Startup Recruiting Quintiessentials
A comprehensive guide for new grads trying to break into early stage software companies for business-focused positions.
I just received a full-time partnerships offer to join Whatnot, one of the fastest growing marketplace startups in the US.
Whatnot is a Series E livestream commerce platform disrupting traditional shopping experiences. I believe that an environment like Whatnot sets me up well for my current goal of founding a consumer company while safely adjusting for risk.
Let’s take a second to clap it up for me.
I know you didn’t actually clap; you’re just going to keep reading because you’re optimizing for efficiency. That’s totally okay, but do feel free to congratulate me with a charitable Venmo donation (@justinbguo).
I know you didn’t Venmo either. What an impatient society we live in.
New grad startup recruiting can be difficult and opaque, especially for business roles. Every hire needs to be valuable, so companies often index on candidates with more industry experience. Additionally, I found that hiring is significantly more focused on technical functions than it is for GTM.
To secure a business role at a startup, I had a ton to figure out by myself with the help of my friends and mentors. Now, I want to redistribute that knowledge back to you.
In this piece, I cover a framework demystifying startup recruiting for business new grads, resources and tools I personally used, and some of my anecdotal experiences.
As this was my first time recruiting, take everything here with a grain of salt. This essay only exists to give you a starting point with your own process.
Common Misconceptions
The word “startup” often triggers assumptions about working for 3 smelly Waterloo/Stanford dropouts that code B2B AI SaaS in a garage.
I want to clarify an important point here: maturity often mitigates the misconceptions that people have about startups.
Startup myths and how they change over time:
“Startups are risky” — It’s statistically true that most early startups fail, but generally there is very little existential risk past Series C. If you join at the right time, you’ll work in a dynamic growth environment without fear of the company exploding. If your startup is venture-backed by reputable investors, their chance of failure overall drops to 33%, with the other 66% breaking even or producing upside.
The riskiest part of startups is the potential opportunity cost if you join the wrong one, which is why it’s important to choose carefully. You don’t want to spend years at a startup that fails to find product-market fit or grow appropriately, when you could be learning more in another environment.
“Startup work is unstructured” — If you join early, you will likely be expected to wear multiple hats (e.g. product and sales) and navigate ambiguous work. But as hiring ramps up, the isolation of roles and responsibilities becomes much more prominent.
“Startups have no work-life balance” — If you join early and the founders aren’t grinding on the weekends, it’s probably going to fail. Later stage is still relatively demanding, but WLB is more balanced because there’s less work per person.
“Startups pay poorly” — Earlier on, your compensation is primarily based on equity, so a temporary stint of ramen and ice cubes for dinner isn’t out of the question. Later on, established startups need to pay competitively to Big Tech in order to incentivize top talent to join. However, the employee earnings will shift more towards salary and benefits than equity.
Business Roles at Startups
Startup are very easy to understand.
Build a great product.
Sell it to customers.
Listen to customer needs.
Build a better product.
Sell it more.
As someone on the business side, your main job in the flywheel is the selling part. These business roles are execution-centric and objectively measured by revenue going up and right. If you want to do sexy “strategy” stuff, go join a consulting firm.
If that wasn’t clear enough, you will be working in sales.
Don’t get too caught up in the title. You can call it Go-to-market (GTM), Growth, Sales Development Representative (SDR), Customer Success, or Partnerships. It’s basically all a form of sales.
I believe sales is actually an incredibly underrated skill to learn.
For one, almost every important career-defining moment is some version of sales. Fundraising from investors is sales, hiring the best people is sales, interviewing is selling yourself, promoting a product is sales, pitching a project to a VP is sales, selling your company to an acquirer is sales, and convincing your friends to go to Costa Rica with you is sales. Sales is much broader than customer acquisition.
For two (has anyone ever said that?), as AI initially lowers the barrier towards building software, the alpha is instead shifting to distribution. Capturing attention, building relationships, and negotiating deals with human beings is more important than ever.
For three (I’m running with this), leverage exists in learning sales because it sounds unsexy, which wards off ambitious people in favor of more prestigious paths. Despite the work being comparably (or more) important, there is 50x more competition in the new grad APM/IB/Consulting market than the new grad SDR market. By entering sales, you can build valuable skills that many of your peers might lack.
