Manager, IT Project Management

When it comes to creating educational travel adventures that enrich the lives and fulfill the dreams of more than 100,000 people every year, there's no organization better than Road Scholar. What's our secret? Dedicated and talented staff who believe in our mission.

At Road Scholar, we are committed to fostering a culture of inclusivity and belonging. We believe that by valuing a wide range of perspectives and experiences, we create a stronger, more innovative organization that reflects the communities we serve.

In addition, we are dedicated to bringing an environmentally sustainable organization. From the way we design our programs to how we operate as a team, we are striving to reduce our environmental impact and create a positive legacy for future generations.

About the role...

Under the direction of the Director, Project & IT Portfolio Management and the project-specific Executive Sponsors, the IT Project Manager is responsible for planning, directing and coordinating all phases and activities for assigned projects. You will provide strategic and tactical leadership to drive on-time and on-budget project completion, aiming to achieve the organization’s strategic goals and high levels of satisfaction among all stakeholders.

Road Scholar offers a remote work environment. The compensation range for this exempt level salaried position is $120,000 - $150,000 based on experience. 

In this role, you will...

• Take ownership of multiple, concurrent IT projects, ensuring timely delivery while adhering to scope and budget. Projects include:
  • Leading a high-profile, multi-year, multi-phase Salesforce implementation, overseeing 10+ workstreams across 5+ departments, with a project team of 50+ members in a multi-level structure.
• Drive collaboration and foster a high-performing team environment.
• Proactively anticipate and resolve conflicts, using project management expertise and creativity to restructure workflows for better teamwork, communication, and efficiency.
• Be a trusted leader, building strong relationships across all levels, internal cross-functional teams, and external vendors to ensure alignment, engagement, and successful project execution.
• Lead all phases of the project lifecycle – from planning and initiation through execution, monitoring, and closure.
  • Define project scope, goals, milestones, deliverables, detailed tasks, and resource requirements.
  • Create and maintain project schedules and budgets, tracking progress to ensure on-time, on-budget completion.
• Manage user expectations and collaborate across the enterprise.
• Oversee vendor performance, ensuring deliverables meet technical specifications and contractual obligations.
• Leverage strong problem-solving, influencing, and decision-making skills to ensure project plans deliver on intent.
• Design and execute communication and change management plans to maximize user adoption and minimize disruptions, actively addressing feedback to ensure a smooth transition.
• Drive resolution of major issues and manage project interdependencies.
• Ensure all decisions and outcomes are well-documented.
• Communicate project status and risks to stakeholders at all levels, serving as the primary contact for user groups and IT management.
• Assemble and coordinate resources, schedules, task assignments, and project plans.
  • Monitor resource utilization and forecast resource needs.
• Contribute to continuous improvement by providing input on project management methodologies, tools, and best practices within the Project Management Office (PMO).

We're seeking...

• Project Management Experience
  • 12+ years of experience managing projects, including complex system implementations and process rollouts.
  • Proven success leading multi-phase, enterprise-scale IT projects (Salesforce experience preferred).
  • Comfortable with large-scale change initiatives impacting multiple departments and business users.
• Leadership & Collaboration
  • Strong ability to build and lead high-performing teams.
  • Trusted leader with excellent stakeholder management skills across 5+ departments.
  • Proven ability to manage 10+ workstreams and guide workstream leaders through planning and execution.
  • Experience working with Executive stakeholders (CIO, VP).
• Project Execution & Problem-Solving
  • Proactive in conflict resolution – able to sense misalignment and resolve issues before they escalate.
  • Expertise in leading project meetings effectively (core team meetings, retrospectives, stakeholder meetings).
  • Demonstrated professional judgment and sound decision-making skills.
• Communication & Organizational Skills
  • Excellent written and verbal communication skills – able to clearly convey complex ideas to technical and non-technical audiences.
  • Strong time management and prioritization skills, able to manage multiple projects in a dynamic environment.
  • Detail-oriented and quality-driven, with a strong commitment to accuracy.
  • Proficiency in Change Management methodologies.
• Vendor & Resource Management
  • Strong vendor management skills, including contract negotiation, performance monitoring, and escalation handling.
  • Ability to manage resources effectively in a fast-paced environment.
• Education & Certification
  • BS/BA in Business Administration, Information Management, or related field preferred
  • PMP certification is a plus
• Technical & Tool Proficiency
  • Proficiency in Agile, Waterfall, and hybrid methodologies.
  • Advanced proficiency in project management tools, including:
    • Atlassian Suite (Jira, Confluence)
    • Microsoft Office Suite (Word, Excel, PowerPoint)
  • Experience with Salesforce is a plus.

Why join the Road Scholar Team...

We offer a competitive compensation and benefits package!  

• Medical, Dental and Vision Insurance (with a substantial employee subsidy!)
• 403(b) Retirement Plan with a company match of 5% after 1 year of employment!
• Up to 20 days of PTO annually, accrued every payroll cycle 
• Enjoy a paid week off, in addition to your PTO, at the end of December to enjoy the holiday season!
• A generous employee discounts on our programs
• Access to obtain a Care.com membership
• As a Road Scholar employee, you can opt-in to receive an IATA membership
• We take professional development seriously which is why we provide LinkedIn Learning access to all employees amongst other professional development opportunities
• That’s right, we’re fully remote!
• To learn more about our benefits offerings, check us out at https://www.roadscholar.org/careers/

Equal Opportunity Employer

Road Scholar supports diversity in our staff, participants, and programs. An Equal Opportunity Employer Road Scholar values and supports individual differences and strives to create an environment that contributes to the success of both the individual and the organization. As an Equal Opportunity Employer, we consider applicants for all positions without regard to race, color, religion, gender, national origin, age, sexual orientation, pregnancy, illness, marital or veteran status or disability or any other status protected by applicable law.

Cybersecurity

At Road Scholar, we are committed to cybersecurity and to providing a safe experience for job seekers. All official communication regarding employment opportunities will come exclusively via email from the official Road Scholar domain or from our applicant tracking system URL recruiting.ultipro.com. We never conduct interviews through texting applications or instant messaging platforms. If you receive an employment offer or other correspondence from an individual at Road Scholar you have not met, or from a non-Road Scholar email domain, it may be a phishing attempt.