Jobs · Information Technology

Implementation Specialist

Bestpass by Fleetworthy · Madison, WI · 4 wk ago
RemoteRemoteInformation TechnologyFull-time

Job Purpose

At Fleetworthy, one of our key values is every trip matters. As an Implementation Specialist, you are the driving force behind a customer's journey from signed contract to successful launch and long-term value realization. You don't just onboard customers— you help them transform how they manage fleets, drivers, compliance, and operations.

Key Responsibilities

  • Lead Customer Onboarding and Time-to-Value

    • Own the implementation process from customer kickoff through successful launch and service activation.
    • Partner with customers to understand business objectives, operational workflows, stakeholder expectations, and desired outcomes.
    • Establish implementation plans, success criteria, timelines, milestones, and governance structures that keep projects on track.
    • Conduct stakeholder interviews and discovery sessions to ensure solutions are configured to support customer goals.
    • Drive timely launches that accelerate customer adoption and value realization.
  • Deliver a Best-in-Class Customer Experience

    • Serve as the primary implementation advisor and trusted partner throughout onboarding.
    • Build strong relationships with customer stakeholders and become a credible expert on Fleetworthy solutions.
    • Facilitate customer kickoff meetings, weekly status meetings, and executive-level communications.
    • Provide personalized training that equips customers to confidently use Fleetworthy's platforms and services.
    • Proactively identify risks, remove obstacles, and resolve issues before they impact the customer experience.
  • Cross-Functional Success

    • Partner closely with Sales, Customer Success Managers, Operations teams, and subject matter experts to ensure a seamless customer journey.
    • Translate customer goals and purchased services into actionable implementation plans.
    • Coordinate with third-party providers, agencies, and vendors to establish required integrations, access, and service readiness.
    • Ensure successful handoffs and alignment across teams throughout onboarding and post-launch support.
  • Drive Adoption and Customer Outcomes

    • Align customers on measurable success criteria and key performance indicators from the start of implementation.
    • Guide customers through solution activation, adoption, and early value realization.
    • Support post-launch engagement and optimization activities to ensure customers achieve their desired outcomes.
    • Help identify opportunities to expand value through additional Fleetworthy solutions and services.
  • Improve Processes and Scale Excellence

    • Contribute to the continuous improvement of implementation methodologies, playbooks, and onboarding best practices.
    • Help standardize processes that improve quality, efficiency, and consistency across customer implementations.
    • Maintain accurate project documentation, implementation records, and progress tracking.
    • Provide feedback on project timelines, resource requirements, and process enhancements.

Qualifications & Experience

  • Associate's or Bachelor's degree in Business, Management, Communications, or a related field, or equivalent professional experience.

  • 1+ years of experience in customer onboarding, implementation, customer service, project management, customer success, or a related customer-facing role.

  • Proven ability to manage multiple projects and stakeholders simultaneously.

  • Strong presentation, facilitation, and relationship-building skills.

  • Experience leading customer meetings, training sessions, and project communications.

  • Proficiency with CRM platforms, project management tools, Microsoft Office, and Excel.

  • Exceptional organization, attention to detail, and time management skills.

  • Strong analytical thinking and problem-solving abilities.

  • Self-motivated with a growth mindset and passion for delivering outstanding customer experiences.

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