Nova Chat with Clara Ma - Founder of Ask a Chief of Staff Network

Jeremy · 0:00

Hey, friends, welcome to another episode of The Leader Assistant Podcast. It's your host, Jeremy Burrows, and this is episode 303. You can check out the show notes at leaderassistant.com/303. I'm excited to share another Nova Chat with my friend Maggie Olson. And in this Nova Chat, Maggie talks with Clara Ma, founder and CEO of Ask a Chief of Staff. They have a great conversation about the role of the chief of staff, and Clara's career journey and lots of fun conversations. So I hope you enjoy it and we'll talk soon.

Speaker 2 · 0:42

The Leader Assistant Podcast exists to encourage and challenge assistants to become confident, game-changing leader assistants.

Jeremy · 0:59

Hey, Leader Assistants, have you heard the Nova Chief of Staff Certification course is about to see a price increase? But don't worry, you can enroll now, lock in the current rate, and start whenever you're ready with lifetime access. Nova's mission is to give you the ultimate student experience. They've packed the course with dozens of templates, self-paced learning, hands-on practice, multiple instructor touch points, peer engagement, and even guest-authored assignments. With over 500 students across 22 countries, Nova is the top spot for Chief of Staff learning and development. Don't wait. Enroll today and join the community at leaderassistant.com/nova.

Maggie · 1:44

So happy to have Clara with us. Clara and I have hit it off from the very beginning. We are a true partnership from a work perspective, and I just love that. So Nova Chief of Staff and the Ask a Chief of Staff community, which Clara leads and founded, we are partners. And if you're like me, you are curious and you want to learn more about all the people in our wonderful space, and that includes Clara. So my goal for these Nova Chats, and if you've been a part of the Nova community for a little while, you've probably been on a few of these. But our goal is to really use this opportunity to go deeper. We chat about vulnerable moments and job transition, do's and don'ts, and career alignment and misalignment, when to move on from a role, how do you know, and more. What's really cool is Clara has chief of staff experience with startups, and she created the Ask a Chief of Staff community. So we're going to dive into both of those areas. But first, let me give a little bit of a background on Clara. So she's the founder and CEO of Ask a Chief of Staff. Ask a Chief of Staff is the premier resource for chiefs of staff looking to secure high-impact roles and drive results. Prior to founding Ask a Chief of Staff, Clara was the chief of staff to the CEO of Hugging Face, a unicorn AI startup, where she helped shepherd the company from its series A to series B. After serving as the chief of staff, Clara went on to become the program director of On Deck, which was series B, Chief of Staff Fellowship Program, growing its membership base from 80 to over 400 chiefs of staff. So talk about career alignment, like clearly Clara is in the place that she should be. Clara's background is a combination of strategy, operations, recruitment, and she's held titles in each of these departments at various early stage startups. So we'll dive into all of that. And Clara really prides herself on being an early stage operator and builder from zero to one. So I want to get into all of that. But first, Clara, we're so happy to have you and welcome.

Clara · 3:49

Thank you so much for having me, Maggie. I know appropriate that we're doing this on Valentine's Day. I feel like you and I were a match made in heaven when we came to talking about and working in the Chief of Staff space. So excited to be here. Thank you for having me and excited to be chatting with you today.

Maggie · 4:05

Yeah, well, so awesome. You know, let's just kind of start at the beginning. I would love to hear you talk about how you found yourself in maybe pre-Chief of Staff roles that led you to Chief of Staff roles. And please share all the startup relevance possible during that time.

Clara · 4:24

Yeah, absolutely. Well, I think my story will probably sound very familiar to a lot of our audience members here, where I, looking back now, feel like I can tell a story about my Chief of Staff journey and career. But while I was going through it, it felt very windy, very messy, and I had no idea that Chief of Staff was even in my purview. So taking it all the way back to my very first job out of school, while all of my friends were becoming consultants and engineers and having all these technical roles, I just wasn't a technical person. I had gone to school for liberal arts, political science and media studies. And when it came to finding my first role out of school, I really had no idea what I could do. But I knew that I liked talking to people. And so what I ended up doing was applying for a small boutique recruiting agency. And from what I was told, I was the very first application that ever went through their system. It was a new company at the time. And so I started my career off in recruiting. And this was a very small, very scrappy boutique firm that the founder had come out of a larger firm and wanted to start her own thing. And so I had the opportunity to really see it from the ground up. And so from the very beginning, I've always had this background and experience at early, early stage companies where it's been less than 10 people. I've gotten to see it grow to over 20, over 50, etc. And it wasn't until I looked back on my career that I realized, oh, I've been working in startups for a very long time. So after about a year and change of recruiting, I wanted to figure out maybe there's something that I can do outside of this. Had I not kind of fallen into recruiting, I wouldn't have known that it was something that I could do. And I had this opportunity to join a very early stage, Bollywood Dance Fitness Startup, which is probably the last thing that most people would expect. But it was actually somewhat of a technical startup, if you will. We built out this online platform for instructors, specifically dance fitness instructors, to learn how to teach this Bollywood Dance Fitness format. And my role there was not only truly jack of all trades, I was teaching the format, but also actually working for the back office as well. So working with our engineering team that was contracted and designers in building out the platform. And it truly was this all hands on deck. That company was four people full time. I worked very directly with the CEO and the other founders of the company. And we really, it was everything from marketing to sales to physically teaching the format and getting people to be excited about this new dance fitness craze that was kind of going on in the, I guess, mid-2010s, if you will. So from there, I worked at that company for about a little over three years, I would say. And I felt like at that point, I had kind of learned everything that I could learn and was interested in kind of really delving into this tech start-up world. I was recruited to go work at AngelList. I specifically worked for the branch that was in Talent Products, which meant we were building out products for recruiters and hiring. And I really credit the head of operations there, who was my manager, to exposing me to this larger world of operations that would later lead me down the Chief of Staff route. Her role was really about experimenting, trying different strategic initiatives, seeing what people might want and what the market was telling us. And then we would try to build small experiments to go and test those things in the market. And if they worked out, then we would go to the engineering team and say, hey, we should build a feature, things like that. And she was the one who opened up my eyes to saying, you don't have to pick a lane, you don't have to specialize and niche down in one thing. You can kind of continue to grow your, your career experience pretty wide. And there is a place for you to do that within companies, whether they're early stage startups or if I wanted to go somewhere else. And so I would say that was a real turning point for me to understand that suddenly, this wide skill set that I had built wasn't a hindrance, but actually a strength. And I could turn that into something more long-term. And from there, that kickstarted my journey into researching what the Chief of Staff role would look like. And it really felt like the next step up for me when it came to moving into more of a leadership position or working closer with executive teams.

