The Job Searches That Landed Netflix, OpenAI, and Abridge

I'm talking to these companies that are AI native or looking for AI experts.

[music] I need to prove why I'm that AI person. Like, oh shoot, well, I haven't

person. Like, oh shoot, well, I haven't built an AI company from scratch. What

stories am I going to tell? Should I

explain that [music] I have a patent because that shows that I'm an innovator? The reality is like the way

innovator? The reality is like the way that you're going to come across most naturally [music] as is this person really a right fit is being able to show your thought process on the ground. The

most successful conversations that I had were when I wasn't trying to explain myself or brand myself in some way. It

was, hey, thinking about the problem that you as a company are working through and based on my own curiosity and research that I've been doing in relevant AI technology. This is how I'm thinking you might be approaching that.

This is how I would be curious to approach that. Is that how you approach

approach that. Is that how you approach that? Like where is my thinking going

that? Like where is my thinking going wrong?

Hi everyone, my name is Nicole Singhal.

I'm your host for the Skip podcast, the podcast dedicated to helping you advance in your tech career. Boy, advancing your tech career is complicated these days

and no more so than for those of you trying to look for a job, particularly an AI first job or an AI first company

role. And what I have found is the best

role. And what I have found is the best source of information often comes from people not about to embark in a job search but actually from people who just

recently made a decision to join a company and have actually joined.

Listening to their postmortem, shall we call it is really informative. And so as part of Skip Coach, which is a group that all of you listening to this can apply to, we had a conversation with

three leaders who had recently joined a bridge, Netflix, and Open AI. And

listening to their stories of what has changed, what's new in terms of interviewing, what companies are looking for, what they're not looking for was really, really informative. I hope you

enjoy the conversation that we had. And

if you want to be part of future conversations, just go to skip.coach in

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Welcome everyone. Uh I am terribly terribly excited to talk to you today um about one of the topics that came up in one of the conversations I had in a live event recently. I was talking to some

event recently. I was talking to some friends and they were like you know job searches are really hard but nobody ever talks about what it's like after you get the job. It's always this super fun,

the job. It's always this super fun, welcome to the new job. But no one ever talks about the difficulties of what it was like to actually go through each and

every one of those misses, wins, decisions, uh, and and thinking through these transitions. And so I'm joined by Ben,

transitions. And so I'm joined by Ben, Julia, and Janie, all of whom recently, uh, took new roles, exciting new roles actually, and went through this

transition. And they're all part of the

transition. And they're all part of the skip group. and we would love to share

skip group. and we would love to share kind of their stories, their learnings and also take questions from you. Uh for

those of you that happen to be joining us live today, we have a Substack going and uh is an opportunity for us to you know hear from people live around the questions they have as they're

contemplating job transitions. And as

we've talked about for the last 6 months, boy, the job market's really dicey and tricky and complicated and and and sort of quoteunquote fun to navigate. And so I'm I'm really excited

navigate. And so I'm I'm really excited about today's episode. So, welcome

everyone. Maybe Ben, I'll start with you. Maybe a quick introduction on kind

you. Maybe a quick introduction on kind of where you were, where you're headed, how long you've been in your new company, and and how long did it take?

>> Uh, yeah. So, hey everybody. I'm Ben

Drier. Most recently, I was working at Door Dash. I was there for about a year

Door Dash. I was there for about a year and a half helping build the new verticals business. So, things like

verticals business. So, things like grocery and retail. And then about 3 months ago, I moved over to Netflix. And

at Netflix, I'm leading our product organization focused on promotional assets and creative technology. What

that means is everything about how we actually promote the content on Netflix.

Think trailers, artwork, synopsis, the things that you see personalized to you on the platform or marketing that content offplatform. There's a huge

content offplatform. There's a huge engine that goes into doing that content justice. And we're building exciting

justice. And we're building exciting technology to make it happen.

>> How long did it take you to make this sort of transition from one to the other company? Was it something that was a

company? Was it something that was a long transition or was it something that kind of happened on the side?

>> It was I would say it was a long and I call it like a half passive half active effort. So I didn't leave my prior job

effort. So I didn't leave my prior job before looking for a new role. I knew

that there was something out there that I was yearning for that was going to push my growth, kind of push my evolution in the evolving AI landscape, that I wasn't quite getting out of my

prior role. And so, even though it was

prior role. And so, even though it was an exciting role, I felt like I was able to have impact, I was looking for what that next move was that was really going to propel the next phase in my career.

So, it was a long journey to ultimately like find the role that felt worth jumping to. And I'm pretty excited about

jumping to. And I'm pretty excited about where I land it.

>> So yeah, I'm gonna call you AI hungry.

I'm gonna call you like, hey, I just felt like I was AI hungry. I really felt like that was the driver for me making a move. Is that a fair is that a fair

move. Is that a fair is that a fair characterization?

>> That's right. And the way I put it is there's no right environment for like you have to be at X company or on Y team to be learning about AI. It's personally

I needed to find the right place that I was going to feel motivated and had the right support and momentum to do the sort of AI learning and growth that I personally wanted to do.

>> I see. I see. That's great. Julia, uh,

welcome. Um, I'd love to hear the same, you know, where were you and what were you thinking uh, you know, in terms of how long were you at the previous role and then, you know, what led you to sort of transition and how did it go?

>> So, hi everyone. I'm Julia. My most

recent role, I was at Pinterest for about nine years on the product team leading the the growth organization. I I

think four or five months ago joined OpenAI to focus on retention as an IC.

And so it was a pretty big transition.

Um I would say my job search overall spanned over the course of a year, although it was not active the the full-time. So I looked for a couple

full-time. So I looked for a couple months while I was still at Pinterest.

Um I knew I was ready to leave. I just

my own learning and growth had kind of felt like it hit a cap. Um looked for a couple months, didn't really have a clear sense of what I wanted. And so I ended up looking at roles that were

pretty similar to what I was doing at Pinterest, just in a different context.