My personal career philosophy is governed by working backwards from a successful version of myself. My long-term goal is to be a founder, where selling is most of the job. I’ve talked to a fair share of founders, and many regret at least not trying sales out in their 20’s when there wasn’t much to lose.
Why not you?
Startup Recruiting Overview
I would approach startup recruiting like a funnel of sequential questions. You shouldn’t move onto the next question until you can answer the previous one well.
Using my 4-year degree in Google Slides, I created this pyramid to better visualize this process.
Again, I would like to emphasize the order of the funnel is very important. Too many people (+ a former version of myself) used to prepare for interviews without being able to get them in the first place. Don’t waste your time. Be patient and only move on when you have the current question answered.
Let’s dive into it.
1: Are startups for you?
This is the first and most important question to ask yourself. Startups require a high degree of conviction and intrinsic motivation. If you just don’t have a strong “why” for yourself, you simply won’t see the process through.
![He who has a 'why' for which to live can bear with almost any 'how'."— Friedrich Nietzsche-[3840*2160] : r/QuotesPorn](https://substackcdn.com/image/fetch/$s_!7mt6!,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2Fe45df904-c886-4565-82a9-109f92305811_3840x2160.jpeg "He who has a 'why' for which to live can bear with almost any 'how'.\"— Friedrich Nietzsche-[3840*2160] : r/QuotesPorn")
Startups are not for everybody. Avoid wasting your time if….
You have no interest in technology (the lifeblood of startups).
You want to keep your personal and work identities completely disjoint. Startup people are passionate about their work, so some blend is somewhat inevitable.
You really care about what regular people think (“prestige whore”). Startups sound sketchy and weird to 90% of people outside of the tech bubble. Chances are that most of the population will not understand or care about what you do.
You are not interested in adjacent work like venture capital or entrepreneurship.
You don’t want to grind.
A decent way to gauge if startups interest you is to watch YC’s startup lectures and see how you feel about the content.
On the flip side, startups can yield incredible operating experience that can set up an extraordinary career. The benefits that I personally resonate with the most are…
Firstly, accelerated rate of learning. Winning startups are intense in the best way possible. They have significantly less bullshit than a typical business job and optimize for actual impact instead of performative work (ex: Powerpoints). Because you also have higher ownership over your work, you can make a bigger impact internally within the company and externally on your customers.
Read Reflections on Palantir by
. While Palantir’s culture is unique, I think this broadly shows what a great startup environment is like.
Secondly, talent-dense networks. Startups attract truly some remarkable and ambitious people. Once you get that initial foot into startup world, you can make some friends who will likely change the world. Warm relationships with talented people often pay off in unexpected ways.
Thirdly, a loose promise of monetary upside. Wealth is created through ownership. While equity returns are variable and highly improbable, the reward upon a successful exit can potentially be life-changing if you join early enough. However, money is a poor reason to enter startups — I would treat it as a second-order effect from learning and network.
Entering startups is like taking a bet on yourself that you will take your experience and multiply it into something much greater. Everybody has their own personal goals, so there truly is no shame in choosing a path more rational for yourself.
2: What traits of a startup are you looking for?
The number of reputable consulting firms, investment banks, and big tech companies is probably <10 each. On the flip side, there are hundreds of great startups out there. How do you narrow down this pool and find the startups that are a great fit for you?
The answer is to develop a criteria for the type of startup you’re looking for. The more specific your criteria is, the easier your search will be.
Your criteria should evaluate these core traits:
Dan Hockenmaier’s essay (How to Choose a Startup) covers most of these traits in more detail if you’re interested.
My personal criteria looked like this:
Stage: Series B to Series E. I built my own startup for two years and realized that I couldn’t quite overcome the ambiguity of the work yet. Thus, I wanted to join a growing, later-stage startup to recognize the principles for success.
I’m starting to recognize that maybe Series A to Series C would’ve been more optimal for building founder-like experience.
Team: Titles don’t mean everything, but I was generally looking for high-signal people (ex-founders, ex-startups, ex-Big Tech, ex-MBB, etc).
Location: SF or NYC (preference to SF).
Traction: I honestly found this harder to screen for, so I didn’t account for it as much. I would just smile whenever I’d see a big number for revenue growth.