Maggie · 8:50

Okay. Wow. Amazing. I personally love dance fitness. It's one of my favorite things. Some of you might know on the call that I moved from Seattle, where there's a ton of resources, like not just talking about food and beverage, but like dance and like all the things, to Lincoln, Nebraska, where there are just a few less. And I finally, like literally this week, Clara found a dance class that I, you know, Zumba is fine, I will happily do Zumba, if that's what's offered. But anyway, I found one and I love that you were doing, I mean, that's like the standout for me, that you were doing Bollywood dance startup. And it's just so cool. It shows that any company, like there are just so many different ways that people build businesses and niches and any of those things need support, right? They need operation support, they need marketing support, they need technical support, they need engineers. It's just super cool to hear your background. So thank you for sharing that. Yeah, amazing. So you talked a little bit about right at the beginning, coming out of school and nobody had told you yet that you didn't have to specialize and you felt like everyone around you was really technical. A couple of questions here. What's your educational background, undergrad, graduate school? Where did you take that journey through?

Clara · 10:12

Sure. So I have an undergraduate degree. I went to the University of California, Berkeley, a stone's throw away from where I grew up. So I was very much in the Bay Area for majority of my life. And also, I like to say that my dad was part of the original Silicon Valley, where they were doing chip manufacturing and things like that. So grew up a little bit around startup culture, had a sense of what that might look like. And so I graduated with a degree in both political science and media studies.

Maggie · 10:38

Okay. And through school and it sounds like your first several jobs, you felt the pressure to specialize and to be more technical?

Clara · 10:47

A little bit. I mean, Berkeley is a pretty big engineering school. That's what they're best known for. So I had a lot of friends who were very much on that engineering track. And even if they weren't in engineering, they were looking at things like, you know, investment banking, consulting, lots of Excel type things. And so even though I was in the liberal arts program, of course, I had a lot of friends who were in political science as well. A lot of those friends were looking at going to law school or taking on political careers, working on campaigns. And that didn't quite feel like what I wanted to do either. And so I was really left with a sense of, I have no idea and I didn't know what other jobs were out there. And if it wasn't more of like a vocational role, I hadn't really heard of too many things that were out there. Back in this time, I would say like product management wasn't as big, then that could have been a route, maybe that could have interest me. But it seemed like a lot of these kind of early stage start ups were all looking for technical talent and I just didn't have that background.

Maggie · 11:44

Yeah, yeah, that makes sense. So thinking about your kind of journey through roles that were pre-Chief of Staff, what are the biggest takeaways you have now looking back on kind of your skill set and what you were good at during that time? Have you heard? The Nova Chief of Staff Certification course price is going up in January of 2025. Enroll now and with lifetime access, start whenever you please. Here at Nova, it's our mission to provide the very best student experience possible. Our course is chocked full of features and resources designed just for you. Dozens of templates, self-paced online learning, hands-on practice, multiple instructor touchpoints, peer engagement opportunities, guest-authored assignments, the list goes on. With 500 students across 22 countries, Nova is the premier destination for Chief of Staff Learning and Development. Enroll today and join us.

Clara · 12:48

Absolutely. One, the first thing I want to say is that Chiefs of Staff truly can come from any background. I mean, from my own background, I was a Bollywood Dance Fitness Instructor and somehow leveraged that into becoming a Chief of Staff. The things that I think that really helped me eventually land a Chief of Staff role was this willingness to do anything. It was this sense of no task is too small or I'll take out the garbage if I needed to. The very first, again, sense of this was when I worked at this Bollywood Dance Fitness Company, they didn't even truly have any opening or role that was what I ended up doing. During my time there, my title eventually became Director of Creative Solutions, which that is probably the most like Chief of Staff-y special project title that you can find yourself at that time. But when I joined that company, a big thing that I was telling the CEO was, look, I don't have a ton of career experience under my belt right now. I know that I can talk to people and I think talking to people and having a high EQ can be one of the strongest skill sets that I bring to the table. I can understand what it is that people are having issues with or problems with and figure out a way to figure those things out for them. When I pitched myself to the CEO and the other co-founders of the company, I said, here, just consider me a resource. Anything that you don't want to do, I'm happy to do it so that you can focus your time on whatever it is that you're good at. If you can just let me in the room so I can watch or listen while you do those other things, that's going to be worth it enough for me to continue to grow my career. I think that it was that willingness and enthusiasm to really be the glue in any part of the organization that compelled them to hire me and then eventually gave me the opportunity to take on a whole bunch of different functions and learn a lot of those functions from scratch.

