Senior Training & Implementations Specialist

Senior Implementation & Training Specialist
This role is pivotal in helping RMS enterprise and mid-market clients succeed with our software, taking them from signed contract to confident, independent use. The Senior Implementation & Training Specialist will focus on two key objectives:

• Leading consultative, end-to-end delivery of complex implementations and training for larger, multi-property, group and mid-market clients, so their teams are ready on day one and get value from RMS quickly.
• Managing stakeholders and acting as a trusted, consultative contact between clients and RMS teams including Customer Success, Support, Product, Engineering and Sales, while mentoring Implementation & Training Representatives and sharing what works.

The ideal candidate will be passionate about client success, comfortable working independently on several complex projects at once, and skilled in consultative stakeholder management, facilitation and project management, and at building credibility with executives, operations and technical teams. Success in this role will be measured by on-time go lives, client satisfaction, and clear knowledge transfer.

KEY RESPONSIBILITIES
Consultative, End-to-End Implementation Delivery

• Own and deliver complex implementations end to end for enterprise and mid-market clients, from kickoff through go live and handover to Customer Success, to scope, on time and against clear milestones.
• Run consultative discovery workshops with client leaders, operations and IT teams to understand their properties, processes, integrations and goals, and turn that into a practical implementation plan.
• Manage several complex implementations at once, including phased and multi-property rollouts, using sound project management to keep scope, timelines, dependencies and risks visible.
• Configure RMS to each client's requirements and test it thoroughly before go live, including integrations and reporting.
• Work with Data Migration colleagues to plan, check and sign off the migration of client data, and make sure clients understand what is moving and when.
• Lead go live readiness and stay close through the first weeks after go live, resolving issues quickly and handing over cleanly to Customer Success and Support.

Training Design and Delivery

• Design and deliver training tailored to each team's role and experience, so large groups are ready on day one.
• Train on site and remotely, to individuals and groups, including train-the-trainer programs so clients can keep their own teams skilled after the project ends.
• Check understanding and adoption during and after training, adjust the approach where needed, and report on client readiness honestly.
• Build and maintain reusable training materials, guides and session plans for enterprise and mid-market rollouts, working with the Knowledge team.

Client and Stakeholder Relationships

• Be the day-to-day lead contact for the implementation and build trust with client sponsors and decision makers, facilitating workshops and steering meetings to align stakeholders and drive decisions.
• Communicate plainly and regularly on progress, risks, trade-offs and what the client needs to do. Raise problems early and say what is not yet known.
• Manage expectations on scope and timelines, and escalate to the Lead or Manager when a scope change, commercial matter or decision sits beyond the role's authority.
• Hand over to the Customer Success Manager or Account Manager with the full picture, so the client never has to repeat themselves.

Collaboration Across RMS

• Partner with Sales, Customer Success, Support, Product and Engineering to keep enterprise and mid-market clients on track, and raise defects and gaps with clear evidence and client impact.
• Share client feedback and recurring patterns with Product so they influence what gets built and fixed.
• Work with integration and technology partners on the client's behalf where an implementation depends on them.

Team and Practice

• Mentor and coach Implementation & Training Representatives through shadowing, reviewing plans and sessions, and supporting them on harder client situations.
• Be a go-to person for complex implementation questions, and share lessons learned through documentation and team sessions.
• Contribute to playbooks, templates and checklists for complex implementations, and suggest improvements to the Lead and Manager.
• Keep project trackers and CRM records accurate and current.
• Use AI tools in daily work, such as preparing project plans and status updates, summarising discovery sessions and drafting training materials, and check the output before it reaches a client or colleague.

KEY BEHAVIOURS

• Committed to our Customer: Looks past what the client asks for to what they actually need, surfaces adoption gaps and risks before they become problems, and follows up to confirm issues are solved.
• Honest words, trusted actions: Flags risks early, is open about timelines and trade-offs, keeps commitments or says early when they cannot be kept, and gives and receives direct feedback without becoming defensive.
• Push boundaries, stay curious: Finds the root cause rather than treating symptoms, uses data to shape decisions, uses AI independently and checks its output critically, and learns from what did not work.
• Own it, make it happen: Works end to end without needing to be chased, unblocks themselves and others, and stays reliable and high quality when workloads are heavy.
• Composed under pressure: Stays calm with frustrated clients and tight go live dates, and keeps the conversation constructive.
• Credible with senior clients: Explains complex topics plainly and is confident with executives, operations and technical teams.
• Collaborative and generous with knowledge: Works well with Sales, Customer Success, Support, Product, Engineering and partners across regions
• Flexible: Comfortable with travel for on-site delivery and working across time zones.

SUCCESS CRITERIA

• Effective client onboarding: Implementations go live on time and to scope, with few configuration defects, escalations and rework after go live. Data migrations are accurate and signed off by the client.
• Client satisfaction: High CSAT scores and positive feedback from clients on their onboarding and training experience.
• Knowledge transfer: Clients can operate RMS independently after training and show confidence in using it, measured against agreed adoption indicators.
• Clean handovers: Handovers to Customer Success are complete, and clients do not have to repeat themselves.
• Team impact: Mentored Representatives grow in capability and confidence, and the playbooks and training materials you contribute are used by the team.
• Accurate records: Project and CRM records are current, and risks are raised early.
• Responsible AI use: AI improves the speed and quality of work, with no accuracy or data privacy issues reaching clients.

SKILLS & EXPERIENCE
Essential

• 3 or more years in implementation, onboarding, training or professional services within B2B SaaS (local SaaS or start-up experience is welcome), including delivering projects for multi-site, enterprise or mid-market clients.
• A track record of consultative, end-to-end delivery of complex implementations, managing several at once, to scope and on time, with multiple client stakeholders.
• Experience designing and delivering training to groups with mixed experience, remotely and on site.
• A working understanding of integrations and data migration, enough to plan and test with technical colleagues and explain the impact to clients.
• Excellent written and verbal communication, with strong stakeholder management and facilitation skills and confidence presenting to senior client stakeholders.
• Strong project management skills, and able to work independently with limited supervision and judge when to escalate.
• Practical AI competence: uses AI tools in daily work and applies sound judgement on accuracy and data privacy.
• Willing to travel to client sites.

Preferred

• Experience in hospitality, with property management systems (PMS) or with RMS is a plus, but not a requirement. RMS product knowledge will be built through onboarding.
• Experience with channel managers, payments or other partner integrations.
• Project management training or certification, such as PMP, PRINCE2 or Agile.
• Experience with CRM and project tracking tools.