Your checklist
Here's everything in one place.
Start here
- Have a Career Clarity conversation with Jack
- Talk to 3–5 people in your network about what they think you'd be great at
- Decide on a direction before you start applying
Set up your infrastructure
- Complete onboarding with Jack (5 minutes, voice or chat)
- Upload your CV to your dashboard and connect your LinkedIn
- Set your email frequency preference
- Create a simple application tracker (spreadsheet or Notion)
Search and apply
- Let Jack's daily matching surface the best roles for you
- Pay special attention to Jill-managed roles — direct introductions
- Tailor your CV and cover letter with Jack for every application
- Ask Jack to identify relevant contacts at your target companies
Prepare and negotiate
- Run mock interviews with Jack for every stage
- Build your story library (8–12 STAR stories)
- Use Jack's salary benchmarking before any negotiation
- Practise your negotiation script with Jack
And most importantly — take care of yourself. Job searching is emotionally hard, and it's okay to take breaks.
01 The job market has changed
Eight months ago, I was looking for a job.
I'd spent the previous few years moving from policy communications to strategy consulting and then into tech. My career has not been linear. At all. Each transition took time, soul searching, and a lot of support from people in my network who helped me see what I couldn't see myself.
When I started searching, I did what everyone does. I opened LinkedIn, scrolled through hundreds of listings, hit up the EasyApply button more times than I care to admit, tailored a handful of applications, and waited. Mostly waited, to be honest. Applications per hire have tripled since ChatGPT launched. Every minute, thousands of AI-polished CVs flood recruiter inboxes, making it nearly impossible for anyone, including the recruiter (bless them!), to separate signal from noise.
The old playbook is broken. Spray and pray doesn't work when everyone is spraying and praying at the same time. Referrals convert at roughly 40%. Cold applications? Somewhere between 2% and 3%. Up to 70–80% of roles are filled before they're ever publicly listed. If you're only applying through job boards, you're fighting over the smallest slice of the pie with the most people.
But here's what I learned: the candidates who win in 2026 are the ones who build a system. Not a stack of disconnected tools. One that helps them figure out what they want, find the right opportunities, prepare thoroughly and thoughtfully, and reach the right people.
That system, for me, was Jack.
I'm Ainhoa. I'm a Founding Operator at Jack & Jill AI, and I work on Jack every day. This guide is what I wish I'd had when I started searching — a comprehensive, honest walkthrough of how to find a job in 2026, from "I don't know what I want to do next" all the way to "I just got an offer and I need to negotiate."
It's mostly about how to use Jack, because he genuinely covers more of the job search funnel than any other single tool I've come across. But it's also about the things no AI can replace: your network, your relationships, and the unglamorous — unless you're fiercely in the Type A camp — work of staying organised and staying human throughout the process.
Let's get into it.
02 Before you search: figure out what you actually want
This is the step most people skip, and it's the one that costs them the most time.
Not everyone has a linear career path. I don't. I went from studying behavioural science to A/B testing comms to working at a startup in Hoxton, with a not so brief stint in consulting. When you've pivoted before, or when you're pivoting now, the question "what do you want to do next?" is quite paralysing. The possibilities are endless, and that's precisely the problem.
I've seen this up close with the candidates I've spoken to — somewhere in the low hundreds region. People come in knowing they want to leave their current job but having no idea where they want to land. They start applying to everything that looks vaguely relevant, burn out, and end up more confused than when they started.
Jack offers a free conversation called Career Clarity that's designed for exactly this. You jump on a call and Jack helps you talk through what energises you, what drains you, and what a fulfilling next step might look like. It's not a personality quiz. It's a structured conversation that helps you articulate things you might not have fully worked through yet.
It's the kind of thing that used to require a £300 an hour career coach, and it's free.
I do love AI agents. But they aren't a replacement for the people in your life who know you. Before or alongside your conversation with Jack, I'd strongly encourage you to talk to the humans who've watched you work: former managers, colleagues, mentors, friends. Ask them what they think you're great at. The combination of Jack's structured approach and the honest, sometimes surprising observations of people who care about you is powerful.
How to do this with Jack
Go to jackandjill.ai/career-clarity and start a call. Let Jack guide you. Be honest — the more you put in, the more useful the output. By the end, you'll have a clearer sense of the direction you want to move in, which makes everything that follows dramatically more effective.
03 Map your landscape
You've decided what you want to do next. The task ahead remains paramount.
When I decided I wanted to move into tech, the next piece of the puzzle was mapping the types of companies I wanted to work at. Early stage or late stage? B2B or B2C? Think of it as the corner piece. It makes everything that comes after easier, and yet most people skip it entirely.
Jack can help you map this. Once he understands your background and preferences through onboarding (a 10 minute voice conversation or quick chat), he starts searching. And the patterns that emerge from his matches are themselves a form of market intelligence.
