[upbeat music] Hey friend, it's David Nebinsky, the community lead at the Chief of Staff Network.
We help chief of staff through the three Cs: cohorts, curriculum, and community via Slack with over 900 people in it. Can learn more about our membership, events, and upcoming courses at chiefofstaff.network.
There you can learn about our upcoming Chief of Staff Connect conferences in New York in October, London in November. Hope to see you there. This episode of, of the Chief of Staff podcast is with Jessica or Jess Li.
She was the first employee and chief of staff at Beacons and worked there for over four years.
In this ep- episode, you'll learn about how she got this role, why she stayed in the role for four years, how it, and how it evolved, considering sometimes chief of staff role is 18-24 months, so really interesting, uh, perspective here and experience here, uh, how she developed a really strong bond with the leadership team, thoughts on having a re- complementary skill set or replacement skill set with your principal, and so much more.
This episode was recorded live at BambooX's NYC office and studio.
BambooX works with seed to late stage startups and their VCs, including Vercel, Hinge Health, Closa, and NEA, helping them hire top talent across software engineering, data, machine learning, and AI, product management, and design.
You can learn more at bamboo-x.com. Excited for you to level up as a chief of staff. Here we go with Jess. Jess, welcome to the podcast. Thank you. Thank you for having me.
We're here in New York kicking off the Chief of Staff podcast. Um, thanks to our friends at Bamboo. Excited to be here.
Um, and, uh, Jess, you've had a incredible chief of staff journey already, and I know that, you know, the future is, is so bright for you.
But we wanna talk about some kind of like atypical e- experiences, even though many chief of staff roles are atypical, but you've definitely spiked on a couple.
Uh, just to kinda kick things off, how would you say that you got your chief of staff role at Beacons? Yeah, so that's a pretty interesting story as well.
Basically, in 2020, 2021, during the pandemic, I was, like, bored and at home and doing a lot of writing online, and one area I was diving into was social commerce.
I'd grown up in China, still have family there, and so was always really interested in, like, China-US and, like, learning from each other and compare and contrast.
And obviously, social commerce was really taking off in China at the time and also in the US in different ways, and I felt like there was a way for the US to learn from China as well as vice versa, um, but probably more the US learning from China since they're pretty advanced there for various reasons.
And so I was writing about that and basically, um, had gotten in touch with the founders, specifically the CEO of Beacons- Mm... actually initially when they had pitched our fund at Soma Capital, so when I was- Mm...
uh, working there in early stage venture back in 2019. Yeah.
And just kind of stayed in touch/got reconnected, reintroduced through an angel friend, um, 'cause I was doing some angel and scouting investing at the time as well after leaving venture full time, and just felt like their idea was really interesting, and we started jamming on social commerce, creator economy.
I also was kind of a content creator in a more atypical way of, like, LinkedIn content, Medium content, um, and so was able to relate to content creators- Mm...
experiences, challenges, and really liked that overall idea of helping people be able to love what they do and do what they love and make money doing it- Mm... and make a living out of it.
And so just kind of jammed on different things. Never thought I would actually join an early stage company 'cause I was, like, actually a pretty risk-averse person- Mm...
at the time, and they were, like, super duper early. It wasn't just a startup. It was just the founders at the time. They'd gone through YC, so some things were de-risked, but it was still really early.
Um, and so, you know, just thought I would kind of help them on the side, like product testing, intro to advisors, fundraising, things like that. But ended up just really loving the team.
Like, felt like spending time with them wasn't, like, work. It felt- Mm... like really fun, and I felt like I could actually be friends with them, which is kind of- Mm...
like a high bar since I am very introverted, and so that doesn't happen- Mm... too often. Um, and so we kind of realized, Neil, the CEO and co-founder, and I, that we were really complementary. Mm.
I can dive more into that 'cause I think that's actually a pretty interesting thing to diagnose as a chief of staff when you're working with a principal, kind of figuring out the complement versus substitute relationship.
But basically just really enjoyed working together on different things informally, and then when they were looking for a chief of staff, I initially was introducing them to people, but kind of was, like, almost, like, jealous of the people who were interviewing, which had never happened to me before 'cause I would do a lot of- Mm...
candidate intros and, like, be happy for everyone involved. But I was like, "Oh, I kind of, like, actually want this role."
And so ended up, you know, being out front with them about that, going through the process, and then deciding to join, um, full time back in, uh, mid-2021. Okay. Let's talk about the complementary versus, uh, substitute.
Yeah. Um, tell me, tell, like, tell us a little bit more how you were thinking about that. Yeah, totally. So Beacons, just the company I was at, they're really big into kind of understanding employees' strengths- Mm...
um, and really focusing on that. And not so much like, oh, you're good at math or you're good at, you know- [laughs]...
reading or whatever, but more like, more innate 'cause I think, you know, math you can obviously learn more or less of, same with other subjects.
And so we would take things like the Clifton Strengths test that I know a lot of people are familiar with, um, and then also this, um, other more, I guess, niche, less well-known thing called Six Working Geniuses. Mm.
Um, and so Clifton Strengths we realized that I was very much, there's like, um, I, I think four or five, some, some number of like- Yeah... categories of strengths. Um, like one is, like, relationship oriented.
Um, but my CEO and I, we were very complementary.
He was very much the strategic kind of strengths, a very, like, visionary, which obviously makes a lot of sense for-A CEO and I was very much the execution oriented, so very much at that like detail level, operational.
Um, and so that was obviously really great. I don't think we actually knew that before working with each other. Mm.
We didn't have the vocabulary for it, but I think we felt it and the Clifton Strengths test gave us that vocabulary for us and the rest of our team as well.
Um, and then with Six Working Geniuses, that one's actually really interesting because, you know, as the name suggests, it's six working geniuses, and so it kind of covers like a project end to end. Mm.
So the acronym is WIDGET. Um, so it's W wonder, that's like the first step, like you figure out what problem it is you wanna even solve.
Like where in the big world do you wanna go after with your project or your startup?
And then the next one is either like innovate or ID, but it's basically like now you have this space, you wanna work on the creator economy or whatever it is, and what are your ideas for solutions, kind of that brainstorming phase.
