[Hiring] Onboarding Project Manager II @Oversight Systems Inc

Role Description

The Project Manager II will be part of the Client Project Management team within the Client Onboarding group. The primary responsibility of this position is to lead client-facing software implementation projects from initiation through go-live, ensuring successful delivery within scope, schedule, and budget. This role is for an individual who resides in Europe and has direct experience working with large external customers to deliver large, complex projects.

This role serves as the primary point of contact for both client stakeholders and internal implementation teams throughout the project lifecycle. The Project Manager II will coordinate activities across Client Onboarding, Software Development, QA, SaaS Operations, Product, and other internal teams while maintaining clear communication with client stakeholders at all levels of the organization.

This is an individual contributor role responsible for independently planning, managing, and executing multiple implementation projects simultaneously, including more complex or higher-touch client engagements. The Project Manager II is expected to operate with a high degree of self-sufficiency, proactively identify and mitigate risks, manage project scope, drive accountability across project teams, and provide clear, timely status updates to ensure successful project outcomes and client satisfaction.

Equally important, this role requires strong relationship management skills, confident and proactive communication, and the ability to serve as a trusted strategic partner to clients. The Project Manager II should be comfortable leading client conversations, navigating challenging situations, and building confidence in Oversight's approach and recommendations.

The Project Manager II is also expected to contribute to team process improvements, identify opportunities to increase efficiency or consistency, and support the continued development of best practices within the Onboarding team.

Responsibilities

• Serve as the primary contact and trusted advisor for client implementation projects, including more complex or higher-touch client engagements, building strong client relationships and establishing credibility through confident, proactive communication.
• Independently develop and manage project plans, timelines, project documentation, resource plans, risk logs, and status reports.
• Establish and maintain project governance, ensuring alignment on scope, objectives, milestones, deliverables, roles, and responsibilities.
• Confidently lead project kickoff meetings, ongoing status meetings, requirements gathering sessions, and stakeholder meetings with clients and internal teams, driving productive discussions, clear decisions, and actionable next steps.
• Coordinate cross-functional internal teams to ensure project tasks, deliverables, and dependencies remain on schedule.
• Monitor project scope, schedule, risks, issues, and budgets, proactively identifying concerns, recommending solutions, and escalating as needed.
• Communicate project progress, milestones, risks, decisions, and next steps to client stakeholders and internal leadership on a regular basis, tailoring communication to the audience and providing clear, actionable recommendations when needed.
• Manage client expectations and drive resolution of project roadblocks to maintain delivery commitments, including navigating challenging conversations and maintaining positive client relationships.
• Lead change management processes, including scope change evaluation, impact assessment, stakeholder communication, and documentation.
• Generate and maintain project reporting, key performance indicators, implementation metrics, and project documentation.
• Ensure project deliverables meet quality standards and client expectations.
• Manage multiple client implementation projects simultaneously in a fast-paced environment with limited oversight.
• Partner with internal teams to prioritize project activities and align resources to meet project objectives.
• Identify opportunities to improve project delivery processes, documentation, templates, or team workflows.
• Develop and maintain Standard Operating Procedures and contribute to continuous improvement initiatives for the Onboarding team.
• Support team knowledge sharing by contributing lessons learned, best practices, and practical recommendations from project experience.

Qualifications

• Strong experience managing client-facing software implementation projects.
• Ability to independently manage more complex client projects with limited oversight.
• Strong project planning, scheduling, and resource management skills.
• Ability to manage multiple concurrent projects with competing priorities.
• Excellent client relationship management and stakeholder communication skills, with the ability to build trust, establish credibility, and serve as a confident advisor to client stakeholders.
• Strong presentation and facilitation skills with the ability to engage both technical and business audiences, lead discussions confidently, and communicate recommendations effectively.
• Experience managing project scope, timelines, budgets, risks, and dependencies.
• Ability to work effectively in a fast-paced environment with changing requirements and priorities.
• Strong business, technical writing, and documentation skills.
• Excellent organizational skills and attention to detail.
• Ability to influence without direct authority and drive accountability across cross-functional teams.
• Strong problem-solving, critical thinking, and decision-making abilities.
• Self-starter with a strong sense of ownership, accountability, and follow-through.
• Ability to identify process improvement opportunities and implement practical solutions.
• Ability to exercise sound judgment, prioritize effectively, and know when to escalate risks or blockers.
• Must be diplomatic and work effectively with client stakeholders, executive leadership, and multiple internal teams, including onshore and offshore resources.

Key Performance Objectives/Indicators

• Successful delivery of implementation projects within approved scope, timeline, and budget.
• Ability to independently manage more complex or higher-touch client implementation projects.
• High client satisfaction and positive stakeholder feedback, demonstrating strong relationship management and client confidence in project leadership.
• Effective management and mitigation of project risks and issues.
• Consistent achievement of project milestones and deliverables.
• Clear, accurate, and timely project communication and reporting.
• Successful coordination and alignment across client and internal project teams.
• Effective management of scope changes, dependencies, and project escalations.
• Contribution to continuous process improvement initiatives.
• Timely completion of assigned responsibilities and project deliverables.
• Ability to successfully facilitate project meetings, confidently guide stakeholder discussions, and drive action-oriented outcomes.
• Demonstrated ability to operate with increased self-sufficiency, ownership, and sound decision-making.

Education/Experience Requirements

• Must have a 4-year college degree (technical, business, psychology, or equivalent).
• 3-5 years experience managing client-facing software implementation or technical projects.
• Experience leading client-facing projects and managing external stakeholder relationships, including serving as the primary point of contact and confidently managing client expectations.
• Proficiency using Jira and Confluence preferred.
• Proficiency using Microsoft Office Suite preferred.
• Proficiency using SmartSheet is a plus. Experience using any project management software is required.
• PMP certification is a plus but is not required.
• Strong English language skills required, and competency in additional languages is preferred.