Director of Product Operations

project44•Chicago, IL

2d•$215,000 - $355,000•Hybrid

About The Position

At project44, we are redefining how global supply chains operate with our Decision Intelligence Platform, Movement. We transform fragmented logistics data into real-time, AI-powered insights, empowering companies to connect instantly, see clearly, act decisively, and automate intelligently. We are seeking a Director of Product Operations to report to the CPO and ensure our biggest cross-functional efforts do not stall. This role is an operator's seat, representing Product in key discussions, unblocking decisions, and transforming multi-team initiatives into shipped outcomes. We expect every team member to actively leverage AI in their day-to-day work, acting as intelligent users of AI tools.

Requirements

Proven experience owning a cross-functional program end-to-end from ambiguity to shipped outcome with minimal oversight.
Demonstrated ability to make decisions under incomplete information and own the results.
Product/technical fluency, including understanding integration timelines, data quality, and technical trade-offs.
Experience partnering directly with engineering to scope work.
Experience building content for a CEO/board/senior audience, distinguishing status updates from decision-ready briefs.
Ability to distill complex, multi-team situations into a concise, one-page summary.
Experience operating with high trust and discretion, accurately representing senior leaders and judiciously determining escalations.
Proven ability to handle confidential information with sound judgment.
Experience running an OKR (or equivalent) cycle that focused a team and connected day-to-day execution to stated objectives for leadership tracking.
Understanding of agentic workflows (non-determinism, autonomy levels, human-in-the-loop, evaluation/monitoring) sufficient to shape governance.
Fluency in using AI tools in personal workflow and ability to drive responsible, governed AI shipping.
Experience standing up or running a QMS, stage-gate review process, or documentation control system, ideally in a regulated environment (GxP/21 CFR Part 11, ISO 9001/27001/62304, SOC 2).
Understanding of CSV/CSA and audit-trail concepts sufficient to partner with Engineering/Security/Compliance.
12+ years in product operations, program/portfolio management, chief-of-staff, or management consulting, with senior cross-functional leadership in complex B2B SaaS; VP-level scope building teams/systems from scratch.
Bachelor’s degree required.

Nice To Haves

Supply chain, logistics, or similarly complex B2B SaaS experience.
Management consulting or program management background.
Experience with Jira/Jira Product Discovery, Confluence, CPQ (Salesforce, Ironclad, etc.).
Board-level content experience.
Experience in a regulated/quality-audited environment (Life Sciences/GxP, 21 CFR Part 11, ISO, HIPAA).
Familiarity with eQMS/eDMS or validation tooling.

Responsibilities

Align Product, Sales, and Professional Services on a unified plan for sales readiness, quoting, FDE scoping, and go-live timelines.
Coordinate Marketing, Product, and Sales readiness to ensure launches are synchronized.
Manage the Product & Design leadership meeting cadence and offsite planning.
Prepare content for OKR retrospectives and board materials, transforming status updates into actionable decisions.
Act as a proxy for the CPO, representing Product's position in cross-functional forums and escalating only critical issues.
Oversee roadmap hygiene, intake SLAs, and release readiness in collaboration with Product Ops, Product Marketing, CX, and Engineering leadership.
Identify initiatives requiring formal programs and establish them, defining scope, owners, milestones, decision rights, and governance through to completion.
Maintain a single, trusted, and current view of program/roadmap status, risks, and dependencies for executive and board reporting.
Establish project44’s product-quality operating system, including a quality management plan, review council, stage-gated development process, documentation controls, and validation/audit-trail/data-retention controls for GxP, SOC 2, ISO, etc., in partnership with Compliance, Legal, Security, and Engineering.
Translate regulatory and audit requirements into concrete product commitments and maintain a defensible source of truth for diligence.
Ensure data quality is a governed key result across PRDs and programs, moving beyond one-off fixes.
Manage roadmap changes, including mid-quarter re-plans based on a single stack-ranked source of truth with documented trade-offs.
Track roadmap work against OKRs and assist the CPO and pillar leads in defining OKRs that focus the organization each cycle.
Own the operating model for AI as a product capability, including review gates for agent behavior/autonomy, evaluation and monitoring with Engineering/Compliance, and cross-functional collaboration for shipping agentic features responsibly.