Industry: My main interests were in consumer, marketplaces, GenAI, VR/AR, and the creator economy. I kept an open mind to other industries if the product was cool (ex: Harvey, AI for law firms).
It should be noted that despite my consumer interest, enterprise software consistently produces better and more valuable businesses.
Investors: Backed by big names like a16z, YCombinator, Sequoia, or Kleiner Perkins were all nice-to-have’s, but not a make or break.
3: Which startups with these traits exist?
Create an Google sheet tracker to store your startup list with the name, description, location, stage, employee contacts, and other details.
For sourcing startups to put on this list, you can use three main methods: screeners, investors, and passive channels.
Option #1: Screeners
The single best tool I found was a startup screener called Prospect (www.joinprospect.com) recommended by one of my mentors (shoutout Andreas).
Prospect aggregates the top startups from all across the US and allows you to directly apply most of your criteria to create an initial list of startups to work with. Additionally, Prospect shows additional information like potential upside, risk, and notable tags (e.g. revenue growth, recent fundraise, etc)
Prospect is completely free and very well-designed.
Sifting through Prospect was by far my most effective method of sourcing. The only downside is if you’re looking for earlier stage companies (pre-seed to Series A), there may be less of them due to lower publicity.
Alternatively, you could check out Breakout List, another screener that seems to have a good track record of predicting the next big startups.
Option #2: Investors
Ian Feeney is widely known as the go-to guy for GTM recruiting.
He runs a selective talent agency called TCP (thecannonproject.com), which takes high-slope candidates and connects them to the industry’s best early stage startups in both GTM and SWE roles. Ian is one of the most knowledgeable, competent, and intense people I’ve ever spoken to, and you can check out TCP here.
In order to supplement this guide with actual expertise instead of some goofy 22-year old yapping, I chatted with him and asked how he would approach recruiting if he were in a college student’s shoes.
“If you were in college looking to break into startups, how would you approach the process?”
Ian Feeney’s Recommendation:
Start looking around January (this would be ~6 months before start date).
Go on Crunchbase and find the top 20 VC funds.
Isolate the top 2-3 partners at each fund who do early stage Series A deals.
To clarify, these are the individual investors, not the entire venture fund.
Alternatively, you can look at the Midas List (Forbes Ranking of the Top VCs)
Find the late Series A, B2B software that these partners invested in.
Late Series A + B2B is where Ian believes the sweet spot is for growth/learning opportunities and equity upside.
Narrow this list down to 10-15 companies based in SF.
Network aggressively through direct cold emails.
College students and new grads often don’t have the credentials that these startups are looking for (unless you’re an ex-founder or an athlete).
If you don’t have these pedigrees, you need to hustle harder to get your foot in the door. Find emails/phone numbers online and make it happen.
Funny story: I was suffering from severe jet lag, so I called Ian at 3 AM in China’s time zone. When he picked up the phone, I started whispering to avoid waking up my sleeping family. At some point it became too ridiculous to continue, so I gave up halfway through the call and started speaking normally.
A word of advice for making first impressions over the phone: Don’t whisper.
Thanks Ian.
Alternatively, you can also look through job boards of these popular VC firms to see if companies are actively hiring for certain positions.
Some examples here:
You can also sort through the VC’s portfolio pages (you can also apply traits like stage and industry) and jot down the companies that are interesting to you like so:
Option #3: Miscellaneous Passive Channels
You can make your discovery more passive by being in the right channels.
Twitter: If you have any interest in startups, read this post by Samay Shamdasani. and create a Twitter (I guess X) account. If you curate your algorithm well, you can easily stay on top of startup news.
Linkedin: Follow all the VCs, PM influencers, and reputable startup folks you can find. Also, turn on job notifications for entry-level GTM, Growth, SDR, and Partnerships positions and set the location to NYC/SF.
Newsletters: Some job boards like iykyk.careers will occasionally aggregate internships or new grad roles for startups (although not exclusive to startups!).
News: Checking Techmeme and Techcrunch are good places to start.
TikTok Startup Influencers who both happen to be Asian women:
Evaluating Whatnot (optional)
My personal experience analyzing Whatnot — feel free to skip if you’re not interested.