It took sort of getting offers to realize that's not necessarily what I what I wanted. And so I decided to quit and do some soularching. So I took sort of six months off. Took a couple months

doing really really nothing and then um maybe three months of active looking before I landed the role at OpenAI. So a

year in total but yeah not not fully looking the whole time. This is a different uh archetype than Ben in the sense that you had had a long tenure at

a company and then you decided not only to search for a new role but you actually took time without you know a job search you know actively and you

know the there's always this anxiety that people have both when they're not being paid as well as like what if I can't get a job and what about the

optics of me like quote unquote not working, you know, and so the the kind of Ben model of looking a little bit on the side, making a decision and then

moving relatively quickly is sort of the the let's call it the default or the norm. What went through your head around

norm. What went through your head around like feeling like you were willing to sort of take that time off and reset when the market was moving as quickly as it was?

>> I think there were two parts of this for me. So my version of looking on the

me. So my version of looking on the side, I sort of end up thinking of that as me like testing the market like are people buying what I'm selling and got enough interest that I felt confident

that like okay I can get a a job if it if I need a job. But I also realized I just needed I'd been at Pinterest so long I just needed the space to really think deeply about what I wanted next.

like the roles that I was going for when I was more passively looking just weren't sitting right and I realized I just didn't have enough space to to realize like I definitely wanted to go

back to being an IC. Um I really wanted to be in a building role with a you know AI focused product to be able to learn that new set of skills and that kind of thing and I just didn't have that

clarity when I was grinding in a in a current role. So

current role. So >> related to that, I just want to build on this point around, hey, I felt like I wanted to, you know, do something different. Did you use that time off,

different. Did you use that time off, you know, to sort of quote unquote upgrade your skills, whether that was a reforge class or building a, you know,

website on the side using cloud code. I

mean, a lot of folks are like, "Look, I don't have time to upgrade my skill, but yet my skill needs to be slightly different because I want a job that's

slightly different. So, I'm going to use

slightly different. So, I'm going to use the hiatus not necessarily to travel and rest, but really to sort of go through that a personal boot camp, let's call

it." Did that enter your mind? Was that

it." Did that enter your mind? Was that

a was that some opportunity that was available to you? How did you think about retraining or upgrading or rethinking some of the skills? Yeah, I

kind of wish I said I would do a personal boot camp, but I did not. I was

definitely on the I was gardening in the afternoon and uh going to Target when no one else was there. So, yeah, I did not do that personally. I felt like for me at least it was more of the

self-discovery to figure out like what I wanted, what that would look like in a job and then kind of giving myself permission to go after it versus a rebuilding of skills.

>> Yeah. And obviously you went from Pinterest to OpenAI and and so it wasn't quote unquote necessary for you to demonstrate a skill that wasn't ab that was sort of absent from yourself, but I think that's always interesting to

understand like what are the different ways people spend their time and what worked and what didn't. Janie, welcome.

I I would love to hear your story around transition and where you were and then how long you you took to kind of get to the next.

>> Hi everyone, I'm Janie Lee. I'm the VP of product at a bridge. We're building

the clinical intelligence layer in healthcare, including in the patient clinician conversation. I've been here

clinician conversation. I've been here for just under six months now. And prior

to bridge, I spent about 4 and 1/2 years at Loom, which was an async video product. The first 2 and 1/2 years, it

product. The first 2 and 1/2 years, it was very much a PLG fast growing company. The last two years, we were

company. The last two years, we were acquired by Atlassian and so loved my time there. every six months felt like

time there. every six months felt like being at a different company and really really loved all the growth that I was able to see. I think towards the end I really had the itch to go somewhere that

was just completely AI native. I think I was lucky in my previous role that we were shipping a lot with AI, but I was probably spending 40% of my time

thinking about offense, but being a pre- AI company, I spending 60% of my time also thinking about defense, whether it's cannibalizing the business, and I

think very very much stuck in where a lot of the preAI companies are. And so I spent about I'd say six to eight weeks once I fully decided I was ready for

something new just going completely deep and figuring out where would I want to be and going through and putting in as much effort as I could. I did do it while I was still at my previous role,

but I think the effort and focus came over weekends, evenings, and was able to thankfully make it work. you know, this is a you're at one of the most interesting companies out there as a

head of product. It's obviously one of these AI growth stars. For those of you that don't know about a bridge, it's, you know, one of those companies that just continues to grow fueled largely by

the growth in, you know, AI technology and and it has a ton of domain expertise inside the building. And I think that you know the the process that you use

Janie the framework of saying look I'm in a company that's growing that's doing well I've had a reasonable tenure both in late stage at lassen and obviously in

growth stage which was loom prior to the acquisition and I think what what you focused on and to some extent Ben what you also articulated is a pretty focused

search around AI native or AI leaning kind of opportunities. Then of course you ended up at Netflix which people wouldn't say is naturally the the sort

of AI startup. Jenny you are absolutely at one of the the hottest companies out there. And so Jenny in your case when

there. And so Jenny in your case when you said I think I want to go AI native what was the process you use that you mentioned over that 6 to8 weeks to to

sort of identify those companies and and start like triangulating towards the right ones to even talk to. I think

that's always the challenge. Did you go to venture websites? Did you talk to friends? You know, how did you make your

friends? You know, how did you make your quote unquote list?

>> Yeah, it's a good question. I spent

probably just a full week, week and a half having, if I had to guess, 50 or 60 conversations just to figure out what is

my list of top five to 10 companies I just want to go all in on. And I'm very much a I need a small set of things to focus on. And so it was a really helpful

focus on. And so it was a really helpful process for me. And there's obviously the set of AI labs and where I spent a lot of time exploring also was across all of the applied AI companies which

ones were the ones I wanted to spend time on. And I think for a lot of these

time on. And I think for a lot of these jobs, they frequently aren't posted online, which means you need to have a lot of conversations. It was everyone

from, you know, I pulled out everyone in my rolodex. It was every VC I knew. I

my rolodex. It was every VC I knew. I

asked, "What are the best companies or more interesting companies that are top of mind for you?" I talked to friends who were at those companies to see what other companies they were exploring in

their job search and also previous mentors. And I think in those

mentors. And I think in those conversations there was a set of companies that rose to the top and came up frequently and that started to give me the beginnings of the list and from

there would do a lot of my own research on listening to the founders of those companies and speak about where they were going and getting to this own my own hypothesis of is this a really

strong applied AI company that I think one has some form of defensibility in 6 to 12 months and two for whether it's because of the people, the distribution or whatever reason I was really really

compelled to learn more about.

