Enterprise Software Implementation Specialist

Role Description

Do you feel more in your element, not less, when a project has six stakeholders, three departments, and a deadline that actually matters to someone's budget? Do fleet managers trust your judgment because you clearly understand what they're actually trying to accomplish, not just what boxes need checking? Can you spot a risk quietly building across two different workstreams before anyone else notices it? Do you already reach for AI to move faster through complex data work, and know exactly when to double-check what it hands you? Are you the person other teams call when an enterprise account needs someone steady at the helm? If so, keep reading...

The team at RTA is looking for an Enterprise Implementation Specialist: our Enterprise Orchestrator, Cross-Team Conductor, and Fleet360 Authority all rolled into one. Reporting to the Implementation Supervisor, you'll own RTA's largest and most complex customer engagements from signed contract through a confident go-live, serving as the primary customer relationship owner throughout implementation while coordinating across Sales, Fleet Consulting, Training, Support, and CSM while personally cleaning, compiling, and migrating each customer's data into Fleet360 yourself.

• Guide fleet managers through high-stakes configuration decisions.
• Catch risk before it threatens a timeline.
• Ensure the customer arrives at go-live confident, not just converted.

This position plays a direct role in RTA's mission to help fleets succeed, on our most important accounts.

Qualifications

• 5+ years of experience in a customer-facing implementation, onboarding, or project management role, B2B SaaS strongly preferred.
• Demonstrated experience managing multiple stakeholders and workstreams across departments simultaneously.
• Proficient with Microsoft 365, including Excel, Outlook, and PowerPoint, with comfort in nested formulas, multi-condition logic, and multi-tab, interconnected workbooks.
• Comfortable guiding customers through high-stakes configuration decisions, including conversations with senior fleet and operations leaders.
• Demonstrated, real-world use of AI tools to increase speed or accuracy in your work, with specific examples you can speak to.
• Excellent written and verbal communication skills.
• Fleet, fleet-adjacent, or public sector operations experience preferred, not required.
• Exposure to SQL or structured databases preferred, not required.
• Bachelor's Degree not required. Relevant experience and breadth of knowledge matters more.

Requirements

• Owns the timeline and sequencing across 6 to 8 concurrent enterprise engagements at once.
• Coordinates explicitly across Sales, Fleet Consulting, Training, Support, and CSM at defined handoff points.
• Proactively surfaces risk, including cross-departmental dependencies that are quietly stalling.
• Guides customers through high-stakes fleet configuration decisions.
• Builds confidence with enterprise customers by communicating proactively and setting clear expectations.
• Personally executes data cleanup, compilation, and migration into Fleet360 for every engagement.
• Assesses data health across multiple workbooks or source systems.
• Comfortable with nested formulas, multi-condition logic, and multi-tab, interconnected workbooks.
• Holds the agreed scope line with customers.
• Operates with an AI-first mindset.

Benefits

• 401(k) with 6% Safe Harbor match (100% vested day one).
• Flexible PTO model built on trust and manager-approved time off.
• Cigna PPO and HSA medical plan options with company contributions ($780–$1,950 annually).
• Garner Health HRA program: up to $1,000 individual / $2,000 family reimbursement opportunity.
• Wellness rewards up to $350 annually.
• Virtual care and mental health support resources.
• Company-sponsored benefits including dental, vision, EAP, life, STD, LTD, legal plan, and identity theft protection options.
• Additional employee perks, wellness initiatives, and discount programs.