Perhaps most of the roles Jack finds for you are at scale ups. Maybe the matches cluster around a specific function you hadn't considered. Turns out the ones you're most excited about — and Jack thinks you'd be a fit for — sit at the intersection of your new found function and scale ups. That's useful data you wouldn't have got from scrolling LinkedIn.
Salary benchmarking is built in. This matters more than people realise when deciding what to do next. What are my potential earnings going to look like if I go down this path versus that one? Jack removes the guessing game. Once he's run a search, he has real data on real roles to base salary estimates on. The benchmarking improves as the search improves; it's not pulled from a generic database. It's grounded in the actual roles he's surfacing for you.
How to do this with Jack
After onboarding, ask Jack to run a search and pay attention to the patterns. Which companies come up? What seniority level? What compensation ranges? Use this as your market map. If you want to narrow it further, tell Jack — he'll refine. You can also ask him directly: "What salary should I expect for a Head of Product role at a Series B startup in London?" He'll give you a benchmark based on live data. Or simply head to jackandjill.ai/salary-benchmark.
04 Let the right jobs come to you
Bid farewell to doom scrolling.
Typically, you need to sift through hundreds of job portals only to come across roles that are already buried under thousands of applications. It's demoralising, it's time consuming, and for most people, it's the part of the job search that breaks them.
Jack does this for you. We've spent loads of time refining our matching algorithm to make sure he finds the roles that are a genuine fit for you and nothing else. This isn't keyword matching. Jack builds a rich understanding of your background, preferences, and ambitions through conversation, and uses that to search across the entire web for roles that match.
Think of it as Jack surfacing the best possible matches for every single version of you — Strategy in an early stage HealthTech startup, Consulting at a boutique firm, Operations at a Series F scaleup — and finding the best 100 odd matches for each. Then comparing all the options against one another to find the perfect fit for your very best version.
He'll reach out over email as often as you want him to — once a day, once a week, once a month — highlighting the jobs that are truly worth your attention. If you want more, you can always head to your dashboard and ask Jack to run another search. He'll keep going until you land on the roles you want to pursue.
But where Jack really shines is when he works together with Jill.
Jill is our hiring manager facing agent. She works directly with employers — real companies, real hiring managers — and she's able to put you directly in touch with them. So you escape the doom loop entirely. No ATS black hole. No silence after applying. A direct introduction from Jill to the person who's actually hiring.
The good news is that this is the closest thing to a warm referral you can get without already knowing someone at the company. And it's the part of Jack & Jill that users consistently describe as the "aha moment."
All you need to do for Jack to start pitching your case to Jill is connect your LinkedIn.
How to do this with Jack
After onboarding, Jack works for you on autopilot. He searches, he filters, he emails you the roles that matter. On your dashboard, you'll see two types of roles: web-sourced roles (jobs Jack found online, tagged with a URL for you to apply to directly) and Jill-managed roles (jobs where Jill has a direct relationship with the hiring manager). For Jill-managed roles, expressing interest can lead to a direct introduction — that's the magic.
05 Make your applications count
Even in 2026, you still need a great CV, a tailored cover letter, and thoughtful application responses. My bet is that this will no longer hold true in 2027, but that's moot given this is a 2026 guide.
The difference is you don't need to do it from scratch every single time.
The reality is stark: a huge proportion of CVs are filtered out by Applicant Tracking Systems before a recruiter even glances at them. ATS software is looking for specific keywords, formats, and structures, and most candidates don't know the rules.
Jack is able to update your CV on your behalf and make sure it passes the ATS test. He can tailor cover letters for specific roles and help you answer application questions. He won't apply on your behalf — that's a deliberate choice, because the best applications still need your judgment and your voice — but he'll make the process dramatically more efficient.
The golden rule here is if you can't confidently explain a bullet point in an interview, it doesn't belong on your CV. Jack helps you sharpen your materials, not fabricate them. The goal is to surface what's already true about you and present it in the way that's most compelling for the specific role.
How to do this with Jack
Upload your CV to your dashboard, via Settings, so Jack has full context. When you find a role you want to apply to, ask Jack to help you tailor your CV and cover letter. You can do this via chat, email, or even a voice call — whatever suits you. Be specific: tell him the role, the company, and any particular points you want to emphasise.
06 Find a way in
Back when I was applying for jobs eight months ago, I found that cold outreach was, by and large, one of the most successful ways to hear back — especially when it comes to hot companies. A thoughtful message to the right person at the right company cuts through in a way that a job portal application simply doesn't.
Jill already does this, and whilst the pool of hiring managers she works with is growing at breakneck speed, there are still a few roles she doesn't have contacts for. Just you wait.
This is still an alpha feature. If you tell Jack you're interested in a specific (web-sourced) role and you'd like to find someone relevant to reach out to, he can search the web to identify the most relevant contact at that company and help you draft a killer outreach message.
The human piece matters here too. Your existing network is your single biggest lever into any company. If someone you worked with two years ago is now at a company you're targeting, I guarantee you have a higher chance of success through that connection than through any other channel.
