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Sr. Director, District HCM Transformations

Description

How you'll contribute to our mission
School districts rely on human capital systems to power everything from recruiting and onboarding to time management and workforce planning. Many districts begin with a single solution, but as their needs evolve, disconnected systems can create friction, inefficiency, and limited visibility.
As Sr. Director, District HCM Transformations, you will help districts take the next step — evolving from standalone HCM tools toward a more unified, platform-based approach that brings greater alignment, automation, and insight across their operations.
This newly created role is focused on building trusted relationships within an established customer base and guiding district leaders through thoughtful expansion conversations. You will help them envision what’s possible when their systems work together as part of a connected ecosystem designed to support educators and staff more effectively.
How you'll drive success

Develop and execute a focused territory strategy centered on expanding existing HCM customers into broader, platform-aligned partnerships
Build executive-level relationships with Superintendents, HR leaders, Finance leaders, and Technology stakeholders
Lead discovery conversations that uncover workflow gaps, integration challenges, and opportunities for greater system alignment
Position Frontline’s platform capabilities as a natural evolution of the district’s existing investment
Guide districts through complex evaluation and decision-making processes with clarity and confidence
Partner closely with Sales, Product, Marketing, and Client Success to ensure cohesive messaging and smooth transitions
Maintain disciplined pipeline management, forecasting accuracy, and long-cycle opportunity strategy
Share market feedback and district insights to inform product direction and go-to-market refinement
Model thoughtful, responsible use of technology in planning, communication, and customer engagement

What you bring to help us grow

Deep experience in EdTech, SaaS, or enterprise solution sales, with a track record of expanding customers beyond initial product adoption
Demonstrated success managing complex, consultative sales cycles involving multiple stakeholders
Strong executive presence and the ability to translate system capabilities into strategic outcomes
Experience selling integrated or platform-based solutions rather than single-point products
Strategic territory planning and account expansion expertise
Comfort navigating competitive landscapes with professionalism and integrity
Ability to collaborate cross-functionally within a growth-focused organization

What you'll need to thrive

A systems thinker who sees connections between products, processes, and long-term district outcomes
A consultative partner who leads with listening and builds trust over time
Resilience and focus in longer transformation cycles
Confidence operating independently while staying aligned with executive leadership
Curiosity about how integrated technology ecosystems can reduce complexity and create clarity
Clear communication skills that simplify complex ideas for diverse audiences

This role will initially onboard and report to our Chief Strategy Officer, who will provide executive alignment, field readiness, and strategic guidance to ensure strong early momentum and successful integration into the revenue organization.

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