And then D is for discernment. So you have all these ideas, like how do you pick the right ones to go after? How do you prioritize within that? And then the next letter is G for galvanize. Mm.
So now that you know what you wanna go after, how do you galvanize your team to get excited and get like high level motivated about doing the things to reach those particular ideas or goals?
Um, and then the next letter is E for, or, uh, yeah, E for enablement.
So that's kind of similar to galvanize, but it's sort of like less of like the big like, oh, I'm get- rallying everybody in this room and more like, how do I unblock you on a day-to-day basis?
Like, keep you motivated like week to week, do good one-on-ones, things like that. And then the final letter T is for tenacity. Mm. So getting that project really over the finish line.
Um, and it was pretty interesting because when you take this, um, test of sorts, um- Mm... kind of like a personality test- Yeah...
it's not like an actual test, but, um, you kind of see like how you rank, so like which letter you're strongest for. And I was like the WIDGET letters backwards, so starting with like- Mm...
the very T-E, like G execution side. And then our CEO was like the WIDGET let- letters forward pretty much. Wow. Uh, more or less.
Um, and so that made a lot of sense and kind of like echoed like what we felt when we were first exploring working together, what I think makes a good CEO versus a chief of staff or like an operations person, and then also like very similar to the Clifton Strengths test.
So that was really helpful and I think being mindful of that when...
'Cause I think it's easy for a principal to be like, "I have so much work, like let me just give like the random like five of them to like [chuckles] my chief of staff. I don't have time to really think about it."
And that's, you know, that's totally fair.
But I think if you're able to, um, like have at least for the most part, like, okay, here's like the 10 things that I typically do as the principal, whether you're the CEO or the CTO or whatever, and here's, you know, three things that are very much like in that like WID phase and that's like better for me as the principal, the CEO to do, assuming that is their strength.
And then these are the ones that are like the execution oriented things and that's better for you, Jess, the chief of staff to do.
Um, or even like, you know, given a project, there's gonna be like a WID phase, there's gonna be a GET phase as well. Mm. So, um, instead of just being like, "Hey, Jess, can you take over this whole project?"
But like, "Hey, yeah, this is important, but let me do like the WID first since like I have that context and that strength and that's what I like to do.
And then once I'm kind of set with that, we can sync up, um, and then I'll hand the GET or the ET off to you."
So, um, I think that was like very helpful for us to kind of think about like, um, oh, in this instance, am I like substituting for you?
Which could totally also be fine 'cause like, you know, maybe it's smaller things like I'm running a meeting or sending an email.
But, um, I think at the high level, kind of like especially if you're complimentary, like really figuring out how to tap into that versus being like, "Oh, we're complimentary, but like, you know, I'm so tired, so just take like half of my things and I'll do half of my things," and then you end up not catering to anyone's particular strengths.
Yeah. And so, um, it sounds like you, you, you have this, this, this, this, this great match here. Um, you were the first employee. Um, what was that like? Yeah.
So it was really fun and I think I honestly like felt, um, I think in other roles before I also really enjoyed them, but it always was like, oh, I'm an employee.
Like, not that it was like me against the company- [laughs]... in any like, you know, crazy way. Right.
But it was very much like, oh, you know, like that's the company, I work there, and I'm an employee, and sometimes our interests are aligned, sometimes they're not as much.
But I think with Beacons from the very beginning, it always felt like I was just like a part of the company- Mm... in a very like true, fundamental, like foundational way.
Like even during salary negotiations, I never felt like I was negotiating against myself. It was like, or against the company or they were negotiating against me.
It always felt like we were like figuring out like the best thing to do together and it was always very collaborative.
And I think it very much felt like, um, you know, like the company was like, not like my baby in like an extreme way- Mm... but a little bit like that where I was like, oh, I want to like, you know, little things.
Like I want to buy my own laptop 'cause I don't wanna like spend the company's money, you know?
Uh, obviously that only goes to a certain extent, like there's obviously still things the company needs to pay for, but I think it was very much like, oh, this is like my startup.
It felt very kind of like a lot of agency, a lot of ownership in a very positive way. Um, and so moved out to San Francisco and, um, it was just the four co-founders at the time.
They'd been working in the company for a little while. Oh. Yeah. And they had- Four co-founders. Yeah. And you. Exactly. Yeah, exactly. And so they were all out in SF.
Um, one person was, uh, sort of more in South Bay, but like the rest were in the city. I think one, one of them took a little time in LA.
But, um, two of them were living in SF at the time, and so I just moved into the same building as the two of them.
And I picked a random room in the building-'Cause it was like a pretty new building, so they had a lot of, like, open units.
I just, like, picked a totally random room that was a studio, 'cause I was looking for a studio, and it happened to be the one, like, right next door. Like, we shared a wall, my CEO and I. What?
Which was, like, really funny. Like, I remember he texted me, he's like, "Oh, congrats on, like, signing the lease. Like, what room are you in?" [laughs] And I was like, "Oh, I'm, like, 263."
And he was like, "Oh, I'm 264." And so that was, like, pretty funny. We had no idea, like, unplanned- Wow... completely. Um, but it was actually, like, pretty great.
Like, I never felt like it was, like, weird or whatever. Like, everybody was, like, really respectful of, like, boundaries and, like- Hmm... work and not, like, work/life balance, but more, like, harmony.
Um, and we actually had, like, um, orthogonal windows, so it was, like, almost, like, closer than if you were just, like, neighbors 'cause you could, like, kinda see into each other's rooms.
Um, and we shared a wall, and my computer was actually closer to his internet router than, um, he was. [laughs] And so a lot of times, like, I would just use his router 'cause I think mine was just not working.
And then he would be, like, blurring out on calls, and I was like, "Oh, sorry, that's probably my bad 'cause I'm using all your bandwidth."
But, um, but anyways, we end up getting an office, and just, like, a lot of the early things were really fun and interesting, like, much more hands-on, very startup-like when we got our first office.
Like, actually, the four co-founders were... Um, they had this, like, tradition of going to EDC, um, like- Yeah... that music festival. Yeah. And so they were there, and I don't have that tradition, so I didn't go.
And so I was in SF, and so I was the one, like, setting up the office initially, like, sitting there waiting for the chairs, like, building the chairs, like, sitting there, like, in the dark 'cause we didn't have lights yet.
