Senior Engagement Manager

ABOUT THE ROLE

"You'll be the person that turns a successful go-live into a long-term partnership, helping customers optimize their operations, solve new challenges, and achieve their business goals."

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 Senior Engagement Manager, you'll own the customer journey after go-live. You'll be the trusted partner customers turn to and the connective thread that keeps Mastery's teams aligned—strengthening relationships, anticipating challenges before they become obstacles, identifying opportunities to deliver more value, and ensuring every customer continues to grow with confidence.

WHAT YOU'LL OWN

• Serve as the trusted strategic advisor for a portfolio of live customers, building long-term partnerships that drive adoption, retention, and business success.
• Lead the post-go-live customer journey, owning Hypercare, guiding customers through new features and releases, and ensuring they continue to realize value from MasterMind.
• Identify opportunities to optimize customer operations, proactively recommending new workflows, features, and best practices that align with each customer's evolving business goals.
• Partner cross-functionally with Product, Engineering, Support, Implementation, and Training teams to advocate for customers, remove roadblocks, and deliver exceptional outcomes.
• Turn customer insights into action by analyzing trends, identifying improvement opportunities, and influencing product enhancements, training strategies, and customer success initiatives.

WHAT YOU BRING

• 5-10 years of experience in customer success, client engagement, account management, consulting, or a related customer-facing role within SaaS, transportation, or logistics technology.
• Track record of managing executive-level customer relationships and serving as a trusted strategic advisor.
• Comfortable leading customers through post-implementation adoption, change management, or ongoing optimization.
• Experience collaborating across cross-functional teams to solve complex customer challenges and deliver business outcomes.

• A relationship-first mindset with exceptional communication, presentation, and stakeholder management skills.
• Ability to think strategically while remaining detail-oriented, balancing multiple priorities across a portfolio of customers.
• A proactive problem solver who anticipates customer needs, identifies opportunities, and drives action before issues arise.
• Strong analytical skills with the ability to identify trends, translate customer feedback into actionable recommendations, and influence internal teams.
• A collaborative leadership style with a passion for coaching others, fostering teamwork, and delivering an outstanding customer experience.

HOW YOU'LL KNOW YOU'RE SUCCEEDING

• Your customers view you as a trusted advisor and consistently achieve strong adoption, satisfaction, and long-term success with MasterMind.
• Go-live transitions and Hypercare engagements are seamless, with customers confidently adopting new workflows and capabilities.
• Customer feedback, product insights, and operational trends result in meaningful improvements across the platform and customer experience.
• Internal teams trust you as a collaborative partner who keeps customers moving forward and helps solve complex challenges.
• You contribute to a high-performing Engagement team by sharing knowledge, mentoring teammates, and continuously raising the bar for customer success.

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.

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.

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.

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