>> Did you stick to that criteria? Like did

you stay with like if it's not AI native and you essentially do a burndown of the broad list and then narrowed it down or did it end up evolving and expanding and you end up talking to companies that

weren't even AI native? Like how how true were you to your hypothesis?

>> It was pretty true. I said, "These are the five to 10 I'm most excited by. I'm

going to give everything I have to these five to 10. If it doesn't work, I'll go back to the drawing board and figure out what else I could do." But I think once I spent the week going really, really

broad, I really quickly shifted into let's give it a shot and see where it goes.

>> Ben, does you had a similar start in that you really wanted to lean into something that was AI native? How much

of how much did what Jaden described match your own experience and process that you used?

>> I used a lot of similar processes especially for understanding earlier stage like true AI native where is there the greatest opportunity and honestly I use probably the same sort of signals

that a lot of people use. Where are the VCs that I tend to respect choosing to put their time and attention and ultimately money? And two, where are

ultimately money? And two, where are people that I've met in my career that I really respect and feel like are constantly on the cutting edge choosing to spend their time and ultimately

committing themselves to? So that's how I navigated the early stage landscape. I

was trying to balance that with okay, what does the AI opportunity look like in latestage world? And the big thing for me that I was searching for was where does it feel like the approach to

AI in a company isn't just oh everybody seems to be doing this thing we should all look out for opportunities to layer it on top. It's where is there such a clear strategic business rationale for

why it's crucial for us to invest in AI transformation. And so it's a very

transformation. And so it's a very different sort of question that I was looking to answer when I was talking with later stage companies. And the only way to really get that is by talking to people. So to Janie's point, like I

people. So to Janie's point, like I wasn't going to job sites and just looking for where the job description sounded interesting. I was finding

sounded interesting. I was finding anybody at Microsoft, anybody at Netflix, anybody at some of these later stage companies and just trying to understand from them how is leadership

thinking about business strategy how where are you seeing celebration of investments in AI and like the sort of use cases that this company really cares about applying it to? And that was the

way that I kind of navigated my way into finding where are the pockets where they are truly motivated for the right reasons to make meaningful investments

into the AI landscape. I think that both of you are describing a very thoughtful, very networkheavy,

very coffee chat type process. Instead

of, you know, starting on LinkedIn and hitting apply now and hoping you get the call back, you're describing a look, in

the next handful of months, I want to enter market. As such, I want to make

enter market. As such, I want to make sure I'm being thoughtful around who I'm talking to. Even before I interview, I

talking to. Even before I interview, I want to have an understanding of how the company's approaching it, what the company's like, what the growth trajectory. So, I'm going to leverage my

trajectory. So, I'm going to leverage my network, the investors, etc. I think that many people that are listening to this might say, you know, that's great for, you know, sort of the Silicon

Valley elite, but, you know, I don't necessarily have that network. you know,

I don't have the 50 people that I could pick up the phone and talk to, you know, I don't have a former co-orker at Netflix. I don't have someone who is an

Netflix. I don't have someone who is an investor that I know at these top tier firms. How how did you end up opening those doors? And perhaps the question

those doors? And perhaps the question maybe more broadly is what advice do we have if you're currently working and you know wanting to eventually get to a new

role? What do I do to cultivate those

role? What do I do to cultivate those relationships in an authentic process that allows me to have those doors available to me when I do enter market?

Maybe I'll start with Janie, you because you you describe the 50 coffee meetings and then maybe I'll get Bennett and move to Julie on this one because this is a good one.

>> I mean, I think there's no harm in reaching out to people who are already there, but I think you need to figure out what is your wedge in or what is the

reason someone would speak to you. And I

probably get tens 50 messages in any [clears throat] given week for people wanting to reach out. And I'd say the range of content coming in looks very,

very different. I've had folks reach out

very different. I've had folks reach out to me cold having created an entire prototype with an idea they have about the product that we're building. That's

going to compel me to look at the message for more than 5 seconds. And if

I learn something new, I will take a call. And so I think there's a way to

call. And so I think there's a way to catch the attention of someone. And if

you think that 50 or 100 people also have the same email address as you, I think you have to send the email with the question of like why would someone respond to me in a sea of 50 to 100

emails. And I think the beauty is we

emails. And I think the beauty is we have so many tools at our fingertips to put in effort and create something that is really compelling for the recipient.

And so I think if if you think about one, you should do the cold outreach.

There's very very little to lose. I'd

say that's step I wouldn't even call it step one. That's step zero. And so don't

step one. That's step zero. And so don't ever just apply. You should always do the cold outreach. And then second, when you are doing the cold outreach, give people a reason to respond that looks

different from 49 other people who might be doing the same thing.

>> And how many of your conversations that you had were were kind of cold versus relationships that you had, you know, had and cultivated over the time?

>> In my most recent search, I think transparently probably less than 10%. I

think where it was cold, it was still through a warm intro, but I always made the ask of someone. And so I'd say that's the other bit is if you have a secondary connection, it also helps a

lot to have someone you know send the intro. It's definitely still warm, but I

intro. It's definitely still warm, but I think as you think about the rules and the companies, look for who your second connections are and ask for the intro.

>> Yeah. And Ben, how did you build that, you know, kind of relationship network so that it was available to you when the time came?