Like, for the internet guy to come and install internet. So it was, like, a lot of, like, pretty typical, I guess, or, like, what you would imagine in a movie, like, early-stage startup things.
And it felt very, like, diverse. Like, one day you were working on the office, one day you were working on marketing, another day you were working on finance.
Um, and so in the early days, it was a lot of, I'd say, those, like, foundational things that you kind of need, ops, finance, office, and then- Yeah...
related to that, recruiting the team members, which I had never done, like, any recruiting really, um, directly myself, not even, like, interviewing people.
I mean, I guess I worked in ventures, so that was some type of, like, interviewing founders and recruiting them for the fund, I guess, but not really in that, like, direct, um, like, actual people management way.
And so that was also really eye-opening and interesting. And this was, like, during the boom of 2020, 2021. Yeah. And so, like, software engineers, it was, like, pretty hard to find them. Mm.
And, um, that was, like, an interesting process to navigate, but obviously we got that done as well.
Um, so yeah, overall, like, a really, I guess, like, typical movie, typical, like, early-stage startup experience and, like, a lot of diverse experiences, but a lot of it was recruiting-oriented to build out that early team.
Okay. Um, what... Like, it sounds like you had an incredible relationship here, a very, like, cordial, social, friendly. Um, how do you think you were able to really, like, accomplish that?
Like, what... Were there certain things that, uh, you did that really, like, help make that happen, especially over the years?
Like, how did you really, like, foster such a strong relationship that felt, like, very, like, kind of, like, natural and organic? Yeah, totally.
So I think a couple things that, um, weren't, like, always intuitive to me, but I think I learned over time, including from advice from the founders and our CEO and from other people.
So a couple things is, like, one as an example, like, really paying attention to the detail around, like, how your CEO, like, acts. Mm.
Like, almost as if you, like, need to, like, play him in, like, a movie or, you know, something. [laughs] Like, I don't know, whatever it's called, like- Yeah... method actors, where they get really, like, into it.
And so it was even, like, little things of, like, okay, noticing how does he take notes? Like, what types of questions does he ask during a meeting? Obviously, I'm not gonna, like, be his substitute. I mean- Yeah...
we compliment for a reason.
But I think when there is a time when I need to substitute for him, which obviously will come up more and more often as our relationship grows, like, knowing how to do that with his full trust.
Um, and so even little things like how does he write, like, smiley faces in his emails, 'cause it actually was pretty different. Like, I think most people use, like, the colon, and he- Yeah... uses the equal sign. Oh.
And, like, I would always have to, like, stop myself when I was, like, drafting an email for him to, like, not do the colon 'cause, like- Mm...
people would think he was, like, kidnapped or something [laughs] now if, um, if it wasn't that.
And so kind of, like, little things, I think paying attention to the details really matter, 'cause I think they might seem, like, small and silly, but it kind of, like, adds up to a lot of trust, um, and a lot of, like, just smoothing over, like, the relationship and any potential frictions, operational frictions that could arise.
So that was one thing.
I think a second thing was understanding what was important to people, 'cause I think people might sometimes think, like, "Oh, if I'm just, like, great and accomplished, um, and competent in general, like, everybody's gonna appreciate that."
Yeah. And sure, to some extent, but I think actually everybody has, like, a different focus.
Like, for example, one person could, like, I don't know, maybe they're really into math, and they, like, really care if you're good at math, and if you can't read a book for your life, that's, like, totally okay.
But, like, another person might have, like, read all these classic books, and if you don't know, like, what Jane Austen is, that's, like, really cringe for them. Mm.
And so, um, I think kind of in the same way, like, understanding what was important to everybody. So for example, our chief product officer, he's, like, a really organized person.
Um, like, he's just, like, really good at, like, organizing his notes and his workflows, and he really values kind of, like, organization.
And so, like, really showing that I was able to, like, help him with that or help our CEO with that or do that myself, I think that kind of, like, builds more of a bond over time.
And then similarly, our CTO, he had, like, particular frameworks that he would use to think about things. He was very, like, outcome and not output oriented. Mm.
So really focusing on, like, not just, like, "Oh, I did X, Y, Z things today, and that's a day goodbye," but, like, even though I did X, Y, Z things, like, I haven't reached, I don't know, whatever the goal is, like, 120 leads, so I'm gonna, like, grind it out or figure out, like, debug, like, what's wrong.
And so I think kind of, like, following that, like, outcome over output philosophy when I was-Recapping what I did or making discussion points, um, I think that like helped, um, with that relationship too.
And so I'd say that's kind of the second thing, just like understanding what each person values, um, in being able to like kinda cast your work in that light when you're engaging with them.
And so that's kind of the second thing. I think the third thing is just like honestly like just being friends with them like outside of work- Mm...
or like find- finding common ground, like jokes or like common interests or like memes or whatever- [laughs]... that you kind of like rely on. Memes. Yeah. Exactly.
And so I think doing that, um, was pretty good, and getting to know like people in their life too, like their girlfriends or their friends or, you know, other people like that were important, even their family if they were like in town.
So kind of like feeling like, you know, you were really welcoming to everybody that they cared about, um, and vice versa. And so I think those were kind of three things that were pretty helpful to do. Yeah.
And did things like, how did that evolve over the four years? Like, I can imagine that, you know, as there's companies growing, maybe like your, uh, the time that you have is different- Yeah...
or there's like more stakeholders, there's more people involved. Like, how do you think... Like, did the, did it evolve over the four years? Yeah, totally.
I think it definitely did, and I think also like the individual people, even without the expansion of the team, like kind of grew or evolved- Yeah... as people as well.
And so I think, um, a lot of it was like even having these, um...
So we actually were like talking in a different context around like relationship advice or something, and one thing that I had heard of was like doing these like relationship check-ins. Mm.
'Cause I think a lot of times like in interpersonal relationships, like you only ever like sit down and hash something out when like there's a- There's a problem [laughs]... problem. Exactly.
It's like, "Oh, I'm annoyed at you for doing X, Y, Z, and I've already been annoyed- Mm... for like the last three weeks and I didn't even tell you."
