AI Senior Project Manager

Ascensus•Boston, MA

1d•Remote

About The Position

A Senior Project Manager is responsible for managing initiatives that increase in size and complexity, such as leading enterprise-wide initiatives, to accomplish organizational strategic priorities. The Senior Project Manager is accountable for owning outcomes end-to-end—not just managing tasks, plans, or timelines—and is expected to drive results, manage risk upstream, and shape decisions that maximize business impact. Expectations of the role include facilitating cross-functional teams in the alignment and prioritization of project objectives that deliver value to Ascensus. This role requires proactive leadership, strategic thinking, and the ability to anticipate challenges, surface tradeoffs early, and bring forward clear options and recommendations. This role will lead initiatives that include the implementation and scaling of AI-enabled solutions (e.g., internal or customer-facing chatbots, workflow automation, decision-support tools), requiring close partnership with technology, data, risk, and business teams to ensure responsible, secure, and measurable outcomes. The Senior Project Manager collaborates closely with business sponsors, product owners, other business and technology leaders, external parties, and teams of subject matter experts to ensure broad organizational readiness, effective risk management, and transparent and timely communications with stakeholders. Senior Project Managers are expected to serve as trusted advisors to leaders demonstrating strong business acumen, understanding leader priorities and constraints, and help leaders see impacts of decisions. The Senior Project Manager also invests in others as a mentor and advocates for agile and lean project management to improve enterprise agility.

Requirements

Bachelor’s Degree or equivalent work experience.
A minimum of 6 years of project management experience within the financial services, recordkeeping or similar field of work.
Demonstrated experience owning outcomes and driving results in complex, highly visible initiatives.
Strong strategic thinking skills with the ability to connect execution to broader business goals and long-term impact.
Excellent verbal and written communication skills.
Ability to communicate with leaders using data, insights, and recommendations—not just status.
Demonstrated ability to anticipate risk, manage tradeoffs, and influence decision-making at multiple levels.
Demonstrated critical thinking skills.
Demonstration of empathy, flexibility, curiosity, and willingness to learn.
Excellent organizational skills including attention to detail and multitasking skills with demonstrated ability to work in time sensitive environment managing multiple, complex initiatives.
Strong working knowledge of Microsoft Office tools and AI-enabled productivity tools (e.g., Copilot/ChatGPT) to streamline analysis, documentation, and communication.
Demonstrated experience leading or significantly contributing to the implementation of AI-enabled solutions, such as chatbots, virtual assistants, or intelligent automation.
For virtual remote positions, we require an uninterrupted workspace during business hours and an internet work speed of 25 Mbps or better.

Nice To Haves

Knowledge and application of agile methodologies preferred.

Responsibilities

Facilitate working agreement and commitment to shared objectives with team of subject matter experts, ensuring clarity of roles and responsibilities.
Own delivery success and outcomes end-to-end, including accountability for results, risk mitigation, and course correction as needed—even when that requires temporarily stepping into execution to move work forward.
Facilitate planning and coordination of broad organizational readiness such as launch, communication and training strategies, while ensuring alignment with technology team deliverables, in support of driving incremental value.
Align with stakeholders to define success upfront using clear, measurable outcomes and indicators; continuously assess whether initiatives are delivering intended business impact, not just meeting milestones.
Apply established best-practices while working lean (eliminating waste), using strategies best-suited to the situational need, and being resilient and adaptable.
Facilitate and support cross-functional teams in aligning to deliver on desired outcomes.
Proactively identify potential risks, dependencies, and issues prior to their emergence; manage dependencies actively rather than providing retrospective updates.
When escalating risks and issues, include relevant context, supporting data, and a well-considered perspective—offering recommended solutions instead of simply reporting status.
Lead end-to-end delivery of AI-enabled initiatives, including chatbot implementations, from discovery and design through launch, adoption, and optimization.
Partner with product, technology, legal, and risk to ensure AI solutions are compliant, secure, and aligned with enterprise standards.
Design ways of working that enable the most effective and efficient execution and resulting impact while reducing downstream risk and minimizing surprises through strong upfront planning and dependency management.
Build and maintain communication channels and methods to provide updates on progress to both internal and external stakeholders timely and succinctly.
Translate progress, risks, and outcomes into clear, decision-oriented insights that enable leadership action.
Leverage data and other assessment mechanisms to facilitate enterprise level transparency and insights that are delivered in a consumable and meaningful format.
Manage project performance using appropriate tools and techniques.
Responsible for protecting, securing, and proper handling of all confidential data held by Ascensus to ensure against unauthorized access, improper transmission, and/or unapproved disclosure of information that could result in harm to Ascensus or our clients.
Our I-Client service philosophy and our Core Values of People Matter, Quality First and Integrity Always® should be visible in your actions on a day-to-day basis showing your support of our organizational culture.
Comply with company and unit policies and procedures and assists others in adhering.
Responsible for protecting and securing all client data held by Ascensus to ensure against unauthorized access to and/or improper transmission of information that could result in harm to a client.
Continually improve workflow and maximize efficiency by eliminating impediments to organizational readiness.
Guide, navigate and support teams if initiatives are forced to adjust due to resource or priority changes.
Proactively surface implications of scope, priority, or resource changes, helping leaders make informed tradeoff decisions.
Advocate for agile and lean project management as well as process improvement across the enterprise; actively engage to implement change well.
Actively engage in approaches to enabling enterprise capabilities to deliver value incrementally, optimize throughput, and improve time to market.
Drive change enablement and adoption for AI-enabled tools, ensuring stakeholders understand capabilities, limitations, and appropriate use of chatbot and automation solutions.
Use and continually develop servant leadership skills and emotional intelligence.
Provide mentoring and leadership to less experienced team members.
Model excellence in program management by setting a high bar for outcome ownership, strategic thinking, and leader partnership; coach others toward these expectations.
Proactively invest in training and learning opportunities to advance team effectiveness.