Senior Project Manager I

CaseWorthy, Inc.; Northern (KY); Hybrid; USD 90,000 - 150,000; Full time

Job summary

CaseWorthy, Inc. is seeking a Senior Project Manager to own the full lifecycle of large-scale SaaS implementations, ensuring on-time delivery and customer satisfaction. You will plan resources, monitor progress, and communicate with stakeholders to drive successful outcomes.

The role requires strategic thinking, risk management, and accountability for project success, with travel up to 15% and a focus on cross-functional collaboration across teams.

Qualifications

• At least 5 years of project management experience with full ownership of outcomes.
• Strong skills in planning, scheduling, RAID logs, and communication plans.
• Excellent customer-facing and internal communication, professionally handling stakeholders.
• Excellent written and verbal communication abilities.
• Solid organizational skills and attention to detail with multitasking ability.
• Ability to make important decisions under pressure and own the outcome.
• Strategic thinking with the ability to assess health and trajectory of engagements.
• Familiarity with Atlassian tools: Jira Software, Service Management, Plans, Confluence.
• Experience leading project teams and guiding large SaaS implementations.
• Bachelor's degree; PMP certification preferred; experience with government contracts is a plus.

Responsibilities

• Act as primary contact throughout the software implementation process, setting tone and cadence.
• Develop and define the complete project plan with artifacts like charter and schedule.
• Forecast and manage issues and risks, flagging concerns early.
• Prepare weekly status reports for executives and run weekly reviews with customers.
• Maintain relationships with customers, reading the room and handling difficult conversations.
• Advocate for customers while protecting scope, timeline, and resourcing.
• Escalate when needed and own the outcome of decisions made.
• Work cross-functionally on enhancements and changes for the broader implementation.
• Assist with system configuration and demonstrate final setup.
• Collaborate with Sales and Account Management on scope changes and margins.
• Provide end-user training and technical support during implementation.
• Ensure knowledge transfer from training to the work environment.
• Willingness to travel nationwide up to 15% per year.
• Performs other duties as assigned.

Skills

Project management

Stakeholder management

Communication

Organizational skills

Decision making

Strategic judgment

Critical thinking

Problem solving

Team leadership

Jira/Confluence knowledge

Education

Bachelor's Degree

PMP Certification

Tools

Jira Software

Jira Service Management

Jira Plans

Confluence

Job description

As a Senior Project Manager, you will own the full lifecycle of large-scale, platform SaaS implementations — on time, on budget, and with high customer engagement and satisfaction. This role requires more than task execution: you will be expected to think strategically about each engagement, anticipate risk before it becomes a problem, and take full accountability for outcomes. You will plan and designate project resources, monitor progress, and keep stakeholders informed throughout the entire process, setting the pace and direction of the engagement from the start. You will be the go-to person for everything involving a project's organization, timeline, and overall success.

Responsibilities

Act as a primary point of contact throughout the overall software implementation process, setting the tone and cadence of the engagement.

Develop and define the complete project plan, including all project artifacts (charter, schedule, RAID log, communication plan, etc.). Ensure project milestones, budget, training needs, and business and technical requirements are met within the agreed timeline and budget.

Proactively forecast, surface, and manage issues and risks associated with the project, flagging concerns early and keeping ahead of them.

Prepare weekly status reports for executives and facilitate weekly status review meetings with customers, using these touchpoints to drive decisions forward.

Establish and maintain effective working relationships with all customers, including demanding or high-friction stakeholders — reading a room, managing difficult conversations directly, and keeping the relationship productive under pressure.

Advocate on behalf of customers by prioritizing and escalating issues when needed, while holding the line on scope, timeline, and resourcing to protect project success.

Exercise sound judgment on when to escalate versus when to resolve independently, and own the outcome of decisions made.

Work cross-functionally with all teams regarding software enhancements, solving problems, and implementing changes as needed, treating the success of the broader implementation as the measure of the job well done.

Assist with system configuration and demonstrate final system setup.

Collaborate with the Sales and Account Management teams to manage changes to the original Scope of Work, protecting margin and delivery quality while maintaining the customer relationship.

Provide end-user training and technical support during the implementation process as needed.

Ensure effective transfer of information learned in training to the work environment.

Ability to travel nationwide, up to 15% annually.

Performs other duties as assigned.

We are unable to sponsor employment visas or support STEM OPT work authorization for this role.

Requirements

Required Skills & Qualifications

At least 5 years' experience in project management, including demonstrated ownership of full project outcomes.

Strong organization and planning skills, with fluency in building and maintaining formal project artifacts (schedules, RAID logs, status reports, communication plans).

Excellent customer-facing and internal communication skills, with a track record of managing demanding or difficult stakeholders professionally and effectively.

Excellent written and verbal communication skills.

Solid organizational skills including attention to detail and multitasking skills.

Demonstrated ability to make important decisions under pressure and own the outcome.

Strong critical thinking, problem-solving, and strategic judgment — able to see the health and trajectory of the overall engagement, not just the immediate task.

Strong working knowledge of Atlassian suite, specifically Jira Software, Jira Service Management, Jira Plans (Advanced Roadmaps), and Confluence.

Ability to lead project teams of various sizes and see them through to completion.

Strong understanding of formal project management methodologies.

Able to complete projects in a timely manner.

Familiarity with Software as a Service (SaaS) applications.

Bachelor's Degree

Preferred Skills & Qualifications

PMP Certification

Experience with Relational Database Management Systems.

Experience working in the Human Services Industry.

Experience with managing government contracts.

Knowledge of AI tools (Rovo, Claude, CoPilot, etc.).