Director of Product Operations

project44•Chicago, IL

1d•Hybrid

About The Position

At project44, we believe in better. We challenge the status quo because we know a better supply chain isn’t just possible—it’s essential. Better for our customers. Better for their business. Better for the world. With our Decision Intelligence Platform, Movement , we’re redefining how global supply chains operate. By transforming fragmented logistics data into real-time, AI-powered insights, we empower companies to connect instantly, see clearly, act decisively, and automate intelligently. Our Supply Chain AI enhances visibility, drives smarter execution, and unlocks next-gen applications that keep businesses moving forward. AI at project44 We expect every project44 team member, regardless of role or function, to actively leverage AI in their day-to-day work. Whether you’re building product, serving customers, managing people, or running operations, AI is a tool you’re expected to use with intent, curiosity, and judgment. We don’t expect everyone to be a data scientist. We do expect everyone to be an intelligent user of AI: able to identify where it adds value, direct it effectively, evaluate outputs critically, and govern it responsibly. We invest in our team’s AI fluency because we believe it’s a competitive advantage for every person at project44, not just our engineers If you’re driven to solve meaningful problems, leverage AI to scale rapidly, drive impact daily, and be part of a high-performance team – we should talk. The Role Product & Design spans eight pillars — from Visibility and Intelligent TMS to our AI Agent/Autopilot portfolio — touching nearly every function on the way to market. We're hiring a Director of Product Operations to report to the CPO and ensure our biggest cross-functional efforts don't stall. This is an operator's seat: someone who represents Product in the room, unblocks stuck decisions, and turns messy multi-team initiatives into shipped outcomes.

Requirements

Operator, not coordinator
Owned a cross-functional program end-to-end from ambiguity to shipped outcome, with minimal oversight.
Made calls under incomplete information and owned the results.
Product/technical fluency
Held their own on integration timelines, data quality, or technical trade-offs.
Partnered directly with engineering to scope work.
Executive communication
Built content for a CEO/board/senior audience; distinguishes a status update from a decision-ready brief.
Distilled complex, multi-team situations into one page.
High trust, high discretion
Operated close to a senior leader — representing them accurately, protecting their time, judging what to escalate.
Handled confidential information with sound judgment.
OKRs
Ran an OKR (or equivalent) cycle that focused a team, not just aggregated existing plans.
Connected day-to-day execution to stated objectives so leadership could track progress mid-quarter.
AI-enabled product ops
Understands agentic workflows (non-determinism, autonomy levels, human-in-the-loop, evaluation/monitoring) well enough to shape governance, not defer entirely to Engineering.
Uses AI tools fluently in their own workflow and can push responsible, governed AI shipping.
Quality & compliance
Stood up or run 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).
Understands CSV/CSA and audit-trail concepts well enough to partner with Engineering/Security/Compliance without being the quality SME.
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.
Jira/Jira Product Discovery, Confluence, CPQ (Salesforce, Ironclad, etc.).
Board-level content experience.
Regulated/quality-audited environment experience (Life Sciences/GxP, 21 CFR Part 11, ISO, HIPAA).
eQMS/eDMS or validation tooling familiarity.
Advanced degree welcome.

Responsibilities

Align Product, Sales, and Professional Services on one plan for sales readiness, quoting, FDE scoping, and go-live timelines.
Coordinate Marketing/Product/Sales readiness so launches land together.
Run Product & Design’s leadership meeting cadence and offsite planning.
Prepare content for OKR retros and board materials that turn status into actionable decisions.
Represent Product’s position in cross-functional forums, escalating only what truly needs the CPO’s attention.
Keep roadmap hygiene, intake SLAs, and release readiness running with Product Ops, Product Marketing, CX, and Engineering leadership.
Identify which initiatives need formal programs, then stand them up — scope, owners, milestones, decision rights, governance — through to completion.
Maintain one trusted, current view of program/roadmap status, risks, and dependencies feeding directly into executive and board reporting.
Stand up project44’s product-quality operating system — quality management plan, review council, stage-gated development process, documentation controls, and validation/audit-trail/data-retention controls for GxP, SOC 2, ISO, etc. — with Compliance, Legal, Security, and Engineering.
Translate regulatory/audit requirements into concrete product commitments and maintain a defensible source of truth for diligence.
Make data quality a governed key result across PRDs and programs, not one-off fixes.
Run mid-quarter re-plans off one stack-ranked source of truth with documented trade-offs.
Track roadmap work against OKRs and help the CPO and pillar leads define OKRs that actually focus the org each cycle.
Own the operating model for AI as a product capability — review gates for agent behavior/autonomy, evaluation and monitoring with Engineering/Compliance, and cross-functional muscle for shipping agentic features responsibly.