Technical Product Manager

About Stable Software

Stable Software builds software for the U.S. customs and international trade industry, a market still largely served by desktop applications from the 1990s, emailed spreadsheets, and manual data entry against federal systems.

We build trade compliance software used across multiple business types — customs brokerages, importers, and freight forwarders. Our products cover duty recovery, tariff classification and duty calculation, reconciliation transmission, denied party screening, and certificate of origin compliance.

We are bootstrapped, founder-owned, and profitable-minded.

The Role

This is a technical product role at a company where product definition is the constraint on how fast we ship. Our engineering team builds with AI tooling and can implement a well-specified feature in a fraction of the time it once took. What limits us now is the quality and precision of the specification itself.

You will own that. Specifically:

- Running requirements sessions with customers and leaving with a precise understanding of what the software must do

- Writing engineering tickets detailed enough to be implemented without follow-up, including edge cases, data conditions, and explicit acceptance criteria

- Deriving requirements from primary regulatory source material rather than from secondhand summaries

- Defining and executing test cases against real customer data, and verifying output before it reaches a customer

- Working directly with AI development tooling to produce first-pass implementations within defined architectural constraints, with engineering review

- Owning the feedback loop between what customers report and what gets built

This is not a roadmap-and-stakeholders role. It is hands-on specification, verification, and delivery.

Why Precision Matters Here

Our software produces financial output that customers submit to a federal agency under their own legal authority. An incorrect calculation is not a cosmetic defect.

Requirements in this domain are set by regulation, not by preference. How amounts are apportioned, how rounding is applied, which transactions qualify — these are legal questions with correct answers, and the specification has to reflect them exactly. Candidates who are comfortable resolving ambiguity by asking rather than assuming will do well here.

Requirements

- 4+ years in technical product management, solutions engineering, business analysis, or a similar specification-heavy role

- Demonstrated ability to write engineering-ready specifications: explicit acceptance criteria, enumerated edge cases, defined data conditions

- Technical fluency sufficient to read code, follow a database schema, review a pull request, and hold a substantive conversation with senior engineers

- Working SQL — you should be able to query production data to validate output yourself

- Direct experience with AI development tooling (Claude, Cursor, or equivalent), including an understanding of where it produces reliable output and where it does not

- Comfort in customer-facing meetings with senior professionals, including running requirements sessions and handling escalations

- Willingness to work from primary regulatory source material to derive product behavior

Preferred

- Background in a regulated domain: customs, trade compliance, tax, insurance claims, payroll, healthcare billing, or financial services

- Experience with data-heavy B2B products involving file ingestion, reconciliation, or calculation engines

- Prior work at a company small enough that you owned outcomes rather than process

Compensation

$120,000–$160,000 base, depending on experience. Full BCBS Gold PPO health/dental/vision coverage. Flexible schedule and location.

To Apply

Email reis@stablesoftware.com with a brief note and links to relevant work. No cover letter required. Please include a specification you have written — a ticket, a requirements document, or an equivalent artifact — with any confidential details removed.

Finalists complete a paid, scoped exercise: we provide a real customer scenario and regulatory source material, and you produce the specification and test cases. Compensated at your rate. Use the AI tooling you would use on a normal workday.