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Description
Every application starts the same way: a new job description, a blank cover letter, and an hour spent re-explaining the same three accomplishments in slightly different words. That's not a writing problem, it's a systems problem. At Bain and Deloitte, I built structured processes for a living — a search just needs the same thing: a tracker, an answer library, and a way to turn any JD into a draft without starting from zero. We build all three live, and put one of your real applications through it before the session ends. What You Get Live Co-Working Build: We set up your entire system side-by-side on screen. Job Pipeline Tracker: A single dashboard to monitor every company, stage, key contact, and next move. Core Answer Library: We document your actual wins, metrics, and career highlights once so you can pull from them forever. Custom Claude Setup: An AI project trained on your tone and facts that reads any job posting and drafts custom resumes, cover letters, and short-answer prompts. One Completed Application: We run a live job posting through the workflow and get it ready to submit during the call. Simple Playbook: A fast, repeatable routine: paste the job description, run the prompt, review, and apply. 48-Hour Follow-Up Window: Direct support after the call to troubleshoot your next applications. Who This Is For You are actively applying but waste hours rewriting the same stories for similar roles. Your AI drafts feel bland and generic, forcing you to rewrite everything yourself. You want a reliable, personal system you own for the long haul. Who This Is Not For Anyone looking for an agency or virtual assistant to apply for them. (This builds the tool; you stay in control.) Candidates looking for interview practice or offer negotiation. (This package focuses strictly on application workflows.) Entry-level job seekers with zero work history. The system relies on real career data to generate strong drafts. How It Works Prep (24h Before): Share your current resume and 1–2 target job descriptions. Story Extraction: We pinpoint your strongest career wins and quantifiable metrics. Live Build (1–6 Hours): We build your tracker, organize your answer bank, and calibrate your Claude project. Test Run: We tailor materials for an active job posting and finalize it live. Handoff: You walk away with a ready-to-run system, a clear checklist, and 48 hours of follow-up support. Tiers range from a one-hour build of the tracker and drafting project to a six-hour build with the full answer library, materials tailored across several roles, and a follow-up session. Pick your tier below.
What you'll get from this package
A clean pipeline tracker to keep every company, stage, key contact, and next step organized in one place.
An answer library built from your real accomplishments, written once and reused everywhere
A custom Claude AI project trained to turn any job link into tailored resumes, cover letters, and application answers that actually sound like you.
Your first application completed live, plus a 48-hour follow-up window so you can submit with total confidence.
Additional details
Coaching delivered via live sessions.
We build your system side by side on a live, screen-shared call—no pre-made templates, just real work on your actual materials. You’ll see the entire process firsthand: how we pull the core rules out of your best writing and how we direct Claude to match your exact tone. That way, you know how to adjust and improve it long after our call wraps up. Every asset we create—your personalized voice guide and your story bank—lives in your own files, fully under your control. The first hour is where the real breakthrough happens. We pinpoint what actually gives your writing its edge and personality. If you skip that step, no clever prompt will keep the output from sounding generic. Once we finish building, you have a 48-hour direct support window to ask questions, troubleshoot drafts, and make sure everything runs smoothly.
Services included:
AI Fundamentals
AI Ethics & Responsible AI
Prompt Engineering
AI Podcast Creation
AI Graphics Creation
AI Agents
AI Automation
AI Research
Talk to a team member
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
More packages from Ashwin
Custom hourly · $399/hr
Get help with AI Fundamentals, AI Ethics & Responsible AI, and .
Ashwin also coaches for Management Consulting and MBA. View all.
Offered by Ashwin S.
Joined June 2024
4.96
Build AI solutions from prototype to production
I coach people who want to build something real with AI, not just get better answers out of a chat window. I run a software business that I built this way myself. No engineering team. That means I have made most of the mistakes already, and I can usually tell within a few minutes why someone's project is stalling. A few things I can help you build: • A working product or internal tool. MBB Prep runs AI case simulations, a large drill library, and a web app I built and shipped without engineers. If you have a product idea and no technical team, this is the conversation I know best. • Content and document pipelines. I generate presentation decks, formatted documents, and PDFs programmatically at volume, with quality checks that catch errors before anything reaches a customer. Most people stop at the first draft. The value is in the checking layer. • Research and data workflows. I run a weekly scraper that pulls listings from multiple sources and returns a clean, formatted spreadsheet. Same pattern applies to competitor tracking, market research, or any task you currently repeat by hand every week. • A house style a model can actually follow. I built a written system that keeps my scripts, sales copy, and coaching explanations in one consistent voice across everything I publish. If your AI output all sounds the same as everyone else's, this is the fix. • A single problem you are stuck on. Bring the project. We will scope it, work out whether a model can realistically finish it, and build the first working version together. • I will also show you where these tools fail. Output that looks polished is often quietly wrong, and business logic and maths are where it goes wrong most. So I will show you how to check a result before you rely on it, when to push back on what a model gives you, and where your own judgment still has to do the work. My consulting background is the useful half here. Structuring the problem before you prompt it is most of the work, and it is the step almost everyone skips.
Starting at $165
1h+ of coaching