Implementation Specialist

Role Overview

• Own the full implementation lifecycle — from requirements gathering and solution design through configuration, integration, data migration, testing, and post-launch review — on complex, multi-workstream, or enterprise-scope projects
• Design implementation solutions that translate complex customer business requirements into technically sound, scalable system configurations — thinking beyond the immediate setup to the customer's long-term workflow needs
• Manage multi-stakeholder customer environments with confidence — navigating competing priorities, evolving requirements, and organizational complexity while maintaining project momentum and customer trust
• Manage timeline risk proactively — identifying delays, blockers, or scope changes early and addressing them with a structured response rather than allowing them to compound
• Handle post-launch stabilization and early adoption challenges as part of the implementation engagement — ensuring customers reach defined value milestones before formal handoff to Customer Success
• Lead technical solution design for complex implementations — including multi-system integrations, advanced data mapping, workflow automation, and custom configurations that require reasoning across the customer's full technology stack
• Maintain expert-level knowledge of all supported platforms, integration patterns, and configuration options — including edge cases, advanced features, and the technical boundaries where custom solutions may be required
• Evaluate the technical feasibility of customer requirements and communicate trade-offs clearly — providing honest, well-reasoned guidance on what is achievable within scope and what requires a different approach
• Independently author and maintain implementation playbooks, configuration guides, data migration templates, integration documentation, and post-launch readiness checklists for use across the implementation team
• Build and maintain trusted relationships with senior customer stakeholders — including IT leaders, operations directors, and executive sponsors — with the credibility and communication quality those relationships require
• Partner with Product and Engineering on feature feedback, integration gap analysis, and release impact assessment — contributing the implementation team's structured perspective on how product decisions affect customer onboarding outcomes
• Collaborate with Customer Success on implementation-to-CS handoffs — ensuring CS teams inherit a complete picture of the customer's configuration, known issues, success criteria, and adoption readiness.

Requirements

• 5+ years of experience in implementation, onboarding, or customer success roles in a SaaS or technology environment
• Demonstrated track record of independently owning and delivering complex, multi-workstream SaaS implementations — with consistent on-time delivery and high customer satisfaction
• Strong technical depth — able to design and troubleshoot multi-system integrations, data migrations, and advanced configurations without requiring escalation for standard technical complexity
• Experience authoring and maintaining implementation documentation — playbooks, configuration guides, data migration templates, integration specs, or onboarding frameworks
• History of acting as an informal peer resource — guiding IS 1 colleagues through technically complex or scope-ambiguous situations with specific, transferable advice
• Demonstrated ability to manage senior customer stakeholders — including executive sponsors and technical leads — through complex, long-running implementations
• Proficiency in project management tools (Asana, Jira, Monday.com) and integration platforms (Salesforce, HubSpot, NetSuite) with hands-on configuration experience
• Strong written and verbal communication skills — able to lead customer governance conversations, produce executive-quality project documentation, and translate technical decisions into business language
• Demonstrated ability to identify recurring implementation patterns and convert them into process or documentation improvements.

Benefits

• Comprehensive Health Coverage: Coverage begins on your first day of employment.
• 401K Plan (US): We match 1:1 for the first 3% of contributions and 0.5:1 for the next 2%. Contribute 5% of your salary and get a 4% match. Choose from pre-tax and Roth options. You’re eligible the first of the month after 90 days and immediately vested.
• RRSP (CAN): We match 1:1 for the first 3% of contributions and 0.5:1 for the next 2%. Contribute 5% of your salary and get a 4% match. Choose from pre-tax and Roth options. You’re eligible the first of the month after 90 days and immediately vested.
• Flexible PTO: Enjoy uncapped paid time off to balance your work and personal life.
• 12 weeks paid leave for all employees.
• Monthly Stipend: Receive $75 USD / $140 CAD per month for phone and internet if you work remotely.
• Generous Holiday Schedule: Benefit from an extensive list of holidays to recharge and spend time with loved ones.