Director, Project Management

Job Details: 

We are seeking a highly skilled and results-oriented Director, Project Management, to support the Services organization. This role will play a critical part in scaling delivery operations, improving implementation predictability, and strengthening portfolio visibility across customer delivery functions including Implementations, Conversions, Add-Ons, and Integrations. 

The ideal candidate operates as a strategic operational leader capable of building scalable governance frameworks, improving forecasting rigor, mentoring high-performing project management teams, and driving operational consistency across a rapidly growing SaaS delivery environment. 

Success Profile:  

This role is anchored in four of our company’s core competencies—Results Driven, Takes Ownership, Drives Efficiency, and Innovative. These competencies reflect the mindsets and behaviors that define success in this role. We outline how each competency translates into real-world actions and outcomes specific to this role.  

Takes Ownership 

• Build, mentor, and retain a high-performing team of Project Managers across all delivery functions, including specialized integration PMs, while establishing clear career paths and performance expectations.  
• Own the selection, implementation, and ongoing optimization of project management tooling, ensuring the project management platform serves as the single source of truth for delivery data, forecasts, and artifacts.  
• Serve as the operational authority for standardized project governance, ensuring all projects adhere to defined tracking, milestone, reporting, and risk management standards.  
• Serve as a selective executive escalation point for at-risk projects and ensure consistent communication of delivery health, risks, and remediation plans to leadership stakeholders.  

Customer-Centric 

• Partner closely with Implementation, Solutions Engineering, Conversions, Add-On leadership, Sales, Customer Success, and Product teams to align delivery expectations, timelines, and operational execution with customer outcomes.  
• Establish and enforce consistent project management methodologies that improve delivery transparency, milestone execution, and customer implementation experiences across all customer segments.  
• Develop and maintain capacity planning models that align project demand with available delivery resources to proactively reduce customer delivery risks and operational bottlenecks.  
• Ensure all delivery teams maintain high standards for project tracking, reporting consistency, and communication quality to improve customer confidence and delivery predictability.  

Results-Driven 

• Own project-level forecasting accuracy, including go-live timelines and phase-based revenue realization, while establishing forecasting methodologies and enforcing adoption across all project managers.  
• Establish baseline visibility into project portfolio health, forecasting accuracy, and capacity constraints, identifying operational gaps and implementing measurable improvements.  
• Improve delivery predictability by continuously evaluating delivery processes, governance models, tooling usage, and reporting structures to support increasing deal complexity and volume.  
• Drive adoption of AI enabled workflows across the PM organization, leveraging automation and intelligent tooling to improve project planning, forecasting accuracy, status reporting efficiency, and documentation quality.  

Strategic 

• Define and evolve the project management strategy aligned to company growth objectives with a focus on scalability, predictability, operational efficiency, and enterprise delivery maturity.  
• Establish a tiered project management framework that supports enterprise, mid-market, and smaller implementations with appropriate governance rigor and operational controls.  
• Provide leadership with data-driven visibility into portfolio health, delivery timelines, resource utilization, forecasting variance, and operational risks to support strategic decision-making.  
• Deliver a prioritized roadmap for PM maturation, including tooling modernization, governance improvements, organizational scaling, and process standardization initiatives.  

Requirements:  

• 8–10+ years of experience in project or program management within a SaaS environment, with a strong record of delivering complex customer implementations.  
• Experience in payments, insurance, or other regulated industries strongly preferred, with a clear preference for candidates with insurance implementation experience.  
• At least 3–5 years of experience leading project management teams or PMO functions.  
• Demonstrated experience building or scaling PMO capabilities in a high-growth environment.  
• Experience managing complex, multi-phase enterprise implementations involving multiple stakeholders and third-party partners.  

Core Competencies & Skills 

• Strong operational and systems thinking, with the ability to design scalable processes without over-engineering.  
• Deep understanding of project lifecycle management, forecasting methodologies, and delivery governance.  
• Proven ability to drive accountability and enforce standards across cross-functional teams.  
• Strong analytical skills with the ability to translate project-level data into actionable insights.  
• Excellent communication skills with the ability to engage both technical and business stakeholders.   

Technical & Domain Expertise 

• Experience with modern project management and Professional Services Automation (PSA) tools (e.g., Rocketlane, SmartSheet, or similar).  
• Solid understanding of SaaS delivery models, integrations, and implementation lifecycles.  
• Familiarity with APIs, data exchange, and enterprise system integrations.  
• Knowledge of payments ecosystems, billing platforms, or insurance systems is highly desirable.  

Benefits:    

We offer a competitive benefits program including:   

• Medical, dental, vision, life & disability insurance 
• 401(k) plan with company match 
• Flexible Time Off (FTO), wellbeing days, paid holidays, and summer Fridays 
• Mental health resources 
• Paid parental leave
• Tuition reimbursement 
• Employee Resource Groups (ERGs)