Program Manager, Strategic Initiatives – Employer Services

About the role

The Program Manager, Strategic Initiatives drives core strategic initiatives, ensures executional excellence on key programs, and collaborates with cross-functional Center of Excellence (COE) and Employer Services partners to optimize results. This highly visible, strategic “utility player” focuses on enabling revenue expansion and protecting the customer base through direct sales campaigns, proactive growth initiatives, and expansion via indirect channel partners. The role acts as a trusted advisor to the leadership team, developing repeatable programs, key performance metrics, and high-level executive communications. It serves as a critical bridge between Product, Technology, Legal, Finance, and frontline Sales stakeholders, managing complex dependencies to accelerate speed-to-revenue and drive strategic organizational effectiveness.

Our schedule is built around 4 days of high-impact, in-office collaboration (Monday–Thursday), paired with Friday Flexibility to wrap up your week remotely.

Responsibilities

• Establish and lead cross-functional strategic initiatives (planning, preparing, launch, execution, follow-up) to achieve business objectives.
• Liaise between Employer Services and COEs on strategic projects to drive business execution and growth.
• Design objectives and work plans to execute on key revenue initiatives.
• Ensure all relevant stakeholder groups are identified and classified for each initiative, consulting them at the appropriate level.
• Drive strategy, provide oversight, and manage accountability for direct sales campaigns.
• Partner with finance, technology, operations, sales, and marketing, using influence to drive progress when things are stalled.
• Act as a trusted advisor to VP-level executives, providing strategic planning guidance and feedback on key initiatives, and advocate for sales team and client needs in all project meetings.
• Present to VP-level and above, as well as plan, coordinate, and host 200+ person virtual and in-person events.

Requirements

• 5+ years of progressive business experience specializing in enterprise program management, strategic planning, business transformation, or specialized management consulting.
• Bachelor’s Degree in Business, Marketing, Communications, or a related discipline required; an M.B.A. or relevant advanced degree is highly preferred.
• Proven track record of navigating complex matrixed organizations and successfully leading multi-disciplinary initiatives that intersect across technology, finance, operations, and corporate legal groups.

Skills

• Assertiveness & Drive: Displays an enthusiastic "owner's mindset," utilizing personal influence and professional diplomacy to push progress forward and eliminate organizational inertia when projects become stalled.
• Confidence & Executive Presence: Comfortably engages with, advises, and presents strategic rationales directly before Vice President (VP) and Senior Vice President (SVP) audiences.
• Elevated Emotional Intelligence: High degree of self-motivation, organization, resilience, and adaptability when navigating nonstandard situations, shifting requirements, and high-stakes multi-stakeholder conflicts.
• Customer Centricity: Remains completely aligned with the strategic vision of our markets, advocating for sales teams and enterprise customer requirements across all internal technical design sessions.
• Project Management Certifications: Deep knowledge of diverse project management methodologies (Agile, Waterfall, and Hybrid frameworks); an active Project Management Professional (PMP) certification is a plus.

Schedule

4 days in-office (Monday–Thursday) with Friday flexibility to work remotely.