Enterprise Manager: Implementation

About Sterling Brokers

Sterling Brokers is disrupting the Group Benefits and Retirement landscape in Canada through our innovative application, integrating with the largest insurance carriers in Canada and global HRIS platforms, to administer a streamlined solution. We are the largest independently owned and operated Third Party Administrator (TPA) and Broker in Canada, and 4th largest overall. Established in 2014, SCB is growing rapidly and looking for talented individuals to join our team.

About the role

The Enterprise Manager plays a vital role in the overall implementation department, both as ahigh level project manager, and as a people manager. The candidate in this position is responsible for overseeing the implementation analysts that directly report up to them, as well as working directly with enterprise level clientele to ensure that there implementation needs are adequately met. They will also be responsible for organizing, managing, delegating, and completing larger scale projects and departmental improvements, while conducing their day today management duties.

Success in this role requires strong analytical skills, attention to detail, problem-solving abilities, people management skill, decision making capability, and excellent communication.

Key Responsibilities

Enterprise Client Implementations & Delivery Leadership

• Lead complex, enterprise-level implementations from intake through post-implementation stabilization, acting as the primary Implementation leader accountable for timelines, scope, quality, and client satisfaction.
• Own the end-to-end delivery strategy for enterprise clients, including implementation planning, dependency mapping, risk identification, and mitigation across carriers, internal teams, and external partners.
• Serve as a senior escalation point for enterprise clients, proactively managing risks, issues, and expectations to support retention and long-term partnership value.

Client Event Management

• Own and manage enterprise open enrollments and major client events from start to finish, ensuring a seamless experience for clients, members, carriers, and internal stakeholders.
• Coordinate closely with Executive Account Managers (EAMs), carriers, and internal teams to align on timelines, responsibilities, and communication strategies.
• Ensure all feeds, eligibility files, rate tables, plan builds, and documentation are prepared, validated, and delivered to the highest standard prior to launch.
• Oversee open enrollment readiness including plan configuration, testing, carrier confirmations, employee communications, and post-event reconciliation and audits.

People Leadership & Team Development

• Lead, coach, and develop Implementation Analysts and Senior Analysts supporting enterprise clients, with accountability for performance, workload balance, quality of output, and professional growth.
• Translate enterprise-level complexity into clear, executable workstreams for direct reports, ensuring clarity on priorities, dependencies, and success criteria.
• Provide ongoing feedback, mentorship, and support to elevate enterprise execution maturity across the team.

Cross-Functional & Carrier Engagement

• Act as a key liaison between Implementation and Sales, EAM, Product, Engineering, Finance, and Carrier partners to ensure enterprise needs are understood and delivered accurately.
• Drive alignment on enterprise timelines, carrier constraints, system limitations, and client commitments to avoid downstream risk and rework.
• Partner with carriers to navigate non-standard setups, escalations, and service challenges inherent to enterprise accounts.

Data, Feeds & Process Excellence

• Maintain strong oversight of data integrity, including eligibility feeds, payroll files, carrier reporting, and billing accuracy.
• Ensure robust QA processes are followed for all enterprise implementations, open enrollments, and renewals, including audits and reconciliations.
• Identify systemic gaps impacting enterprise delivery and contribute to process improvements, tooling enhancements, and documentation that benefit the broader Implementation organization.

Data, Feeds & Process Excellence

• Maintain strong oversight of data integrity, including eligibility feeds, payroll files, carrier reporting, and billing accuracy.
• Ensure robust QA processes are followed for all enterprise implementations, open enrollments, and renewals, including audits and reconciliations.
• Identify systemic gaps impacting enterprise delivery and contribute to process improvements, tooling enhancements, and documentation that benefit the broader Implementation organization.

Risk Management & Reporting

• Proactively identify, assess, and escalate risks related to timelines, data, carrier readiness, or client experience.
• Provide clear, structured updates to management on enterprise delivery health, resourcing needs, and emerging risks.
• Support departmental planning by contributing insights on enterprise complexity, capacity, and scalability.

Block & Team-Wide Contribution

• Maintain a baseline understanding of block implementations and renewals, ensuring enterprise leadership remains connected to broader team workflows and standards.
• Support block initiatives as needed during peak periods or escalations, reinforcing a One Team mindset.
• Contribute to team-wide initiatives, knowledge sharing, and continuous improvement efforts that raise overall implementation quality and consistency.

Required Skills & Experience

• 3+ years of experience in Group Benefits or a related industry preferred.
• 1+ years of people management experience is preferred.
• Strong data analysis skills; experience working with Excel (Pivot Tables, VLOOKUPs, formulas)required.
• Familiarity with HRIS platforms, data feeds, and carrier systems is a plus.
• Ability to conduct business in French is a plus (can be coached on industry specific terms as needed).
• Ability to manage multiple projects simultaneously and meet tight deadlines.
• Experience working with clients in a professional capacity.
• Strong communication and stakeholder management skills to collaborate across departments.
• Detail-oriented with a proactive approach to problem-solving.
• Comfortable working in fast-paced, evolving environments with a continuous improvement mindset

Why Join the Sterling Brokers?

• Career Growth: Be part of a rapidly expanding company with opportunities for advancement.
• Competitive Compensation: Competitive salary and comprehensive benefits package.
• Collaborative Team: Work alongside highly motivated professionals in a supportive, team-oriented culture.
• Remote Flexibility: Work from home while contributing to an innovative, client-focused organization.