Senior Implementation Specialist

Restaurant365; Quinte West; Hybrid; CAD 109,000 - 164,000; Full time

Benefits offered by this job

Competitive pay

Medical benefits

401k matching

Stock options

Flexible PTO

Catered meals

Wellness program

Job summary

Restaurant365 is seeking a Senior Implementation Specialist to lead high-touch onboarding for enterprise restaurant clients. You will design tailored onboarding plans, handle multi-system workflows, and mentor peers to raise delivery quality.

The role combines advanced solution knowledge with project leadership and customer relationship skills to ensure rapid adoption and long-term success. Hybrid work with on-site collaboration is expected.

Qualifications

• 5+ years of hands-on SaaS onboarding or implementation experience.
• Proven track record of guiding customers through technical setup, training, and go-live.
• Experience managing complex, high-touch implementations.
• Strong client-facing communication and presentation skills.
• Ability to mentor junior team members and improve delivery processes.
• Demonstrated ability to work cross-functionally with PM, engineers, product, and success teams.

Responsibilities

• Lead enterprise-scale implementations from discovery to adoption, aligning customer requirements with platform capabilities.
• Conduct advanced discovery sessions to map multi-location workflows and configurations.
• Deliver expert-level training (virtual or onsite) to drive user adoption.
• Advise on complex use cases, integrations, and best practices for maximizing platform value.
• Mentor and coach junior specialists, contributing to internal training.
• Collaborate with PM, Solutions Architecture, Product, and Support to resolve issues and ensure on-time delivery.

Skills

Project management

Training delivery

Customer relationship

Analytical thinking

Mentorship

Cross-functional collaboration

Job description

Restaurant365 is a SaaS company disrupting the restaurant industry! Our cloud-based platform provides aunique, 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!

TheSenior Implementation Specialistis a key expert within the Professional Services team, responsible for delivering high-touch, high-complexity onboarding experiences for our most strategiccustomers—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, andsetthe 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 serves 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 capabilitiesto 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 productexpertiseto 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 improvementbyidentifyingprocess gaps, suggesting enhancements toimplementationplaybooks, 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.

KEY METRICS FOR SUCCESS

• UtilizationRate

• Project Completion Throughput

• On-Time Delivery Rate

• Customer Satisfaction (CSAT)

What you’ll need to be successful in this role:

• 5+ years of hands-on experience in SaaS onboarding or implementation, with a proventrack recordof successfully guiding customers through technical setup, training, and go-live across varied business types and user groupswhileconsistentlyachieving key performancemetrics.

• Experience managing complex, high-touch implementationswith proven project management skills.

• Deep understandingof 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-facingtrainingsand translate technical concepts into clear, actionable guidance for both technical and non-technical stakeholders.

• Highly analytical andsolutions-oriented, able to assess requirements, troubleshoot issues, and maketimely, 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.

• ProvenSaaS tool fluency, sound technical knowledge,and detail orientation.

PREFERREDQUALIFICATIONS

• Familiarity withrestaurantor 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.

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.

$78,800 - $118,200 a year

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