Strategic Initiatives Director

Location Requirements: Hybrid to Wayne, Naperville, or Austin. Remote candidates will be considered. 

Your role on the team:  

The Strategic Initiatives Director drives the successful execution of our corporate strategy through the expert leadership of our company OKR program and initiatives supporting our strategic objectives. This role partners with executives, functional leaders, and functional experts to define and successfully execute OKRs and project plans, and measure and communicate progress and outcomes. This role will also drive continuous improvement within our strategic initiative management discipline. The Strategic Initiatives Director reports to the Chief Transformation Officer.  

You can expect to: 

OKR Management  

• In collaboration with executive and functional leaders, lead the process to define company key results and related team OKRs. 
• Document all company and related team OKRs in our system of record. 
• Partner with Finance and other systems experts to ensure reporting is built to track achievement toward OKR targets. 
• Partner with all OKR owners to ensure regular status updates are entered in our system of record. 
• Proactively identify, escalate, and resolve risks to the successful completion of OKRs. 
• Lead regular OKR progress reviews with the Executive Leadership Team and facilitate decisions related to OKR changes. 
• Create OKR progress reports for our parent company and company-wide audience. 
• As our OKR practice leader, we provide support to teams on their implementation of OKR processes. 
• Define, document, and implement processes that improve and scale our OKR discipline. 

Strategic Initiative Management  

• Partner with executives, functional leaders, and subject matter experts to define goals, timelines, and desired outcomes for company high-level strategic initiatives. 
• Build robust, agile plans to define and track the work necessary to achieve initiative objectives. 
• Build and apply extensive knowledge of the business to draft necessary project components and identify and engage needed stakeholders and project participants. 
• Lead regular and ad hoc meetings to inspect and drive progress toward defined milestones and end-state objectives. 
• Provide frequent updates to executives and stakeholders on the status of strategic initiatives, including reporting on key metrics. 
• Proactively identify, escalate, and resolve risks that could limit the successful completion of objectives. 
• Adjust and adapt project plans and scope in response to new inputs, learnings, and issues, always informed by the strategic objective. 
• Define, document, and implement processes that improve and scale our strategic initiative management discipline.  

What you bring to the role:  

• Excellent relationship-builder and collaborator who inspires action through relational rather than positional authority. 
• Highly organized, detail oriented, and demonstrates consistent follow-through. 
• Analytical and strategic thinker who relentlessly pursues results. 
• Ability to navigate effectively through ambiguity and technical complexity to proactively identify issues and solutions. 
• Ability to communicate effectively with executives, functional leaders, and cross-functional team members. 
• Ability to quickly build expert-level knowledge of business strategy, systems, processes, teams, and roles. 
• Focus on achieving vital outcomes, not just defined outputs. 
• Experience leading and managing an OKR or similar program preferred.  

This role requires: 

• Successful experience leading executive-level strategic projects and initiatives.  
• Experience designing highly effective, repeatable processes, and structures to manage and execute work. 
• Experience effectively managing multiple projects concurrently. 
• Possesses 8+ years in roles of increasing responsibility in a corporate environment. 
• Strong proficiency in MS Excel, PowerPoint and Word.  

Who we are:  

Frontline Education is a pioneer of school administration software purpose-built for K-12 districts. We provide innovative, connected solutions for student and special programs, business operations, and human capital management with powerful data and analytics to empower educators and administrators. We earn the trust of K-12 leaders across the U.S. by serving as a consistently high-performing, forthright partner of school districts through every dimension of the company. 

We're a group of unique and talented individuals that love what we do. We've been lucky enough to land jobs with a