Director, Project Management

InvoiceCloud•Boston, MA

About The Position

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. 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.

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.
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.
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.

Responsibilities

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.
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.
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.
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.