How I built a personal AI bot that found $4,300/year of unused workplace benefits

Most employees in Canada use 30-40% of the benefits their employer pays for. The rest expires December 31 every year. It’s not because people are lazy. It’s because:

• Benefits booklets are 50+ pages of dense insurance jargon
• HR departments can’t legally tell you what to claim (liability)
• Brokers don’t push optimization - their incentive is selling new plans, not maximizing existing ones
• “I’ll figure it out later” turns into December, then it’s gone

I’ve been building a personal AI assistant called Life OS for the past year. Python, LLM APIs, 100+ tools across 20 Python modules. It helps organize private logs, notes, scheduling, finance context, health context, and daily decisions without putting the raw data on this site.

A few weeks ago I asked it a simple question: “Audit my workplace benefits. Tell me what I’m missing.”

Thirty minutes of conversation later it had:

1. Parsed my 50-page employee benefits booklet
2. Read claim-history screenshots I provided
3. Built a complete YTD usage tracker for every bucket
4. Identified ~$8,500 of unused annual benefits - most of which I had no idea I had
5. Walked me through filing eligible purchases I’d already made as a $900 wellness-account claim

Net of tax: roughly $600 in my bank account, for two receipts I’d forgotten I had.

That session also surfaced benefit categories I genuinely should have known about but didn’t:

• $1,200/year paramedical bucket shared between massage, chiro, physio, and dietitian
• $1,500/year mental health bucket completely separate from paramedical
• $400 vision bucket I had not touched
• $150 home health-device coverage available every 5 years
• $130 annual recovery-device coverage sitting unused

It matched unused benefits against my actual life context and eligible purchases without forcing me to read the booklet like a lawyer.

Why this works as a service

The pattern is repeatable:

1. Read the plan booklet - extract every cap, percentage, and exclusion
2. Pull the claims history - see what’s already used vs available
3. Build a YTD usage tracker - surface unused buckets with deadlines
4. Match against personal context - life stage, relevant needs, purchases, and deadlines
5. Recommend specific high-value claims - not vague “you may be eligible” advice, but concrete actions to file next

Most insurance carriers in Canada use similar plan structures (Green Shield, Sun Life, Manulife, Canada Life, Blue Cross cover ~80% of the market). The booklets are dense but the patterns are repeatable. A specialized AI agent can deliver this audit in 30 minutes - work that would take a human 6-10 hours.

What I’m building from here

The Benefits Maximizer is becoming its own module inside Life OS - and probably the cleanest first service because the value is easy to understand:

I help employees find unused workplace benefits before they expire.

If you work in Canada with a typical extended health plan and want to know what you’re leaving on the table, get in touch.

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If you want to follow along as I build more of this, the rest of the writing lives on the blog. Travel videos on the JustJor YouTube channel.