arm places Chiefs of Staff (and increasingly COOs, BizOps leads, and Heads of Operations) into roles. The community arm runs a 500-member paid Slack, a 16,000-strong substack, weekly webinars, executive group coaching, in-person events across cities like New York, Chicago, DC, Boston and Seattle, and an annual compensation benchmarking survey.

What are the top three things a new Chief of Staff should do in their first 90 days?

Run a listening tour that includes ICs and managers, not just leadership. Agree with your principal how the role will be publicly introduced and what falls inside its scope. Start thinking from day one about what this role is setting you up to do next, and shape your ownership accordingly.

Can an AI agent replace a Chief of Staff?

Clara's view is no. AI can automate the manual layer of the work, but the time-reallocation conversations with the principal, the change-management work, and the discernment about what to escalate and how all need a human in the loop. The role is becoming more valuable because of AI, not less.

Full Transcript

Episode Transcript

Introduction

Bea [00:00]

Hi and welcome to Top of the Ops, the podcast where we have real conversations about what happens behind the scenes of startups. I'm Bea, ex-VC at Lakestar and now Chief of Staff at Praktika.

Ceci [00:10]

And I'm Cecilia, ex-VC at Talis Capital and FD at PortalOne. Today it's not just us. We're happy to be joined by Clara, founder of Ask a Chief of Staff, a community and recruiting agency for Chiefs of Staff, ex-Chief of Staff at Hugging Face, and former program director of the OnDeck Chief of Staff fellowship. Welcome, Clara.

Clara [00:32]

Thank you so much for having me.

The Accidental Chief of Staff

Ceci [00:33]

I'd love to start with you and your career. Can you walk us through how you ended up as a Chief of Staff? I read that you had never heard the title outside of politics, and then you were running it at an AI unicorn, Hugging Face. How did you get there?

Clara [00:51]

It's a fun story that makes more sense in hindsight, but felt very windy at the time. I started my career in recruiting, at a boutique firm that worked with the first D2C startups. I loved it so much I decided to go and work at one. I worked at a few different startups, the smallest with just four people, where titles don't matter and you do whatever needs doing. From there I went to AngelList, in the AngelList Talent division, doing a lot of operations and triaging across the company.

While I was there, the CEO of AngelList Talent started talking about hiring a Chief of Staff. I had no idea what that was. He kept comparing it to The West Wing, the president's right hand, and I tried to figure out what that looked like in a corporate context. The idea was a right hand to the executive who frees them up to focus on their zone of genius. That was my first touch point with the role. It set me on a path to find one at a company where my talents would be better suited. That's how I ended up at Hugging Face. Looking back it makes sense. At the time I just knew I had a wide generalist skill set, I wanted to sit closer to leadership and watch how decisions actually got made, and I thought I might want to work for myself one day. The Chief of Staff role gave me a crash-course MBA. Taking it completely changed the trajectory of my career.

Series A to Series B at Hugging Face

Bea [03:39]

At Hugging Face you saw the transition from Series A to Series B. For listeners who haven't done that, what did you own in a company that grew from 40 to 200 people?

Clara [03:59]

When I started I was employee number seven through ten, depending on the day. Four of us started at once. I was the only operations person. Everybody else was an engineer or a scientist. The better question is what didn't I own. I didn't work on product, I didn't code. With my CEO I divided and conquered business operations. We didn't have a COO, and that was a track I wanted to explore, so I had that conversation early and it shaped what I built.

I put the hiring system in place. By the time I left at about 45 people we had raised our Series B. I wrote the first parental leave policy, something I'd never done before. I managed our third-party accounting and finance firms and made sure everything was in line. And then everything in between: ordering t-shirts for the community, writing the first marketing newsletter, running the LinkedIn presence. It was a little bit of everything all at once. That's why this role is so transformational. It exposes you to parts of the business you'd never touch if you were in a functional role.

Bea [05:36]

Did you end up hiring for specific roles you'd built out? Did you delegate as you went, or hold the ownership?

