Project Manager Representative Jobs in Chicago, IL

ABOUT THE ROLE

"You'll be the person who keeps a complex implementation calm, organized, and moving — turning a long list of moving parts into a customer's confident go-live."

MasterMind is the cloud-based TMS built for everyone who moves freight — shippers, carriers, private fleets, IMDL, and brokerages — all operating in one platform. Getting a customer fully onto that platform is its own kind of complexity: timelines, dependencies, internal teams, customer stakeholders, and a hundred small decisions that all must land in the right order.

As our Project Manager, you'll own that complexity from kickoff to go-live. You'll be the steady hand customers trust and the connective thread that keeps Mastery's internal teams aligned — managing scope, surfacing risk before it becomes a problem, and making sure every implementation ends the way it should: on time, on scope, and with a customer who's confident in what they just adopted.

WHAT YOU'LL OWN

Customer & Stakeholder Management

• Represent the Mastery brand in every customer interaction — building trust through clarity, consistency, and follow-through
• Build strong relationships with customer stakeholders and internal teams that translate into smoother decisions and fewer surprises
• Define communication and engagement strategies for each project, adapting as stakeholder needs and expectations shift
• Keep information flowing — clear, timely, and proactive communication throughout the project lifecycle

Project Planning & Execution

• Lead projects end-to-end, from initiation through go-live and handoff to Customer Success
• Define project strategy alongside the project team — goals, success metrics, milestones, deliverables, and timelines
• Build and maintain project plans that balance scope, schedule, quality, and resource constraints in the real world, not just on paper
• Monitor project health against milestones and success criteria, catching drift before it becomes delay

Scope, Risk & Dependency Management

• Define and protect project scope in partnership with customers and internal teams
• Manage scope changes through clear, documented change control — no surprises, no scope creep by accident
• Identify risks early and build mitigation and contingency plans before they're needed
• Coordinate cross-functional dependencies, communicating impacts clearly when one team's timeline affects another's
• Escalate when it matters — knowing the difference between a risk to monitor and one that needs immediate attention

Team Leadership & Process Improvement

• Foster accountability and ownership across every team involved in an implementation
• Turn lessons learned into better delivery, continuously refining how Mastery runs implementations
• Champion project management standards and drive adoption of the tools and processes that make delivery repeatable
• Define go-live readiness and post-implementation success criteria, and make sure every box is checked before a customer goes live

WHAT YOU BRING

Experience

• 5–10 years of project management experience, ideally in software implementation, SaaS, or technology environments
• Track record managing customer facing implementation projects from kickoff through go-live
• Experience with enterprise software implementations
• Comfortable managing multiple projects simultaneously without losing the thread on any of them
• Transportation, logistics, supply chain, or freight industry experience preferred

Skills & Approach

• Strong organizational, planning, and prioritization instincts
• Excellent written, verbal, and presentation communication
• Sharp problem solving and critical thinking under ambiguity
• Familiarity with Agile, Scrum, or hybrid PM methodologies
• Fluent in tools like Asana, Slack, Teams, and Microsoft Office
• PMP, CAPM, or equivalent certification a plus

HOW YOU'LL KNOW YOU'RE SUCCEEDING

• Customers go live on time, fully scoped, and confident in what they've adopted
• Internal teams know exactly what's expected of them and when — because you made it clear
• Risks get caught and resolved before they become escalations
• Customer Success inherits a smooth handoff, not a cleanup job

ABOUT MASTERY

Most TMS platforms are tolerated. We've proven a better way — one platform built for every facet of transportation: shippers, carriers, private fleets, and brokers, all under one roof. Built to be loved. We're still the only ones who mean that.

Mastery Logistics Systems exists because the transportation industry deserves better. For too long, shippers and carriers have been forced to stitch together a patchwork of outdated, inadequate systems — one for dedicated fleet, another for brokerage, another for LTL, another for intermodal — none of them talking to each other, all of them slowing things down. Mastermind TMS changes that: one platform for every mode, every function, every stakeholder. Flexibility, visibility, and control — finally in one place.

The timing matters. Global supply chains are under pressure like never before, and the transportation industry is at the center of it. We're building the platform that helps this industry move faster, smarter, and more efficiently — tackling everything from AI-powered data ingestion to intelligent automation.

We are a masterful mosaic of specialists, builders, and genuinely good people. Different backgrounds, different talents, one shared obsession: creating something the industry has never had. We believe in diversity of thought, deep respect for each other, and the relentless pursuit of getting it right. We're small enough that every person makes a real impact — technically and culturally — and deliberate enough that we only add people who make the whole better.

If you're passionate about humanizing a complex industry, building for scale, and touching every corner of the global economy — welcome home. Let's build a masterpiece.

BENEFITS — BECAUSE YOU SHOULD LOVE WHERE YOU WORK AND HOW YOU'RE TAKEN CARE OF

We don't do "bare minimum" here — not in the product, not in the culture, and definitely not in how we take care of our people. Mastery's benefit package is built to give you real coverage, real flexibility, and real peace of mind.

  Medical, Dental & Vision

Comprehensive health coverage so you can focus on the work, not the what-ifs.

️  Life & AD&D Insurance

Company-paid life insurance at 1× your salary, plus AD&D and additional voluntary coverage options.

⚖️  Legal & Employee Assistance

Legal assistance and employee support programs — for life's messier moments, big and small.

  401(k) with 4% Match

We invest in the platform and in your future. Save for retirement with a competitive company match.

️  Flexible PTO

Manage your life and your schedule. We trust you to do great work and take the time you need to recharge.

❤️  Giving Back — St. Jude Children's Research Hospital

Our philanthropic partner is St. Jude Children's Research Hospital. Because doing good work and doing good in the world aren't mutually exclusive.

Robust benefits. Real flexibility. A team that has your back. That's the Mastery standard.