Canada Remote (Country) Employment

Fellow Insights Inc is hiring an Enterprise Implementation Specialist

Responsibilities

  • Lead full-cycle implementation for major enterprise clients, from contract signing to organization-wide deployment and measurable outcomes.
  • Develop and manage comprehensive deployment strategies across departments, units, or regions, including phased rollouts, key milestones, and performance indicators.
  • Act as the main post-sales contact and strategic advisor for enterprise stakeholders such as IT, security, procurement, and executive leadership.
  • Conduct discovery sessions to assess client organizational structure, technology environment, security needs, and change readiness, then design customized implementation approaches.
  • Oversee technical setup for large-scale deployments, including SSO/SAML configuration, calendar and CRM integrations, data transfers, and bulk user provisioning.
  • Collaborate with client security, legal, and IT teams to complete required compliance assessments, security questionnaires, and documentation for regulated environments.
  • Lead change management initiatives such as executive onboarding, internal champion programs, train-the-trainer sessions, and communication strategies to drive broad user adoption.
  • Manage multiple concurrent enterprise implementations, identifying and resolving risks related to scope, schedule, and budget.
  • Recognize opportunities for additional product usage or expansion during implementation and coordinate with Sales and Customer Success teams.
  • Develop and improve standardized implementation guides, templates, and best practices to support scaling with growing enterprise demand.
  • Produce and maintain documentation, training resources, and enablement materials specific to enterprise and compliance-sensitive clients.
  • Work with Product, Engineering, and Customer Success teams to share client insights, escalate critical issues, and influence product development priorities.
  • Track and report on deployment progress, user adoption rates, and risk factors for both internal leadership and customer executives.

Benefits

  • Competitive and equitable pay aligned with market standards.
  • Comprehensive health and dental benefits, including prescription and life insurance coverage.
  • Paid parental leave of 12 weeks at 80% salary for new parents.
  • Generous time-off policy: three weeks vacation, paid sick days, and a company-wide paid break at year-end.
  • Remote-first work model within Canada.
  • Professional growth support through learning funds, internal learning sessions, and end-to-end ownership of initiatives.

Compensation

Competitive and market-aligned

Work Arrangement

Remote within Canada

Team

Enterprise-focused implementation team supporting complex, large-scale deployments

Other

  • Work remotely within Canada.
  • Excellent written, verbal, and presentation abilities in English are required.

Not offered

About company
Fellow Insights Inc
Fellow gives every employee their own AI-powered Chief of Staff, an assistant that understands meeting discussions, surfaces key insights, answers questions, and takes action. A remote-first, Series A startup backed by Craft Ventures, iNovia, and Felicis, helping teams from Shopify, HubSpot, and Warner Media to startups make meetings more productive with AI.
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Job Details
Department Customer Support and Implementation
Category other
Posted 17 days ago