Restaurant365 is a SaaS company disrupting the restaurant industry! Our cloud-based platform provides a unique, centralized solution for accounting and back-office operations for restaurants. Restaurant365’s culture is focused on empowering team members to produce top-notch results while elevating their skills. We’re constantly evolving and improving to make sure we are and always will be “Best in Class” ... and we want that for you too!
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 implementations from 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 sessions to 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 expertise to 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-functionally with Project Management, Solutions Architecture, Product, and Support to resolve issues, address custom requirements, and ensure delivery excellence.

Contribute to continuous improvement by 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.

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.

PREFERRED

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.

Key Metrics for Success

Utilization Rate

Project Completion Throughput

On-Time Delivery Rate

Customer Satisfaction (CSAT)

R365 Team Member Benefits & Compensation

This position has a salary range of COMP. The above range represents the expected salary range for this position. The actual salary may vary based upon several factors, including, but not limited to, relevant skills/experience, time in the role, business line, and geographic location. Restaurant365 focuses on equitable pay for our team and aims for transparency with our pay practices.

Comprehensive medical benefits, 100% paid for employee

401k + matching

Equity Option Grant

Unlimited PTO + Company holidays

Wellness initiatives

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DYN365, Inc d/b/a Restaurant365 is an equal opportunity employer.

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