Senior Business Project Manager

Senior Business Project Manager

Established in 2000, InsureMyTrip is the nation’s original travel insurance comparison site and a member of the Tokio Marine HCC group of companies. For more than 20 years, we have connected travelers with trusted providers to help them understand travel insurance and find the right plan for their needs. We are a technology company that sells insurance, but more importantly, we care about our customers and employees and take pride in conducting business honestly and ethically.

Joining the InsureMyTrip team means having the advantages of being part of a leading company while enjoying many of the benefits of a startup culture. This you will have the opportunity to make an impact, influence key strategic decisions, and create or improve processes. We are looking for experienced and motivated individuals who can turn company priorities into coordinated action and measurable results.

Position Summary

The Senior Business Project Manager leads the execution of company designated strategic and significant operational initiatives across InsureMyTrip. Reporting to the CEO, this role serves as the central coordination and visibility point for the company project portfolio and works with department Heads and project sponsors to turn priorities into clear, executable plans and measurable results.

The role establishes ownership, sequencing, milestones, resources, budgets, dependencies, risks, and success measures; coordinates work across functions; drives follow through on commitments and decisions; and provides concise, accurate reporting to the CEO and senior team. Success requires strong business judgment, direct communication, project discipline, and the ability to influence without direct authority.

Department Heads and project sponsors remain accountable for business outcomes, resources, and functional deliverables. This role ensures the work is clearly defined, coordinated, visible, and escalated when needed. It includes both business and technology initiatives but is not a dedicated product owner or technology delivery manager.

Key Responsibilities

Strategic Planning and Project Intake

•  Partner with the CEO and senior team to clarify priorities, intended outcomes, scope, timing, and measures of success.

•  Facilitate project intake and ensure initiatives have a clear sponsor, accountable owner, business objective, success criteria, and sufficient readiness before execution begins.

•  Translate priorities into plans with defined milestones, deliverables, resources, budgets, dependencies, risks, decisions, and ownership.

•  Recommend sequencing and prioritization based on business impact, capacity, dependencies, urgency, and readiness, and support business cases, cost and benefit analyses, budgets, and return on investment measures.

Portfolio Management and Delivery Coordination

•  Maintain an accurate view of the portfolio and backlog of approved strategic and significant operational initiatives.

•  Establish and maintain project plans, schedules, milestones, deliverables, ownership, and status across participating departments.

•  Coordinate execution across business and technology teams and coordinate internal and external resources as appropriate.

•  Track departmental commitments and follow up with project sponsors, owners, and functional leaders to keep work moving.

•  Identify dependencies, resource constraints, scope concerns, risks, and slipping timelines before they affect results.

•  Facilitate resolution of obstacles, push for timely decisions, and escalate issues when progress is stalled or executive action is required.

•  Ensure technology related initiatives have sufficient business context, ownership, timing, and readiness while respecting functional ownership of solution design, estimation, and execution.

Executive Reporting, Governance and Accountability

•  Maintain accurate visibility into active initiatives and provide concise updates to the CEO and senior team on status, business impact, delivery confidence, risks, decisions needed, and recommended next steps.

•  Develop practical portfolio dashboards and status reporting that support timely decisions and avoid unnecessary administration.

•  Facilitate portfolio reviews, project governance meetings, and decision discussions, with clear documentation of decisions, owners, and due dates.

•  Drive follow through from leaders and project owners on commitments, decisions, deadlines, and deliverables.

•  Challenge assumptions, unclear ownership, incomplete plans, and missed commitments directly and respectfully, and recommend changes to priority, scope, timing, or resourcing when evidence supports it.

Implementation, Change and Outcome Review

•  Coordinate implementation readiness, including communications, operational changes, documentation, training, deployment, adoption, and ongoing support.

•  Monitor milestones, cost, scope, quality, and critical dates, and coordinate mitigation plans when risks or issues emerge.

•  Conduct post implementation reviews, confirm whether the intended business outcome and return were achieved, and identify remaining gaps, lessons, or next steps.

Project Management Process Improvement

•  Use and reinforce the existing project process and improve intake, prioritization, planning, reporting, risk management, governance, and closeout where needed.

