Sep 15, 2026 · 21 min · 9 segments
Jack and Jill just raised a $40m Series A led by Air Street Capital with Madrona joining the round, and participation from existing investors. This brings total funding to $60m, just ten months after…
Matt WilsonGuestSeb JohnsonHost
Yeah, so we launched in San Francisco at the start of 2026, and San Francisco has been growing faster than London was at the same time, indexed by launch dates.
And New York is following the same trajectory, although it's only a couple of months in.
And I think with going international, I think you either want to do it early in your life as a company, where it just becomes the default operating model of the company from day one almost, that you are multi-market, that you are operating with teams in different time zones and teams in different offices, and that it's just part of your DNA in terms of how you operate.
You know, we think winning in what we see as kind of key tastemaking markets, winning in the US as being fundamental to our long-term success as a business and our ability to win globally.
So we thought it was really important to get out there and put our stake in the ground and push on those markets.
of action done from London, from our London HQ, as well as building out the office on the ground there in San Francisco and spending a whole bunch of time out
What was your thinking or strategy in getting those users, right? Because you need to get people on the platform.
When you're going to a new city or ecosystem, what is the marketing or, I don't know, overall strategy of getting those first thousand, 10,000 people on the platform?
So I think, you know, first of all, marketing is built on a foundation of product.
So where you've got some, we've got a kind of marketplace product where we've got companies on one side with Jill and professionals on one side with Jack.
How do you build some density into that marketplace so that you can get over this cold start problem? We have a marketplace, we also have standalone products.
So Jack works brilliantly well, regardless of Jill, at understanding who you are.
So Jack is scouring every public job listing in the world and identifying them, regardless of whether we've got a direct relationship with that company or not.
So Jack is kind of continuously monitoring every day, is there something interesting that's coming to the market for you? So you don't have to be browsing job boards.
Yeah, so we launched in San Francisco at the start of 2026, and San Francisco has been growing faster than London was at the same time, indexed by launch dates.
And New York is following the same trajectory, although it's only a couple of months in.
And I think with going international, I think you either want to do it early in your life as a company, where it just becomes the default operating model of the company from day one almost, that you are multi-market, that you are operating with teams in different time zones and teams in different offices, and that it's just part of your DNA in terms of how you operate.
You know, we think winning in what we see as kind of key tastemaking markets, winning in the US as being fundamental to our long-term success as a business and our ability to win globally.
So we thought it was really important to get out there and put our stake in the ground and push on those markets.
of action done from London, from our London HQ, as well as building out the office on the ground there in San Francisco and spending a whole bunch of time out
What was your thinking or strategy in getting those users, right? Because you need to get people on the platform.
When you're going to a new city or ecosystem, what is the marketing or, I don't know, overall strategy of getting those first thousand, 10,000 people on the platform?
So I think, you know, first of all, marketing is built on a foundation of product.
So where you've got some, we've got a kind of marketplace product where we've got companies on one side with Jill and professionals on one side with Jack.
How do you build some density into that marketplace so that you can get over this cold start problem? We have a marketplace, we also have standalone products.
So Jack works brilliantly well, regardless of Jill, at understanding who you are.
So Jack is scouring every public job listing in the world and identifying them, regardless of whether we've got a direct relationship with that company or not.
So Jack is kind of continuously monitoring every day, is there something interesting that's coming to the market for you? So you don't have to be browsing job boards.
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