Maggie · 14:42

Yeah. Okay. Let's recap those for people listening. No task too small, willingness to do anything with some enthusiasm for being that glue and letting you listen in. And then that emotional intelligence that I know Clara and I, we both talk about a lot. It's woven throughout the Nova Chief of Staff Certification course. Clara, I think you write about EQ a lot as well, and probably talk about it with your members. And I think just the ability to talk to people and clearly Director of Creative Solutions, that is a very Chief of Staff like title. So I'd love for you to share a little bit more about, you were mentioning that you pitched this role to the founders. So what company was that for and what role were you in? And then what role were you pitching to move into? And how did you navigate that?

Clara · 15:28

Yeah, so this was the second job that I had at the Bollywood Dance Fitness Company. I came in, my previous experience was in recruiting. And at the time, I knew that they were a small team and I figured small teams could use help. And at that time, I felt like my time in recruiting was kind of done, or at least I had learned everything that I could learn there. And I wanted to expand my horizons a little bit, pick up some more skills. I've always had a dream to be an entrepreneur or like found another company or even work on the VC side because I wanted to be at that kind of initiation stage of a lot of companies. And so I figured if I could go to another early stage company and have the opportunity and access to try out a lot of different functions, then that's gonna give me a better skill set moving forward in my career as well. And at that time, it was only my second job out of school. So there was still so much that I didn't know about running a business, period. And I just was willing to take kind of any experience that I could do that was outside of recruiting. So yeah, very opportunistic. I would say I happened to know that I had a alumni friend who worked at this company. She was leaving to go somewhere else. And I figured there was some sort of a vacuum that was going to be there. And so I reached out and first, I had an informational call with one of the other employees who was working there and asked her, what are things that you're doing right now? How is this company looking to grow? What are things that you're having problems with or things that you would like to, if you could like snap your fingers, like have fixed in the next three months or whatever it was. And after I had that call, I reached out to the CEO and asked him, you know, this is what my experience is. I don't have a ton of it, completely frankly, but I'm willing to learn and I'm willing to try and do a bunch of things. If you're willing to take a chance on me, I will try to pay it forward as much as I can. And so he set me up with a little bit of a take home. I pretty much remember like, I was like, I think I'm killing it. And then I sent it in to him and he was like, okay, let's like talk about why you decided to format it this way. And he gave me some pretty blunt feedback on that and had me kind of resubmit it. And after that, he was like, okay, great. Like, it was good to see that you're able to take this feedback and reformat your take home in a way that we actually think, like there's a lot of learning potential here. So, you know, we're going to be happy to bring you on and hopefully you can grow with the company. So it was definitely, I think luck plays a lot into, of course, your career journey, but also being persistent about talking to people in the company and really understanding what it is that they need help with and pitching yourself to help fill in those gaps.

Maggie · 18:16

Yeah, I love this. And we will get to The Chief of Staff experience here in a minute, but I want to stay here for just another second. So I'm hearing, Clara, and I think I hear some similarities in my story, too. You know, you weren't afraid to raise your hand. You weren't afraid to have a conversation and put yourself forward. You weren't afraid to. And really, it wasn't even probably not being afraid. I'm guessing it just felt natural to you to to continue to have a network that you nurtured, to have a friend that you knew was moving from a role that's like, you know, kind of maintaining your network and keeping it nourished. And then I think, you know, another piece there is just kind of that informational interview. You're not afraid to pick up the phone and ask questions. You're persistent. So where do you think that you learned or got the kind of bravery or understanding that you can just raise your hand and ask for what you want? Because a lot of people don't feel comfortable doing that.

Clara · 19:16

Yeah, that's a great question. And I wish I could chalk it up to, you know, something that I learned or was in my life. And part of it is, I really like talking to people. I'm very outgoing. I'm very extroverted, as you can probably tell. And I really just don't mind having a conversation with anybody and everybody. And so it felt very natural to just be curious about what people were doing and ask those questions. The other part of it is, I think I just had that early 20s bravado that, like, you think you know a lot more about the world than you actually do. And I encourage people to tap back into kind of that childlike wonder and curiosity when it comes to asking people for information, right? Like, don't go and ask people for a job. That's not what my main, like, first conversations were. It wasn't coming in and saying, hey, like, hire me, you know, do this, do that. It was more so coming at it from a place of curiosity to say, I'm curious about this business. I'm curious about this dance fitness thing because I have a background in dance. I love dancing. So it was a very natural point of connection for me to be talking to the people who are working there. Clearly, we both had passions for dance and coming at it with that kind of mentality makes it a lot less of an ask and like giving me something and more so a collaborative conversation between the two of us to talk about something we're both passionate about.

Maggie · 20:41

Yeah, yeah, I absolutely love that. It reminds me of a conversation I was having recently around networking and how it can feel really big and daunting and scary. And personally, like the last thing that I want to do is go to like a Lincoln startup event or just a big broad networking event. I have, it kind of gives me like, no, I don't want to do it. I can't, I can't find the time. And I've kind of been aware of that. But when it's broken down into something or a person or a category of things that I'm really passionate about, like food and beverage or restaurant startups or, gosh, my background is in Nordstrom fashion industry. Like if it's specific enough, if it's personal enough, if it's the people that I want to connect with, like I think that is key to figuring out how do you put yourself out there in those ways. So hearing you say, you know, I was passionate about it, I cared about it. And it's just fun to have a conversation about something that you enjoy. It becomes a lot more digestible to think about putting yourself out there or, you know, driving an hour to go to a networking dinner or lunch instead of a massive event and like so super broad.

