Strategic Implementation Specialist

Flywire•Boston, MA

1d•$65,000 - $80,000•Hybrid

About The Position

The Opportunity: The Strategic Implementation Specialist ensures seamless rollouts for strategic customers by delivering a white glove implementation and adoption experience across Sertifi and Flywire solutions. This role owns the full lifecycle of customer success, leading change management and project management efforts to integrate Sertifi Payments (Sertifi Pay), which may include any combination of credit card, ACH, surcharging, and reconciliation, into customer workflows that impact sales, events, finance, accounting, and daily operations. By driving consistent usage, efficiency, and long term adoption, this role establishes Sertifi Pay as the primary collection method and supports sustainable outcomes across single properties, property management groups, and strategic brand names.

Requirements

3+ years of experience in implementation, SaaS, or customer facing roles with ownership of strategic or high value customer lifecycles.
Demonstrated experience leading complex implementations and driving post go live adoption across payments, workflows, and operational teams.
Strong understanding of payments and collections workflows, including credit card, ACH, surcharging, and reconciliation, with the ability to translate complexity into clear guidance.
Exceptional communication and stakeholder management skills, with experience engaging cross functional teams and executive level audiences.
A solutions first mindset focused on removing barriers rather than creating them, with the ability to proactively identify risks, unblock progress, and keep customers and teams moving forward.
Proven ability to apply project management and change management principles to navigate ambiguity, manage competing priorities, and deliver outcomes.
Comfortable working independently while partnering closely with Sales, RevOps, Product, and Technology teams to achieve shared goals.
Committed to delivering a high touch, trust based customer experience that supports long term adoption and measurable success.

Responsibilities

Manage high impact implementations for strategic customers, owning the full implementation and adoption lifecycle across single properties, property management groups, and strategic brand names.
Deliver a white glove experience by tailoring Sertifi and Flywire solutions to customer workflows across sales, events, finance, accounting, and operational teams.
Lead the implementation and adoption of Sertifi Payments (Sertifi Pay), establishing it as the primary collection method and driving consistent usage across daily operations.
Partner cross functionally with Sales, RevOps, Product, and Technology teams to remove roadblocks, manage dependencies, and ensure successful outcomes.
Apply change management and project management best practices to navigate complex implementations, optimize workflows, and support long term customer success.
Facilitate trainings, working sessions, and executive level touchpoints as needed to reinforce adoption, address gaps, and align stakeholders.
Track implementation progress, adoption milestones, and key risks, ensuring timelines are met while maintaining a high quality customer experience.

Benefits

Competitive compensation
Employee Stock Purchase Plan (ESPP)
Flying Start - Our immersive Global Induction Program (Meet our Execs & Global Teams)
Work with brilliant people that will keep you on your toes, learn more about their journeys by checking out #InsideFlywire on social media
Dynamic & Global Team (we have been collaborating virtually for years!)
Wellbeing Programs (Mental Health, Wellness, Yoga/Pilates/HIIT Classes) with Global FlyMates
Competitive time off including FlyBetter Days to volunteer in your community and Digital Disconnect Days!
Great Talent & Development Programs (Managers Taking Flight – for new or aspiring managers!)

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