Clara [06:04]

I ended up holding most of it during my time there. By the time I left, instead of hiring a replacement Chief of Staff, the company broke my role into individual functions. They brought in a finance manager for the accounting and finance work, a part-time legal person for the legal review work, and so on. So I was doing and owning a lot of that throughout.

What She Most Underestimated

Ceci [06:45]

What was the thing you most underestimated about the role going in?

Clara [07:00]

How much access you really have. There was never a room someone said no to me being in. I'd never had that level of access anywhere before. You don't need to ask permission, you just absorb. If I did the role again, I'd take more advantage of that. That's where you learn. My CEO got to a point where he said, "I don't need you to ask me anymore. I'll rein you back in if you overstep. There's nothing you can't be a part of."

What She'd Rebuild Today with AI

Ceci [07:58]

If you were dropped in the same seat today with the AI tools that have been built since, what would you rebuild first?

Clara [08:14]

Meeting prep, by a long way. It used to mean digging through email threads, old Google Docs, sometimes LinkedIn, sometimes a 30-reply email chain, just to walk into a meeting prepared. Today you can condense all of that into a five-minute briefing right before the meeting. As a Chief of Staff you hold context for yourself, for your principal, and for the organisation. That context is your power, because pattern-matching across the company is how you become effective. But organising all of it manually was hard. With today's tooling I think I could cut meeting prep alone by 50%, which is significant.

Bea [09:52]

Do you think Hugging Face would have made a different decision about backfilling your role today? Hiring a generalist instead of four functional people?

Clara [10:00]

It's a good question. Hindsight is 20/20, but yes, I think some of those things could still roll up under a single generalist with a bit more depth in one or two areas. You still need a human in the loop, even with all the AI tooling. I'm never going to send an email AI drafted without reading it through. The replacement after a Chief of Staff today could be a slightly more specialised Chief of Staff with workflows and agents underneath. One term I'm seeing more often in the space is "Chief of Agents", the person managing the agents across different functions and workflows, doing the final check before anything ships. The first iteration of an agent isn't going to be perfect. Iterating it is high-leverage work, and being on the cutting edge of that is great for the Chief of Staff too.

Bea [11:54]

Is there a category of work a Chief of Staff used to do in 2022 that just isn't a human task anymore, beyond meeting prep?

Clara [12:03]

Inbox triage. I use Superhuman and it's amazing. It buckets my pitches in one place, accounting and finance in another, the actually important emails in another. As a Chief of Staff I had access to my CEO's inbox, and he wanted to be CC'd on everything. With today's triage I could have surfaced only the urgent things and tagged the rest as spare-time reads. Huge time saver.

What Still Needs the Human Touch

Ceci [12:57]

We're seeing both the rise of agents and the rise of the Chief of Staff role. What still needs the human touch?

Clara [13:08]

Three things. One, every executive wants time back. A Chief of Staff helps them automate, delegate, or kick to the curb. An AI agent will agree with you. A Chief of Staff will say, "If this is the new priority, here's what you're deprioritising, and here's what that looks like day to day." Two, change management. You can't just say "everyone use this tool now." You need buy-in, hearts and minds, and the Chief of Staff is usually the person with the most trust across the organisation to drive that. Three, discernment. AI is black and white. Doing business is gray. The relationships, the macro context, the internal context, that's all human. So I'm not surprised that as agents trend up, the Chief of Staff role does too. AI literacy is now a hiring criteria that didn't exist five years ago, but the seat itself is more valuable, not less.

Bea [15:32]

I had not heard "Chief of Agents" before and I will repeat it endlessly. Thank you for the inspiration.

Ceci [15:41]

My own use of AI has skyrocketed even since the start of this year. The context surface you hold as a Chief of Staff and as a generalist is huge, and people hire you for your judgement and your ability to read what's not spelled out. Agents take the manual layer, and you bring the discernment.

Bea [16:25]

Also: be the challenger and the prompter of the AI. Use your discernment to make it better.

