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Request for Startup: Is It Possible to Build a Recruiting Company People Actually Love?

August 18, 2025 · By Garrett Wolfe · Originally published on Substack

Genuine question here:

Is it possible to build a successful company in the recruiting space that actually delights people - helping recruiters find and hire talent, and candidates find roles that excite them?

Recruiting is one of those problems that never seems to get solved. Everyone agrees it’s broken - startups struggle to attract the right talent, candidates drown in noise, and recruiters are caught in the middle. We’ve had two decades of LinkedIn, billions poured into ATS systems, and a wave of new hiring startups - yet the experience still feels frustrating and fragmented. So the real question is: what actually works, and why does it feel so inconsistent?


The Two Sides I See Every Day

A handful of my posts on LinkedIn these days have been about finding your next gig and connecting friends to open roles. It’s honestly sad that I know two fundamentally siloed parties that I can’t connect easily:

  1. Startups solving large and rewarding problems, but either A) struggling to get applications or B) drowning in too many to sift through. Companies like Hebbia, Tennr, Legora, Harvey, Harmonic, Permitflow, Footprint, Owner, Rogo, Unify, Clay, Pylon, and dozens more.

  2. Candidates from my banking days, Duke days, and even younger kids who DM me now because they want to make the jump into startups. Unfortunately, a lot of them occasionally a) lack initiative or persistence, b) are risk averse, or c) aren’t truly ready to take the leap.

From the candidate’s perspective, the journey is just as painful. You send 100 LinkedIn messages or Ashby applications and hear nothing back. You can be perfectly qualified, but you’re invisible unless you have a referral or a personal connection. What candidates want isn’t just more job postings - it’s signal. They want to know which startups are actually worth the leap, and they want a warm path in. That’s why brand and network matter more than any polished careers page.


People Choose Startups for Different Reasons

A subway train is arriving at the station.

People join companies for different reasons depending on stage IMO.

At each stage, companies hire in different ways:


Why Hiring Feels So Hard

Because there’s no consistent methodology. Unless you decide to make hiring an internal priority, you’re winging it stage by stage.

And the tools we all use weren’t built for this. LinkedIn is noisy and full of spam. ATS systems like Greenhouse and Ashby are designed for process, not connection. Even Slack groups and Notion lists end up being glorified spreadsheets. The reality is that when I try to connect someone to a startup, it doesn’t happen because of software - it happens because I personally DM the founder, or I know someone on the team. The tech hasn’t caught up to how hiring actually happens in practice.


The Real Unlock: Brand

building brand means sexy monochrome tshirts <3 :)

My hot take (which actually isn’t hot whatsoever): the best way to set your company up for optimal hiring outcomes from the very beginning is to make brand (and network) the centerpiece of your GTM and hiring.

We’ve seen what happens when a company nails its brand. Look at Pylon, Linear, Clay - their content and design make them aspirational places to work. Candidates line up because they want to be part of the story those brands are telling. On the flip side, when a company has no brand presence, recruiting becomes a grind. You default to agencies, outbound sourcing, or endless filtering through applications. Same market, same comp bands, completely different hiring outcomes - all because of brand.

Today we see companies like Pylon, Clay, Cluely, Icon, and more captivating people with dangerously entertaining content. I will actually pause in the middle of my workday to watch the latest Roy Lee shit-post or see Yoona Kim and Marty Kausas cook up a beautifully choreographed Pylon feature drop. We’ve even seen Adara Parker start to do this at Unify. It’s fun, it’s interesting, and most importantly: it makes me want to work there.


My Accidental Recruiting Marketplace

I know this firsthand because I’ve accidentally been running a mini recruiting marketplace out of my inbox. I have a running list of 50+ startups I admire and 75+ friends or acquaintances who want to break into startups. Every week a number of people ask me for an intro. It’s objectively not scalable and there’s no tool that makes that simple - it’s all trust and brand. And honestly, that’s the lesson: recruiting works when people trust the connector and when the company’s brand is strong enough to get people excited. Everything else is noise.

I remember seeing one of the recruiting SaaS founders share years ago just how difficult it is to build successfully in this space, because of the fragmented stakeholders and preferences. That’s still true today.


The Challenge

If you’re building a startup today, your real recruiting advantage isn’t comp, perks, or headcount - it’s whether people think you’re cool enough to join. That might sound superficial, but it’s the honest truth: the companies that win talent are the ones people talk about, not the ones with the slickest ATS.

What if we rebuilt recruiting from scratch with brand + network at the center instead of treating them like afterthoughts? My bet is that the companies who do that will find hiring not just easier, but genuinely delightful.

So if you’re a founder, forget the ATS for a second. Ask: does anyone outside your team want to work at your company? If not, that’s the real recruiting problem.

The Solution?

What could the solution look like? Well, maybe something like:

If you’re trying to solve the hiring / recruiting problem, please reach out - i’d love to hear about what youre building and help to the extent I can!

Garrett

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