20 Feb 2026 2 min read

My first AI app - tools for job hunting

Me talking to my AI agent about my emails

The AI wave is changing the professional landscape and I want to ride that wave. At careercaddy.online, I've been building tools that helps me with my job applications. For example, in the (intensely boring) image below, I demonstrate putting a job-post URL into my service. AI scraped the website and created a job-post record for my own accounting. Then, I use AI to compare my resume with the job description and score it from 1 to 100.

Logs of my AI agent talking to my API — The logs of my AI bot smartly creating records on my job website

Among the open-source AI-assisted SaaS products (of which there are impressive contributions), Career Caddy aims to simplify the process of prompting AI. The purpose is to answer application questions by supplying past responses to guide it in mimicking my writing style.

By supplying my past answers, I benefit in two ways. First, I am training AI what I've done beyond what my resume says. Second, I am more likely to write authentically when I provide answers in a job application.

When training AI, Career Caddy aggregates my resumes, cover letters and application questions as part of a giant prompt to give the AI material in order to write like me. This is handy when I come to that section of a job application that asks me a question like:

Can you share an example of a complex bug you encountered in a project? How did you identify the root cause and what steps did you take to resolve it?

For me, I always freeze at a question like this. I've answered it before a dozen times, but each time I re-experience an aversion to self promote. This is part a reluctance in regurgitating a canned answer and part, "I don't even know where to begin." With Career Caddy, I don't have to choose between letting AI write drivel or crafting my own bespoke answer. I write it once and can reference it always.

Career Caddy also helps me write in my authentic voice. Yes you've read that right, an AI tool helps me write more like me. When I use my writing to inform AI, I am incentivized to produce my own words and not slop. This makes the AI sound more like me and not vice versa.

Career Caddy is currently a barely held together collection of Agents, MCP, Prompts, API, HTML, templates, scripts, CI/CD, files, folders, and free time that amount to a hill of dog food. My goal is to coalesce it all together into an open source MVP that can be demoed for a small audience next week. After I have a large enough corpus of data, maybe it will even apply to jobs for me.

One of the major hurdles to MVP is the atrocious UI. As a backend engineer, I really want to get the functionality working and then shore up the aesthetics. I'll probably lean on AI for that.