From Chief of Staff to Founder

Bea [16:35]

We wanted to touch on life after Chief of Staff. You went from Hugging Face to becoming a founder. Walk us through that. Did the Chief of Staff role help you found a company?

Clara [17:01]

After Hugging Face I went to OnDeck, where I led the Chief of Staff fellowship. It was my first time building platforms specifically for Chiefs of Staff. The community was around 80 people when I joined and we grew it to over 400 over two and a half years. It gave me a lot of fuel to build for Chiefs of Staff. By the time I left, OnDeck had downsized and deprioritised those community roles. I gave myself a three-month sabbatical. I told myself my next role would be head of community somewhere. What I actually found over those three months was that I couldn't stop thinking about Chief of Staff stuff. I was on a tapas crawl in Spain still thinking about Chief of Staff stuff. That has to be a sign.

So I figured, what can I do in the Chief of Staff space that extends my personal runway and lets me keep traveling. The first iteration of Ask a Chief of Staff was pure recruiting. I had a network of Chiefs of Staff and a network of executives who wanted one. I started the LLC to separate my business and personal money. That's why I always say I was an accidental founder. I told myself if I made one placement by the end of December 2022, I'd consider doing it full-time. I made three. Fast forward to March 2023, the people I'd placed were coming back to me confused, overwhelmed, not sure they were doing it right. I recognised myself in them. That's when we launched the community platform. We're now at over 500 paid Slack members. Being a Chief of Staff and being a strong operator served me from day one. I built with the end in mind, so when the team grew there was no operational debt to dig out of.

The First 90 Days

Ceci [22:06]

You see hundreds of Chiefs of Staff land in roles. What are the top three things a new Chief of Staff should do in their first 30, 60, 90 days?

Clara [22:37]

One, do a listening tour. Talk to as many people as you can. Yes, leadership, but also the ICs and managers actually shipping the work. They'll tell you what the culture is really like, where the strategy is or isn't translating, where the friction is. The first 90 days is the best time to ask anything you could possibly want to ask. If you're six months or even a year in and haven't done one, it's never too late.

Two, agree with your principal how the role gets introduced to the company. My CEO told everyone at Hugging Face on day one to come to me first for anything people, payroll, or finance related. Not to cut off access to him, but to set my credibility publicly and force me to learn the systems. Once I delivered, trust built fast. This matters double if you're an internal transfer: distinguish what you used to do from what you do now. If someone asks you for the old thing, point them to who owns it now. Do not just do it.

Three, start thinking ahead from day one. It sounds counterintuitive, but most Chiefs of Staff don't stay in the role for more than two years. If you're not deliberate about where this role is taking you, you end up with a wide CV and a weak narrative. I told my CEO early I was on a COO track. That changed how he assigned things to me. So you've got the evidence you need when you move on.

What Changed in CoS Job Descriptions

Bea [27:23]

What would our audience need to be aware of about competencies that have changed in Chief of Staff job descriptions from 2023 to 2026?

Clara [28:17]

We ran a community all-hands earlier this year with our recruiter, looking across every job description we've worked on. Two things stand out. AI literacy is a non-starter. If you haven't touched it at work, do it in a personal project. You need to be able to talk through how you'd systematise a workflow with AI. The second one, which surprised me, is go-to-market. Understanding how a product launches and reaches profitability. With VC capital tighter for non-AI companies, founders need a right hand who can stretch into growth and revenue. Two years ago that wasn't in the job description. Now it is, often.

On Compensation

Ceci [30:02]

Has the approach to salary changed from 2023 to now? Are we seeing AI inflation or deflation?

Clara [30:26]

It's a wide range, because so much of the work is hard to pin down. When a Chief of Staff is great, nobody can quite point to what they're doing. When the role falls apart, everything gets pinned on them. It's thankless that way. Salary usually sits between the executive layer and the manager layer, with stage and experience pulling it up or down. We run an annual compensation survey to bring transparency. A Chief of Staff who started a new role on Monday told me at our Chicago happy hour last week that she used our salary data to negotiate tens of thousands of dollars more. Two practical tips: benchmark off the survey, and never anchor below your previous role's salary, because the scope of a Chief of Staff is always larger than it looks.

