152: Ben Orenstein - How to Stand Out When Applying for a Job at a Small Company
Episode
47 min
Read time
2 min
Topics
Career Growth, Startups, Design & UX
AI-Generated Summary
Key Takeaways
- ✓Application quality over quantity: Submit deliberate, customized applications instead of mass-applying to hundreds of positions. Read job postings carefully, follow instructions exactly, and reference specific requirements in your response to demonstrate attention to detail and genuine interest.
- ✓Derisk yourself as a candidate: Small company founders fear bad hires intensely. Demonstrate competence upfront by doing small amounts of actual work—analyze their product, suggest improvements, or share a relevant code commit with trade-off explanations rather than linking to your entire GitHub profile.
- ✓Showcase cross-functional abilities: Highlight skills beyond the core job requirement—developers with design sense, anyone with strong writing ability, or side projects completed independently. Small teams value generalists who can execute across domains without constant oversight or specialized departmental support.
- ✓Create your own opportunities: Email founders directly with specific project proposals showing first-day work completed, potential business impact, and execution plans. Many hires at small companies never had job postings—demonstrating initiative and alignment with company goals can create positions that didn't previously exist.
What It Covers
Ben Orenstein and Adam Wathan share hiring insights from small company founders' perspectives, covering application strategies, interview tactics, and how candidates can demonstrate competence while reducing perceived risk for resource-constrained startup teams.
Key Questions Answered
- •Application quality over quantity: Submit deliberate, customized applications instead of mass-applying to hundreds of positions. Read job postings carefully, follow instructions exactly, and reference specific requirements in your response to demonstrate attention to detail and genuine interest.
- •Derisk yourself as a candidate: Small company founders fear bad hires intensely. Demonstrate competence upfront by doing small amounts of actual work—analyze their product, suggest improvements, or share a relevant code commit with trade-off explanations rather than linking to your entire GitHub profile.
- •Showcase cross-functional abilities: Highlight skills beyond the core job requirement—developers with design sense, anyone with strong writing ability, or side projects completed independently. Small teams value generalists who can execute across domains without constant oversight or specialized departmental support.
- •Create your own opportunities: Email founders directly with specific project proposals showing first-day work completed, potential business impact, and execution plans. Many hires at small companies never had job postings—demonstrating initiative and alignment with company goals can create positions that didn't previously exist.
Notable Moment
One candidate stood out by structuring his application to mirror the job posting's format, including why he might not want the role alongside why he would, demonstrating self-awareness and reducing the founder's concern about cultural misalignment.
Episode Transcript
This episode of Fullstack Radio, I talked to Ben Orenstein about how to stand out when applying for a job at a small company. This is Fullstack Radio episode one fifty two. So, yeah. We are doing this podcast today because you messaged me saying I think we've actually talked about this in the past, but doing an episode about this, which is, like, hiring tips from the applicant side because both of us are sort of more newly on the hiring side, I think. And it's interesting to be on the other side and sort of realize, like, what, we're looking for in people who apply for jobs at our company while at the same time remembering probably, like, what we did to apply for jobs ourselves and, what we maybe would have done differently, kinda understanding both perspectives. Does that sound about right? Sounds just right. Yes. And it was kind of it's kind of spurred by I've seen a wide variety of application quality, from people. And I I kinda feel compelled to, like, put some advice out there to sort of help because I think there's some people that are kinda just not doing it quite that well. And I think we can maybe give some guidance. Totally agree. Okay. So I guess, like, where do you wanna start? How how big of a net do we wanna cast on this topic? Well, I was thinking kind of starting at, may like, the way to kind of cheat the system a little bit. Okay. Like, so I most of my advice that I've written up is kind of like, what are you what do you what should you do if you're cold applying for a job? Yeah. And I think that's worth talking about, and that's where I think we'll focus on. But I I did wanna kinda mention before we got here that I think, really, the best way to get hired at a company is to, like, have some friends or contacts in that company. It's like that's, like, really, like, the easy mode version of this is, like, you've been going to meetups or something and met someone that works there. So this is my if I had to kind of, like, summarize what I think the most important thing to do is to get hired from, like, the perspective of someone hiring is to figure out how to, like, maximally derisk that person hiring you. Because that's how it feels, like, from my side of things anyways. And that is very similar to what you're talking about. If someone else on your team knows someone and can vouch for them, like, that does a lot to derisk Totally. The hiring process. Right? Or if you know someone because they've come to your meetup for two years and they've given presentations or, you know. So Totally. Yeah. I think it definitely ties into that. Exactly. And and this didn't I didn't quite appreciate …
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