Clara · 21:55

Yeah, absolutely. And I'll give a piece of advice, if you will, to people who know that everybody knows you should be networking, right? Everybody knows that you should be going out there, talking to people, things like that. If you are feeling hesitant or, you know, you're like, oh, I'm just not super extroverted or like, I don't know how to just pick up a conversation with people. I was actually talking to a friend about this yesterday and she says, you know, I'm an introvert at heart, but again, I know I need to be going to these networking things or I go and support my friends. If there's food, if there's a snack table or pizza, I go there and I talk to those people because I know those people are feeling just as uncomfortable or just as awkward, just as introverted as I am. And so we go and we bond over the food and the food becomes the kind of catalyst for us to talk about something. And so I feel like that was a really great piece of advice that, you know, you might meet someone there and talk to them, be like, oh, you're also looking at the orders. I'm also looking at the door, there's like, gosh, like, isn't this a great place for us to hang out? And also you don't have to feel like you need to talk to every single person. Like she said, I try to talk to three people. If I can talk to three people at, however many people are at this networking event, like that feels like a good number of connections to make. And you just need one, you just need one good connection. So three is a great place to aim. And once you do three, you're like, okay, I'm done. I'm ready to go home. Just make sure you follow up with those three people and see where that leads you.

Maggie · 23:21

Yeah, I love that. And I know that we will get to this later, but I know that you run some really cool networking events with Chiefs of Staff. So let's make sure we chat about that. But let's now dive into your move from kind of close to, but not quite Chief of Staff roles at startups to then, like truly kind of moving into more of a Chief of Staff like role. And how did that happen and where in your career? If you want to kind of share with us about that.

Clara · 23:46

Absolutely. So post Bollywood Dance Fitness Company, I was recruited to go work at AngelList where I worked under the head of operations. Truth be told, that head of operations was very Chief of Staff like to the CEO. So I was almost a Deputy Chief of Staff, if you will, now that we can go back and actually give titles to these things that we were doing. And then the head of operations ended up going on sabbatical about a year and a half after I had been there. And so now I was kind of left without a manager. And again, I was still very much in this floating position of filling in the gaps. And so at that time, our team was growing pretty rapidly and we didn't have a designated recruiter. So this is where the story kind of like comes back full circle, where the CEO looked at me and said, well, you have a recruiting background and we build talent products. So how would you feel about taking on the recruiting for our team? We need to hire like 10 more engineers by the end of the year. And given that you have a little bit of experience here, would you be willing to do that? And I said, yes, with a caveat of, I would also like to learn more about product. I would like to learn more about what it's like to build product because that's a big part of our team. And I understand what the product is, but I want to see what goes into it. So kind of copy-otting the yes and like, I like to use the improv like, yes, and like, yes, I'm willing to do this. And can I learn this thing? He was like, that sounds like a very fair trade. So what he let me do was I was able to sit in on product meetings and start to just pick up like engineering talk and how our product managers and product designers worked with other people very much fly on the wall. And eventually we got to a point where the CEO himself started to consider hiring a chief of staff. And that was the first time I had ever heard of this phrase in a tech startup environment. Of course, West Wing heard of that, have seen, you know, a variety of staff in the political world. And funnily enough, the CEO of the company loved the West Wing. And that's where he got the idea from. He like saw the other day and he's like, what year was that?

Maggie · 25:46

What year was this?

Clara · 25:49

2018, I believe, maybe.

Maggie · 25:51

2018?

Clara · 25:51

Yeah.

Maggie · 25:52

Okay.

Clara · 25:54

And so 2018, 2019, something like that. And so he was like, I could really use like a Leo McGarry for myself. And so I was like, what, what is that? Like, what does this person do? Because if you're going to hire this person, I'm going to have to lead the chart. I'm going to have to help you write the job description. So I need to understand what this role is. And the more that he described it to me, the more I was like, I think that might be something that I'm interested in. That being said, the company at that stage, I think was Series D. So it was a pretty later stage startup. And one of the skill sets that he was really looking for was Excel and really being able to kind of manipulate data, use it to make decisions, things like that. And that was just not a skill set I had. But the scope of the role in terms of sitting by his side, helping him manage priorities and just being this right-hand person was super interesting to me. And I figured, OK, if our CEO at a tech startup is looking for a Chief of Staff, other CEOs at other startups must be looking at Chief of Staffs as well. And so that was kind of the impetus for me to start looking around, to see what Chief of Staff roles were out there and starting to apply to them on my own time.

Maggie · 27:08

OK, amazing. Can we back up a little bit and share? I'm guessing that some people on the call are very familiar with startup structures, Series A, B, C, D. I am much less familiar than you are, but probably have had exposure to it and understand a bit. Can you walk us through, in layman's terms, what is a Series A? What is bootstrapping? What is A to B? You've mentioned a few of these transitions and company structures. What does this mean for those of us that are learning more about the startup world?

Clara · 27:40

Yeah. I'm not going to claim to be an expert here either. I'll tell you what I know from my experiences.

Maggie · 27:46

Yeah, that's fine. Your experience is enough.