•  Apply the appropriate level of structure based on the size, complexity, risk, and business impact of the work, and drive greater transparency, accountability, and predictability.

Success Measures

•  Company priorities enter execution with clear outcomes, ownership, scope, timing, dependencies, and measures of success.

•  The CEO and senior team have timely, accurate, and actionable visibility into the project portfolio.

•  Material risks, resource constraints, missed commitments, and decisions are identified and escalated early with recommended next steps.

•  Strategic and significant operational initiatives are delivered with greater predictability and fewer delays caused by unclear ownership, unresolved dependencies, or delayed decisions.

•  Implementation plans address communication, training, operational readiness, adoption, and ongoing support.

•  Completed initiatives are reviewed against the intended business outcome, cost, and return on investment.

Qualifications

Required

•  Bachelor’s degree in a related field or equivalent professional experience.

•  At least eight years of progressively responsible business project, program, or portfolio management experience.

•  Demonstrated success leading complex initiatives that require coordination across multiple business functions.

•  Experience partnering with executive leadership and influencing senior leaders and teams without direct reporting authority.

•  Experience managing scope, timelines, budgets, resources, dependencies, risks, change, and intended business outcomes.

•  Strong business judgment and the ability to challenge assumptions, address conflict, push for decisions, and determine the appropriate level of structure and escalation.

•  Strong facilitation, negotiation, planning, problem solving, organizational, and stakeholder management skills.

•  Excellent written, verbal, presentation, and executive communication skills.

•  Experience preparing portfolio reporting, dashboards, status updates, business cases, budgets, and return on investment analysis.

•  Ability to work effectively across business and technology initiatives and manage multiple priorities with accuracy, urgency, and follow through.

•  Demonstrated adaptability, self awareness, sound judgment, and responsiveness to feedback.

Preferred

•  PMP or an equivalent project management certification.

•  Experience working with Agile software development teams.

•  Experience with Jira, Confluence, Microsoft Project, Smartsheet, or similar project and portfolio management tools.

What We Offer

• Hybrid Schedule, 2 days work from home and 3 days in office (fully remote work not available)
• Strong learning culture with ongoing development opportunities
• Comprehensive medical, vision, and dental coverage, with eligibility beginning on your first day of employment
• Basic life and disability insurance
• 401(k) plan with 6% company match
• 20 days of PTO, two floating holidays, approximately 11 paid holidays, and volunteer time off
• Paid parental leave
• Access to our award-winning wellness program, including mental health services, fitness network membership, and a complimentary Headspace subscription
• Student loan matching program

If you are a motivated professional with the skills and experience to succeed in this role, we encourage you to apply and join our team. Join a team where your success is our priority and you can make a real impact!

InsureMyTrip is an equal-opportunity employer. If your experience aligns with the listed requirements, please apply!

The pay range for this position is $117,200 - $175,800 which includes geographic adjustments, where applicable. The pay range is the range THMCC, in good faith, believes is the range of compensation for this role at the time of this posting. The hired applicant will be offered pay within the entire range based on the candidate’s geographic location, qualifications, work experience, education, and/or skill level. The Company is fully committed to ensuring equal pay opportunities for equal work regardless of color, race, sex, national origin, sexual orientation, religion, age, veteran status, disability, pregnancy, citizenship status, genetic information, or any other basis protected by federal, state, or local pay equity laws.  

You do not need to disclose your criminal history or participate in a background check until a conditional job offer is made to you. After making a conditional offer and running a background check, if the Company is concerned about a conviction that is directly related to the job, you will be given the chance to explain the circumstances surrounding the conviction or challenge the accuracy of the background report. 

As an insurance company, we comply with certain federal, state and local laws such as the Violent Crime Control and Law Enforcement Act of 1994 (18 USC § 1033(e)), which restricts our ability to employ individuals with certain types of criminal convictions. Where not restricted by law and for criminal history not covered by this law, the Company will consider qualified applicants with arrest or conviction history in compliance with applicable law.     

#LI-KP1

#Hybrid