And then it's almost like too late for you to do anything to appease me, and then, you know, it kind of spirals and it becomes an ugly fight or whatever. Yeah.
Um, and I think what I heard from, I forget where I heard it from, probably like some type of blog or something, but, um, this person was like, "Yeah, we actually just have like a biweekly or like- Mm...
an every Sunday we just check in," and there's like a list of questions they go through as a couple. And it's like, uh, when, um, something like, uh, what did I do that was good, or what did I do- Right...
that was maybe not like bad, it was a little bit of a charged word, but that I could improve on.
Um, or what were the favorite things that I did that you liked and appreciated, and what were like the less good or less favorite things.
And so, um, I think kind of like implementing that in our like one-on-ones in addition to being like, "Oh, here's like the list of three things that are on my mind to talk about that are just like urgent but maybe not like foundational," I think kind of checking in on like, do we feel like we're communicating enough?
Mm. Um, like kind of meta level questions- Yeah... like that. Less of like, oh, the marketing campaign, let's review that, but more...
I mean, that obviously too, but also like, do we wanna like spend more time in the office together? Or even like kind of little nuances- Mm... that do make a big difference.
Like, do we wanna like sit in the same office or like have certain days where like we're both sitting in like...
'Cause our office structure was like there was an open space, but there was also like an office office inside, and like we spent a little bit of time just the two of us, like our CEO and myself, like in that office.
And then we switched to like open office plan too, and we were trying to work more with the team. So I think stuff like that was really helpful to do, like these meta level check-ins- Mm... on like how things were doing.
And then we also did that at a broader level with the entire like leadership team, which included the founders and a couple other function heads.
Um, which usually those were a little bit more like, um, kind of operational topics, like, oh, you wanna talk about this thing or this situation, um, or this metric or whatever. But also there would be time.
And I think, um, some people on our team, like our chief product officer, he was really good at like thinking about those things. Mm.
And so, um, other people would kind of bring topics that were more like, "Oh, this metric is going up or down. Let's review it."
And then he would also bring in, in addition to that, more topics around like, "Hey, do we feel like this meeting is still helpful?" Like, do we want to like reorient this meeting?
Do we feel like the process we're putting together, the agenda for this meeting is still helpful? So kind of those meta level questions that people don't often think about or ask.
I think that was really helpful to be able to do at like an individual one-on-one level with your principal, and then also at that like leadership level with the founders and the other department heads. Yeah.
Do we need to do a relationship check in here? [laughs] Yeah. [laughs] Okay. The podcast is going well- Yeah... from like a output perspective, but how are you doing as a- Yeah... as a human? Yeah. You know? Exactly. Um,
and so that's like the relationship side. Um, what was it like for you as, in four years in the role, like how did you continue to grow and evolve as well?
Like, I, I can imagine in the beginning it was like, you know, very in the weeds and, and kind of, you know, building, you know, f- fixing problems and kind of getting things going.
And then I can imagine as like your, or as the company grown and your role has like evolved over the four years, like I can imagine it was probably hard- Yeah...
but to like, to stay in the role for that long, considering almost just like you've seen so much and have done so much. Like- Yeah... how did, like how did you stay motivated? Yeah, totally.
I think what was really helpful was kind of like you said, the role really like evolving in discrete phases. Mm.
Um, I think sometimes like for other folks maybe, or situations, it could be like more just like random evolutions or spikes. [laughs] You know, like every day you're doing the same thing, but like on- Right...
a random Thursday you'll like be doing something randomly else. And so I think that could probably be more, maybe that's exciting to some people, but probably more like weird or frustrating or less coherent. Yeah.
Um, I think for me, the way I kind of thought about the different phases, and a lot of it was kind of like hindsight too.
Um, so it was less like totally intentional going into it, 'cause you can't always like see around corners. But I'd say in the early days it was very much like setting up those foundational functions that- Mm...
any company needs no matter what before they really think about much else, which was obviously the recruiting.Side and then the ops and finance side, and then eventually passing those onto folks who join kind of like within that first year of me being at the company who were like more full-time focused- Yeah...
on that, and customer success was one as well.
Um, and then after that, after those kind of like foundational functions were more covered or at least like kinda built out and passed on to people, um, I ended up focusing more on growth and marketing. Mm.
Um, since that was an area that obviously was important, but we didn't have like a point person for until we hired a marketing person. And then I ended up managing her throughout her time from product- Wow...
marketing lead to head of marketing. Um, and so that was really fun. She was great to work with, and the folks who reported to her as well.
So kind of doing all things marketing, um, and then also kind of thinking a little bit about product in different ways. I think that was something that, you know, it's a very buzzy, um, function- Mm...
and I think it was something that I actually didn't like- Like chief of staff. [laughs] Um, yeah, exactly. [laughs] Yeah, it's like the new hot thing, or I mean, the old hot thing.
Um, but I think it was something that I had obviously heard a lot about and people wanting to go into it, but I actually didn't personally, like it wasn't like, oh, I wanna be like a product person- Mm...
for, you know, no reason at all. [laughs] 'Cause I think a lot of times people will want these roles without like totally knowing why or what's involved. Mm.
And I think for me it was like, obviously, it sounds really interesting and important, but like I don't like wanna shove myself in there.
But because our CEO, he's a very product-minded person, um, and so he likes to get involved with product and adds a lot of value there, and product was really or still is really important to the company, um, as a function and that kinda like everybody was sort of contributing to it in different ways, even if they weren't explicitly a product manager.
And so I ended up seeing a lot of that. Um, and I think product ends up being more of like the strategic, like WID phase, going back to those like- Yeah... different, um, strengths.
And so I think it was less natural for me. But I think what was interesting is that I kind of felt, um, what was interesting to me was actually more the technical product side- Mm-hmm...
which I kind of discovered in my last year there. Um, and we were building out this, um, more B2B product, basically the semantic search marketplace for brands to find content creators on our platform.
And so, um, we were doing kind of like more of the novel AI things that were coming up at the time, like a year, two years, or a year and a half ago.
Um, and I had a background in math and computer science, but hadn't like really gone into it like in a dedicated way full-time. Yeah.
Um, but kind of missed it, I think, after a while, 'cause I think after college, I was like, "Oh, I'm so done." Yeah. Like, I never want to like do this [laughs] again.