First, I found Whatnot through Prospect.
Weighing against my criteria:
Series B to Series E ✅ (Series E)
Ex-founders, ex-startups, ex-Big Tech, ex-MBB ✅ (all)
SF or NYC ✅ (SF, NYC, LA)
Consumer, Marketplaces, Creator Economy, GenAI, VR/AR: ✅ (first 3)
a16z, YCombinator, Sequoia, or Kleiner Perkins ✅ (a16z, YC)
Conclusion: Great fit!
Qualitatively, my analysis looked something like this. At a high-level, I understood that Whatnot is a livestream shopping marketplace. Sellers hold live auctions on physical items (ex: sneakers, clothing, etc) that consumers can bid on in real time.
Conceptually, livestream selling sounded a little silly. I was skeptical about the TAM and the channel’s effectiveness. Then, I did a bit more research.
For consumers, you can get very impressive deals on name brands. I downloaded the app and immediately saw a pair of brand new On Clouds (retail $150) sell for $60. This is compelling to collectors in niches like sneakers, fashion, toys, and trading cards.
If you’re interested in trying Whatnot out, please use my referral link: https://whatnot.com/invite/justinbguo. We can both get free money to buy things!
For B&M businesses, livestream selling allows operators to sell spare inventory extremely quickly and create a notable secondhand revenue stream. Instead of passively listing everything in the discount section and praying, businesses can go live and actively make room for higher-margin, better-selling products.
Notable Metrics: $3B 2024 GMV, $359M 2024 revenue, 102% YoY growth, $25K/year average seller earnings, $1M/year average seller earnings for the top 500 sellers.
The metrics around seller earnings really sold me — Whatnot facilitates the creation of entirely new viable businesses layered on top of it. The same principle is alive for Airbnb hosts, YouTube creators, Apple iOS developers, and Shopify merchants. A single supply-side user can bring in millions of dollars of GMV into the platform, and these metrics of seller revenue are proof of that.
Livestream shopping is also huge in China (market size is $700B compared to a growing $50B in the US) and growing rapidly. I found that the record for dollar value of items sold in one stream is $1.9B USD (🤯🤯🤯), held by a single influencer on Alibaba’s Taobao over 12 hours. Whatnot is the equivalent for the US and Europe.
You can read more comprehensive reports on Whatnot from Contrary and Greycroft.
4: Who’s working at these startups?
If you cold apply, you’re probably DOA unless you have a generational resumé. Startups are all about warm referrals and being proactive about networking before the job even opens. One of my mentors, an early employee at Brex, told me that 90% of the early hires were from employee referrals (shoutout Scott) — it is all about connections.
Use Linkedin to find school alumni working in your role, preferably 2nd degree connections. 2nd degree connections give you credibility, and the more common ground you have, the better conversion you’ll have in your message.
Consequentially, a clean and interesting Linkedin profile will increase your conversion rates. This means implementing a somewhat professional headshot, a concise headline, and sharing enough about your experiences in the description instead of 1-2 words vaguely describing the team you were on. Coding up a personal website is also generally a good sign for people interested in startups.
5a: How can you contact startup employees?
Linkedin Connection Request
Linkedin connection requests are your top-of-funnel channel. Since Linkedin is the main platform to source employees, it’s also convenient to reach out on there.
Your conversion rate will be lower than a cold email because it is harder to stand out with a limited character count of 300, but you can optimize for volume because everybody is right next to each other. It’s generally really easy and *kinda* works.
When writing your message, be concise and direct while balancing a somewhat casual tone. The general structure that I personally used mostly followed some variation of…
Brief intro + common ground if applicable
Demonstrate interest in startup
CTA (provide advice, hop on a call/chat, etc)
Thanks or alma mater shoutout
Some examples of messages that converted:
Hey [alumni name] - I'm a Ross senior looking for fast-growing startups to join post-grad. Whatnot caught my eye w/ the raise & I'm wondering if you have any advice for getting my foot in the door. Go Blue!
Hi [alumni name]! My name is Justin, I'm a current senior at Michigan Ross. I'm looking to work at a growing startup post-grad and Scribe caught my eye. If you have time, I'd love to chat for 15 minutes and learn more about your career path from Michigan all the way to now. Any help would be much appreciated!
