What it was like to be employee #1 at a YC B2B startup
After leaving my first W-2 job to go back into founder mode, figure it might be interesting to share about life as employee #1
Having grown up in Silicon Valley and reading about tech news, I always knew about the “lore” behind Y Combinator (YC).
Paul Graham’s essays were quite legendary and I always found them to be incredibly thoughtful and on point.
I spent my 20s in non-profit, real estate, and education, so I was never really “in” tech besides having friends in tech.
From Sept 2019 to Sep 2021, I joined the Searchlight.ai team, led by Kerry and Anna Wang, and got my first taste of W-2 life (which I reflected briefly about here) and B2B tech startup life at the same time.
Of course, it was a wild ride with all the typical ups and downs of navigating ambiguity with a small group of people. Not everyone has the skillset to be an employee #1, so my intent is to illuminate what my experience was like beyond the soundbites and highlight reels.
BUT FIRST, the highlight reel (for context 😆).
TLDR of Searchlight
Talent Intelligence Platform (basically, helps companies find the best hires smarter and faster using data)
Team Size: 15 (as of this writing)
HQ: San Francisco + Remote
Leadership: 30U30 Founders
Funding: $20M; with $17m Series A, led by Keith Rabois
Read More on Techcrunch
G2 Reviews Here
Teams that implement Searchlight get:
+45% employee retention
+40% hire speed
+72% length of employee tenure
How I Arrived
In July 2018, a full year before I joined Searchlight, one of the folks on my team at Orenda Academy asked if it was ok if twin sisters from a YC Startup could come visit, shadow, and learn about the work we were doing teaching teens soft skills at summer camps.
Why?
These two sisters were trying to see if building a company around coaching/mental health might be viable. And our summer program was a mix of class curriculum and life coaching.
We figured, why not? It wouldn’t have changed what we were doing, so having two people be a fly on the wall couldn’t hurt.
They came, they watched, we chatted a bit, and we stayed in touch.
I offered the twins informal coaching, space to process and soundboard as they were figuring out what business they wanted to build in the midst of YC.
We spoke a handful of times and by September 2018, it seemed like they settled on a path and we fell out of touch.
In January 2019, my co-founder and I decided to wind down Orenda because we weren’t confident in the founder-business match. We were early in our careers and education services were a pretty low margin business. We thought that it might make more sense for us later in our careers, so we made the hard decision to wind down operations.
This led a lot of soul searching, exploration, and experimenting to figure out what my next reinvention would be.
In August 2019, I decided that I was finally ready to jump into the tech world. A fellow founder and friend, Candace Wu, nudged me to announce it publicly in case people in my network might be able to help. So I made a post on Facebook asking friends to help with my search, but was ultimately skeptical that it would lead to anything.
Within 24 hours of making the Facebook announcement, one of the sisters texted me.
It’s funny.
My text to Kerry was a soft way to say, “Hey, if it’s super early stage, I don’t think that’s my cup of tea right now.”
Clearly, she didn’t get the message, because her response was, “Let’s talk!!!”
I ended up shadowing Kerry and Anna at their office 2–3 times for a couple weeks so I could get the feel for what it’d be like to work with them.
I also told them that I was committed to seeing through the rest of my job hunt (I documented my results here) because I had never done it before.
Long story short, in September, I had 3 offers on the table, and I became Searchlight’s first hire.
Why Did I Join?
There was really only 1 other offer I was seriously considering besides Searchlight’s.
LiveRamp made one of the highest offers they made to SDRs (Sales Development Representative). I felt pretty good about the manager there, they ran a smooth interview process, and it felt validating to likely make >100k/year in my first W-2 job (base + performance).
One of the main things I was looking for in my next step was to be able to learn and be part of a bigger team. I didn’t want to be responsible for so many things after 10 years of founder-level work.
I called Kerry to let her know where I was at in the decision making process (leaning towards LiveRamp), but I wanted to give Searchlight the last say as a friendly courtesy.
They ended up changing the offer to a sales role (from Business Operations) and assured me that I’d be able to learn from their sales coach.
Direct learning from a seasoned sales vet? Higher base & performance comp? That checked off enough meaningful boxes for me and that’s what led me to join.
Early Pivot
Within 2 months, we all realized that I wasn’t in the right role (sales).
I wasn’t getting as much guidance as I needed from their sales coach and without any prior tech sales experience, it was hard to hit ground running.
According to Jim Collins in his book Good to Great, he talks about the concept of “First Who, Then What,” and that the best strategy is to have a busload of people who can adapt and perform brilliantly no matter what comes next.
The founders at Searchlight prioritized having me on the bus, knowing that we’d figure out how to best leverage my abilities along the way.
I ended up switching into Customer Success — making sure that our early adopting customers 1) were WOWed 2) knew how to get the most value from our platform 3) and had an outlet to talk about bugs, make feature requests, and guide our product development.
