Enterprise Implementation Specialist

Jaide Health; Ottawa; Remote; CAD 90,000 - 130,000; Full time

Benefits offered by this job

Health and dental coverage

Parental leave

Vacation and sick leave

Remote-first within Canada

Learning budgets

Job summary

Fellow is seeking an Enterprise Implementation Specialist to lead large-scale deployments across enterprise customers, spanning multiple departments and hundreds to thousands of users. You will own end-to-end implementation from contract signature through org-wide rollout, including SSO/SAML, data migration, and cross-functional coordination with security, IT, and executives.

This role requires 5+ years in B2B SaaS implementations, CRM experience, change management, and strong executive

Qualifications

• 5+ years in implementation, onboarding, professional services, or technical PM at a B2B SaaS company.
• Proven record leading large-scale, org-wide software rollouts.
• Experience with CRM and project/professional services tooling.
• Strong change-management and executive engagement skills.
• Excellent written, verbal, and presentation skills in English.

Responsibilities

• Own end-to-end implementation for large enterprise accounts from contract through rollout.
• Design rollout plans spanning departments, regions, and milestones with success metrics.
• Serve as primary post-sale contact for IT, security, procurement, and executives.
• Lead discovery on org structure, tech stack, and security requirements.
• Manage deployments including SSO/SAML, data migration, and user provisioning.
• Collaborate with security/legal/IT to complete reviews and documentation.
• Drive change-management programs to achieve high adoption across users.
• Manage multiple concurrent implementations, monitor risks to scope, time, budget.
• Identify expansion opportunities with Sales and Customer Success.
• Create playbooks, templates, and enablement content for enterprise clients.
• Partner with Product/Engineering/CS to surface feedback and inform roadmap.
• Report rollout health and adoption metrics to leadership and sponsors.

Skills

Enterprise rollout leadership

Change management

Executive communication

Independent ownership

Cross-functional collaboration

Tools

Salesforce

HubSpot

Smartsheet

Asana

monday.com

Jira

SSO/SAML

Job description

About Fellow

Fellow is the AI meeting assistant that helps teams turn conversations into decisions and action, built from the ground up with privacy and security in mind. Fellow supports the entire meeting workflow, from pre-meeting briefs to note-taking and recording to human-level recaps, so organizations can have fewer, better, and shorter meetings. Today, Fellow is evolving beyond notetaking into an AI Chief of Staff for the whole organization.

Founded in 2017 by the team behind Fluidware (acquired by SurveyMonkey), Fellow is a Series A company backed by Craft Ventures, iNovia Capital, and Felicis Ventures. We're a remote-first company headquartered in Ottawa, and leaders in 100+ countries rely on Fellow, including teams at Shopify, HubSpot, WarnerMedia, Tucows, and Dynatrace.

Our mission is simple: make work better for everyone. Because when meetings run better, work feels better.

About the Role

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, elevate 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 offer

At 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.