Um, I also had like nightmares where my problem set isn't done. But like, um, I think after a while I was like, oh, I'm kind of like missing doing this. Mm-hmm.
And I was like reading textbooks and papers on my own as like AI became a bigger thing. My little brother is still in college, and so he was...
He's studying computer science and I think a minor in math, and my dad works in engineering, and we're all like very close.
Um, and my mom used to as well, and so we would talk about things, and I just kind of got more like technical and was like playing around with code myself, thinking about starting- Mm... my own company.
Like, not really like t- super seriously, but more just like playing around with different things.
And so, um, ended up doing more of the technical PM-ing in the early days of that product, which I really liked, actually. Mm. And I was like, um, I don't actually really like kind of like doing user experience.
I mean, I think that's very important, but I think, um, I'm not like a very design-oriented person. Like, I don't really think about like aesthetics. Like, my outfits and like my room- Yeah...
is just like pretty not aesthetic. [laughs] It's just like whatever it needs to be. Um, and so I think I'm just not like naturally like that.
But I think kind of like marrying like the user experience or the product with the technical side, kind of like getting more in the weeds was actually really interesting to me.
And so that kind of led to what I'm gonna be doing next. But I think that was like, um, an interesting kind of shift, too.
So basically, in summary, I think early on it was like those foundational functions, and I think those things are more like output oriented, so they're more like things you can kind of like- Mm... control. Um- Yeah...
like, you know, did you do the books? You know? There isn't like a, "Oh, I tried, but it didn't work" [laughs] or whatever.
You know, it's just like, "Oh, I did them," or like, "Did you respond to all the customer support emails?" Like, you know, you just kind of do it.
Um, it's less of like a growth thing, where it's like you could work really hard but just not get any users, and obviously that's still bad.
But I think with customer support, you can't be like working really hard responding to the emails and none of the [laughs] emails get responded to, 'cause like something... That would be really strange.
And so, um, I think that was like a comfortable on-ramp for me, having done mostly like output-oriented work and like more junior level roles before coming into this role, um, and feeling like, you know, things were more in my control or had a grasp of things, and then moving into more of that outcome-focused role and managing people around marketing and then kind of like dipping my toe into something that was like, um, pretty new, but I think pretty important for the company and pretty interesting to me personally.
And so that- Mm... was like kinda where I found some alignment, um, as well. It sounds like it was easy. Yeah. [laughs] Exactly. Just one, two, three. Yeah, exactly. Four years- Yeah...
just, you know, bang, bang, bang, boom. Um, tell me about a time when it wasn't easy.Yeah, that's a good question.
I think really, like, um honestly, what I felt and what I was kind of saying towards the end when I was like um leaving the company and like saying goodbye to everybody, um, I think like a lot of times for people, like work is like the worst part of their life.
They're like, oh, you know- Mm-hmm... it's Monday or like you know, whatever. It's the worst. Yeah, exactly. Um, or like whenever I would catch up with friends, like they would...
Their, the main drama in their life would be like, "Oh, like my work, I wanna quit," or, "My boss is this or that." Um, yeah. And I think the main drama in my life was always like outside of work, [laughs] um, you know?
And so, um, I think that was like very fortunate.
Like I felt like with work, even when things were like more difficult or when the company wasn't like growing as much as you would've liked, um, during certain periods of time, I think, um, what really helped was that our CEO, he was...
I think I'm like actually a pretty pessimistic person, I think especially when it comes to my own life.
I think I'm pretty good or hopefully pretty good at like cheering up friends, um, or like seeing like the positive side of their situation.
But I think for me, like I always like assume like the worst case scenario, you know? Like if my train is like a little bit delayed, I'm like, "Oh, I'm gonna totally miss my flight," or like whatever. Um- Same.
Yeah, exactly. [laughs] Like even if it's like a couple minutes, I'm like, "Well, maybe a couple minutes delay, could be like 20 minutes, and then that could turn into an hour, and then- Yeah...
I'll miss my flight," you know? And so I think I'm like a pretty pessimistic person and tend to like extrapolate negative data- Mm... pretty hard and not as much the positive.
But I think maybe that's like a common thing, you know, people always like focus on the negative, you know, or like see the worst parts about themselves or whatever. Um, but I think our CEO, he was just like...
And this was also like beyond our like kinda skills being complementary.
I think he was like just a very complementary-minded person, or may- maybe he was just like a healthy-minded person, [laughs] and I was like enough healthy-minded.
But you know, he had the good side in so, um, he was like really good at like, um... And he would tell me this, like was true throughout his life too, not just in the company. Mm.
Like it wasn't just like he was putting on a strong face or something. Like whenever like something, you know, negative happened to him, like obviously he would like notice it and process it and learn from it.
But he would kind of like honestly forget about it like after a few days or certainly a few weeks. Like whereas I think a lot of people, including myself, will tend to like ruminate on that. Mm-hmm.
Um, and so I think working with him and talking to him a lot and like, um, sometimes I'd bring things up like, "Oh, are you worried about like X, Y, Z?" Like he wouldn't be worried. Um, and that like helped me a lot.
Um, you know, it's kinda like if you have, if you're a little kid and you like go to your parents and you're like really worried, and they're like, "Oh, don't worry. Like that's totally fine," and you feel a lot better.
And so, um, I think that was like really helpful, just like kind of like hearing him like not be like not worried, like, "Oh," like, "Whatever," but like he had a very like educated way to think about it.
And it kind of felt like he was able to do what he could that was in his control, but like he wasn't super worried about it.
Like I think, um, like I guess like there's maybe like a different, different combinations of people who think about competitors.
Some people just like don't even know competitors exist [laughs] and they're just like delusional. Yeah. Maybe they're happy, but like that's pretty concerning still.
Um, some people, like no competitors exist, and they like obsess over it, and they're like really like depressed about it.
And I think our CEO was like the really good like quadrant of like he was actually super aware of all the competitors and honestly probably knew more about them than most people.
Um, but he wasn't like really worried about it, but not in like an arrogant way.
It was more just like, "Hey," like, "I'm un- I understand like what's different or what's better, what's worse about them, and I'm doing like what I think is like the right strategy.
