Senior IT Project Manager

Careington International is a benefit solutions-oriented company. An established leader, we have been a trailblazer in the field of discount health care since 1979. Over the years, our mission has remained the same, to create discount health programs that are marketable to the employer, profitable to the provider and economical for the member. In response to a growing demand for our products and services in recent years, our growth means that we continuously strive to recruit innovators to join our fast-paced, forward-thinking team. 

This role is currently Hybrid in nature - Three days in the office, two from home. 

We are seeking a highly motivated and results-oriented Senior IT Project Manager with excellent verbal and written communication skills to join our team. The ideal candidate will follow the Servant Leadership concept to lead and manage multiple projects through the full project lifecycle, ensuring that the projects are delivered on time, within budget, and to the highest quality standards.   

EXPECTED WORK AND PERFORMANCE 

• Spearhead end-to-end planning and delivery for complex, enterprise-scale IT initiatives, ensuring alignment with overarching business strategy, organizational priorities, and ROI/benefit realization.
• Architect comprehensive project roadmaps by translating strategic objectives into actionable phases, defining clear milestones, resource allocations, financial budgets and success criteria.
• Orchestrate interconnected workstreams in highly matrixed environment, assigning clear accountability and seamlessly coordinating cross-functional dependencies to maintain program integrity and momentum.
• Lead change control and governance processes; authorize and manage interventions to safeguard scope, schedule, and budget against scope creep.
• Monitor and report delivery performance using quantitative metrics (timeline forecasts, burn rates, KPIs), and recommend corrective actions to senior leadership.
• Drive release management and deployment governance— drive go/no-go decisions, ensure definition of done, and coordinate rollbacks and post-release remediation when required.

Executive Stakeholder & Governance Management

• Cultivate executive relationships, routinely presenting program status, risks, financial trade-offs and strategic recommendations to steering committees and executive sponsors.
• Navigate strategic stakeholder landscape, synthesizing diverse requirements, negotiating competing priorities, security decisions, accelerating approvals, and influencing outcomes to balance technical realities with business imperatives.
• Tailor dynamic delivery methodologies (Agile, Scrum, Waterfall, Hybrid) to project needs, leveraging PMO standards and enterprise tooling to ensure transparency, traceability and auditability.

Cross-Functional Leadership & Team Enablement

• Lead, mentor and motivate cross-functional matrixed teams, setting clear objectives, actively removing impediments, and fostering a collaborative culture of accountability and excellence.
• Optimize resource capacity and utilization, accurately forecasting personnel needs and vendor/third-party relationships to ensure optimal skill alignment across all project phases.
• Champion continuous improvement by identifying process optimizations, institutionalizing best practices and establishing repeatable delivery frameworks (Agile/Waterfall/Hybrid).

Risk, Issue, & Vendor Management

• Proactively identify, assess and prioritize risks across technical, operational, security and compliance domains; design and execute robust mitigation and contingency strategies before issues impact delivery.
• Drive critical issue resolution and escalation processes, orchestrating rapid cross-functional remediation and ensuring seamless, transparent communication with stakeholders and leadership.
• Manage strategic vendor relationships and supplier performance, contracts and SLAs; ensuring third-party delivery meets quality, timeline, and budget expectations.

Program Performance Tracking, Documentation & Continuous Improvement

• Maintain impeccable program artifacts, including comprehensive program plans, RAID logs, test plans, change registers, release communications, and compliance documentation.
• Serve as the single point of accountability for stakeholder communications, delivering transparent, data-drive status reports, executive dashboards, and milestone summaries, highlighting progress, risks, decisions required and recommended actions.
• Facilitate comprehensive post-implementation reviews, systematically capturing lessons learned to continuously elevate governance, delivery predictability, and organization maturity.

QUALIFICATIONS

Required

• Bachelor’s degree or equivalent experience
• 8 years of experience in project management, with at least 3 years of experience managing complex projects across multiple departments with competing stakeholder priorities.
• Must have a proven track record of successfully delivering projects within budget, schedule, and scope.
• Exceptional communication and interpersonal skills, enabling effective collaboration with diverse stakeholders, including the ability to explain a server migration to the CEO and a business requirement to a Lead Developer without losing anything in translation.
• Experience in project management methodologies (Agile Development frameworks) and tools (Jira, Azure DevOps, Confluence, SharePoint, ServiceNow).
• Strong understanding of risk management principles and techniques.
• Proficient in MS Office Suite, including Visio and MS Project.

Preferred

• PMP certification desirable
• 2 to 3 years of formal Agile/Scrum experience desirable
• Insurance or other compliance-heavy industry experience a plus, insurance experience a big plus

SKILLS

• Solid understanding of software development models and knowledge of both Agile and traditional project management principles and practices and the ability to blend them together in the right proportions to fit project needs.
• Ability to understand technical software development concepts and terminology
• Self-starter with ability to work independently and follow through to successful completion of each initiative.
• Ability to think creatively, problem solve, and work with others to find the best solution. 
• Excellent organizational and time management skills to prioritize tasks and meet deadlines.
• Adaptability and resilience to handle unexpected changes and maintain project momentum.
• Precision in work and attention to all details.
• Excellent organizational, multitasking and time management skills
• Excellent people skills