Jack & Jill vs Shortlisted: What Each One Actually Does (October 2026)

Jack & Jill and Shortlisted do different jobs, and plenty of people would do well to use both. Jack is a free AI agent that finds roles, rates your fit, suggests resume changes, and introduces you when one of its client companies asks to meet you. Shortlisted runs a human-led job search: a person reads every role and sends you hand-built applications you approve before anything goes out, for $95 a month.

Jack & Jill raised a $40 million Series A in September, so you're likely to hear a lot more about it. Here's what each one does as of October 2026, based on Jack & Jill's own pages and our own test of Jack.

What does Jack do?

Jack starts with a conversation. Its site says "a short conversation is enough" to talk through what you've done and what matters to you. From there, Jack says it scans 15 million jobs a day and sends you the matches it thinks fit. It also offers mock interviews, salary benchmarking and career coaching, all free for candidates.

When we tried Jack on 6 October 2026, it offered something newer too. A tool called the Application simulator, marked new, read a job ad alongside the resume we'd uploaded and rated how well they fit. It then listed numbered fixes, such as keywords the posting asked for and a date that didn't line up. Each fix opened in an editor with tracked changes, where you accept or reject the edit and export the result, and the same flow included a step for writing a cover letter.

That's useful, and it's free. You do the finishing yourself, though. You review the suggestions one at a time, decide which ones are true of you, and send the application when you're happy with it.

What does Jill do?

Jill is the employer side, and it's how Jack stays free. Companies pay Jack & Jill 10% of a new hire's first-year salary, with a full refund if the hire leaves in the first three months.

Introductions start with the employer. A hiring manager browsing candidates on Jill clicks "Request Intro", Jack pitches the role to you by email or WhatsApp, and if you say yes, Jill introduces you both over email. Jill lists London, San Francisco and New York as its markets, and the companies on its page are mostly startups, such as Ramp, Attio and Multiverse. For every other match, you apply through the listing yourself.

What does Shortlisted do?

We take each role all the way from the listing to a finished application. A person reads every role before it reaches you and tells you why it fits and where you'd be stretching. You say yes or no. For each yes, software drafts a tailored resume and cover letter from what you've told us, and a person edits it and checks every claim against your own background. Nothing goes out until you've approved it. You send each application yourself, so it goes out under your name and the replies come to you.

With your go-ahead, we also email the hiring manager or recruiter at the companies that fit you, whether or not they hire through a recruiting platform. We've sent more than 1,250 of those emails so far.

Our intake takes longer than a short conversation because every line in your resume and cover letter has to trace back to something you told us, so we ask detailed follow-up questions about what you did and what it changed.

How do they compare side by side?

Everything in the Jack & Jill column comes from its own website, checked on 6 October 2026, apart from the Application simulator, which comes from our own account. Both services change quickly, so check their pages before you decide.

	Jack & Jill	Shortlisted
What you pay	Free	$95 a month
How it's funded	Employers pay 10% of a hire's first-year salary	A flat monthly fee from you, with no placement fee
Who finds the roles	Jack's software, scanning 15 million jobs a day	Software scans the listings, and a person reads every role before you see it
Who finishes each application	You, working through Jack's suggestions	Software drafts it, and a person edits and checks it for that role
Checked against your background	You decide what's true of you	A person checks every claim against what you've told us
Who sends it	You	You, after you've approved it
Contact with employers	An introduction when one of Jill's client companies requests one	With your go-ahead, an email to the hiring manager at any company that fits
Where introductions happen	London, San Francisco and New York	Any company, wherever you can work
Guarantee	Its terms say it can't guarantee interviews	No interview guarantee, and a full refund of your first payment if you ask within 15 days

Which one is right for you?

Jack suits you if you're happy to finish your own applications and want free suggestions. It's a strong free option if you're aiming at startups in New York or San Francisco, where Jill's client companies hire.

Shortlisted suits you if you want the finished application in your hands and a person to handle each role. You get a resume and cover letter built and checked for each one, and we reach out to hiring managers at companies that may never use a recruiting platform.

Using both makes sense for a lot of people. Jack can bring you introductions from its client companies, and we can cover everything else. If you do use both, tell us about the companies Jack introduces you to, so you don't end up applying to the same one twice.

Where to start

If you'd like to see how we work before you pay anything, try our free resume review. It shows how we read a resume and what we'd change first. For the wider market, our guide to what reverse recruiting costs compares seven paid services.

---

Sources, each checked on 6 October 2026: Jack & Jill pricing, jackandjill.ai/pricing; Jack, jackandjill.ai/jack; how introductions work, jackandjill.ai/docs/introductions; Jill, jackandjill.ai/jill; terms of service, jackandjill.ai/terms; Series A announcement, jackandjill.ai/blog/series-a. The Application simulator description comes from our own Jack account on 6 October 2026. Our outreach count is from our own records, counted on 2 October 2026.