Director, Project Management

About InvoiceCloud:

InvoiceCloud is a fast-growing fintech leader recognized with 20 major awards in 2025 including USA TODAY and Boston Globe Top Workplaces multiple SaaS Awards wins for Best Solution for Finance and FinTech and national customer service honors from Stevie and the Business Intelligence Group. Judges also highlighted our mission to reduce digital exclusion and restore simplicity and dignity to how people pay for essential services as well as our leadership in AI maturity and responsible innovation. Its an award-winning purpose-driven environment where top talent thrives. To learn more .

Position Overview

The Director of Project Management Office (PMO) is responsible for establishing and operating a centralized PMO that drives consistency predictability and visibility across all customer delivery functions including Implementations Conversions Add-Ons and leader owns project management standards tooling forecasting discipline and portfolio visibility ensuring that all projects are executed within a consistent framework and that leadership has accurate real-time insight into delivery health and revenue timing.

This is a hands-on leadership role that blends operational rigor systems thinking and team development. The Director will build and scale a high-performing PMO that serves as the control tower for delivery execution while partnering closely with Implementation and Solutions Engineering leadership who retain ownership of execution outcomes.

As InvoiceCloud scales and moves further up market delivery complexity and volume will increase significantly. The Director of PMO plays a critical role in ensuring that growth does not come at the expense of predictability efficiency or customer experience. This role establishes the operational backbone that enables the Services organization to scale with confidence.

Success Profile:

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

Strategic

• Define and evolve the PMO strategy aligned to company growth objectives with a focus on scalability predictability and operational efficiency.
• Establish a tiered project management framework that supports enterprise mid-market and smaller implementations with the appropriate level of rigor.
• Partner with the VP of Services and functional leaders to align delivery operations with company revenue and growth targets.
• Continuously evaluate and improve delivery processes artifacts and governance models to support increasing deal complexity and volume.
• Identify and implement AI driven capabilities such as predictive risk detection automated status summarization and intelligent timeline forecasting to improve delivery predictability and reduce manual overhead.
  • Tooling and Systems Ownership
    • Own the selection implementation and ongoing optimization of PMO tooling including the transition from SmartSheet an equivalent platform.
    • Ensure the project management system is the single source of truth for all delivery data forecasts and artifacts.
    • Define and enforce data standards usage expectations and reporting structures within the tool.
    • Eliminate shadow systems and ensure consistent adoption across all teams.
  • Team Leadership and Talent Development
    • Build mentor and retain a high-performing team of Project Managers across all delivery functions including specialized integration PMs.
    • Establish clear roles career paths and performance expectations for PMs at different levels.
    • Coach team members on both tactical execution and strategic stakeholder management.
    • Foster a culture of accountability transparency and continuous improvement.

Takes Ownership

• PMO Governance and Delivery Standards

  • Establish and enforce standardized project management methodologies including project planning milestone definition risk management and status reporting.
  • Own the definition of delivery health and ensure consistent objective reporting across all projects.
  • Ensure all projects including those led by Implementation Managers without dedicated PMs adhere to defined minimum standards for tracking and reporting.
  • Serve as the system of record authority for all project data and artifacts.
  • Define and execute an AI strategy within the PMO that leverages automation and generative tools to improve project planning status reporting risk identification and documentation quality.
  • Drive adoption of AI enabled workflows across the PM organization ensuring teams effectively leverage automation and intelligent tooling to improve efficiency consistency and scalability.

Results-Driven

• Forecasting and Portfolio Visibility

  • Own project-level forecasting accuracy including go-live timelines and phase-based revenue (MRR) realization.
  • Establish forecasting methodologies and enforce consistent usage across all project managers.
  • Provide clear data-driven visibility into portfolio health risks and delivery timelines.
  • Partner with Implementation leadership who own portfolio-level commitments by providing accurate and timely project-level data and variance tracking.

• Capacity Planning and Resource Modeling

  • Develop and maintain capacity models that align project demand with available delivery resources across Implementations Conversions Add-Ons and Integrations.
  • Identify capacity constraints bottlenecks and risks early enabling proactive planning and decision-making.
  • Provide leadership with visibility into resource utilization and future demand to support hiring and prioritization decisions.

Customer-Centric

• Partner closely with Implementation Solutions Engineering Conversions and Add-On leadership to ensure alignment between process execution and outcomes.
• Act as a key operational partner to Sales Customer Success and Product in aligning delivery expectations and timelines.
• Serve as a selective executive escalation point for at-risk projects in partnership with Implementation leadership.
• Ensure clear and consistent communication of delivery health and risks to executive stakeholders.
• Travel onsite as needed to support large enterprise and strategic customer implementations leading project kickoffs discovery sessions executive stakeholder meetings and escalation discussions to ensure successful project outcomes

Requirements:

• 810 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 35 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 ( 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)

InvoiceCloud is committed to providing equal employment opportunities to all employees and applicants. We do not tolerate discrimination or harassment of any kind based on race color religion age sex nationality disability genetic information veteran or military status sexual orientation gender identity or expression or any other characteristic protected under applicable laws.

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