Operations · IT · AI Automation

Jonathan
Henderson

I keep things running, connect the dots, and build the AI that handles the rest.

Fifteen years across a software company and government missions abroad

Jonathan Henderson

What I Build

I am not a developer by background. I build with AI. Here is the proof: small, working tools built on my own time, each one live and clickable.

Ledger Lens

Live AI

Drop in a messy receipt or statement and get back a categorized, reconciled report with duplicate and anomaly flags. Live AI does the reading; the totals are recomputed in code so they always reconcile. The interactive version of the automation I have used to replace paid expense software at a fraction of the cost.

Live demo
Ledger Lens showing a reconciled credit-card statement with category and duplicate flags
Crosswalk CV showing a source CV with country-specific details struck through

Crosswalk CV

Live AI

Rewrites a CV from one country’s hiring conventions to another’s: it strips what hurts in the target market, restructures to local norms, and explains every change. Trilingual (English, Portuguese, and Spanish), with a live AI model behind it.

Live demo
Sentinel showing a vendor risk dashboard with renewal countdowns and risk tiers

Sentinel

Live AI

A vendor risk and renewal console: a live dashboard, an AI contract analyzer that ranks the concerning terms and pulls out the key dates, and risk scores computed in transparent code. The AI does the heavy reading; the scoring stays objective and the weighting stays a human decision.

Live demo
Self-Check showing a banded, non-diagnostic result with a plain-language explanation

Self-Check

Live AI · explainer

A calm, accessible self-check that is scored on the server, never in the browser, and returns a banded, explicitly non-diagnostic result. A live AI explainer puts the result in plain language and stays supportive throughout. Fictional questions, nothing stored.

Live demo
Secure Handoff showing the six-step file handoff walkthrough

Secure Handoff

Systems · security

A sandboxed walkthrough of a self-hosted service for moving large files between organizations: one-off, unguessable links, no accounts, and automatic expiry. Built with AI assistance, but the product itself runs no AI. The story here is systems and security engineering.

Open walkthrough
The Ask assistant showing its opening message and suggested questions

Ask

Live AI

Have a question about my work? Ask the assistant. It answers only from a curated, public fact file, shows its own prompt and the cost of every reply, and says plainly when it does not know. It speaks about me, never for me, and conversations are not stored.

Ask it something

Every one is a sandboxed demo: it stores nothing you enter and carries its own notes on what it does. The tools run on fabricated data; the assistant answers only from a public fact file.

About

A practical operator with fifteen years across a software company and government missions abroad, who taught himself to build the automation that takes the busywork out.

“I bring a practical, figure-it-out approach to whatever the work needs, whether that’s managing systems, running an event, or building an AI tool to take the busywork out.”

I’m an operations person who also builds the automation. That is the job now: operations and administrative support across the central office of the Association of College Unions International, with a focus on putting AI to work on the repetitive parts of everyone’s week.

For six years before that, I was the one an 80-person software company counted on to keep the back office running: IT and SaaS administration, vendor and expense operations, trade shows, and marketing. When a process was slow or manual, I taught myself to build a practical AI tool in Python to fix it, even though I don’t come from an engineering background.

Earlier still, I spent eight years coordinating events and programs for Global Affairs Canada at missions in New York, London, Dublin, and Ottawa. What ties all of it together is a knack for catching the work that falls between the teams and getting it done, then making sure it doesn’t have to be done by hand twice.

When I’m not at a keyboard, I’m usually teaching myself to fix something around the house. Same figure-it-out instinct, different tools.

Expertise

From keeping the lights on to building the tools that make the work lighter.

AI & Automation

Self-taught builder of practical AI tools in Python and the OpenAI API: an expense processor that beat a paid platform at about a penny a report, a lead-enrichment pipeline across Apollo and HubSpot, and an interactive ROI calculator that doubled as a lead-capture tool.

Operations & Administration

Expense processing, vendor and invoice management, and third-party risk and compliance. About 20 expense reports a month and audit-ready vendor records, keeping the business side steady.

IT Administration

Microsoft 365, LastPass, and 300-plus SaaS licenses across 80 employees in the US and abroad. Onboarding, offboarding, license right-sizing, and the person people call when something has to work.

Events & Logistics

Nine trade shows a year, run single-handedly end to end: booth design, freight, travel, collateral, and a budget of about $100K. Earlier, roughly 30 events a year for government missions, from 50 to 1,000 guests.

Marketing & Communications

B2B campaigns, SEO, analytics, paid ads, and brand. Built marketing and analytics stacks, ran a website overhaul to a number-one Google ranking that has held since 2013, and turned a $300K marketing program into a board-ready deck.

Background

Professional experience and education.

  1. Current

    Administrative Operations Manager, ACUI

    Operations and administrative support across the central office of the Association of College Unions International, with a focus on applying AI tools and workflow automation to take repetitive work off people’s plates.

  2. 6+ years

    Operations, IT & Communications, OneVizion

    Kept IT, vendor and expense operations, trade shows, and marketing running for an 80-person software company, and built AI automation that replaced manual workflows and cut costs. Grew from a part-time coordinator into a full-time manager reporting to the CEO.

  3. 8 years

    Program Coordination, Global Affairs Canada

    Coordinated events and programs for Global Affairs Canada at missions in New York, London, Dublin, and Ottawa, including UN General Assembly weeks and events from 50 to 1,000 guests, with the budgets, communications, and logistics behind them.

  4. Education

    BA Political Science, McGill University

    Bachelor of Arts in Political Science, with minors in Communication Studies and East Asian Studies. Bilingual in English and French, with an international outlook built from studying and working across several countries.

Let’s connect.

If something here is useful to you, or you want to compare notes on building this kind of thing, I’d be glad to hear from you.

The fastest way to reach me is email.

jonathan@jslhenderson.com linkedin.com/in/jslhenderson
Based in Michigan, working remotely

Bilingual in English and French.