Hi [cold contact name] - my name is Justin, I’m a senior at UMich looking to explore post-grad opportunities at awesome startups. It's clear that AI is going to revolutionize knowledge work as we know it, and Hebbia is at the front of this trend. Would love to know if you're hiring scrappy new grads. Thanks!
Hey [cold contact name]! My name is Justin, I'm a senior at UMich. I started watching Suits and was wondering if "Harvey" comes from Harvey Specter. More relevantly, Harvey would be an amazing place to work, and I’d love to learn if you have tips for getting a foot in the door. Are you open to chatting here or a short call? Thanks!
If you have any impressive achievements, it also might be helpful to call them out in your intro (ex: internship at name brand company, ex-founder, student-athlete, etc).
Another best practice is to offer asynchronous availability to ask questions over text. Startup people are typically busy, so offering async availability shows consideration for their time.
The Art of the Cold Email
Much of this section will be plagiarized from a much better essay called How to Get Hired from Quarter Mile, so feel free to just read that instead.
When you really want to work for a specific startup and you find a particularly interesting prospect (ex: founder or someone working in your function), you should send a cold email in addition to a Linkedin connection request.
Email converts much higher than Linkedin messages because it demonstrates grit and that you actually give enough of a shit to find that person’s email.
If you want to stick around in the startup world, sending a good cold email is one of the most important skills to master. It opens up a world of opportunities with virtually zero risk.
With smaller startups, you can typically guess emails with the employee’s first name with their company domain (ex: justin@notion.com). However, there’s no guarantee that this email will be sent to the right address.
A safer way to do this is to use an extension called Apollo (shoutout Shrey) that can find someone’s email from their Linkedin with relatively high accuracy.
When writing your email, aim for it to be attention-grabbing, personal, and succinct.
Here’s a good template from How To Get Hired:
Hey, Jordan - my name is Carter. Reaching out to suggest we work on some writing/content together.
I used to write for [X company], where I built [X thing] that drove [X outcome]. I’ve also written with [notable client] and [notable client].
Enjoy the stuff you have put out so far. Think there is a lot more we could write about (that could be valuable for [X] and [Y]) and would love to share ideas (here’s a link to a memo I put together for you).
Have 15m this week or next for a quick chat?
Carter
This is something I wish I knew earlier: if you feel like there is a specific area of the business that you can create value in (ex: increase profitability, growth), call it out and write a short memo about it. This can be somewhat difficult because you won’t always know what the internal needs of the business are, but it will make you a far more compelling candidate.
Here are three of my cold emails that converted. They’re not the best, and I’m still working on my cold outreach ability, but they got the job done.
“Hey [cold contact name]! My name is Justin, I'm a senior in college right now thinking about working for a startup post-grad. Captions really excites me. I've tried the product on a couple of short-form videos and I can testify it feels like magic.
You currently have my dream job as a PM at Captions, and it looks like we have common interests in...
> Content creation (I used to have a TikTok compilation channel with 2M+ views)
> Product (I interned as a PM at several times and read product content obsessively)
> Software entrepreneurship (founded a consumer social app).
If you have some time next week, I'd love to meet you for 20 minutes to hear 1) some advice that you'd tell your 22 year old self before entering career 2) how I could get my foot in the door at Captions.
Happy to ask questions asynchronously too if better for your schedule - thanks!
Justin”
“Hey José and Dan,
Congratulations on the Series A! My name is Justin, I'm a senior at UMich interested in building delightful products for artists. I'd love to explore the opportunity to work with you after I graduate if you guys are open to hiring.
A bit about me:
> Helped grow a dope music artist (Habe) from 80K to 250K Spotify monthly listeners
> Interned as a product manager at Mastercard last summer
> Working on a consumer social app (currently at 175 WAUs)
> Scaled a YouTube channel up to 2M views and 8M impressions
> Focus areas in product, growth, and design
Fun fact: My dream job was to be a product manager at Spotify for Artists.
If there's no current openings, thanks for your time regardless! I truly believe what you guys are building is incredibly cool and is going to solve a critical pain point for thousands of artists at scale.
Justin”
This wasn’t a direct cold email for a job, but the degree of personalization was very well-received.