>> I couldn't agree more with Jamie. like

early now I feel very lucky that I spent years working at companies that now have broad networks and so I have some more natural connections to be able to tap into especially second and third degree

especially earlier on in my career I was cold calling the heck out of people and and what I found a different style is going to work for everybody for me I'm

not a natural networker it doesn't feel comfortable to me to reach out for a reason but the thing that guides me is curiosity I'm an incredibly naturally curious person. And the thing that feels

curious person. And the thing that feels most genuine to me is reaching out to have a conversation with somebody not because I'm looking for a connection or I'm looking for an in somewhere, but I'm legitimately interested to learn more

about the way they're thinking about something and the way that they're approaching something. And so I found

approaching something. And so I found that the personal style that worked best for me was doing the cold emails, accepting the fact that maybe I'm going to hear back from 10% of them, but the

10% that reach out resonated with the why behind why I really wanted to talk with them, not just somebody at the company that they worked at. Um, and

that that honestly that's what got me my first real job in product. And I think that's continued to be how I've built kind of an organic network over the years. Julia, you've been listening to

years. Julia, you've been listening to sort of the process in the pipeline that these two built, heavily network-based, very very focused on AIcentric

companies. You had mentioned your

companies. You had mentioned your interest was to be moving a little bit from a a hands indirect kind of a leadership role into a hands-on role and

you also had a deliberate search going.

What was your process like? How did you build your quote unquote pipeline and how much did it change as you went through your your journey?

>> Yeah, I think mine was definitely a little bit different than than Ben and Janie. So, when I was looking while I

Janie. So, when I was looking while I was still at Pinterest, it's a much trickier situation because you want to sort of be mindful of who you're telling that you're you're looking. And so, I

was doing much more of the sort of cold apply, you know, talking to sort of trusted people outside the company to to get leads on what was was out there.

Once I decided to leave, it became a lot easier to, you know, tell people that I was looking and I started getting a lot more inbound, I would say, of just opportunities that are out there that that people might have thought of me for. One thing that was different, I

for. One thing that was different, I think, also than the the stories we've heard so far so far is I found a lot of value from exec recruiters or sort of specialized recruiters. And I got

specialized recruiters. And I got connected with some of them, you know, a lot of you probably have messages in your your LinkedIn DMs from exact recruiters or recruiters over the years.

And so I sort of went back through those messages to find, you know, maybe someone had messaged me a year ago and now they're at a new spot and kind of responding and using that as like a warmer intro and then just taking a

bunch of calls. So the exec recruiters were really great at sort of understanding what I was looking for and trying to do that matching to opportunities that I wouldn't have thought about, wouldn't have known about cuz they weren't posted or just like

companies that weren't on my radar. So

the network was a big part of it, but it I also ended up with offers from places I had cold applied to or had gotten connected to from a sort of side recruiter.

>> And were the recruiter conversations useful to open up like, oh, I I know there's this company that's hiring that might be great for you, or were they useful to sort of figure out like, oh,

this is how the market might see you, Julia. this is the level, the seniority,

Julia. this is the level, the seniority, the skills, this is our suggestion as to which type of company to go after or void. How much

of the sort of guidance came from the recruiters or as you ended up deciding where to go, where did the guidance come from more broadly?

>> I think the guidance from recruiters on the market was interesting. It probably

wasn't a like a game-changing element for me. I just like found it interesting

for me. I just like found it interesting of like what kind of roles are out there, what they were seeing. It's

really nice when there's a recruiter too that's not at the company. They're it's

very much easier to see them like on your team than on the company's team.

Like their job is to just find, you know, the best person, but they also want to be able to place you for other roles if it's not going to work. So,

they have a sort of more like, yeah, we were playing for the the same side than it is when you're just speaking directly with the company. in terms of ultimately making decision if that's what you're asking off for guidance. It was um a lot

of sort of talking to trusted mentors, people who knew me really well and then really digging deep at OpenAI sort of once I had an offer to do some due diligence. I'm like, is this going to be

diligence. I'm like, is this going to be a good fit for me? I'm someone who I I tend to like to like get the role and then do like litigate if I want it versus doing a lot of the litigation up

front before I start the process. Now,

for the three of you, did you end up like looking at one or two offers and interviewing at a very small number of companies or did you end up like going

through a much broader pipeline? I'm

kind of looking for like what was the width of your pipeline? You know, I think people all the time have different approaches, which is the spray and prey model versus the very targeted rifle

shot model. You know, Julia, in your

shot model. You know, Julia, in your case, did you end up like being pretty narrow or did you go really broad in terms of the companies you talked to?

>> Probably somewhere in between. I

definitely wasn't like I need to work at an AI lab. I'm only talking to to these couple companies. I was mostly looking

couple companies. I was mostly looking for So, when I look at any role, I'm most interested in like the people.

Like, are the people there good? The

product itself. It's like, do I like the product, use the product, or can I at least understand like I need to understand the motivation behind the product? And then just like the personal

product? And then just like the personal growth opportunities like is this going to give me an opportunity to really be in a builder role again? And that could show up for me in a lot of different ways. So I was looking yeah somewhat

ways. So I was looking yeah somewhat broadly not not a full like anything goes but within that set of criteria I was flexible on sort of how that manifested >> and ultimately when you know there's a

question around where did the job come from in the end of the day you know in the open AI case did you just apply through the front door or were there folks that you knew through your

previous network or was that a venture introduction like how did you open that door I guess is the question >> so I had cold applied to a role in my first like while I was still at Pinterest, they had reached out to me

about an interview. I ended up being sick and so I had to cancel and then I just like fell off my radar and then they reached back out to me about this role like I guess it was like maybe 8 months later. I think I right once you

months later. I think I right once you sort of apply you're just in their system. So it wasn't it wasn't like a

system. So it wasn't it wasn't like a referral or sort of a network based I still think of it as somewhat of a a cold apply in that sense. So in some ways you were passive but you were

reached out because of your work at Pinterest when you were when you were there. Ben, in your case, you know,

there. Ben, in your case, you know, curious around the width of your pipeline, how broad did you go? And then

ultimately when it comes to Netflix, you know, where did that introduction ultimately come from?

