State of AI with Nathan Benaich - Our investment in Jack & Jill: a job market that works for you

0:00You're listening to Our Investment in Jack and Jill, a job market that works for you on Air Street Press. Earlier this year, a founder in the Air Street portfolio whose product taste I trust tried Jack and Jill and what's apt me. If you can invest in Jack and Jill, do it. Honestly, it's a top tier AI product. I spend much of my time searching for and nurturing a network of talent, founders to invest in, experts who can riff on the nuances of a market or technology, members of our Air Street AI community, and people to join our portfolio companies. Each search involves learning what makes someone tick, what they're great at, what they'd love to do next, and what they definitely don't want next, and who could help them get there. So when Matt Jack and Jill's CEO and I grabbed lunch in SF this spring, much of what he described resonated with me. Today we're announcing that Air Street Capital has led Jack and Jill's $40 million series A with Madrona joining the round.

0:57and existing investors, including CreonDoom and entrepreneurs, first investing again. This follows a $20 million seed round less than a year ago. Together, we believe agents that understand and represent both candidates and employers can build a much better global marketplace for talent. A candidate is much more than their resume. Your resume and LinkedIn profile describe your professional past, where you worked, what you studied, and the projects you shipped.

1:26But how much do they say about your next career challenge? You might have spent years managing a team and want to build again, inspired by what you can now do with AI. You might want to switch fields, join a startup, or move across the world. It takes a conversation to learn that about you. Meet Jack, the AI agent helping you work out your next career move and find opportunities that fit. People tell him about the team they want to leave, the salary they're nervous to ask for, and the work they would take a pay cut to do.

1:55Jack helps them think through those decisions, prepare for interviews, and negotiate an offer while searching millions of job postings on their behalf. People have spent 12,000 hours talking to Jack in the past few months alone. Many return every week, continuing conversations that have been running for months. One person has called him 144 times and spent 44 hours discussing their career. Each return conversation gives Jack a chance to learn what has changed, which opportunities appealed, which fell flat, or whether your priorities have shifted. That should help him make more relevant introductions over time. Being useful between job moves gives people a reason to keep talking and jack a fuller understanding of whom they should meet. We see an opportunity to build a consumer brand that people trust with their careers. Someone in your corner who gets to know your skills and passions and goes out into the world to find opportunities for you. Most people have had to do that work themselves, calling on friends and their network when they can.

2:54LinkedIn made our professional lives searchable. Jack and Jill can make personal representation a normal part of working life, helping you discover where you could do your best work long before you know you want to move. Meet Jill, your company's recruiting agent. We're equally focused on building a brand that companies trust to help them hire the people who will shape their future. Jill earns that trust by getting to know your business, what makes someone successful in your organization, and where previous hires haven't worked out.

3:23You refine the job description together, and she recruits from the network of people who've spoken with Jack and opted into opportunities. Jack understands what the candidate wants next, and Jill understands what the company needs. When the two agree there's a strong match, they introduce the candidate directly to the hiring manager. You get to have the conversation without first spending hours filling out a cold application. Jack and Jill has arranged 25,000 interviews and is arranging another 5,000 each month.

3:53More than 385,000 people have spoken with Jack, while Jill has worked with over 5,350 companies in the US and Europe, including Ramp, Atio, Multiverse, and Corgi. These agents are doing the legwork for a decision that can change someone's life. You still decide whether you want the job or want to make the hire, but the agents have helped you find each other. Your next career move might surprise you. One Jack user wanted more time to build AI projects.

4:24Within a week of their first conversation, Jack introduced him to a pre-seed accelerator. It opened up a path to becoming a founder that he hadn't known was available. It's why I think of Jack and Jill as a global opt-in network for talent. The same understanding of people that makes a good hiring introduction could help connect co-founders, collaborators, and experts too. Matt and his co-founder, Saras, started Jack and Jill in March 2025. Matt previously co-founded Omnipresent.

4:52helping companies employ people across borders, while Sara's co-founded Coolar, backed by Y Combinator. Today, 15 of their 25 team members are former founders. We're partnering with Matt, Sara, and the team to help remarkable people meet ambitious companies, starting with further expansion across the US. Whether you're considering your next move or hiring someone to help build your company, give Jack and Jill a try. I'd love to hear whom you meet. Thanks for listening to our investment in Jack and Jill.

5:22a job market that works for you on Air Street Press.