Director Of Strategic Initiatives Jobs in Ridgefield, CT

This position is open to both remote and hybrid work

The Director of Strategic Initiatives serves as a key member of the FLIK Independent School Dining leadership team and reports directly to the President.

This role is responsible for driving the successful execution of FISD's most important operational, strategic, and cross-functional initiatives. The Director of Strategic Initiatives ensures that priorities move from planning to implementation, accountability is maintained, and projects deliver measurable results across the division.

The role combines project management, operational leadership, change management, and business transformation. Success requires a hands-on leader who can work effectively with Operations, Finance, Culinary, Human Resources, Procurement, Technology, and Compass Group support teams to remove obstacles and deliver results.

This position is expected to spend significant time working directly with district leaders, support teams, and school operators to ensure initiatives are implemented successfully and sustained over time.

Strategic Initiative Management

• Lead and manage FISD's portfolio of strategic initiatives, including new account launches, client retention programs, operational improvement initiatives, and cross-functional pilots
• Develop project plans, timelines, milestones, ownership structures, and success metrics for key division priorities.
• Drive accountability across departments and ensure commitments are completed on time.
• Identify project risks, remove roadblocks, and escalate issues when necessary.
• Provide regular executive-level reporting on initiative status, risks, and outcomes.
• Own the cadence of business reviews, leadership team meetings, and planning offsites - preparing agendas, capturing decisions, and driving action

Operational Excellence Execution

• Partner closely with the Operational Excellence team to ensure corrective action plans resulting from audits are fully implemented.
• Establish and manage a centralized tracking process for audit findings, action plans, and resolution timelines.
• Work directly with District Managers and support teams to drive completion of required actions.
• Validate completion of corrective actions and ensure sustainable process improvements are achieved.
• Identify recurring operational challenges and recommend systemic solutions.

New Business Mobilization and Unit Openings

• Serve as project lead for major account mobilizations, new unit openings, and significant operational transitions.
• Coordinate activities across Operations, Human Resources, Finance, Technology, Procurement, Marketing, and Culinary teams.
• Develop and manage opening readiness plans and milestone reviews.
• Ensure schools are operationally prepared prior to launch.
• Conduct post-opening reviews and support stabilization efforts during the first 90 days of operation.

Systems Implementation and Business Transformation

• Lead implementation of operational and technology initiatives including POS conversions, reporting enhancements, client-facing tools, and process improvement projects.
• Partner with Compass Group technology teams and external vendors to coordinate implementation activities.
• Translate operational needs into business requirements and implementation plans.
• Support change management, communication, and training efforts to drive adoption.
• Identify opportunities to improve efficiency, reporting, and client experience through technology and process improvements.

Client Commitment and Retention Support

• Maintain visibility to key client commitments, strategic initiatives, and retention-related action plans.
• Partner with Operations and Account Management leaders to ensure commitments are delivered on schedule.
• Track progress against major client initiatives and provide visibility to leadership.
• Support strategic retention efforts and high-priority client projects.

Compass Group Partnership, Cross-Functional Leadership, & Executive Support

• Develop strong relationships across Compass Group support functions and centers of excellence.
• Serve as a resource for field teams navigating Compass processes and support structures.
• Help accelerate implementation of enterprise initiatives within FISD.
• Serve as a trusted thought partner and operational extension of the President - translating strategic priorities into clear plans, owners, and outcomes
• Lead high-priority special projects assigned by the President, including business development support, new partnership evaluations, and operational pilots
• Identify organizational gaps, escalate risks proactively, and bring forward well-developed recommendations

Required

• 8-12 years of progressive experience in project management, business transformation, implementation leadership, or a related field.
• Proven ability to lead complex cross-functional initiatives across multiple stakeholders.
• Strong organizational and project management skills with exceptional attention to detail.
• Demonstrated success driving accountability and achieving results without direct authority.
• PMP certification or equivalent project management experience.
• Excellent communication, presentation, and relationship-building skills.
• Ability to balance strategic thinking with hands-on execution.
• Strong analytical and problem-solving capabilities.
• Willingness to travel to support projects, openings, and operational initiatives.

Preferred

• Experience within food service, hospitality, education, retail, or multi-unit operations.
• Experience leading mobilizations, implementations, or operational improvement initiatives.
• Familiarity with Compass Group systems, processes, and organizational structure.
• Experience with POS systems, reporting platforms, operational technology, or business transformation projects.