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.
We move quickly, share work early, and help each other get unstuck. We believe work should be fun, and we do our best work when people are curious, collaborative, direct, and genuinely excited to solve hard problems together.