You can't be better than someone in every single way." Yeah. "But like I'm kinda sticking to the strategy."
And so I think that was really helpful, um, actually like being able to like have more of that, like positivity, but like not like empty positivity.
'Cause if someone's just like, "Oh, don't worry about it," it's like, "Why? I should though," you know? But he had like good reasons for that.
And so I think that was like really helpful to kinda like keep that perspective in mind, even during like harder times.
And I think just like everybody was really good friends with everybody, I think, outside of work too, and just like really cared about people.
So even if there were like disagreements at work, like, you know, people would be like arguing pretty intensely, like, um, after, you know- Yeah...
during like the meetings, but then afterwards just like be totally like good and like good friends.
And so I think people were really able to like separate like the work and the not work of it all, um, because there was that like...
So I think if you're not friends outside of work, it's like I only know you o- in one context, and you're just screaming at me, and, or not screaming, but you know, disagreeing or whatever, um, in, in a meeting.
But if it's like, you know, like your siblings or something where like you can be mad at them and have a fight, but like you also have all these great memories of like- Mm-hmm...
everything fun that you guys do and all the good conversations you have or with parents or an SO or something, I think that's kind of what it felt like with the different team members. So that was also really helpful.
Yeah. On this like topic of outside of work, um, and you don't h- have to answer this if you don't want to, but you mentioned you were like, "Oh, I would talk to friends-" Yeah...
"and like they would say how their job was, you know, tough," or whatever. And then you had mentioned like, "Oh, like my drama was the stuff that was outside of work." Yeah.
Is that a function of because the role was really demanding and you weren't able to maybe like put a lot of time and care and resources in those other areas, or was it just like something else?
Yeah, that's a good question. I think growing up, like my focus was always like work or school, you know, obviously- Yeah... when I was younger.
Um, and I was just so focused on school, and I think also being an introvert, like there wasn't too much like that I was doing like for fun, like outside of school.
Especially during high school and even during college, like I would do like groups that were like a little bit like out of the pre-professional track, but like not really, honestly.
Um, and so like the, the most like non-pre-professional was like teaching kids computer science, and so like- [laughs]... it was still like pretty like academic in nature.
Um, and so I think I always like just focused a lot on work, and like knew how to deal with problems there or issues, or like always thought very positively about it, where I was like- Mm...
even if it's tough, like I feel like I'm gaining something, I'm learning something. Mm. Like this is like a useful, important part of my life.
And I think, um, a lot of times, like I remember in high school, I just like never exercised, and- Mm... that was like honestly in hindsight very bad and obviously finding balance like later on.
But I think-I kind of like de-emphasize a lot of things outside of work mostly just it was work and like some friendships, and I think everything else I was like not really sure like how to navigate, um- Mm... as well.
Um, and I think also, um, w- it's always been like this kind of evolving journey where like I remember when I went from high school, I really crafted my identity around my strengths where it was like, "Oh, I'm the person who's good at math," and like, "That's who I am," and like, that's great, and I was like the best in math at my high school.
But then moving into college at Harvard, it's like everybody was kind of like that, you know, especially if you're majoring in math or taking these harder math classes.
And so like half of you by definition are gonna be like below average- Yeah... and you've never d- y- haven't even been like top five percent instead of like top whatever one person before.
And so I think it was this process of like recreating my identity to be centered around interest.
Um, and I think kind of in the real world, like moving out to SF to like not living at home, like doing things more in person, it was like a little bit of like that same transitional period of like- Mm...
figuring out what are hobbies that I wanna do, like outside of work, like how do I become a balanced person, and I think that never came really naturally to me.
Even like we were talking before this about my sabbatical, but like I was like, "Oh, like sabbatical is great. Like you don't work. Like what could possibly go wrong?"
Especially if you like are able to do so financially, you don't have to worry about that. Um, but and my family was really supportive and friends, et cetera. But I was just like so miserable for a lot of it- Mm...
'cause I was like, "Oh, my whole identity was work," and like this was like, you know, just everything for me, and now it's kinda gone.
And so I think kind of like figuring out those things outside of work were like, um, kind of more challenging, I'd say, 'cause I had less of like a playbook for it- Mm...
and had less like reps in like thinking through it. But now you've got a couple. We gotta wrap it now. Yeah. Yeah, yeah. [laughs] So for the next sabbatical, I'm not saying you should do it. Yeah.
But, you know, um, the first rep I think is the hardest. Totally. Yeah, exactly, and I think like not fighting it and more just like- Mm... "Hey, this is what it is."
And, um, 'cause I think the worst thing is to be like, um, "Oh, like I'm kinda sabbaticaling, but I'm also kind of recruiting, and I really don't wanna like sabbatical, but I also really do," you know?
[laughs] And I think just being like, "Okay, like not recruiting for this period of time, and I'm gonna sabbatical, and here are my goals.
Here's like the countries I wanna visit or like skills I wanna learn or things like that." Um, so I think, yeah, definitely like kind of being more intentional- Yeah... that will be really helpful. Um,
is there anything else you wanna share about the chief of staff role or like tying, uh, yeah, identity to work or being the first employee or, uh, working f- four years in the role?
Is there anything else that you think that we like missed that you definitely wanna talk about?
Yeah, I think one thing I'll add that I think is maybe a little bit related to that point around like strengths and interests- Yeah...
and identity, um, and things like that is, um, I think like, you know, as a weird analogy, but I remember applying to college, and I think the conventional wisdom is to be like, "Oh, I'm gonna play a m- instrument and do a sport and be like the newspaper president or whatever, and then president of something else."
Um, and that's like great. That shows- Yeah... that you're like really high achieving and really smart and hardworking, but I think, um, there isn't really an identity there.
It's just like, "Oh, this is the person who does like three things and like does it like pretty okay," but like what really is the draw?
And I think kind of similarly, like in the quote, unquote, "real world" or within a company, I think chief of staff, obviously by definition your role is really diverse, and that's one of the benefits and one of the things that you're good at.
But I think also like kind of having this mind around like, "What is it that I want to be known for in this company- Mm... or in my career in general?"
Almost like, um, I had this one boss who I'm still really close to from when I was an intern in college, and he had us write...
