About the RoleThe 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.
Required Skills & Experience- 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.
What we offerAt Fellow, we invest in the people who make our mission possible:
- 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.