Clara · 27:52

There's a couple stages of funding is how we refer to companies. That's where the letters come from. We use that to just denote how many rounds of funding a company has gone through. At startups, generally speaking, they don't have any money to start, so they need some money from somewhere so that they can start to build out product or whatever it is that they want to sell down the line. When they go to venture capital firms to raise a round of money, they'll label that the seed stage is usually the earliest. If you go even earlier than that, sometimes they will have what they are called angel investors, where they are individuals, like think of Ashton Kutcher, who invested very early in Spotify and Uber. But people who have a good amount of money and they'll come in as what they call angels and put in money to help the company start to have a stream of money to use to hire people, to buy laptops even, you can really use this money for everything and anything to get your company off the ground. After angel round is a seed round, so it's usually a smaller, and this is where you might go to an institution like a venture capital firm to get, can be anywhere from half a million dollars to 10 million dollars to more than that. There's no real cap on what you can call your seed round before moving into A, B, C, D, E, F, G. You just keep going down the line until you decide that the company is going to go public and be NASDAQ traded, at which point you no longer have any series after that. Or if you get acquired or whatever, it might be down the line. So it's a very rough kind of thing.

Maggie · 29:34

I think that's helpful. I think, yeah, I think that's helpful. So when you share, you know, you helped a company go from Series A to Series B, that is from one funding round to another, raising a significant amount of more money to fund the company.

Clara · 29:51

Exactly, yes.

Maggie · 29:52

Okay, cool. All right, so what did you love about being a Chief of Staff at a startup? And what else can you share about that experience around just kind of Chief of Staff work and startups before we move into your next part of your journey with Ask a Chief of Staff?

Clara · 30:09

Sure. So the thing that I loved and when I joined as a Chief of Staff to the company, it was called Hugging Face, we had just raised our Series A right before I joined. So essentially, we are very early stage in the Series A for context. At that point, I believe our Series A was about $10 million. The team itself was 10 people when I started, and I like to say that I was employee number 6 through 10, depending on when we walked in the door that day, four of us started all at the same time. What I loved about being that early stage is that there's really no precedent in terms of operations or playbooks or processes. So you really have the lay of the land when it came to putting these things in place and really building the scaffolding of the company. One of the stories that I like to tell is that on my second day, one of my employees or colleagues came up to me and said, my wife just had a baby, what is our parental leave policy? And we just didn't have one. We were so early stage, nobody else had had a baby before at the company. And so I basically hopped in and I was like, I don't know, but give me till the end of the day, let me do some research, figure out what exactly we need to be able to provide that for you. And I'll come back with you, whatever we end up doing. So I spent the day on Google. I called up a lot of friends who work at a variety of different companies to kind of see what policies might look like, what insurance we needed to get, what was a good amount of time relative for people to take off or be able to take off and put together our first parental leave policy that then became kind of the standard moving forward. And it was a really exciting time to be able to do that. And the company was also going to be growing very rapidly with that Series A. We were planning on hiring a ton of people. And so we didn't have a strong recruiting process or pipeline, but we knew we needed to hire. So I helped build a lot of that out. And it was just a really, I know a lot of startups use this phrase, but you know, drinking through the fire hose, there was always something to do. And there was no right or wrong way to go about doing these things, because there simply was not a way that these things were done at this company before.

Maggie · 32:28

Yeah, that's honestly one of the things that I think that I know I love about the Chief of Staff role, and I think draws a lot of people to the role, is that we are constantly working on new and different things. And it's this really cool blend of building and creating and then executing and then moving on and doing something else, you know, another topic or procedure policy creation or gosh, return to office or, you know, seat mapping. I mean, it's just like from the finance, like we could just go on and on. There's so many different things that Chiefs of Staff can do. And within those things, it's like a combination of the art and the science, the build, the create that, you know, I just love that about the Chief of Staff role. And one other thing that makes me think about this kind of this element of the role is it's also normal for us to want to take on a new challenge or a new role once we feel that we have set up the infrastructure and have set up the processes and systems and we tack out all the needs. And we want to go do that again somewhere else or in another role or another thing. And I think especially maybe generationally prior to us, there's been this emphasis on staying in your company for years and years and decades and decades and, you know, moving around. Can we talk about that? Is it okay? And this is just my PSA that, yes, it's okay. And Chiefs of Staff are great at what we do because we love the adventure and the problem solving and the creation and building of these things and then doing it again and again. So I don't know, Clara, if you have anything to add there, but I think it's a fun part of the Chief of Staff role, for sure.

Clara · 34:04

Yeah, absolutely. And I know some people had mentioned, like, the startup world is not super familiar to some of you. And so I would say Chief of Staff roles, they can be very, obviously, they can vary very differently depending on who you're working with stage of company. And so if you're interested in Chief of Staff roles, it can be a variety of roles as well. You know, a Series A company that's very early on is going to be very different from a Series D or E or F even, where there are a lot more operations that have been established, there's a lot more people in the team, you have department heads to work with and things like that. So even within the startup world, it can look very different. And so I'm happy to delve into that more as well, or if anybody has questions, I'm reading the chat, I'm happy to answer anything else that could be helpful in terms of setting context for being a Chief of Staff in this early stage startup world.

Maggie · 34:56

Yeah, so before we get to Ask a Chief of Staff, what advice do you have for people who are curious about or definitely know that they want to pursue Chief of Staff work at a startup?

