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. It's an award-winning, purpose-driven environment where top talent thrives. To learn more, visit InvoiceCloud.com.


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 Integrations. This 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 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.


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:

• 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)

Base salary is one component of total compensation. Employees may also be eligible for an annual bonus or commission. Some roles may also be eligible for overtime pay. The above represents the expected base compensation range for this job requisition. Ultimately, in determining your pay, we'll consider many factors including, but not limited to, skills, experience, qualifications, geographic location, and other job-related factors.


Base Compensation Range

$180,000-$210,000 USD

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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