For many job seekers, startups hold a special allure.
There’s the chance to help build something from the ground up, gain experience that might take years to acquire at a larger company, and, if things go well, share in the upside through an IPO or other liquidity event.
Getting a foot in the door, though, can be difficult, especially now that startups OpenAI and Anthropic have reached eye-popping valuations. Consider that Andrew Benson, founder of pre-IPO trading platform Hill Markets, estimated the SpaceX IPO will mint 4,400 new millionaires, Business Insider previously reported.
We asked the people making hiring decisions at Harvey, Lovable, and other buzzy startups what candidates should do — and avoid doing — to improve their chances of getting hired.
Here’s what they had to say:
Join the community before you apply
Don’t wait until you’re job hunting to engage with a startup, said Stacey La Torre, chief people officer at Replit, an AI-powered software-creation platform. Participate in its user community forums, attend virtual or in-person events, and become an active user of the product.
This can help you build relationships inside the company, gain a deeper understanding of what it does, and potentially get noticed by hiring managers, she said, adding that the strategy helped a grade-school teacher with no sales experience land a sales job at Replit.
Do deep research
Ryan Stanford, a people leader at the prediction-markets startup Kalshi, advises job seekers to read founders’ blog posts and media coverage to gather talking points for interviews.
She said she appreciates candidates who find and reference Easter eggs hidden throughout the company’s careers page because that shows they’ve done their homework.
Flex your creativity
At the AI-powered search engine Perplexity, a sales applicant once mailed the company a custom-engraved clock bearing its logo and the slogan, “time kills all deals”— a nod to the sales maxim that opportunities die when deals move too slowly.
Jesse Dwyer, Perplexity’s chief communications officer and a hiring manager, said the gesture got his foot in the door. The applicant had a strong résumé and references, and when offered a phone conversation, he volunteered to fly across the country at his own expense to meet face-to-face the next day.
Both stunts showed knowledge of the sales process and demonstrated conviction, said Dwyer, adding that this person ultimately got the job.
Show that you get startup culture
Demonstrate speed and initiative because those traits mirror the fast-paced nature of startup work, said Kalshi’s Stanford. She pointed to applicants who responded to her messages almost immediately and volunteered to interview outside traditional business hours. Recently, an applicant impressed her by sending her a calendar invite for an interview before she had a chance to do so.
“It shows that someone’s committed to what our culture can be like,” Stanford said.
Engage on social media
That can mean participating on X, LinkedIn, or other channels where a startup’s leaders and staff are active. Perplexity’s Dwyer said the tactic can be especially effective at startups, as they often have more flexibility in how they identify and engage with job seekers.
“We’ve met some of our best candidates on social media,” he said.
Show you can thrive in ambiguity
Startups tend to want people who can navigate uncertainty and find solutions when no playbook exists, said Katie Burke, chief operating officer at Harvey, an AI software company for lawyers. Job seekers can demonstrate they fit this mold by describing how they built a process from scratch, fixed something broken, or solved a problem without a clear owner, she said.
“What we want to hear more is, here’s how I took a process at my company or a customer problem at my company and here’s how I actually solved it,” Burke said.
Prove you’re a builder
Share something you’ve built with the company’s product if that’s possible, said Ariel Brito, head of talent, and Marisa Rack, head of people, at AI mortgage-servicing startup Valon. They pointed to a candidate for a recruiting position who arrived at a final-round interview with a website that synthesized what he had learned about the company and made a case for why he would excel in the role.
“It was kind of sloppy, but we were so excited because they took initiative,” Rack said. “They differentiated themselves.”
One of the strongest signals that someone is a strong startup candidate is evidence that they’ve created value on their own, said Cameron Zoub, cofounder and chief growth officer of Whop, a startup that operates a marketplace for online entrepreneurs to sell digital products and services.
When interviewing job candidates, he said he looks for examples of people launching a business, running a side hustle, building a product, or growing a community.
Don’t focus on what’s in it for you
Candidates can hurt their chances by focusing too early on compensation, equity, benefits, and other personal perks, warned Perplexity’s Dwyer. Those conversations are important, but he said startup leaders are often looking first for signs that a candidate is excited about the mission, product, and company.
“If you walk into a startup that’s in hypergrowth and your first questions in the interview are what’s in it for me, then you’re probably not the ideal candidate for a startup,” Dwyer said.
Don’t be afraid to critique the product
Many startup founders appreciate candidates who engage critically with the business rather than simply praising it, said Kalshi’s Stanford. If you’ve used the product, come prepared to discuss bugs you encountered, friction points in the user experience, or areas where you think the company could improve, she said.
The goal isn’t to be negative or show off; it’s to demonstrate that you’ve spent time understanding the product and are already thinking like an owner, she said.
Don’t be an AI spectator
At Lovable, candidates stand out when they’re actively using AI to enhance their expertise, said Charles Guillemet, who leads recruiting at the Swedish vibe-coding startup. The ideal hire combines deep domain knowledge with an AI-native mindset — whether that’s a marketer speeding up campaign creation or a salesperson building custom demos, he said.
“The perfect combo is someone strong in a specific vertical and has domain expertise augmented by AI,” Guillemet said. “We care more about domain expertise versus general skills.”
That said, you don’t want to be seen as overly dependent on AI. At Valon, recruiters occasionally encounter candidates who appear to be using tools like ChatGPT to generate answers in real time during virtual interviews, said Brito and Rack. The problem is that interviewers are trying to evaluate a candidate’s judgment, reasoning, and ability to work through challenges independently, they said.
“You can’t just outsource your thinking completely to AI,” said Brito. “Judgment and taste and craft and reasoning and human principle matter a ton.”
