Enterprise Implementation Specialist

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take charge of the comprehensive implementation of Fellow for major enterprise accounts, from the signing of contracts to complete organizational rollout and realization of value.

• Develop and implement detailed rollout strategies that encompass departments, business units, or regions, including phased approaches, milestones, and success indicators.

• Act as the main post-sale contact and trusted advisor for IT, security, procurement, and executive stakeholders.

• Lead the discovery process of the customer's organizational structure, technology stack, security/compliance requirements, and change-management necessities.

• Oversee SSO/SAML configurations, calendar and CRM integrations, data migration, and user provisioning on a large scale.

• Collaborate with security, legal, and IT teams on security assessments, questionnaires, and compliance documentation.

• Spearhead change-management and adoption initiatives, including executive briefings, champion networks, train-the-trainer programs, and communication strategies.

• Manage multiple concurrent enterprise implementations while mitigating risks associated with scope, timelines, and budgets.

• Identify opportunities for expansion and upselling in collaboration with Sales and Customer Success.

• Create implementation playbooks, templates, and establish best practices.

• Produce documentation, training materials, and enablement content tailored for enterprise and regulated customers.

• Collaborate with Product, Engineering, and Customer Success to gather feedback, escalate issues, and guide the product roadmap.

• Report on rollout health, adoption metrics, and risk status to leadership and customer executive sponsors.

⛳️ Requirements

• A minimum of 5 years of experience in implementation, onboarding, professional services, or technical program management within a B2B SaaS environment.

• Demonstrable success in leading large-scale, organization-wide software implementations across various departments and/or for over 500 users.

• Proven experience managing intricate, multi-stakeholder enterprise implementations from kickoff to full adoption.

• Familiarity with CRM systems such as Salesforce or HubSpot.

• Experience with project/professional services tools like Smartsheet, Asana, monday.com, or Jira.

• Practical knowledge of SSO/SAML and SCIM provisioning.

• Understanding of enterprise IT/security review processes.

• Strong skills in program management and change management.

• Ability to craft rollout plans and oversee timelines and risks across multiple projects.

• Capacity to drive adoption on a large scale.

• Executive presence and comfort in presenting to IT, security, and C-suite leaders.

• Outstanding written, verbal, and presentation skills in English.

• Ability to work independently, take initiative, and collaborate across functions in a fast-paced environment.

🏝️ Benefits

• Comprehensive health and dental insurance, including coverage for prescription medications and life insurance.

• 12 weeks of paid parental leave at 80% of salary.

• Three weeks of vacation time.

• Paid sick leave.

• Paid company-wide break at the year's end.

• Remote-first flexibility — Work remotely from within Canada.

• Learning and professional development budgets.

• Lunch-and-learn sessions.

• Autonomy to manage your work from start to finish.