[Hiring] Enterprise Implementation Specialist @Fellow Insights Inc.

Role Description

The Enterprise Implementation Specialist will lead the successful launch and org-wide adoption of Fellow across our largest, most complex customers' deployments that often span multiple departments, hundreds to thousands of users, and a wide range of cross-functional stakeholders. This is a senior, high-ownership role for someone who has run large-scale software rollouts before and knows how to turn a signed contract into company-wide adoption, not just a well-onboarded pilot team.

You'll thrive in this role if you are:

• A seasoned program/project manager who can plan and run multiple complex, multi-stakeholder rollouts at the same time.
• Comfortable being the primary point of contact for stakeholders ranging from end users to IT, security, and executive sponsors, often all on the same account.
• Skilled at change management - able to drive adoption at scale across a large, distributed organization, not just train a handful of admins.
• Energized by the extra rigor (security reviews, compliance requirements, procurement processes) that larger and more regulated organizations bring to a rollout.

Responsibilities

• Own end-to-end implementation of Fellow for our largest enterprise accounts, from contract signature through full org-wide rollout and value realization.
• Design and execute detailed rollout plans for org-wide deployments spanning multiple departments, business units, or regions, including phased rollout strategies, milestones, and success metrics.
• Serve as the primary post-sale point of contact and trusted advisor for enterprise stakeholders, including IT, security, procurement, and executive sponsors.
• Lead discovery to understand a customer's org structure, tech stack, security/compliance requirements, and change-management needs, and translate them into a tailored implementation plan.
• Manage the technical aspects of enterprise deployments, including SSO/SAML configuration, calendar and CRM integrations, data migration, and user provisioning at scale.
• Partner with customers' security, legal, and IT teams to complete the security reviews, questionnaires, and compliance documentation that regulated or highly structured organizations require.
• Drive change-management and adoption programs - executive briefings, champion networks, train-the-trainer programs, and communications plans - to ensure high usage across large, distributed user bases.
• Manage a portfolio of concurrent enterprise implementations, proactively identifying and mitigating risks to scope, timeline, and budget.
• Identify expansion and upsell opportunities that surface during implementation, partnering with Sales and Customer Success to pursue them.
• Build and refine implementation playbooks, templates, and best practices to help scale the function as Fellow's enterprise base grows.
• Create and maintain documentation, training materials, and enablement content tailored to enterprise and regulated customers.
• Partner cross-functionally with Product, Engineering, and Customer Success to surface enterprise customer feedback, escalate issues, and inform the roadmap.
• Report on rollout health, adoption metrics, and risk status to internal leadership and to customer executive sponsors.

Qualifications

• 5+ years of experience in implementation, onboarding, professional services, or technical program management at a B2B SaaS company, with a proven track record of leading large-scale, org-wide software rollouts (multiple departments and/or 500+ users).
• Demonstrated experience managing complex, multi-stakeholder enterprise implementations from kickoff through full adoption.
• Experience working with a CRM (Salesforce, HubSpot, or similar) and project/professional-services tooling (e.g., Smartsheet, Asana, monday.com, Jira).
• Working knowledge of SSO/SAML, SCIM provisioning, and common enterprise IT/security review processes.
• Strong program and change-management skills: able to build rollout plans, manage timelines and risk across concurrent projects, and drive adoption at scale.
• Executive presence comfortable presenting to and building trust with senior stakeholders, including IT, security, and C-suite leaders.
• Exceptional written, verbal, and presentation skills in English.
• Ability to work independently, take ownership of outcomes, and operate cross-functionally in a fast-paced, evolving environment.

Preferred

• Experience implementing SaaS solutions within regulated industries (e.g., financial services, healthcare, insurance, government, or other compliance-heavy environments), including familiarity with requirements such as SOC 2, HIPAA, or data residency.
• Experience mentoring or supporting more junior implementation or onboarding team members.
• Formal project management certification (e.g., PMP, PRINCE2) or equivalent experience.

Benefits

• Fair, competitive compensation — we benchmark against the market and pay fairly for every role.
• Health and dental coverage, including prescription drugs and life insurance.
• Parental leave — 12 weeks of paid leave at 80% of salary for any parent welcoming a child into their family.
• Time to recharge — three weeks of vacation, paid sick leave, and a paid company-wide break at the end of the year.
• Remote-first flexibility — Work remotely within Canada.
• Room to grow — learning budgets, lunch-and-learns, and the freedom to own your work end to end.