Hiring With AI

We’re in the process of hiring an investment associate (or two!).

We’ve been working through our networks and usual channels - but I wanted to try out some of the new AI recruiting platforms.

I love AI recruiting. Recruiting is one of those categories that feels so perfectly aligned with AI’s capabilities because, at its core, it’s mostly a data problem.

Most of the time you have someone in mind who would fit the role, but you just need the right population of people - and a way to rank and reach out to them. And this is exactly the type of problem that AI is good at.

I tried out a handful of the latest AI recruiting platforms and wrote a quick review below.

What was interesting was that it felt like the biggest difference between the products was how conversational and productive they felt. I thought search quality was going to be the biggest differentiator (and Jack & Jill does seem to have the best search), but a lot of it came down to product design. The platforms still needed to be engaging and well-designed to hold my attention.

Jack & Jill - Amazing branding and the most impressive platform of the group - I love that Jill helps companies hire and Jack helps candidates find jobs and negotiate. The UI/UX design is smart and makes you feel like you’re making progress on finding the perfect candidate with it constantly recalibrating based on who you request introductions to, and who you pass on. So far I’ve made 14 requests for candidates - scheduled 3 interviews - and have become obsessed with looking at the dashboard pipeline to see if anyone else has responded. While I continue to refresh the dashboard, it gives me non-invasive notifications that more people have been added to my search pipeline (but never adds more than 10 people, which I’m guessing is a product decision to make the list manageable).

Contrario - Ended up not fully onboarding since it requires companies to classify as a startup, private equity, or public company. But to their credit, the CEO sent me a LinkedIn message within 6 hours asking for feedback & said their team will improve the onboarding flow.

Serra - Kept erroring out. “This search encountered an error. Partial results are shown below.”

Juicebox - Wow, the team needs to work on the UI/UX - it has to be improved; I lost momentum on the search. The only moves you can make on the platform are hide and shortlist. It never felt like the review was going anywhere.

Prism and Clera - Both early and worth watching.

I tried Wellfound, and it immediately felt Boomer to me, and for Paraform, I didn’t want to be connected to a recruiter.

Here is a quick market map of the companies for some visuals -

But even though I love it as a data problem, every AI recruiting company we’ve looked at, we’ve run into the same venture questions about making an investment in the space:

• Recruiting isn’t very frequent for most companies. Once they have hires locked down, they no longer need recruiting services - this creates a natural user churn.

• Companies can use multiple platforms at once, so there isn’t any loyalty or lock-in.

• A data moat here is hard. Everyone is searching the same LinkedIn, GitHub, and public web data, so the question is what becomes proprietary over time.

• The best search and discovery product will win initially, but the long-term winner likely needs to become part of the broader recruiting workflow - or even the HR stack - to increase market size, expand into larger enterprise contracts, and create real defensibility.

It also feels notable that two of the highlighted companies have already been acquired rather than scaling into standalone venture outcomes.

That said, I still think we’re early. AI is changing what recruiting software can do, and markets can be unlocked with new capabilities.

I’m only 24 hours into my AI recruiting search, but I’m feeling optimistic.

Hopefully one of these products finds our next investment associate! I’ll let you know how it goes.