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Indigo Grady (he/him) · Humacao, Puerto Rico · Remote · Atlantic Time (UTC−4)
Open to Product Manager, Program Manager, and Operations roles
I build teams and systems that bring vision to life.
Product and operations leader. I was the second hire and, for three years, the entire product function at a remote SaaS and edtech company. Today I build Claude-based agentic workflows as Founding COO at AutoPilotPR.
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Selected work
Razor Sparrow · General Manager · 2023–2026
Stabilizing a growing company
First response time fell from weeks to under 24 hours. With that foundation in place, I led the shift to growth and launched three new products.
How I did it
Situation
I joined as the second hire. Support was buried: at its peak, the backlog held about 300 tickets plus hundreds of unanswered emails, and customers waited weeks for a first reply.
What I did
I found that about three-quarters of the tickets traced back to bugs. I hired a senior engineer to fix them, and wrote the backlog that guided the work. I turned the founders' ideas into scoped, prioritized tickets with user stories and acceptance criteria, and rebuilt the support process around a new ticket system.
What happened
First response fell from weeks to under 24 hours, with a team of five: two engineers (one of them the founder), a support specialist, a billing lead and me. We stayed lean on purpose, aiming to grow while bootstrapped before hiring more engineers.
The launches
GradeSight, Email My Students and ClassCloak shipped in August 2026, weeks before I left. GradeSight and ClassCloak were new products. Email My Students was a full rebuild from scratch for Chrome's Manifest V3, under its existing listing.
District renewals stayed strong while school budgets fell, and new district customers kept overall usage steady.
How I did it
Situation
School district contacts changed constantly, so quotes and invoices got lost, and every renewal needed a fresh quote.
What I did
I built an account model that tied documents to the district instead of the person and routed each message to the right stakeholder. I redesigned district pricing, and co-designed a new admin portal with tiered permissions, including the authorization system and database schema behind it.
What happened
Quotes and invoices stayed attached for about 300 districts, and a renewal no longer needed a new quote each year. Renewal rates stayed strong, and new district customers offset the accounts that shrank as budgets tightened.
An admin portal wireframe I built with AI (ChatGPT) to test the design before engineering started, shown here redrawn with sample data.
Razor Sparrow and AutoPilotPR · AI workflows
AI where it actually helps
It saved enough time that when the support role opened up, we didn't need to rehire for it. I now design Claude-based agentic workflows at AutoPilotPR, with a focus on keeping token costs low as usage grows.
How I did it
Situation
Routine support questions took up time the team needed for harder cases.
What I did
I built an AI support-drafting system in Cursor with Claude models and evaluated it against the replies the team had actually sent. I scoped it to routine inquiries on purpose and left escalations to people. I also prototype admin workflows with AI before handing them to engineering, so requirements arrive already tested.
Part of the AutoPilotPR reply flow. The model writes the words, and code places the facts from the source systems, so a draft can't invent a price or a date.
Code Power (an Optic Power company) · Product Coordinator · 2021–2023
Client goals into buildable software
One client's president wrote that his product "undeniably benefitted" from that involvement.
How I did it
Situation
A software consultancy running many client projects at once, each with shifting scope.
What I did
I oversaw eight projects across six industries and was the main liaison for seven clients. I ran up to three projects at a time in Jira, owned requirements and backlog grooming, and tested builds before release, filling the business analyst, scrum master, and project manager roles at times as each project needed.
Client project: BUILD's Fam-Biz CEO simulation game for students in grades 7 to 12.Sample work: the roadmap slide from a biweekly status report I wrote for a marketing agency's internal task manager, redacted. Each report also covered recent deliveries and open risks, like this one on limited user testing.
Oct 2026 – nowFounding COO (part-time), AutoPilotPRBusiness strategy and Claude-based agentic workflows
Aug 2023 – Sep 2026General Manager, Razor SparrowProduct, support, billing, renewals, and operations for a remote SaaS and edtech companyTeam of five · about 70,000 users · about 300 district accounts
May 2021 – Jul 2023Product Coordinator, Code Power (an Optic Power company)Requirements, backlogs, and delivery for eight client software projects
Sep 2018 – Jul 2020Environmental Specialist, Triumvirate EnvironmentalOversaw migration of the FDA's chemical inventory to a new system; Rookie of the Year 2019
Feb 2017 – May 2018General Manager, Bistro 360Hired and trained a team of 12 to 20, managed more than 15 distributors, and wrote the employee handbook and training manual
Jun 2016 – Feb 2017Assistant Front-of-House Manager, CheesetiquePromoted within five months; launched the store's first liquor program
Tools: Jira, Taiga, Confluence, Airtable, Stripe, GoHighLevel, REST APIs and webhooks, Claude, Claude Code, Cursor, MCP, HTML, JavaScript. Education: BS in Environmental Studies, Elon University.
Let's talk
I'm looking for remote product, program, and operations roles where the work has a large impact on the team or company, especially where AI can help.