Bea [32:21]

What helped me on the equity side was working backwards from an end number. If the company exits at a billion plus, what percentage ownership would feel fair given how stretched I am? Then I backed out the present-day ask. Almost an NPV calculation.

Ceci [32:58]

What worked for me, because I already had trust with my CEO, was joining on a placeholder salary with a reassessment built in at three months. Neither of us knew what the role was going to be. That was a special situation though.

Clara [33:24]

A Chief of Staff isn't on a standard performance review cycle. I did the same thing at six months. A fundraise is also a natural trigger. Founders pay themselves more after a raise, and your scope grows too. Every principal is happy to reward good work. If you've given them real time back, that's what you're optimising for.

Why the Role is So Lonely

Bea [34:27]

You built the community to how many members now?

Clara [34:31]

We're 500 in our paid Slack community, 16,000 substack subscribers.

Bea [34:37]

Huge. What surprised you about what people come to the community for?

Clara [34:47]

On paper, we offer the tactical stuff: weekly webinars, mentorship, executive group coaching, templates. People sign up because they want something they can take back to their principal on Monday morning. What actually keeps them coming back is the feeling of belonging. Knowing they're not the only one managing a big personality, not the only one whose OKR rollout keeps confusing the team, not the only one trying to figure out AI. It's lonely in a really specific way. You're the only one doing that role inside your company. You're in the leadership team but also outside of it. You hold context that can't leak, including layoff information, while also being the person people come to with their insecurities. That weight is hard to talk about with friends or family. Other Chiefs of Staff get it instantly.

Ceci [38:46]

I feel really seen right now. Shall we jump into the rapid fire?

Rapid Fire

Bea [38:50]

One AI tool you pay for and would absolutely not give up?

Clara [38:55]

Granola. It's been a huge game changer as a founder, and the ability to group meetings together and get cross-context is something I wish I'd had as a Chief of Staff.

Ceci [39:14]

One AI tool that is overhyped?

Clara [39:17]

Anyone building an "AI Chief of Staff". I think you can build systems for Chiefs of Staff and automate the manual parts of the work. The role itself, no. Both AI and Chief of Staff are trendy, so putting them together sounds like a great idea, but as three Chiefs of Staff in the room we can all say: if AI is replacing what you do, you're not doing it well.

Bea [39:58]

One book or substack every Chief of Staff should be reading?

Clara [39:58]

Molly Graham's substack. She writes about building and scaling teams, and recently became the host of WorkLife. Her philosophies on hiring high performers and building systems that don't break as you scale are excellent.

Ceci [40:25]

Best single piece of advice you've been given?

Clara [40:31]

"Give time to time." From my principal. Early in the role I thought it was impressive that my calendar was fully booked nine to five. I realised I wasn't actually getting any work done, or only checklist work, not deep work. My principal blocked two-hour thinking windows on his calendar every other day for the deep work and the context-processing. He pushed me to do the same. As a founder now, I try not to take substantial meetings on Wednesdays and Fridays so I can think about the state of the business.

What's Next for Ask a Chief of Staff

Bea [41:45]

Last question. What's next for Ask a Chief of Staff?

Clara [41:49]

Growing the community towards the next milestone, 750 paid members. Doubling down on in-person events: full-day summits in New York, networking dinners and happy hours in Chicago, DC, Boston, Seattle, possibly San Francisco. And we've expanded beyond Chief of Staff recruiting into BizOps leads, Heads of Operations, and last year we placed our first COO. We are not limited to the title anymore.

Ceci [42:45]

That brings us to a close. Thank you so much for being here, Clara. It's been so fun getting to know your career.

Bea [42:54]

I concur. Thank you so much for joining us. To everybody listening, please like, subscribe, and share. This was Top of the Ops.

Clara [43:01]

Thank you for having me.

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