I ended up running/building the Customer Success function for the next 18 months until we hired our current Head of Customer Success.
Life as Employee #1
Different Hats
One of the most fun aspects about being an early employee is that there’s so much room to get involved in different things. Unofficial list of different hats I wore for various amounts of time:
Webinar project manager
Product Strategy/Development
Culture Strategy
Hiring manager
QA-er
Data project nerd
“Auto-magic” operations
Live chat support
Form-builder Extraordinaire
Customer Marketing
Content Producer
Vendor Manager
Coach
Orderer-of-office-snacks
One of the most enjoyable functions I served was as a strategic partner to the founders. The three of us had countless late nights at the office (pre-pandemic) where we’d talk about the high level direction of the company, sales strategy and messaging, proactive planning for key initiatives in the months ahead (hiring, big customers, fundraising, product launches, special projects). These huddles were part of the quintessential experience of startup life and I will remember those nights with fondness. The problems we were tackling weren’t easy, but it was fun to wade through with people you could trust and have a good time with.
Work-Life Balance
This shouldn’t surprise anyone, but startups require a lot of work! When we were less than 5 people, 10+ hour days were pretty normal, every customer request was important, every bug seemed existential, and every meeting needed to be maximized.
When COVID hit, 12+ was more normal as we (and probably the whole planet) scrambled to figure out what to do.
Once we started hiring, leading up to our Series A, it eased up a little to actual 8 hour days.
One of the things I’ve appreciated since day one has been our norms around work/life balance. Of course, it’s probably not the first thing people think of at a startup, but I found myself having better balance with this than my significant other who was working as a designer at Facebook.
She’d often get frustrated because she’d have meetings thrown on her calendar for the following morning, 10pm at night. She’d get criticism from other team members about not being responsive to messages being sent at similar hours.
Yeesh.
Meanwhile at Searchlight… our team agreed that after 5pm, no one is required to answer Slack messages except in emergencies. The expectation is that you’d get to those messages the following morning. And from memory, I only remember being asked to respond after work hours a few times during the crazy first few months after COVID shutdowns went into effect.
Culture
A lot of people talk about “culture add” or “cultural fit.” These probably mean different things to people, but ultimately, the culture of the team is shaped by everyone in the room/company based on what is 1) accepted/tolerated 2) discouraged 3) or celebrated.
In practice, that means everyone on the team has a voice in deciding how behaviors are responded to at any point.
Early on, I made multiple suggestions like creating a “winning” channel in Slack so that we could publicly celebrate each others’ successes (this was a call back to when I was running Orenda, my own team brought up how they didn’t feel like there was enough acknowledgement/affirmation/appreciation).
One of our early engineers suggested we also make an “oops” channel so that it would foster a norm around making mistakes and learning from them. It would reinforce the idea that mistakes are inevitable and that we value the dividends of learning over the temporary pain of a mistake.
I also made a suggestion around talking about “Personal Wins” in addition to our existing “Professional Wins” of the week because I wanted to make sure that there was room for the “humanity” of our lives. I didn’t want to be in an environment that felt sterile, cold, and transactional.
Down the road Kerry decided that we’d have team members decide on a rotating basis what we’d do during our weekly team dinners, a subtle way to share ownership, spark creativity/expression, and a way for the team to feel more ownership in shaping how we connect with each other.
Behind the scenes, myself and other team members encouraged the founders to take *real* vacations. Partly because we cared about their longevity, energy, and engagement, but also because we knew that it sets a tone with how the rest of the team thinks about taking time off. If the founders never take time off, it creates a subtle hint that no one else should be taking time off.
When I was running Customer Success and one of our biggest customers (contract value-wise) churned, I expected my head to be chopped off (kind of, not really). Of course, the team wasn’t happy about the news, but ultimately we ran a retrospective, documented what we thought went wrong, and identified the key things we could do to prevent it from happening again. This kind of response is what creates a problem-solving culture instead of a finger-pointing culture that is critical to create the psychological safety to make mistakes (they WILL happen, it’s just a matter of when).
Culture really starts at the top. Whatever the leaders and most senior employees allow/celebrate, those are likely the things that continue to perpetuate and become acceptable behavior. That’s why it’s so important early on to have the right people because they will continue to reinforce behaviors that fit the original vision of the founders to the newest hires much further down the road.
Which brings me to the next point.
Leadership
Even before I joined Searchlight, I was optimistic about the leadership. This is partly because I already knew Anna/Kerry prior and had coached them informally for a few months.
There are 5 core traits I think early stage leaders need to have (not exhaustive, but just a quick list from my experience) that Searchlight’s founders have in spades.
1. A Strong “Why”
When everything looks bad, when you’re pinned against a wall, when a pandemic hits and everyone stops buying software, what do you do? What will motivate you to find clarity or direction when everything looks bleak?