>> Yeah. So, I think my approach tends to be I I almost have the opposite mindset from Julia maybe, which is I need to be so confident that I'm really excited about a role to be able to engage myself

in the interview process. So, I did a ton of upfront dating is what I'll call it. I took first, second, and third

it. I took first, second, and third calls trying to really understand a company and assess the fit of the company overall and then figure out if there was an interesting role. I did

very very little actual interviewing. By

the time I got to the interview phase, there was I'm trying to even remember if I technically interviewed at a second company this time around or if Netflix was the only place that I truly

interviewed. But I like having that

interviewed. But I like having that motivation that I really care about a role to be able to then put my best foot forward and really give it my all in the

interview process to secure the role.

And you asked, where did this role come from? Nicole, there's maybe where you

from? Nicole, there's maybe where you think this one came from, and then there's an original backstory here. So,

this this time around, I did happen to know somebody at Netflix in this organization that I ended up joining.

And so, that's where the conversation started 6 months ago about the role that I ended up taking. The reason I knew that person originally was because I called applied to Netflix 7 years ago.

And I almost joined Netflix. Primary

reason being I was so enthralled with the team impressed by the culture and the people and particularly the hiring manager at that time and the hiring

manager 7 years ago 6 years ago agreed to keep in touch with me and serve as a deacto mentor over time even though I ultimately decided not to join the team back then. And so all of this really

back then. And so all of this really traces back to a cold application on the Netflix website six or seven years ago.

That's that's really interesting and and I I love both of these points for a second. I want to just stay on it. You

second. I want to just stay on it. You

know, I think because I'm always interested in like what you do today influences what may happen tomorrow. That's why the whole property that we work on is called

skip because it's very much like careers are long-term and job searches are also long-term. Janie described look I want

long-term. Janie described look I want to when I became time to it only 10% of the people I talked to of the 40 or 50 are people that were new most of them

were were soft relationships and encounters that I had had so I had built that level of trust and I'd been on the receiving side of that as people were asking me questions as well and that was

the time you know Julia mentioned that you know because of the role that I had there were reachouts that were coming in through the LinkedIn etc and I was able to respond and even at the moment it

didn't work out it was actually important and Ben took it to the next level and said look 7 8 years later I still end up engaging in some conversation that happened in the past

so I think that all of this describes like look what we work on now has sort of a an impact in the future even if it doesn't seem timely or transactional or

valuable in the moment you know building this network creating this kind of connection and maintaining these relationships ultimately brings a lot of luck. You know at the highest level we

luck. You know at the highest level we could say oh yeah this was just a lucky thing that worked out but this luck was highly highly engineered. Now and Jenny in your case you know sim similarly when

we talk about the breadth of the pipeline and then ultimately where did a bridge come from was it a relationship that either reached out directly to you or you held in the past or was it

something that you literally kind of opened the door on or used a recruiter?

How did how did that go through? Similar

to to Julia, one of the the calls I had was with an exact search firm and a recruiter that I had known over the years and it just happened to line up with the the sets of companies I was

really interested in. And I think there's a piece to your point of of luck that the timing worked out when I originally created that list of 10 companies. Five of those probably

companies. Five of those probably weren't really valid companies because they weren't hiring or there wasn't necessarily a role fit. And so it was a lot of serendipity.

>> Do do you maybe not just for you but all three of you, do you maintain relationships with recruiters even as employed people? Like are you mentioned

employed people? Like are you mentioned that there's a recruiter that you knew?

Are you only talking to recruiters or venture folks while you're in transition or are you constantly, you know, having those discussions?

>> I'm constant, but probably not from the angle that you would think. I think

mostly as a person who's hiring, I frequently continue to stay in touch about the roles I'm now hiring for to see if there are folks in their network or in their conversations who are

looking for new roles. I think they tend to draw in a lot of really really high density talent and and folks who are actively looking who we may just not

know about. And so I found it helpful to

know about. And so I found it helpful to also share in the other direction the opportunities that I'd love to get on on their radar.

>> Ben, what about you? Are you who are you staying in touch with?

>> I'd say similarly, there are just recruiters that I've ended up building relationships with over time that I naturally end up checking back in with every couple years. But I'm not

constantly grabbing coffee or reaching out to say, "What are you seeing in the market?" It it's just not my style.

market?" It it's just not my style.

Well, it's not like how I've cultivated the relationships.

>> Got it. And and Julia, do you have like these authentic relationships that you maintain or is this just like just one thing too many for you to manage?

>> I think it's maybe more similar to Ben.

It's not a a constant thing. I've had

enough friends that are recruiters over the years that whenever time permits, I try to respond to these like when recruiters cold outreach me on LinkedIn, like I will do a pass like every couple

months and just go through and say like, "Thanks for thinking of me, not not interested right now." And I actually think that that has had some value just because so they they don't hear back

from so many people in general that they appreciate just even the like not looking type response. So I keep sort of a a very passive, you know, touch back

and forth with people, but sort of ends up being a large volume of people.

>> And you know, Ben, you mentioned this story that that I want to go back to, which is, you know, there was a relationship that you had even as you interviewed with with Netflix, but it

was years prior. You were impressed the manager and you kind of maintained some type of connection. I'm curious,

do you or others do the same thing?

Like, do you maintain connections with your past co-workers or even in the extreme case, people that you've interviewed that didn't work out that you were excited about? Is that a natural thing that any of you do?

>> Yes. And I I only do it when it feels natural is kind of the point to me. like

I I'm embarrassed to ask people to mentor me if it doesn't feel like a natural fit that gosh I respect and enjoy talking with this person so much that I really want them on my you know

personal board of directors. Similarly,

I've interviewed people over the years that whether it was the right fit and I extended an offer and they didn't accept or maybe it wasn't even the right fit in that role and we didn't extend an offer,

there are people that I just so clearly clicked with, respected their approach to product and like who they were as a person that I asked if they would be willing to stay connected. And you know,

it doesn't mean that we're grabbing coffee once a week. Um, you know, some of these people I check in with maybe every six months, every 12 months. I

want to be an open line for them if they're looking for advice or want a sounding board for things, but yeah, I I've maintained a lot of relationships that kind of just happened through a random interview process over the years.

