Enterprise Implementation Specialist

About the Role

Responsibilities

• Own enterprise implementations from contract signature through full rollout and value realization.
• Design phased rollout strategies, milestones, and success metrics for multi-department deployments.
• Act as the primary post-sale contact for IT, security, procurement, and executive stakeholders.
• Lead discovery and translate customer needs into tailored implementation plans.
• Manage SSO/SAML, calendar and CRM integrations, data migration, and user provisioning.
• Coordinate security reviews, questionnaires, and compliance documentation with customer teams.
• Drive adoption through executive briefings, champion networks, train-the-trainer programs, and communications.
• Manage concurrent implementations and mitigate scope, timeline, and budget risks.
• Identify expansion opportunities with Sales and Customer Success.
• Create playbooks, templates, documentation, training materials, and enablement content.
• Partner with Product, Engineering, and Customer Success on feedback, escalations, and roadmap input.
• Report rollout health, adoption metrics, and risks to internal and customer leadership.

Required Skills and Experience

• 5+ years in implementation, onboarding, professional services, or technical program management at a B2B SaaS company.
• Experience leading large-scale organization-wide software rollouts involving multiple departments and/or 500+ users.
• Experience managing complex enterprise implementations from kickoff through full adoption.
• Experience with a CRM and project or professional-services tooling.
• Working knowledge of SSO/SAML, SCIM provisioning, and enterprise IT and security reviews.
• Strong program and change-management skills across concurrent projects.
• Executive presence with senior IT, security, and C-suite stakeholders.
• Exceptional written, verbal, and presentation skills in English.
• Ability to work independently, own outcomes, and operate cross-functionally.

Preferred Qualifications

• Experience implementing SaaS solutions in regulated industries or other compliance-heavy environments.
• Experience with SOC 2, HIPAA, data residency, or similar requirements.
• Experience mentoring junior implementation or onboarding team members.
• PMP, PRINCE2, or another formal project management certification, or equivalent experience.

Workplace

• Fellow is a remote-first company headquartered in Ottawa.
• The role can be performed remotely within Canada.

What We Offer

• Competitive market-benchmarked compensation.
• Health and dental coverage, prescription drugs, and life insurance.
• Three weeks of vacation, paid sick leave, and a paid company-wide year-end break.
• Twelve weeks of paid parental leave at 80% of salary.
• Learning budgets, lunch-and-learns, and autonomy to own work end to end.