2. Humility
Great ideas can come from anyone, anywhere. Having a novice’ mindset helps you learn faster, helps you stay optimistic. Also, mistakes happen. Being able to acknowledge and own mistakes is incredibly rare and one of the things that make leaders trustworthy and worth following.
3. Resourcefulness
In startup life, ambiguity is the status quo, so it’s very o-k to not have the answer from the get go. What’s 100% necessary is the perseverance, creativity, and willingness to find the answer.
4. High Processing Speed
There’s an infinite amount of information available in this day and age. In the rush to make a startup succeed, there’s also a lot of things that can happen in a day, lots of meetings to debrief. The faster a leader digests and implements new information, the more of an edge they have. This is an advantage that compounds over time.
5. Willingness to get hands dirty
In the early stages of a company, there’s so much to do and a lot of it isn’t glamorous. Running payroll, manually pulling up metrics, QA-ing, fielding support tickets, buying gifts for key stakeholders, updating typos on the website, managing the team’s credit card limits… it just needs to get done.
But of all these traits, I think the rarest of these from a leadership perspective is #2 (humility), and both founders at Searchlight have an abundance here.
More often than not, I hear about leaders not listening, not taking feedback, not creating psychological safety and I think humility (or lack thereof) is a huge part of it.
Searchlight is incredibly lucky to have sharp, humble, and thoughtful founders. I truly believe it’s one of their competitive edges, it’s one of those intangibles that make a huge difference.
Why Did I leave?
In May 2020, I ran an experiment with my network. I was helping people understand more about their “Zone of Genius” and it got a decent amount of sign ups. After a year, I had done 100+ sessions, made a decent amount of revenue (without trying to make money), and it had an incredibly high NPS. It was surreal to experience demand pull for once, something I didn’t experience very frequently in my past ventures.
Even with a decent amount of success, the idea of venturing off on my own didn’t have enough appeal.
But in June 2021, one of the early supporters of my Zone of Genius work proposed the idea of building a school around Zone of Genius and asked me what I’d need in order to be excited to build it. A few conversations later, it seemed apparent that they wanted to angel invest in me building out this school.
Did not expect that.
As soon as the angel investor made the offer, I gave Anna/Kerry a heads up. I didn’t have enough clarity/conviction to give a hard yes or no, but I wanted them to be in the loop and be a part of the discussion.
It wasn’t the easiest decision. I had been a part of Searchlight… even before it was Searchlight, I felt a lot of ownership in the product and the company direction. We had built a fantastic culture, team, and we were also coming off the cusp of raising Series A funding.
Ultimately, by July, I made my decision to go for Zone of Genius because… how often do you come across an angel investor who wants to fund your side project? That and, the freedom and flexibility to define my own schedule as well as not needing to worry about runway for more than a year.
So here I am! Working on building Zone of Genius, full time, you can learn more about it here.
I exercised all my Searchlight options, and still support Searchlight on the side as the team heads into growth mode.
Post-Searchlight
Having been a part of Searchlight since the early days, as I mentioned, has created a huge sense of ownership. I got to play a huge role in shaping the product, processes, culture, and organizational habits, so I still wanted to be involved in a few ways.
Nowadays, I still hop on regular calls with Kerry to think through hairy people/strategy/hiring problems, I still own a small project with one of our customers, I’m still part of the team’s Slack channel so I’m still exposed to a lot of the company happenings. I still work with our Head of Customer Success (who I helped hire/onboard) to talk about strategic Customer Success priorities and plans.
Overall, I kept the parts that I felt excited about and am also good at.
I was/am super grateful that the team was open to transitioning me from a full-time employee to a consultant on the side — it’s not something that I hear people doing, so I wasn’t sure if they’d be open to it. Again, I think this speaks to the open-mindedness of the leadership there and willingness to just problem solve and make the most of their employee #1 leaving to work on their own company.
Closing Thoughts
Searchlight isn’t a perfect organization because no organization is perfect. But IMO, the most important things are there. The willingness to learn from mistakes, the desire to improve how things are done, and not punishing people punitively when mistakes happen.
We’ve not been immune to the challenges of hiring, we’ve had some hiccups with customers, had some launches/pilots not work as well as we wanted, we all dropped various balls at certain points… like I said, things aren’t “perfect.”
I think Searchlight gets a lot of the big things right and I think it’s evident in how far we’ve gotten, results we’ve driven for our customers when it comes to hiring efficiency and effectiveness, and why customers are routinely surprised when they find out that, “We’re only a team of 10!”
So, in closing, if you’re looking to join a down-to-earth team on a mission to make hiring more equitable, that has open-minded and sharp leaders, check out their careers page since they’re hiring a bunch, and maybe I’ll see you in our team’s Slack 😉
I also understand that this isn’t completely exhaustive of my entire experience at Searchlight, so if you have any further questions, feel free to ping me and I’d be happy to answer any questions you have about my experience.
As I’ve mentioned, I’m now working on Zone of Genius full time, if you’d like to learn more about it, check it out here!