>> Yeah, I love that point. And and part of the reason I'm I'm I'm making this and staying on this point for a few extra minutes is I I really feel that a lot of

the story that you folks mentioned wasn't the it wasn't a typical sales pipeline. It wasn't like look in order

pipeline. It wasn't like look in order for me to get a job I need to talk to 100 companies. And so if I apply to a

100 companies. And so if I apply to a hundred and I'll get through process at maybe 10 and maybe five are things that I'm willing to do then I'll go through it and boy that's going to take a bunch

of time. I'll have to quit and instead

of time. I'll have to quit and instead it was like this careful cultivation and then a very rifle very targeted search that made sense. And so when you're

cultivating those conversations it has a lot to do with those relationships that you've built over the years or in your current employer or how you think about

past relationships, mentors etc. Skip as a community where you folks are members, you know, it's a it's now it's over 100 people, but in the initial stages there

were a few dozen. Almost everyone that were in the few dozen were people that had interviewed at one of my previous jobs and actually had chosen not to take the job, which is sort of a hilarious

start to the group because I was very excited because the company was in hyperrowth. We were able to recruit and

hyperrowth. We were able to recruit and talk to some of the best in Silicon Valley and they would come and they would interview but for a variety of reasons it may not have worked out but the ones that really caught my eye kind

of the reverse situation what you described Ben are the ones that I stayed in touch with cuz I said look you know though it didn't work out here and though you chose someplace else that

made sense and so you rejected us I would love to be able to sort of stay on your journey to see where you went and see if we can be helpful or I can be helpful not for the purposes of trying

to somehow hope that they fail in their next role and they come back. It was

much more of a genuine understanding like look, they were strong enough for us to give them an offer. Those are

folks that over time I'd like to be part of their orbit either to help them and perhaps they may help me and I would like to learn from them. And so I I just feel like there's so many opportunities

in our current workplace or in our current neighborhood or in our current social circles or even through you know podcasters and other there's so many opportunities to build those

relationships that will help you when you need it. But that is sort of genuine networking and I I love the fact that that was such a core part of the search that you folks did. I'm going to

transition for a second over to interviewing because I think that, you know, the a good chunk of questions that are coming in, you know, are based on,

you know, what what worked, what didn't, what was a surprise, etc. So maybe I'll I'll I'll throw this up for grabs, but you know, maybe I'll start by saying like when you went through this

interview process, you all had a perception of what the process would look like and and then you ended up seeing what it ended up being and obviously you've talked to a lot of people that were going through process

at the same time. So maybe you can identify what was kind of the most surprising parts of it or perhaps the most notable as you think through guidance for others that are maybe

preparing for an interview. Julia, maybe

I'll start with you particularly because you went through the open AI process.

It's an a process that a lot of people are contemplating. Any surprises or any

are contemplating. Any surprises or any gotchas or any tips and techniques and and things that you want to make sure people are thinking through? So I think with the OpenAI process, there are parts of it that look very similar to what you

would expect with other product processes and other parts that are maybe a little different. So they have the the typical slate of sort of PM fundamental interviews, you know, product sense,

product execution, etc. You should expect them to be, you know, AI focused versus design a alarm clock for the blind. Like they're going to be a little

blind. Like they're going to be a little bit more specific. One thing that was very different though that I ended up enjoying a lot was that the crossf functional interviews and the later loops were almost all also sort of case

study live working sessions. Um so

instead of the behavioral tell me about a time when it was like here's a problem we're working on just like how would you start and it was either things that they had done very recently or were actually thinking about and that was great for me

because it broke me out of the sort of typical interview mindset. you got to see what it would be like to actually work with this person on the other side, which was really useful information for me. And I think I got to show up in just

me. And I think I got to show up in just a much more of like my natural habitat than this like contrived story about something I did in the past. So, I found their process to be much more focused on

demonstrating what you can do today versus just like regurgitating what you've done in the past.

>> We'll we'll come back to that. But but

what I'm hearing from you is the storytelling aspect that a lot of us prepare for. What did you do in the

prepare for. What did you do in the past? What problems did you solve etc

past? What problems did you solve etc perhaps were less relevant than you being thrown into kind of a a you know almost like a problem solving or working

session. And so it was less about you

session. And so it was less about you know how did this work at in your case Pinterest and more about you know imagine if you were struggling with is what questions would you ask etc. Is that a is that a fair way of

understanding? It's like sort of what

understanding? It's like sort of what what you've felt played out at OpenAI.

>> Exactly. Yeah. I think that the set of behavioral questions I got are things about my past I interpreted as being demonstrated at making sure that I was someone who had been in the weeds enough

in my past role and that I was going to be okay as a as an IC. like that I really wanted to be an IC and could show that I had operated at least with some of that mindset

historically but yeah most 90 plus% of it is sort of live problem solving >> interesting so it was less about give me examples where you were hands-on and

more about here's the problem how would you solve and then they were able to glean is this person you know essentially in the weeds or not in the way they answered the question

>> I think so yes an example like the engineering cross functional interview right I was sort of just getting yeah pushed to go deeper and deeper deeper on like know specifically what would you

build like what's the first experiment what are the groups like what is the behav you know just um trying to make sure that you could show that depth >> yeah that's interesting and and Ben tell me a little bit about this sort of

question around storytelling and you know describing the past versus describing for example an AI specific skill a lot of people are asking you

know how AI did you have, you know, and then perhaps how hands-on like walk me through how you thought about preparing and what was the surprise.

>> It was a hilarious emotional journey is the way that I'll put it. I think I I I felt this pressure of, oh gosh, I'm talking to these companies that are AI native or looking for AI experts and so

I need to prove why I'm that AI person.

And I'm like, oh shoot, well, I haven't built an AI company from scratch. What

stories am I going to tell? And I had some early things that I was doing of I'm like, I don't Oh, I have a I have a patent for work that I did in the past.

