Build Your Job Search OS with Claude
A real job search is a volume game you lose to friction — rewriting the same answers from scratch, losing track of who you talked to, staring at a blank cover letter at 11pm. I built my own Job Search OS to kill that friction, and in this session we build you yours. You leave with a pipeline you can see, a profile you write once and reuse everywhere, and a Claude project that turns any job description into a tailored draft in your voice. WHAT'S INCLUDED • Live working session, screen-shared — we build it together, end to end. • Your pipeline tracker: every role and its stage (spotted → applied → interview → offer), company, contact, and next action. • A "universal profile" + answer library: your background, stories, and best answers written once, reused everywhere. • A Claude project that drafts tailored resumes, cover letters, and application answers from your profile — in your voice, matched to each job description. • Your first real application, run through it live, start to finish. • A repeatable per-application routine: paste the JD, get a tailored draft, review, apply. • Optional Chrome auto-fill workflow for application forms. • 48-hour post-build support window. BEST FIT IF • You're applying to a lot of roles and drowning in one-off rewrites. • You want every application tailored without starting from a blank page. • You keep losing track of where you stand with which company. • You want a system you own, not another monthly job-tracker subscription. NOT A FIT IF • You're applying to one or two roles — you don't need a system for that. • You want me to find jobs or make introductions — I build the machine, not your network. • You want your applications written with zero input — your stories come from you; Claude amplifies them, it doesn't invent them. HOW IT WORKS 1. Pre-call brief (~24h before): your target roles, plus your current resume and any materials. 2. Live build (1–10h by tier): we build the tracker, profile, answer library, and drafting project together. 3. First real application, live: we run an actual job description through it, start to finish. 4. You leave with the keys: the whole system is yours, plus the per-application routine. 5. 48-hour post-build support window — anything breaks, message me and we fix it. Tiers run from a 1-hour scoping consult to a full 10-hour build with the drafting brain, Chrome auto-fill, and a follow-up session. Pick your tier below.
What's included
I run this as a live, screen-shared build — we make the real system together, I don't hand you a template. You'll watch exactly how I prompt Claude to tailor a resume and answers to a specific job description, so you can run it yourself for every future application. Your materials and stories stay yours, in your own files. I commit to a real turnaround, and there's a 48-hour support window after we build.
- A pipeline tracker for every role — stage, company, contact, and next action, so nothing slips
- A reusable "universal profile" and answer library — your stories and best answers, written once
- A Claude project that drafts tailored resumes, cover letters, and application answers from any job description — in your voice
- Your first real application run end-to-end live, plus a 48-hour post-build support window
Meet your expert
Ben L.
• Stanford GSB Alum, Class of 2021 -- see relevant background & experience below: • Coaching | Advised 400+ admits into Stanford GSB, HBS, Wharton, Kellogg, MIT Sloan, INSEAD, Haas, and more (see ~100 Leland reviews), while teaching multiple courses through Leland • What I'm Doing Now | Based in NYC, building a publication 'Staying Human', working on a stealth, marketplace startup, coaching and playing chess profssionally, and advising a slate of Seed to Series C startups through Elevate LLC • Public Policy | Prior to Stanford, worked on the Policy Team for the Chicago Mayor's Office under Mayor Rahm Emanuel, focusing on 5G infrastructure policy, criminal justice policy, and citywide corporate/economic development deals • McKinsey | Before policy, worked at McKinsey & Co , with casework focused on job training for the formerly incarcerated and workforce development for at-risk youth • PE / VC / Startup Advising | After Stanford, worked in Bain's Private Equity Group on various due diliegences, managed deals with several venture capital firms, and advised multiple startups on growth and go-to-market strategy • Professional Writing | Speechwriting in public policy & political environments, Lead Editor for Nondisclosure (Stanford GSB's magazine) and Managing Editor for the Stanford International Policy Review • Additional Writing | Crafting op-eds, ghostwriting for major publications, developing a fictional short story collection, policy deep dives, a book on chess applications to life, and application essays of all sorts • GMAT / Test-Taking | Scored in the highest percentile of GMAT test-takers, but more importantly I've honed my ability to help others extrapolate top test-testing strategies in the areas they're weakest • Additional Coaching Details | 5+ years experience working with >750 individuals on essay writing and resume professionalization for top consulting firms, MBA programs, execs, and the broader job market • Interview Training | I was interview-trained with McKinsey, helping me give high-quality mock interviews for MBBs and any MBA program; I've also held 10+ events through Leland on interview prep for McKinsey's PEI and GSB's interview process in particular