Clara · 35:09

Yeah, for people who are unclear or you don't know yet, the best thing that you can do for yourself is talk to people who have done it. I think that having informational interviews is it's not asking for a job, so making sure that you know the distinction there. But the best way you can find out about the role other than obviously working in the role yourself is to talk to many people who have been in the role before, and that way you can start to pattern match to understand. Because just being an early-stage startup chief of staff can mean, like I said, a lot of different things, just like being a corporate chief of staff can mean a lot of different things. If you're a chief of staff at T-Mobile versus LinkedIn, those two things are going to look very different because one is a telecommunications company and one is more of a tech company. So within startup, what kind of startup do you want to work in? What kind of industry? How big? How small? How late stage? How early stage? Really familiarize yourself by talking to other people and that's going to help you hone in on that as well. And then, sorry, your second question was around...

Maggie · 36:14

I think you hit it, like when you know you want to work in a startup, how does somebody cross that bridge and get there? And you did mention having those informational interviews. Anything else to add there?

Clara · 36:25

Yeah. And then the other thing I would say is looking at startup focused job boards, like things like Well-Found or Crunchbase, Y Combinator, I know I'm just throwing a bunch of names out there, but these are all companies that work in the startup space that have job boards that are specific to the startup world. So LinkedIn, of course, also has a lot of job postings as well, and you can take a look and see how many people are at that company. But you can always cross-reference with another website I love called Crunchbase, which will tell you what stage that company is at.

Maggie · 36:57

Okay. Awesome. Well, Clara, why don't you take us from Chief of Staff's startup world to, you know what, actually, I want to just be an advocate for Chiefs of Staff, create a membership community, bring hundreds of Chiefs of Staff together. Tell us how you found yourself creating and building Ask a Chief of Staff.

Clara · 37:18

Sure. So one of the hardest things I think about the Chief of Staff role, which also makes it one of the best things, is that it really opens up your career opportunities to everything and anything else. You can really become anything after the Chief of Staff role. So even before taking on a Chief of Staff role, and this is something I know in hindsight now, is to think about where you want your career to be in the long term. I wish I had given that more thought when I took on my Chief of Staff role, because after about a little over a year, I felt like I was hitting my mark in terms of, okay, I think it's time to move on, but I have no idea what that might look like. And so throughout my time at Huckingface, we did go through our Series B, so we did raise another round of money. And what that meant also was that now all the operation stuff was at least in place. We had a foundation on which to go off of. And the next thing that we needed to think about was like, how do we grow the company to the next stage? Did that mean monetizing a product? Did that just mean acquiring more users? Did that mean now it's time to consider, like, what next thing we can build? And so with the, with Hugging Face in particular, they were in the AI space. And because we started to need to think about what that next stage would look like, it would really look like me needing to build more knowledge in the AI space. In that earlier stage at Series A, I needed to know what AI stuff we were building, but I didn't need to get as deep into it. Once we hit our Series B, I really had to start to pick up more industry knowledge. And that was the point where I was thinking to myself, okay, if I really build myself into this space, I'm going to start to build a career in AI. Is that what I want? For me, I think AI is important. Obviously, looking at the state of the world now, we can see how prevalent it is, but it wasn't necessarily where I needed or wanted to build my career. What I really enjoyed doing was people, like I think this is a commonality or common thread throughout my entire career, is talking to people, helping people, building communities, bringing people together. I had the opportunity to go to OnDeck and build out their Chief of Staff fellowship. It was actually a fellowship that I myself had gone through. It was an eight-week program at the time. By the time I took it over, it became a year-long program. It was really this opportunity to continue to build in the Chief of Staff space, and really start to provide some of the resources that I wish I had had earlier in my career. The community space was somewhere that I knew I wanted to continue to build in. We did have somewhat of a community within the AI space when I worked at Hugging Face, and I really enjoyed being able to interact with people there. This opportunity at ONDEC, again, using the power of network, I knew that the founder or the program director of the fellowship was moving on to a different role within ONDEC. I knew that there was going to be this vacuum and put myself up for that role. I basically volunteered and said, I really enjoyed my time in this community space. Having gone through it myself, I think that there are some things that I could bring to the table as a consumer of the product and now being on the other side to help improve it. And I'm really passionate about the Chief of Staff role, so I would love to continue to bring people together here. And so that was the transition from being a Chief of Staff to now building communities of Chief of Staff.

Maggie · 40:44

Amazing. Okay, so tell us about Ask a Chief of Staff and what it is, what your members get, how people interact with each other, and what does the day to day look like for you as the leader of Ask a Chief of Staff?

Clara · 40:57

Sure. So here at Ask a Chief of Staff, we do have a community. It's an online community that's mostly run through Slack. We have two tiers of membership. One is for our current Chiefs of Staff, so people who are already in the role and they're looking to network with other Chiefs of Staff to share best practices, learn from each other, and really take your career to the next level. One of the hardest things about being a Chief of Staff is that you just don't know what you don't know. A lot of the times when you're encountering something, it's the first time you've encountered it and you're expected to deliver at an executive level. But the good news is that it's not the world's first time encountering this kind of problem. Other people have gone through this before, so using this collective knowledge, we can help accelerate Chiefs of Staff to create more impact at their current companies. Our second membership tier is our Aspiring Chief of Staff tier, which is great for people who are looking to either land their first or next Chief of Staff role. There we really focus on job search, resume review, interview prep, things like that. Again, it's really great, I think, to have people who are in a similar career mindset or similar situation. They're looking for a job and bringing together this community so that you don't feel so alone when you're going through this job search. The role itself is inherently a little bit lonely, so having people who get it is really helpful. One of the things that we pride ourselves on is that we like to uncover the hidden job market and basically find opportunities that are not posted online anywhere else, and make introductions to those CEOs for our members, and so that they are able to really get in front of the people that they want to work with and put their best foot forward, instead of being one of hundreds of applications that now go through a LinkedIn ATS system.