Like, should I explain that I have a patent because that shows that I'm an innovator? Like, it's it's this branding

innovator? Like, it's it's this branding exercise that I felt the pressure to go through very early on. And the reality is like the to Julia's point, the way that you're going to come across most

naturally as is this person really a right fit is being able to show your thought process on the ground. And so I I found that actually the most

successful conversations that I had were when I wasn't trying to explain myself or brand myself in some way. It was hey thinking about the problem that you as a

company are working through and based on my own curiosity and research that I've been doing in relevant AI technology.

This is how I'm thinking you might be approaching that. This is how I would be

approaching that. This is how I would be curious to approach that. Is that how you approach that? like where is my thinking going wrong? And it it was really in being able to engage with

problems that that I felt like teams were able to assess whether I was really going to be the right thought partner for solving them.

>> Did you end up having like a sort of a longer take-home or uh you know an exercise which really kind of showcased that thinking.

>> I know people have hot opinions about the value of take whether it's worth doing takeh homes. Uh, I love a good takehome when I'm interviewing because it gives me the opportunity to really be

able to deeply engage with these problems. And this was one where so my my experience interviewing with Netflix, I had already had a couple, you know, crossunctional one-on-one more behavioral interviews and I actually got

feedback after one of the interviews from the recruiter which is very generous. They said, "You didn't come

generous. They said, "You didn't come across as showcasing your AI mindset in how you approached that problem." I'm

like, "That's fair." It's also because to be honest like I didn't really have an AI mindset when I tackled that problem in the past. But so I took it as the gauntlet for okay when I get into this homework I need to be able to demonstrate that I can engage deeply

with the AI aspects and an AI first approach to this problem. And that

didn't mean that I already had to have all of the experience and paradigms that I could apply on top of it. I took it as a challenge to say how deep could I go?

how much could I really learn about relevant AI technologies that maybe I wouldn't have even considered 2 years ago that now are the obvious way that I need to approach the problem and then there's maybe one element that I had

thought less about in the past that I tried to apply more now which is that the technology is evolving so quickly that to say uh I understand the tech and

how it's going to apply here so this is the right solution you're going to be stale 6 months from now and so instead I had to actually engage with that as like another dynamic in the problem solving

itself which is this is what we know about the technology today is where it seems like the technology is evolving the most quickly and where I would expect the greatest advances to be but to be honest who knows like we don't

know where the research is necessarily going and how quickly new capabilities are going to be unlocked so this is how I would think about setting up a team to actually engage with that evolving technology and the path of well what if

this problem gets solved for us 6 months from now versus what if Nobody has built that technology 6 months from now. So it

was it was a different way of scenario planning and like thinking through what strategic execution means in a world with evolving capabilities. I think

there's such gold in this point, Ben, that I want to make sure that we emphasize, which is the authentic curiosity

and the questions and the humility to essentially note that, you know, I don't know, but here's how I would approach

it. Is it relatively unobvious way to

it. Is it relatively unobvious way to conduct an interview? You know, if you think about it, if I'm going to ask you a series of questions in an interview, you think about SAT preparation. It's

either A, B, C, or D. You're there is no like, I don't know, let's talk about it.

But it turns out there's a lot of power in nuance because in reality of the scenario that you're working through, a lot of these questions are unanswerable.

A lot of these you don't have enough context to be able to really nail it.

And so, they want to hear how you think.

And when they see that you're open and thinking through and dealing with suggestion and changing it or that recognize that that technology changes and your learning will change, it gives

people a sense that hey, this is the type of person who comes across as a problem solver that would fit in our environment. And that also sort of

environment. And that also sort of applies to your note, Julia. I I'm I'm curious because you're in the most AI native art company you could argue and you went from Pinterest which is not

known to be AI native. You must have had quite a bit of anxiety that you know Ben also shared around hey how am I going to come across as like AI you know expert

in this interview? How did you end up like what turned out to be the secret sauce or did you end up having to brush up or prep on this or how did that end up playing out?

>> When I was going through the opening interview loops, I made sure that I was yeah going much deeper than I would have normally gone on the announcements they were putting out, reading like maybe the

papers behind the announcements, that kind of stuff to to try to build my own inner working knowledge. But one thing I think I found is that at least on the product side and I'm, you know, I'm still in a growth focused role at

OpenAI, but the knowledge that they're missing is not necessarily AI knowledge.

Like I think I had a skill set around growth and and doing product in a different way that sort of was able to complement what people inside the building that had been there for a while could already do. And so I I didn't get

the sense that they were looking for an AI expert, but somebody who, you know, could have the ability to sort of learn and think in sort of new and novel ways, if that makes sense. So it didn't it

didn't end up being a huge a huge thing.

Like it was much less important at least at OpenAI than I had anticipated.

>> Yeah. Also slightly unintuitive. And you

know, I'm curious Janie, you know, you're this question would apply very much to you. I mean, you're one of the hottest AI companies out there. You also

came from Atlassian and Lube which wasn't necessarily companies that were known for being AI first yet you had to you were targeting these first AI AI first companies and so a how did you

think about the prep to demonstrate your AI knowledge and then as you ended up unfolding not only was it an AI first company but it was a head of product role so something that was a fairly

substantive uh leadership position so you were probably being asked on two fronts And those were the kind of roles you were hunting as well. So I'm really curious around how you did the prep and

what ended up playing out.

>> On the prep side, I really anchored on the things at previous companies, whether at Loom when we were shipping some of our first AI features or at Open Door when I was primarily working with

our ML pricing teams on learnings there that extend to how I think about shipping product now. And then I think for just broader prep, similar to Julia,

just did a lot a lot of reading to get smarter. And so I do think there is,

smarter. And so I do think there is, especially coming from a nonI native company, a lot of prep that I think helps you be a lot more dangerous. And

in the process itself, similar to Ben, I love a take-home or a whiteboarding session. It's also a good signal for me

session. It's also a good signal for me to figure out like am I getting excited about this work and can I see myself doing this 5 days a week and in the

approach process we had a whiteboard session on something that was very specific to healthcare and I had no experience with healthcare but I I

actually think doing a take-home now in the age of AI is incredibly fun because you can become an expert a lot quicker and also go through a lot more content

and depth in a much shorter period of time. And I think that's where I got to

time. And I think that's where I got to showcase how would I actually do the job. And so did deep research across

job. And so did deep research across multiple products to learn about this very very specific use case and topic that we were looking at and within you

know an hour or two of reading became deep enough to know what it was when two hours ago I didn't know what the whiteboarding topic was about and then got really curious. I couldn't find an

existing version of the product online.

