Project Manager - IT Delivery & Execution - Insurance Industry

Why Jencap? We are one of the largest wholesale insurance intermediaries in the United States with expertise in wholesale brokerage, binding authority, and program management. The common thread woven throughout our success story is our collaborative and driven team of people. Our teams are empowered and work together to find solutions. We have a passion culture – with teamwork, collaboration and a focus on growing individuals and giving them the tools & development opportunities to have a successful career. 

The Project Manager is responsible for leading the planning, coordination, execution, and delivery of technology initiatives across the organization. This role operates within the IT Delivery & Execution function and is accountable for driving projects from initiation through completion with a strong focus on execution, transparency, accountability, and business outcomes. The Project Manager works closely with key leaders and functional areas to analyze, support, manage, lead, monitor, and report on projects across the organization.

Unlike a traditional stand-alone PMO model, this role is embedded within IT leadership and works closely with business leaders, technical teams, vendors, and stakeholders to ensure projects are delivered on time, within scope, and aligned to organizational priorities. The Project Manager serves as a delivery leader who brings structure, visibility, risk management, and momentum to projects while helping teams achieve successful outcomes. This position may require periodic travel based on project needs and is expected to work remotely or from a local office as appropriate.

This role can work a hybrid schedule in any of our Jencap locations or Remote. 

Responsibilities

Project Leadership & Execution

• Lead assigned technology and business-facing projects through all phases of the project lifecycle, including initiation, planning, execution, monitoring, and closure.
• Develop and maintain detailed project plans, timelines, milestones, dependencies, and deliverables.
• Drive project execution with a focus on accountability, follow-through, and measurable outcomes.
• Ensure project scope, objectives, and success criteria are clearly defined and aligned with business priorities.
• Coordinate project activities across cross-functional teams, including business stakeholders, IT resources, vendors, and third-party partners.
• Monitor progress against plan and proactively address issues that may impact delivery.
• Track and report on project status, including budgets/expenses, and surface potential budget revisions needed to accomplish objectives within time and budget targets.
• Monitor compliance with project policies, standards, and governance requirements and address gaps proactively.

Stakeholder Communication & Coordination

• Serve as the central point of coordination for assigned projects.
• Facilitate regular project meetings, status reviews, working sessions, and stakeholder updates.
• Provide clear, concise, and timely communication regarding project status, risks, issues, decisions, and next steps.
• Build trusted relationships with stakeholders across IT and the business to support effective collaboration and decision-making.
• Escalate concerns appropriately and ensure leadership has visibility into project health and critical decisions.

Risk, Issue, and Dependency Management

• Identify, track, and manage project risks, issues, assumptions, and dependencies.
• Develop mitigation and contingency plans to support successful delivery.
• Proactively surface roadblocks and coordinate resolution with the appropriate stakeholders.
• Assess changes in scope, priorities, or resourcing and communicate impact to timeline, budget, and delivery expectations.

Delivery Governance & Project Discipline

• Apply consistent project management practices, templates, tools, and reporting standards established within the IT Delivery & Execution function.
• Maintain project documentation, decision logs, RAID logs, action items, and status reporting artifacts.
• Support governance processes by preparing materials for leadership reviews, steering committees, and project checkpoints.
• Ensure projects are managed with appropriate discipline while remaining practical and adaptable to the size and complexity of the initiative.
• Conduct post-implementation assessments/evaluations and capture lessons learned to improve future delivery.Perform various project management, coordination, and PMO-related tasks (including ad hoc analysis and reporting) as needed.

Business Partnership & Outcome Focus

• Partner with business and IT leaders to understand project goals, operational impacts, and desired outcomes.
• Help translate strategic priorities into executable project plans.
• Support change readiness, user adoption, implementation planning, and transition to operational support where applicable.
• Contribute to continuous improvement of project delivery practices, tools, and team effectiveness.

Qualifications

• Bachelor’s degree in Information Technology, Business, Project Management, or a related field, or equivalent combination of education and experience.
• 5+ years of project management experience leading technology, systems, or cross-functional business initiatives.
• Demonstrated experience managing multiple projects simultaneously in a fast-paced environment.
• Strong understanding of project management principles, methodologies, and delivery practices.
• Experience working closely with technical teams, business stakeholders, and external vendors.
• Proven ability to manage timelines, priorities, risks, dependencies, and stakeholder expectations.
• Strong organizational, analytical, and problem-solving skills.
• Excellent verbal and written communication skills.
• Proficiency with project management and collaboration tools such as Smartsheet, Microsoft Project, Jira, or similar platforms.
• Demonstrated experience in requirements gathering, setting quantifiable goals, data collection/analysis, and measuring results.
• Strong change leadership skills, customer focus, and strategic thinking.
• Self-directed, process-oriented, strong business acumen, attention to detail, and ability to drive consensus in decision-making and problem solving.
• Flexible, adaptable, and resourceful when managing changing timelines and multiple deliverables in a fast-paced environment.
• Motivated to build relationships across teams and partner groups and comfortable collaborating at various levels.
• Demonstrated creative and innovative thinking with a strong desire to improve service, relationships, processes, and systems.
• Comfortable interacting with all levels of management, including executive leadership.

Preferred Qualifications

• Insurance industry experience; exposure to Agency Management Systems (AMS), Underwriting, MGA, Wholesale/Brokerage, Binding Authority, and Program Management; and experience with Insurity SureMGA/ConceptOne (highly desired).
• Experience working within IT organizations delivering enterprise applications, system implementations, integrations, upgrades, or transformation initiatives.
• Experience in environments where project management is embedded within IT delivery rather than a separate PMO.
• PMP, CAPM, Scrum Master, or other relevant certification preferred, but not required.
• Familiarity with change management, testing coordination, cutover planning, and post-go-live support activities.
• Experience supporting governance and executive-level reporting.

The base salary offered for the successful candidate will be based on compensable factors such as job-relevant education, job-relevant experience, training, licensure, demonstrated competencies, geographic location, and other factors.  Discretionary incentive compensation may be awarded. Jencap also offers a range of benefits and programs, based on eligibility, which currently include but are not limited to; comprehensive health care coverage, a 401k plan, and tuition reimbursement.  Jencap is an emerging and rapidly growing leader in the industry and as such, we approach talent acquisition as an opportunity to identify the best talent. Therefore, the level of the role and compensation may vary depending upon the best available candidate. 

Want the opportunity to build something new? Expand your knowledge and stretch your experience through new and emerging risks? Have your voice heard, your skills properly applied, and to add tangible value to an organization? You’re in the right place. 

Jencap is dynamic, bold, tenacious, and trusted in the industry. Here, you are not just one of the many, you are one of us.  We truly are better together. 

Jencap is an Equal Opportunity Employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin or citizenship status, sexual orientation, gender identity or expression, pregnancy, marital or familial status, disability status, medical condition, genetic information, military or veteran status, political affiliation, or any other characteristic protected by law. We are committed to fostering a work community where every colleague feels welcomed, valued, respected and heard, as we believe that that creating an environment where every employee feels included and empowered, helps us to deliver the best outcome to our clients.