“Hey [cold contact name],
I initially was going to reach out on the off chance there were any new grad opportunities at ElevenLabs. But I read some of your writing (Tufts.io, D3 lacrosse, stuttering in AI) and just wanted to say I really admire your work and the way you think.
A bit about me:
> Senior business student @ the University of Michigan
> Founded a social app that failed (did not reach Balbus levels of success)
> Almost played D3 soccer; chose to focus on academics/professional life instead
I'd love to ask you three other things if that's alright!
1. How technical do you need to be in growth roles at technical companies? Debating whether to learn more engineering before I graduate.
2. How did you find your niche in EdTech? Would just be a helpful anecdote to help me understand how other successful people specialize.
3. What do you think is the biggest problem with college education? I'm thinking of writing a blog post reflecting on my business school experience.
Thanks!
Justin”
Make sure you follow up on your cold email if you don’t receive a response. Another great way to grab someone’s attention and show that you care is by following up on other platforms (particularly Twitter).
If you’re really desperate for the job, you could try Instagram DMs.
5b: Quick Advice for Coffee Chats
Stay authentic, loose, and relaxed. These are supposed to be fun!
Be cognizant of time by asking if they have a hard cut-off.
Come prepared with 3-5 questions to use as a crutch.
Mine default towards career goals, day-to-day responsibilities, why startups, and how they got into their current company.
Stalk their entire digital footprint for more personalized questions.
If the chat is going well, I’ll directly ask about hiring new grads.
Don’t strictly center your conversations around the questions. When an interesting topic comes up, double-click into it.
Make sure to share your own stories and experiences to ensure that the conversation doesn’t feel like a one-sided interview.
My best coffee chats always involved laughing and even a little cussing.
Don’t be afraid to ask more personal questions (e.g. opinions, hobbies, etc) and crack a joke here and there.
There’s a lot of opportunity in the “How are you doing?” or “What have you been up to?” to get to know someone as a person.
Prepare something interesting for yourself to share as well.
When you see past the professional employee mask and recognize them as just another human being, the conversation becomes 5x easier.
Remember that most of the connections you make will not end up hiring you, but it’s almost always advantageous to meet more smart people. Again, you never know how they might come back into your life in the future.
6: How can you prepare for the interview?
Since every startup has different needs and hiring practices, interviews are the most variable part of the process. However, here are the most likely scenarios you will encounter and how to best prepare yourself for them.
3-8 rounds of interviews.
Use Glassdoor to find past interview questions.
Ask your recruiter plenty of questions on interview advice and expectations.
Demonstrate an understanding of the product and how it delivers value.
Read investor memos and listen to interviews with the founders (literally search the startup’s name + “podcast” on Spotify and see what comes up)
If the startup is consumer-facing, try the product out yourself and look through App Store Reviews/Reddit/TikTok/Twitter to gauge sentiment.
If the startup is B2B, you could try scheduling a demo.
Use Perplexity/ChatGPT to conduct deep research on the startup, founding story, key metrics, market dynamics, and competitive differentiation.
Why are you interested in this startup?
Reflect upon your personal career goals and how working at the startup would fit into the narrative (reference “Are startups for you?” section)
Areas to focus on: learning opportunities, contributing to a worthwhile mission, how you want to impact the startup.
Look through the startup’s careers page for their hiring propaganda.
Why are you interested in this role?
Read every word of the job description carefully and try to draw parallels between your past experiences and the responsibilities of the role.
Demonstrate knowledge of general business/product theory.
Read literature on product/startup stuff and do something entrepreneurial.
Heavy emphasis on behavioral ability (e.g. autonomy, leadership, collaboration)
While in internships or projects, actively jot down your experiences and accomplishments in a notes document.
This will ensure you have a solid story bank to practice with.
Take-home assignment that mimics real work/on-the-job thinking.
Ask yourself what they’re looking for, then optimize for that.
Do it quickly to show that you care.
Interviewing for Whatnot
The Whatnot Partnerships position opened on February 12th, and I received my offer on April 9th. The process looked something like this:
Resumé Screening
Recruiter Call
Behavioral Interview I
Take-Home Assignment
Take-Home Assignment Review, Behavioral Interview II (Skills Interview)
Behavioral Interview III (Principles Interview)
Reference Check
Offer Letter!