So, I scoured through YouTube videos of the founder speaking. Found a sample of the product and started creating mocks and prototypes of what this would look like. And then started thinking like as

like. And then started thinking like as if I were a PM at the company, what would it take to ship this thing? How

would I actually commercialize or monetize it? and probably over the

monetize it? and probably over the course of a weekend went through the whole idea to commercializing plan, created a prototype and I think got

really really deep in what that would look like and in an AI first world you have to inevitably answer things like what would it take to ship this thing?

What do evals actually look like? And if

you just force yourself to go to go through the endto-end process of shipping a product at the company you're looking to be at, I think you inherently both have to learn yourself a lot about

the company, but also about all the AI considerations you might not have in your old job. But you also have an opportunity to show your ability to learn and think in the context of

already being there. And I I'd encourage everyone who is going through a process with a take-home to go very very deep if you know when I I I think my recruiting

partner told me I was in over 120 interviews in Q4. When I think about what I've seen in some of the patterns, I feel like prototypes are the standard now in any take-home. But what the lens

I look at it at with is is this a prototype I could have created myself in 30 minutes or is this someone who's thought really deeply and has gone above and beyond that showcases that they they

can think about what it actually means to ship at at a bridge. And so I think especially as tools are getting better it seems like weekly are you taking advantage of them and are you going

really really deep and taking on the mindset of a PM who's already here?

There's a balance between showing acumen in real time and being able to apply

oneself to a problem at the company and pedigree and brand. And what the three of you are essentially saying is the

pendulum for a variety of reasons have relatively significantly shifted towards demonstration of skill problem solving

and less about where you've been, what you've done, what title you've held in the past. That is a highly optimistic

the past. That is a highly optimistic point for those that perhaps have not had the opportunity to work for, you know, these quote unquote brand names.

Now, on the flip, the brands help them connect with people, open up opportunities, you know, explore positions, bounce ideas, help shape the pipeline, etc. So, there's a balance. Of

course, it's not, you know, people that are completely unknown that are able to open these doors, but that the today, if you have the ability to demonstrate with your own hands how you think and

how to solve the problem at the company that's in front of you through some research, through some reading and target a handful of companies that have open roles, you can really stand out in

process. That's that's what I'm hearing.

process. That's that's what I'm hearing.

I would love as we kind of wrap up here, maybe each of you to give kind of a single takeaway as to like what piece of advice do you have for our group

listening to this, contemplating a search perhaps now, actively or perhaps in the in the coming months of 2026?

What what advice do you have that you wish you perhaps had when you were going through your own, you know, this past year? um what what anything come to mind

year? um what what anything come to mind that you want to want to that we haven't covered so far?

>> I mean I think for me what ended up being the key to my job search and like landing in a role that I felt really good about was the the sort of soularching piece about what I wanted

and being okay with where that landed even though it was different. I think a lot of people think of, you know, I had a a big team at Pinterest, so moving from like a director role with a big

team to an IC role as like a like a step back. And I ended up really not thinking

back. And I ended up really not thinking about it that way. Like an IC role is just a very different type of role than I had before. The sort of, you know, constraints of my life at the time were different than I had before. And so I

think just getting comfortable with what it is that you want up front would have probably saved me a lot of time from that that initial search I did that was a little bit more undirected when I wasn't really clear with myself about

what I actually wanted or needed for for this stage of career in life. So if you have the the space to do that upfront, I think it'd be really helpful.

>> Yeah. I mean there's a lot of courage in your story, Julia. Courage to sort of perhaps take a role that that you know in the past was something that you held.

courage to take some time off even though there wasn't a clear kind of clarity on what was next. I I love I love your your journey, Ben.

>> Yeah, I think maybe echoing similar sentiments to what Jamie was mentioning to me, especially this phase in my career, I'm realizing has to be anchored in following the fun and following the

genuine curiosity. And it's so easy in

genuine curiosity. And it's so easy in this moment looking at the job landscape to try to look for where is the prestige, where do people seem to say that you can learn the most. But at

least personally, the the motivation is going to come from being so genuinely interested in the problem to be solved that it feels natural that you're going to learn something there. And I think that's something that maybe I knew in

the back of my mind going into the process and ultimately was like the single greatest decision-m like factor when it came down to really choosing a job.

>> And and Jamie, as we close out here, you know, you're obviously growing your team, so you're in hiring mode. you're

on the opposite side of the table now as you think about advising people that come to you. What counsel do you have now that you've gone through this journey? Yeah, I mean I recognize it's a

journey? Yeah, I mean I recognize it's a very very noisy and and busy market. And

I think in a world that feels so noisy, I'd say, you know, the the moments where I'm so impressed or so thrilled to talk to candidates is the high agency, high

effort. Has this person put them the

effort. Has this person put them the themselves in the shoes of someone who's already here? and have they shown and

already here? and have they shown and demonstrated real excitement, curiosity about what it would be to to build a product here. And so I think for for

product here. And so I think for for folks who have the sets of companies that they are potentially curious about or excited by, I'd really encourage the the depth. And it's become, I think,

the depth. And it's become, I think, easier than ever and probably more fun than ever to actually do those things in a way that I think allows you to get a lot closer to learning about the product

and building it before you even get in.

And so would really encourage folks to to use the tools at pretty much all of our fingertips right now.

>> Well, Ben, Jamie, Julia, thank you so much for sharing your stories and for being available for our our community and our group here. I'll share out a

recording of this for those of you that didn't get a chance to watch it and uh look forward to our conversation next month. Thanks again and enjoy the rest

month. Thanks again and enjoy the rest of your weekend.