I know LinkedIn's search isn't the friendliest, and it's quite hard to keep track of what your 10,000 odd connections are up to these days. But take the time. Search your connections for the companies on your target list. Reach out. A short, honest message goes a long way.
This isn't schmoozing for the sake of it. It's reaching out to people you've worked with and asking for help. Most people are happy to do it.
07 Prepare like it matters
When the email comes that tells you they'd like to have a first chat, Jack doesn't leave your side. This is personally my favourite feature.
Mock interview coaching is one of Jack's deepest, most sophisticated capabilities. He helps you prepare for interviews, and he adapts to the type of interview you have coming up. Simply let Jack know what you're preparing for and who you're interviewing with, and he'll help you crack it.
Jack simulates realistic screening calls tailored to your background and the specific role you're targeting. He asks the questions real interviewers ask, gives you space to work through your answers, and helps you find what works. After each session, he provides detailed feedback on what landed and what didn't.
Voice is strongly preferred here — 93% of mock interview users choose to do it on a call, and that makes sense. Interviewing is a spoken skill, not a written one. Practising out loud, hearing yourself articulate your experience, getting comfortable with pauses and follow-ups — that's what builds confidence.
The best way to prepare
Build a library of 8–12 stories from your career, structured around the STAR framework (Situation, Task, Action, Result). Cover:
- Ownership moments (3–4 stories)
- Mistakes and what you learned (2–3)
- Cross-functional or conflict situations (2–3)
- Big wins with specific metrics (1–2)
Jack will help you build and refine this library. Then, before each interview, map the most relevant stories to the likely questions for that specific role and interviewer.
How to do this with Jack
You can do this via any channel you wish. Head to jackandjill.ai/mock-interviews. Jump on a call with Jack, chat to him, or do it over email. It's entirely up to you and whatever suits your schedule and comfort level — it's completely fair if you don't want your fellow commuters to hear you talking about fixing a bug you'd introduced. Tell Jack the role, the company, the interview stage, and ideally who's interviewing you. He'll take it from there.
08 Negotiate with confidence
You got an offer. The instinct, especially in a tough market, is to accept immediately and be grateful. I get it. Last time I tried negotiating, I lasted about five seconds before folding. But this is one of the highest-leverage moments in your entire job search, and leaving money on the table costs you for years.
Jack will help you prepare. He can benchmark the offer against market data for similar roles, help you identify which components of the package are negotiable, and run through likely objections and counterarguments.
The data here is interesting: research from Harvard's Program on Negotiation has found that AI negotiation tools can actually reduce the gender gap in negotiation outcomes. When people practise with an AI, they negotiate more assertively regardless of gender.
Jack won't negotiate for you. But he'll make sure you walk into that conversation knowing your worth, having rehearsed the hard parts, and feeling confident rather than anxious.
09 Your dashboard: mission control
Everything Jack does converges in your dashboard. Think of it as your job search command centre.
Even now, happily in a job, I still check my dashboard every week to have Jack run a few searches on my behalf. It's important to keep an eye on the market even when you're not actively searching. You never know when something unmissable pops up, and it's of course much easier to go at it from a position of strength.
From your dashboard, you can chat with Jack about anything — a role, a company, a career question, or just to ask for advice. You can scroll through new job matches and keep an eye on the ones you've shortlisted. You can attach documents — your CV, a job description, interview notes — so Jack has more context on you. And you can call Jack directly from the dashboard if you'd rather talk than type. You can even dictate if that's more your gist.
The dashboard is the single place where everything Jack knows about your search comes together. Use it to stay on top of your matches, revisit roles you've saved, and keep the conversation going.
10 What Jack won't do for you
There are a few things Jack can't help with (yet). Wink wink. I'd encourage you to do them manually in the meantime.
Leverage your network
We talked about your network being your single biggest lever in section 6. Right now, that requires manual work. Going through LinkedIn, cross-referencing connections, sending messages. And as tedious as this is, it's also incredibly worthwhile. Now, imagine if Jack knew who in your network works at the companies you're targeting, and surfaced those connections for you automatically. Wouldn't that be something.
Company deep dives and interview memos
Right now, if you want to research a company before an interview, you're stitching together Glassdoor reviews, LinkedIn posts, news articles, and whatever you can find on Crunchbase. What if Jack could pull together everything you need to know about a company and the people interviewing you, packaged into a brief you can read as you saunter into their office? Think of it as your pre-interview cheat sheet.
Track your applications
There's nothing more embarrassing than applying twice for the same job — and believe me, I've done it. Beyond that, tracking lets you spot patterns. Maybe you're hearing back more from a certain type of role, and you should zero in on those.
We are building application tracking into the platform. In the interim, I'd suggest you keep a simple spreadsheet or a Notion database with your applications: the company, the role, the date you applied, the stage you're at, and any notes. It takes five minutes and saves you hours of confusion later.
A favourite thing of mine to do is also reference what version of my CV I attached. You can then quickly start to see whether any one version trumps all others. Perhaps that one line about how you optimised X system leading to Y minutes saved per day is doing the heavy lifting.