It sounds like morbid and weird, but like he had us write our obituaries of- Oh, I've done it too. Yeah. Yeah. It's actually like a great exercise. Yeah. Um, and it's- Should find it. Yeah.
I don't know where it is- Exactly... but like I did do it. Like to see if it was like close- Yeah... you know. Yeah.
I think like and he was saying that like, um, you know, he's had many interns over the years, and it ends up not that they've like died obviously, [laughs] but like, um, they're all still living.
But like, you know, their lives have kind of like mirrored- Mm... like a lot of what they said.
And so I think kind of like being able to like work backwards from things, which I think is like just really important in general. It's like, you know, if you're trying to build something or- Yeah...
build a relationship with someone, like working backwards of like here's the goal of like how I want this sales or partnership or whatever relationship or even personal work relationship to be.
What should I do today to like set me up for that, and what should I do tomorrow, et cetera, et cetera? And so I think we're like, "Oh, I wanna run a marathon in like a, you know, a year or whatever.
Like, what is my training plan for each week to be able to build to that?" So I think similarly, like, um, with your story and your journey and your brand at that company of like, yes, I am chief of staff.
I am doing a lot of different things, and, um, people might not always know what I'm doing. But like how can I make it, um, so that I'm s- you know, obviously doing the things I gotta do- Yeah...
and that's diverse, but like also building towards that particular brand and being able to be known for some things.
I think if you're known for everything, you end up being known for nothing, unfortunately, even if you're really great and doing a lot of good work the whole time.
And I think related to that too is a lot of times people, um, as a chief of staff, like you mostly work with your principal, and so obviously- Mm...
they know everything you're doing, and they probably know what you're doing more than they know a- about anything else, [laughs] um, you know, in the company. But that's not really true for other people.
And so even if they're like well-intentioned and you have a good like friendship with them- Mm... they might be like, "Oh, what is, you know, this person doing?" You know? Mm.
Like, I mean, they seem to be working hard, but like what is it? And so I think kind of like finding ways to like almost manage up or like manage sideways- Mm...
or manage throughout the company of like sharing and showcasing things that you work on.
And I think, um, a lot of times it's like the chief of staff is really behind the scenes, and then the principal is the one to like if you write an investor update, they're the one to send it, and that makes a lot of sense because the investors- Mm...
would be like, "What is going on?" You know, otherwise. But I think when there is room for you to like be more of the face of that, I think our CEO- Mm...
was really supportive of me doing that and honestly like would go out of his way to think about ways for me to do that.
And, um, I think, you know, if you have a CEO who doesn't do that naturally, not like bad intention or anything, but just like falls off his radar- Mm...
I think kind of like-Being proactive yourself as chief of staff of, like, thinking about, like, um, yeah, I did all this work, and, like, obviously, you know, so and so principal is the one to send it out.
That makes sense.
But, like, how can I, like, share updates with people on, like, what I'm doing so that they can, like, share feedback or even just feel, like, authentically enrolled in my success because they feel like, you know, I'm asking them for feedback.
It's like, you know, if I have an idea and I just run with it, and then you're probably gonna, like, end up disagreeing with certain things, and you're like, "Ugh, why didn't Jess consult me?"
But if I'm like, "Hey, David, like, here's what I'm thinking," um, and then even if I, like, only, like, incorporate one or two of your comments- Yeah...
after I, like, present this project, you kinda feel ownership of it in some constructive way, and you want to support it 'cause you're like, like, "I gave feedback. I was involved. Like, Jess included me.
Like, this is, like, a little bit of my project, too. I want to see it succeed. Let me do whatever I can." And so I think doing that with your career, like, inside the company is really helpful. Okay. Um,
you mentioned about the new role, uh, but how would you say, like, your chief of staff role has helped you with this new role that you're about to take on? Yeah, totally.
So I think, um, one is, like, more directly, too, because actually the founders of, um, Beacons, they w- did their PhD program with the founders of Cartesia, which is the company I'm joining. Oh. So it was like- Yeah...
yeah, pretty direct. It was, like, kind of a funny story. Like, I was on sabbatical, not really thinking of... I was, like, in a yurt somewhere, like, on a [chuckles] you know, a vacation. Yeah.
Um, and my brother, um, he's graduating this year, but he- That's your younger brother? He's younger. Your younger brother. Yeah. Yeah. So he's six years younger, so he's... or six school years.
And so he's graduating, like, this year, but in December, and so he has, like, one more internship to do. Um, and he's technical, and so he's looking into, like, more machine learning research opportunities.
And he had just messaged me, and he was like, "Hey, have you heard of, like, Cartesia?" I was like, "Yeah, I've heard of them. Like, they're, like, a pretty big, buzzy, like, AI company."
And he was like, "Oh yeah, I just, like, had an interview, and it was, like, first round, but it was, like, with the CEO." I was like, "Oh, that's super cool."
Like, you know, usually it's passed off to, like, a recruiter or something. Um, and he was like, "Yeah." Like, he said that he knew the Beacons founders. They went to, like, Stanford together- Mm...
and he's, like, seen me around on LinkedIn, 'cause I think I was, like, liking different or reposting or whatever- Right... like, Beacons posts. Um, and so I was like, "Oh, cool.
I'm gonna be in SF, like, next week for something else, and we'll just, like, reach out and get coffee." Um, and so we did that, um, and then kind of like, um, started talking about, like, a potential role.
Initially it was more growth, and then now it's more, like, product and data ops, um, which is what I'm ending up doing. And we did a work trial to kind of, like, feel that out with the team. Mm.
And so, um, it ended up, like, working out really well, and I really enjoyed, like, doing that work trial, which I actually think is a really great idea to, like, find that mutual fit. Yeah. You know?
Like, actually, like, experience working at the company, and they can experience you working there and see if they kinda can see that fit. Totally. Um, and it feels very, like, natural, and so, um, that was great.
So that's kinda like a more direct, um, way. But I think, um, another way, too, is kind of, like, that technical product experience of, like, knowing, like, oh, this is actually...
'Cause I think I was someone who had, like, a lot of... Like, I think some people are like, "Oh, I wanna be a doctor, and that's, like, what I'm gonna be- Yeah...
and I'm single-handedly focused on that," or, "I'm gonna be a ballerina," or whatever. I think for me it was like a lot of things were interesting.