Maggie · 42:43

Yeah, that's amazing. So if I'm in the aspiring Chief of Staff tier looking for a job, and then I find a Chief of Staff job, do I just move to the other tier, and now I'm in the tier among existing Chiefs of Staff, and I still have this great community?

Clara · 43:01

Yes, absolutely. So we would upgrade you into our current Chief of Staff tier so that you have the peers around you that are, again, at the same career level that you're at.

Maggie · 43:09

Cool. Okay. Awesome. And you do a lot of events. So we kind of alluded to this earlier, but Clara, you're in Chicago, you're in New York, you're in California, and you have Chief of Staff dinners, right, that are a way to get local Chiefs of Staff together and network, kind of how we were talking about earlier, like the little easier to network with people who you know are doing the same thing as you, and they're looking for the same thing. And you host these events, right, pretty often?

Clara · 43:35

Yes, pretty often. We try to do all the major geographies that we're in at least once a quarter, San Francisco and New York are, of course, our biggest. But we are, I'm going to Chicago tomorrow night. We have a 10-person Chief of Staff dinner in Chicago. We are going to be doing a three-day summit. You're hearing it here first. If you're not in our community already, but we're doing a three-day Chief of Staff summit in Santa Rosa coming up in April, where we're bringing together Chiefs of Staff to learn from each other and do a fun wine tasting as well. And we're also doing a lot more happy hours throughout the country as well. So actually, let me see if I can drop this link for all of you. But we do online workshops, we do in-person events, everything and anything. So if you want to come join us for any of those, please feel free to sign up for any of them. And all these events are free for our members. So it's a little park incentive to join, so you can meet people in person or online virtually.

Maggie · 44:34

Very cool. And as a reminder, for the Nova students that are on, any student of Nova gets their first month with Ask a Chief of Staff complimentary. You just have to email Clara, you can see me, we can make sure that you're covered there. But just a reminder that we have this great partnership. I think that what Clara is doing is awesome. I mean, it's a lonely world sometimes out there as a Chief of Staff. And having resources, like Clara said, who've been through these challenges before, you're probably not the first person to approach a problem. It might be a little bit different, but to have people to reach out to is so clutch. And it was really important to me in my beginning of my Chief of Staff journey to have someone to say, here's a template. Oh my gosh, gold, right? Okay, so if you have questions for Clara, please pop them into the Q&A portion of the chat. I'm trying to see if there's any questions yet in the chat chat area, but Q&A works best for this. So feel free to pop them in. Clara, what is your favorite thing about being a Chief of Staff? Is it talking to people?

Clara · 45:42

Talking to people is definitely, I mean, it's a great part of it. I think like as a Chief of Staff, you're required to talk to people throughout the company to get a pulse of what's going on. For me personally, being a Chief of Staff was just the opportunity that you got. You had such a wide array of different responsibilities, special projects, strategic initiatives. So you would really just have a chance to work on everything and anything. I think that breadth was what was really got me most excited about waking up every day and seeing, like, what are we going to tackle today or this week or this quarter?

Maggie · 46:19

Amazing. OK, we're going to do some rapid fire questions. So what is a day in the life right now of Clara Ma? And what are the tools you use each week and day?

Clara · 46:29

Just to clarify, is this a day in life of my life right now or Chief of Staff stuff?

Maggie · 46:32

Your life. We're going to take Clara's life for this one.

Clara · 46:37

So I'm doing obviously a lot of community work. So I like to time block my day. That's probably the biggest tool that I can recommend, is that I have a really great EA, and she knows that I take meetings from 10 to 12 every day. And then after that, it's like deep work time for me. So I really try to time block, and that's probably the best tool that I can recommend. Otherwise, I mean, I love using ambient for all of my note-taking during my meetings, so I don't have to take notes talking with somebody. It can take the notes for me and summarize everything. And then I'm a big just G Suite user. I love Gmail. I love Google Calendar. I think all of them work together super well. And the last tool I will say is I use Crisp for my Zoom meetings, and it's great at filtering out all the background sounds and also doing noise cancellation. So if you're like me and you like to work from anywhere, cafes, hotel lobbies, things like that, it's really great to clear out the ambient noise so everybody can come across crystal clear.

Maggie · 47:43

I love that. I hadn't heard of Crisp before, but it does make sense for a New Yorker for sure. Yeah. All right. So favorite resource in terms of like books or podcasts for scaling startups.

Clara · 47:59

Okay. Zero to one is one that I can recommend. I think most people have probably heard of it is written by Peter Thiel. It's all about scaling from zero to one. Other ones that I'm trying to think of.

Maggie · 48:12

That one's called Scaling from Zero to One. Is that what you said?

Clara · 48:15

It's called Zero to One.

Maggie · 48:17

Zero to One. Okay. Correct.

Clara · 48:19

And then podcasts wise, it's been a little while since I've done the podcast. When it comes to startup things. Let me get back to you on that.

Maggie · 48:29

Okay.

Clara · 48:30

It's been a little while. Yeah. I think also take a look at Renny. Lenny Raditzky, I think, is how you spell his name. He does a lot of great articles on his sub-stack about product and scaling. So that's probably a really good one to check out as well.

