Director of Product Operations at project44 in Chicago, IL

Why project44?
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.
Headquartered in Chicago, IL with a 2nd HQ in Bengaluru, India we are powered by a diverse global team that is tackling the toughest logistics challenges with innovation, urgency, and purpose.
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.
What You’ll Do
Cross-functional coordination: 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.
Meeting cadence & executive communication: Run Product & Design’s leadership meeting cadence and offsite planning. Prepare content for OKR retros and board materials that turn status into actionable decisions.
CPO proxy: Represent Product’s position in cross-functional forums, escalating only what truly needs the CPO’s attention.
Operating system ownership: Keep roadmap hygiene, intake SLAs, and release readiness running with Product Ops, Product Marketing, CX, and Engineering leadership.
Program management: Identify which initiatives need formal programs, then stand them up — scope, owners, milestones, decision rights, governance — through to completion.
Reporting: Maintain one trusted, current view of program/roadmap status, risks, and dependencies feeding directly into executive and board reporting.
Quality & compliance system: 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.
Regulated-market readiness: Translate regulatory/audit requirements into concrete product commitments and maintain a defensible source of truth for diligence.
Data quality: Make data quality a governed key result across PRDs and programs, not one-off fixes.
Roadmap change management: Run mid-quarter re-plans off one stack-ranked source of truth with documented trade-offs.
OKRs: Track roadmap work against OKRs and help the CPO and pillar leads define OKRs that actually focus the org each cycle.
AI governance: 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.
What We’re Looking For
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.
Experience & Education
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; advanced degree welcome.
Nice to Have
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.
Work Authorization: Candidates must be authorized to work in the US without current or future employer-sponsored visa support.
In-office Commitment:Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for candidates who are enthusiastic and committed to joining our team on-site,in our beautiful headquarters 4 days a week. Together, we’re building something extraordinary—learn, grow, and thrive in our fast-paced, transformative environment.

We continually evaluate our pay ranges to reflect skills, experience, and market conditions. The base salary offered will be determined by assessing a candidate’s experience and skills relative to the scope and responsibilities of the position, as well as the specific geographic location where the job will be performed. Base salary is one component of project44’s total compensation package, which also includes stock options for all EOR and project44-employed team members, bonus or commission eligibility depending on role, and a benefits package tailored to your country of employment. Specific benefits package offerings vary by country and may include health, dental, and vision coverage, retirement plans, and paid time off, in line with local market standards and statutory programs. The base salary range for this position is $215,000 – $355,000 + bonus eligibility.
Diversity & Inclusion
At project44, we’re designing the future of how the world moves and is connected through trade and global supply chains. As we work to deliver a truly world-class product and experience, we are also intentionally building teams that reflect the unique communities we serve. We’re focused on creating a company where all team members can bring their authentic selves to work every day.
We’re building a company that every one of us at project44 is proud to work for, and our journey of becoming a more diverse, equitable and inclusive organization, where all have a sense of belonging, is shaped through the actions of our leadership, global teams, and individual team members. We are resolute in our belief that each team member has an equal responsibility to mold and uphold our culture.
project44 is an equal opportunity employer seeking to enrich our work environment by creating opportunities for individuals of all backgrounds and experiences to thrive. If you share our values and our passion for helping the way the world moves, we’d love to review your application!
For any accommodation needed during the hiring process, please email   recruiting@project44.com. Even if you don’t meet 100% of the above job description you should still seriously consider applying. Studies show that you can still be considered for a role if you meet just 50% of the role’s requirements.

More about project44
Since 2014, project44 has been transforming the way one of the largest, most important global industries does business. As transportation and logistics continue to evolve and customer expectations around delivery become more demanding, industry technology must rise to the occasion. In just a few short years, we have created a digital infrastructure that eliminates the inefficiencies caused by dated technology and manual processes. Our Advanced Visibility Platform is used by the world’s leading brands to track shipments, collaborate with supply chain partners, drive operational efficiencies, and create outstanding customer experiences.