Like, there were a couple things that weren't, but, like, it honestly was like everything is, like, kind of pretty interesting.
Um, and so, um, I think kinda being able to, like, narrow things down a little bit of, like, here's what I don't wanna do or do wanna do, um, at Beacons, that was, like, really helpful.
Um, and I think also being able to, um...
I think what I really like, actually, is that the Beacons founders, obviously they're PhD, uh, folks, and so they kind of had this, like, very research-oriented mentality when it came to building a company, which I think was actually very unique and very useful and impactful.
So even things like thinking about, like, hypothesis testing instead of, like, oh, let me just try some random ideas and, like, see what works.
But, like, in a more structured way of, like, what's a hypothesis that I can, I can prove or disprove, um, with an experiment, you know, even outside of, like, a traditional, like, you know, research setting, but, like, at a company with growth or with really anything else.
And so I think that's, like, helped a lot of, like, matching, like, the type of culture and thinking that's happening at this other company and getting exposed to AI, too, and, like, figuring out- Mm...
like, what within different functions is, like, most interesting to me. Um, and so I think those things, like the interpersonal connection, like the kinda cultural similarity- Mm...
and the figuring out which function was, uh, most interesting to me were really helpful. Such a small world sometimes. Yeah, exactly. [laughs] Yeah, exactly. Yeah.
Um, is there anything else you wanna share to existing or aspiring chiefs of staff? Yeah.
I think honestly the chief of staff role is one that's super exciting because I think what people often think or maybe, like, get wrong is, like, they think of their career as, like, okay, I'm, you know, 22 years old, just graduated college.
At the peak of my career, I want to be, um, COO or whatever it is, um, CTO, et cetera. Yeah.
And I think they kinda see it as this, like, very much like, okay, I'm just gonna, like, keep climbing, like, this mountain to become COO or become whatever.
But I think actually what it really is, 'cause you might end up, like, climbing this mountain and then reaching the top and being like, oh my God, like, this is so ugly or terrible or, you know, whatever.
I'm, like, sick, and I spent my whole life up this mountain. Mm. I can't even get back down, you know, or even look at another mountain peak, um, whatever.
And so I think kind of, like, the way to, I would say, to think about it is more like you have this, like, fuzzy idea. Like, you're like, okay, I wanna be a C- COO rather than a CTO, 'cause that's, like, different. Yeah.
Or I wanna work in tech versus I wanna work in biotech or whatever. That's different.
So, like, a fuzzy idea of, like, which direction you wanna be, um, going into, so you're not, like, going after the whole world of things.
But I think a fuzzy direction, and then each step kinda thinking about that more is like almost like a journey of finding product market fit, 'cause it's, like, very much a seesaw. It's not just like you lock- Mm...
yourself in a room, and then you're, like, product market fit, you know? [chuckles] It's like you kinda launch things, and you're like, "Okay, this was good. This was bad. This is how I'm gonna change the product."
And then the market kinda changes, too, and then you, like, rebalance that, and that's very iterative.
And, you know, some people get to it, some people don't, but I think ideally in this case you do get to your career goals. But I think having, like, okay, this next job, like, it's not gonna be...
Maybe it is the end-all, be-all, but, like-If it's not, like what's one skill that I really want to learn- Mm... and what's one thing about myself that I want to learn? Of like- Mm...
um, here's, I learned, uh, maybe, you know, you hated the job or whatever, and, um, that seems like a wash, but it's like what did you learn? You learned that you didn't like, you know, this particular industry. Totally.
Yeah. Or you learned that you didn't like these particular types of people or culture.
Um, and so I think kind of like having that mindset, like nothing really feels like a wash, and then you don't end up like, you know, COO and being like, "Wait, I just worked 20 years, but I hate this," [laughs] or you know- Mm...
whatever. Um, or like I would, would have much rather been something else. And so I think that's like really helpful 'cause in college I was like very single-handedly focused on going into investment banking- Mm...
and private equity and then just like chilling there until MD and like being done with that. But obviously, like my whole life has not at all been very different from that.
And so I think, um, if I had kind of like just been like, "Okay, heads down, let's just become like an MD," because, you know, I don't know why. I think every- everybody at Harvard wanted to do that.
[laughs] Like that's their mentality. And so, um, I think kind of like, um, doing that, um, would've been pretty bad 'cause I probably would've not enjoyed myself and- Mm...
like ended up in this path that wasn't really aligned with me. But I think, you know, doing a banking internship and then picking your head up and being like, "Okay, cool. I learned these things.
Now I can open these doors, but like which of those doors do I actually wanna do based on like what I learned I was good at, what I learned I enjoyed?" Um, and finding the intersection of that.
And I think being really reflective at like each stage of your career or each job of your career, each experience, I think that's really helpful. One skill and one thing about yourself. I really like that.
That's like less about really like the role. Yeah. It's more about just like, hey, I have this hypothesis or I'm attempting to do these things. Yeah.
And like, you know, again, like obviously it matters whether the, like, how like how the work actually happens. Yeah.
But just in general if you're about this is like, like for me, it's like, you know, I've gotten a lot better at events. Yeah. And through that process I've learned like, uh, how to host more events. Yeah.
And then I've also learned about myself of like how to like be more confident. Yeah. And those are just things that like have happened, and not necessarily really a function of like, like the job.
It was just like more of like that- Yeah... those are, those are things that like were kind of like in my control or more- Totally... any that, that happened.
And so now there's all these other things that are happening, but like if I just look at those two things- Yeah... like that's like, that's worth the journey. Totally. Uh- Yeah. So, wow. Okay.
We covered a lot of ground here. Yeah. There's lots of different tests to look into. Um, and yeah, this has been so great, Jess. Yeah. And sounds like people can stay in touch with you on LinkedIn. Yeah.
Anything else you wanna leave us with? Yeah.
And I can drop my email like in the actual episode too, so people can reach out, like if they're looking to become a chief of staff or thinking about if that's right for them or, you know, thinking about what's next like after- Mm...
or how to make the most of their time as chief of staff, like always happy to chat about that. Amazing. Thank you so much, Jess. Yeah. Thank you so much. Woo.
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