Software Implementation Specialist Jobs in Chicago, IL

"You'll be the hands-on builder who turns complex workflow blueprints into a fully configured, battle-tested reality for our clients."

Getting a customer live on MasterMind requires turning strategic implementation plans into precise technical setups, accurate data moves, and seamless user experiences.

As our Implementation Specialist , you'll be a key execution engine behind that process. Working closely with Implementation Leads and Managers, you'll get under the hood of our TMS to handle hands‑on system configuration, guide initial data migration, and execute rigorous validation testing. This is an entry point into Mastery designed for someone who is detail‑oriented and eager to build technical depth, master logistics technology, and directly impact how our clients operate day to day.

• Build the foundation: Execute hands‑on configuration tasks within the TMS platform—setting up data dictionary terms, user roles, scopes, permissions, and system settings to match client requirements.
• Power the data move: Support data migration by helping create templates, executing initial data migration activities, and making precision adjustments along the way.
• Translate client needs: Develop a deep understanding of client‑specific future workflows to ensure every setting aligns with their operational goals.

• Ensure go‑live readiness: Prepare, execute, and validate User Acceptance Testing (UAT) test cases to confirm the platform performs flawlessly before client handoff.
• Squash defects: Partner with broader implementation and product teams to identify, track, and resolve system defects early.
• Protect quality: Validate that system behavior meets both functional standards and client expectations prior to deployment.

• Become a subject matter expert: Build and maintain deep technical proficiency in the MasterMind platform through hands‑on experience and structured training.
• Stay ahead of updates: Actively participate in ongoing enablement programs to keep pace with new features, platform updates, and industry's best practices.
• Drive efficiency: Apply product insights back into your day‑to‑day work to make future implementations faster, smoother, and more effective.

• Stay in lockstep with leads: Partner closely with Implementation Leads, Managers, and Product teams to align daily technical tasks with overall project milestones.
• Bring clarity: Participate in team meetings and client touchpoints to provide clear task updates and technical context when needed.

• Early‑career professional looking to build a foundation in software implementation and SaaS technology.
• Background, coursework, practical experience in Business, Supply Chain, Information Systems, or a related field.
• Demonstrated ability to manage detail‑heavy execution tasks and organize competing priorities effectively.

• Uncompromising attention to detail: You double‑check configuration settings and catch data discrepancies that others miss.
• Growth mindset & curiosity: High energy, self‑motivated, and eager to pick up technical skills and industry domain knowledge quickly.
• Strong communication skills: Clear, professional written and verbal communication whether syncing internally or speaking with clients.
• Logistics & SaaS instinct: A basic understanding of enterprise software platforms or transportation, logistics, and supply chain. It would be a differentiator if you have specific experience in the Intermodal, Drayage or LTL spaces.

• Configurations land right the first time: System settings, permissions, and data templates match client requirements with minimal rework.
• Testing cycles run smooth: UAT test cases are thoroughly validated, and defects are caught and resolved well before go‑live.
• You become a platform authority: Implementation Leads trust your platform knowledge and rely on you to execute complex technical setups.
• Project timelines stay protected: Your execution keeps technical and configuration milestones moving without creating bottlenecks for the broader project team.

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.

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.

• Comprehensive health coverage so you can focus on the work, not the what‑ifs.
• Company‑paid life insurance at 1× your salary, plus AD&D and additional voluntary coverage options.
• Legal assistance and employee support programs — for life's messier moments, big and small.
• Robust benefits. Real flexibility. A team that has your back. That's the Mastery standard.

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

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

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