Senior Implementation Specialist
The Senior Implementation Specialist is a key expert within the Professional Services team, responsible for delivering high-touch, high-complexity onboarding experiences for our most strategic customers-typically enterprise-level or multi-unit restaurant groups. This role combines advanced solution knowledge, project leadership, and customer relationship skills to ensure implementations are executed efficiently, drive rapid adoption, and set the foundation for long-term customer success.
The Senior Specialist will partner closely with Project Managers, Solutions Architects, and Customer Success Managers to design and execute tailored onboarding plans that address unique customer workflows, integrations, and operational structures. Beyond direct delivery, this role serve as a mentor and quality benchmark for other Implementation Specialists, helping raise the bar on consistency, methodology, and customer experience across the team.
How you'll add value:
Lead complex, enterprise-scale implementationsfrom discovery to adoption, ensuring alignment between customer requirements and R365’s platform capabilities to manage milestones on time and within budget to deliver smooth and complete project experience for customers.
Conduct advanced discovery sessionsto deeply understand multi-location, multi-system workflows, and configure solutions to maximize operational efficiency.
Deliver expert-level training(virtual or onsite) that drives confident end-user adoption, tailoring content to different audience levels-from executives to frontline staff.
Apply deep product expertiseto advise on complex use cases, integrations, and best practices, ensuring customers maximize the full value of the platform.
Mentor and coach junior Implementation Specialists, providing feedback, sharing best practices, and contributing to internal training programs.
Collaborate cross-functionallywith Project Management, Solutions Architecture, Product, and Support to resolve issues, address custom requirements, and ensure delivery excellence.
Contribute to continuous improvementby identifying process gaps, suggesting enhancements to implementation playbooks, and piloting new delivery approaches.
Proactively manage risk, surfacing adoption blockers early and developing mitigation strategies to keep projects on track.
Other duties as assigned.
Utilization Rate
Project Completion Throughput
On-Time Delivery Rate
Customer Satisfaction (CSAT)
KEY METRICS FOR SUCCESS
What you'll need to be successful in this role:
5+ years of hands-on experience in SaaS onboarding or implementation, with a proven track record of successfully guiding customers through technical setup, training, and go-live across varied business types and user groups while consistently achieving key performance metrics.
Experience managing complex, high-touch implementations with proven project management skills.
Deep understanding of multiple R365 product lines: Accounting, Operations, ExpandShare, and HIRE
Exceptional organizational and time management skills, with the ability to manage multiple projects simultaneously, prioritize effectively, and meet tight deadlines without sacrificing quality.
Excellent verbal and written communication skills, including the ability to lead client-facing trainings and translate technical concepts into clear, actionable guidance for both technical and non-technical stakeholders.
Highly analytical and solutions-oriented, able to assess requirements, troubleshoot issues, and make timely, data-informed decisions that support customer success.
Self-starter with the ability to work independently, while also demonstrating strong collaboration skills when working cross-functionally with Project Managers, Engineers, Product, and Customer Success.
Demonstrated coaching or mentorship experience.
Strong analytical and problem-solving skills.
Proven SaaS tool fluency, sound technical knowledge, and detail orientation.
Familiarity with restaurant or hospitality environments.
Experience in structured certification programs or internal training content.
Experience shaping onboarding frameworks and internal tools.
Comfort adapting to evolving playbooks and tools.
Basic understanding of accounting principles.
PREFERRED QUALIFICATIONS
R365 Team Member Benefits & Perks
- Competitive compensation package
- Comprehensive medical benefits
- 401k + matching
- Team member stock options
- Flexible Time Off + Company holidays
- Weekly catered lunches + snacks
- Wellness initiatives
This role is hybrid, balancing flexibility with the value of in-person collaboration. To support connection, partnership, and team effectiveness, employees are expected to work onsite each Tuesday and Wednesday.