I’m going to share three crucial lessons that I used to land the role. Had I missed out on a single one of these, I wouldn’t have a job.
Get your foot in the door.
I can’t stress enough how important it is to find a warm connection who can vouch for you internally. Throughout my entire college experience, I only received a very small amount of interviews relative to my peers despite having a self-proclaimed strong resumé (you can be the judge of that). For some reason, I could never crack the screening step, even with referrals.
In late January, I saw that Whatnot raised a Series E and reached out to a UMich alumni via Linkedin to chat. At the time, no new grad positions were even available, but he said that he would keep me posted if anything opened.
Just a couple of weeks later, my contact sends me an email notifying me that the team had just opened up a position. He directly forwarded my resumé to the recruiter, and I immediately entered the interview process, bypassing the initial screen.
For me, this was arguably the most important step of the entire process.
Do the job before the job.
In a weird way, most of my interview prep actually happened two years in advance when I founded a consumer app called Push. Building my own startup 0-1 was by far the most formative professional experience I’ve had to date, and it came back to give me a tremendous edge in Whatnot’s interview process. How did the dots connect?
On the intellectual side, I learned the core principles for success in consumer social through studying all the biggest consumer software businesses.
Reading The Cold Start Problem while building Push was incredibly helpful.
Andrew Chen wrote multiple chapters entirely dedicated to marketplaces, where I learned about supply/demand sides, economic network effects, magic moments, and virtuous cycles.
He also joined Uber in 2015 around its Series E, so I found many strong parallels between growing Whatnot sellers and Uber drivers.
I made strong relevant references to these things in my Whatnot interviews.
The distribution work for Push taught me about the importance of doing things that don’t scale (AKA: Sales) to hustle and acquire the early adopters.
This mirrored the responsibilities of a Whatnot Partnerships associate, and generally I felt like I could answer nearly any behavioral question with some anecdote from Push.
Push also demonstrated the qualitative traits (grit, autonomy, agency) that startups generally look for.
After I shut Push down, I wrote a semi-viral essay that caught the attention of an awesome founder. I also took a GTM-focused internship for his early AI startup, where the main role was acquiring early users, which reinforced my interest in sales/distribution.
My Push co-founder and this founder served as both of my references in Whatnot’s final “round.”
My friend Joey advocates for always having a great story/example about something you worked really hard on. If nothing comes to mind, this is your sign to start.
Compete on differentiation.
I would’ve hated to compete against myself if I was another candidate. Here are the three things I did to stand out from the pack.
To familiarize myself with the consumer UX, I actually went on Whatnot and spent $70 of my own money to order two items (a gold chain and a pair of shorts). When asked about my Whatnot interest, I flashed the chain on the Zoom call and passionately described my experience.
In other words, my interviews were pay to win.
In the third round, candidates were given three days to complete a take-home assignment about category expansion. I submitted the take-home so fast that my recruiter thought I forgot about the 36 hours allotted.
The minute I received the email, I locked in for 11 hours straight and wrote a 3,000 word, 11-page deliverable complete with research, graphs, visuals, and citations.
Lastly, in my final interview, I screwed up a behavioral question somewhat badly. My interviewer was looking for a very specific instance and limited it to a subset of my experiences. I stumbled and totally thought that I shat the bed.
Before my turn to ask questions, I took a risk and asked to pause the interview to revisit my answer. My interviewer was receptive, and I shared a much more comprehensive experience answering his same question.
Then, based on two podcasts that he had featured in, I asked several tailored questions about his scope of work, entrepreneurial interests, and favorite sneaker from his 20-year collection.
Your tolerance for risk is a differentiator.
Wrapping Up
I hope this piece helps. It’s something I wish I could’ve read a couple months ago. Recruiting for startups is no joke, but trust that you’ll make it work in the long-term. If you proactively build experience, network like crazy, and differentiate yourself, I have no doubt that you can make it happen!
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Email: jbguo@umich.edu
Twitter: https://x.com/guo_dini
Linkedin: https://www.linkedin.com/in/justinbguo/
Very quality post Justin, and very enjoyable. Helpful to understand the startup scene all around.
Congrats! Very helpful post!