Maggie · 48:43

It's a great resource. And How I Built This Podcast, I just love it. It does feature massive companies now that have raised hundreds of millions of dollars. But it's so cool to hear about their journey when they were, you know, bootstrapping and working at McDonald's. And now they're, you know, these major, major company owners. Calendly, they have an episode on Calendly. And the founder is from Nigeria. Incredible story. So if you want to start with one of them, I would start there. All right. So Ms. Clara, with the understanding that every industry varies, what would you suggest a starting salary range for a Chief of Staff? This is a hard one because it is a huge range.

Clara · 49:26

Yes, it's a range that depends on the size of the company, how much money they've raised, how much experience you have. So let me redirect you. I know this is a little self-promo, but our sub stack actually has a compensation survey. Maggie, I'm trying to type things in the chat, but I think it's only going to the hosts and panelists. So if you want to follow up with everybody after, it's I think, gosh, I don't know what issue of it is, but if you go to askachiefofstaff.com and take a look at our blog, we do have our compensation survey there, and that will help you figure out where you are in that range.

Maggie · 50:08

Okay. I am resending a couple of the things that you sent. The setting might just be on your chat was to hosts and panelists. So resending a couple of those. But yes, Clara has some awesome resources out there for salary. To throw it out there, just to give you a number, Jodi, I would say Chief of Staff minimum these days, and gosh, it's so geographic. It's so company dependent, startup, maturity, all the things. But minimum would probably be 120 to 140 with a max of 200 to 300. Huge range, but you'd probably find yourself somewhere in there, and to help relate a bit to maybe EAs. I would say if an EA is at around 100, a Chief of Staff, I have seen usually is probably around like a 140 from a comparison standpoint. So very, very rough, but I want to give you a little bit of context there. Okay. So next question here, for aspiring Chiefs of Staff, long-term goal, it's not next job, it's my long-term goal. What are some transitional rules that I should be looking for? Like right now or next job, what should I be aiming for to help get me to Chief of Staff?

Clara · 51:19

So depending on where you want to be a Chief of Staff, right? So if it's within, let's say a larger corporation, there may be a track within that corporation that you might want to look into. Sometimes it can be like a project manager role or like a strategic initiatives lead, it could be a variety of things. I mean, EAs also can make that leap into a Chief of Staff role. So if you're working with like an executive or a head of business unit, if you are looking at early stage startups, I would say if you ever see at an early stage startup careers page, there is a title listing that says, don't see the job that you want and want to apply anyway, that is the chance for you to build yourself into that role. That's very much the, I will do anything type of role and really trying to figure out, as long as I can get my foot in the door. With startups, titles are so leading, it doesn't necessarily mean you only do that thing. If you can get your foot in the door with whatever functional background you have at the startup that you would like to be a Chief of Staff at down the line, that is going to be much more valuable than any specific job title that makes sense.

Maggie · 52:33

Yeah. It's always easier to move into the role you want at the company you're already at. Like Claire is saying, can you put a proposal together? Can you identify what that looks like? I think another thing to look for, especially, I guess internally or externally, if you're trying to identify what is a Chief of Staff role or what is close to a Chief of Staff role, it's roles and even just job responsibilities that are for a person more so than for a separate line of business or a separate work stream or product or whatnot. So is there a person behind the computer at your all-hands event? That person's probably somewhat on this Chief of Staff team or this back office team. Is there a person running around for other events doing logistics? Is there a person helping ghost writing? Is there like, who are the people supporting the leader? Those are the back office chief of staff roles. And it can sometimes help to understand that kind of visual or kind of an example when looking at job descriptions, job descriptions, especially to figure out like, what is this role? Is it doing all these things for a leader to support a leader? Or is it like, I'm running this product program management or whatnot? So that's probably another little thing to look for there. Okay, well, that's the end of our questions. Clara, do you want to leave us with any final thoughts, how to get ahold of you, how to reach you? Ask a Chief of Staff, I'm happy to post some things in the chat too.

Clara · 54:03

Absolutely. Best way to get in touch with me is on my LinkedIn. I love connecting with all of you. So please send me a LinkedIn request and I'm happy to accept it. And that's where I'm posting about the newsletters we write, and posting about different things like Maggie and I both cover EQ a lot about how that's one of the most important things a Chief of Staff can do. And everything that I work on, you will see it on my LinkedIn first. So please send me a request there. I saw a question in the chat about repeating the details for our aspiring Chief of Staff. So yes, the aspiring Chief of Staff membership, you have access to our Slack community, you have access to our resume review, help, interview prep, job search, exclusive jobs that are not posted anywhere else, as well as mentorship. So many of our current and former Chiefs of Staff are happy to be mentors to you as you go through your own Chief of Staff search. So hopefully that's helpful. Otherwise, you can go on our website, askachiefofstaff.com, and there's more details there. And I think that's pretty much everything. I mean, I hope that this is the start of many conversations that I have with many of you. I'm also happy to do career chat, so one-on-one 30-minute calls, if that's something that you want to explore further. And thank you, Maggie, for having me. This was so wonderful to get to chat with you in this setting.

Maggie · 55:21

Absolutely. It's so fun to get to know you a little bit better and hear about your journey. It's inspiring and I think it's really helpful to hear how you balance all the things and what you recommend looking back. So thanks everyone for joining. Have a wonderful night. Have a great Valentine's Day. Also, Valentine's Day is silly. If it's not for you, that's okay too. So we'll see you back in the workspace tomorrow, everyone, and have an awesome day. Thanks, Clara.

Clara · 55:48

Bye, everyone.

Maggie · 55:49

Bye, everyone.

Speaker 2 · 56:01

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