Director of Implementation

About us and why we’re hiring...

Road Sync is revolutionizing the logistics industry with intelligent, simple, and innovative financial solutions. Our digital platform streamlines payment processes for warehouses, carriers, brokers, and repair/tow operators, dramatically reducing processing time and maximizing revenue collection.

We are seeking a Director of Implementation to lead onboarding, activation, and early-lifecycle success for new customers. This role owns the critical early customer journey, from kickoff to first transaction to full ramp. It is directly accountable for time-to-value, feature adoption, and seamless transition to the Account Management team. The ideal candidate operates as a systems leader who builds early momentum, not just technical completion, and ensures every new customer is actively using the product, not merely set up.

• Own the end-to-end onboarding process from deal close through first transaction, driving toward strong in-month onboarding completion.
• Accelerate time-to-transact by removing blockers, sequencing implementation steps effectively, and holding the team accountable to activation milestones.
• Drive activation by ensuring customers complete configuration, training, and initial live transactions early in the post-kickoff window.
• Ensure the team validates business requirements upfront so implementations are scoped correctly and set up for early success.

• Drive ramp-up achievement by monitoring velocity weekly and intervening early when customers fall behind expected transaction-volume curves.
• Own revenue- and margin-driving feature attach rates, ensuring hardware and special promotions deliver measurable ROI.
• Develop and execute playbooks that move customers from basic setup to full-platform utilization, defining success as active product usage rather than technical completion.

• Maintain at-risk revenue at healthy levels within the implementation portfolio through proactive health monitoring and early intervention.
• Manage the Implementation-to-Account Management handoff, ensuring customers transition with a solid foundation: active transactions, feature adoption, and a clear success trajectory.
• Partner with the Account Management Team Lead to ensure warm, documented transitions that preserve customer momentum and minimize post-handoff churn risk.

• Lead, coach, and develop a team of Implementation Managers, ensuring each team member meets their KPIs/SLAs with a clear understanding of what to do and how to execute.
• Build a team that performs consistently even when you step away—invest in repeatable processes, documented playbooks, and knowledge management.
• Dedicate meaningful weekly time to direct coaching on activation and ramp strategies, using real customer data and at-risk account reviews.
• Proactively identify process improvements and engage Revenue Operations to implement fixes that improve team efficiency and effectiveness.

• Provide regular, proactive updates to leadership throughout the week on onboarding progress, at-risk accounts, and team performance.
• Prepare and present a business overview during monthly business reviews to executive leadership.
• Deliver crisp, data-backed feedback to Product (activation and ramp blockers), Rev Ops (process and tooling friction), and Support (SLA and escalation inefficiencies).
• Escalate thoughtfully and in a solution-oriented way, always include context, data, and a recommended path forward.

• 3-5 years of experience in customer success, implementation, or onboarding management within a SaaS or payments technology environment.
• 2+ years of direct people management experience, with a demonstrated track record of coaching individual contributors to exceed performance targets.
• Experience owning end-to-end onboarding or implementation funnels, with accountability for time-to-value, activation, and early-retention metrics.
• Strong analytical skills with the ability to inspect data, identify at-risk accounts, and translate metrics into coaching actions.
• Proficiency…