Sr. Project Manager

Overview: If you're looking for the stability of a profitable, growing company with the entrepreneurial spirit of a startup, we’re hiring. SageSure, a leader in catastrophe-exposed property insurance, is seeking a Senior Project Manager, Strategy Implementation. This exciting role will be pivotal in helping us continue to optimize how we execute against our strategy and allow scale for growth.

This position offers exposure to leadership via the engagement of key stakeholders across all levels of the organization. If you are results-driven, have a growth mindset, and are enthusiastic about collaborating across the organization to drive business outcomes, we’d love for you to apply.

What you’d be doing:

• Drive the development and execution of strategic project roadmaps aligned with corporate OKRs, directly supporting growth initiatives and enterprise integration efforts.
• Serve as a trusted strategic partner to senior leadership and C-suite executives—translating high-level strategy into actionable, results-driven project plans.
• Provide program management support for high-impact initiatives, including post-merger integration activities that align people, processes, and platforms across the organization.
• Collaborate with executive stakeholders to define project objectives, success metrics, and milestones that align with organizational priorities.
• Participate in executive-level governance forums to deliver strategic updates, integration progress reports, and issue escalation briefings that inform high-level decision-making.
• Act as a thought leader in strategic planning and project delivery, offering insights and structured approaches to accelerate execution and drive measurable outcomes.
• Optimize resource planning and cross-functional coordination to ensure initiatives are properly resourced and risk is effectively managed.
• Lead end-to-end project planning and execution—managing scope, timelines, budgets, resources, and risk mitigation with a focus on transparency and stakeholder engagement.
• Monitor and manage risks throughout the project lifecycle—proactively escalating issues to maintain momentum and strategic alignment.
• Conduct post-implementation reviews and lessons learned workshops to continuously refine project delivery practices and inform future strategy and integration efforts.
• Engage with internal and external stakeholders to understand business needs and design scalable, secure solutions that address enterprise challenges and support long-term strategic goals.
  
  
  

We’re looking for someone who has:

• Demonstrated ability to articulate the strategic rationale (“the why”) behind key initiatives, decisions, and project objectives—especially to executive and cross-functional audiences.
• Strong executive presence with the ability to confidently engage and influence C-suite leaders, fostering alignment around strategic priorities and integration goals.
• Proven success in building trust-based partnerships across diverse stakeholder groups, including corporate strategy, operations, and integration teams.
• Exceptional analytical and problem-solving skills; able to think strategically in order to connect high-level business goals with detailed execution plans.
• Balances long-term vision with day-to-day execution, demonstrating both systems thinking and precision in delivery.
• Able to lead through ambiguity, drive clarity in complex situations, and guide teams through dynamic or transitional environments (e.g., during post-merger integration).
• Effective multitasker with strong organizational skills and the ability to manage competing priorities without losing momentum.
• Comfortable challenging the status quo and developing innovative, scalable solutions to enterprise-level problems.
• Exceptional written and verbal communication skills, with a focus on clarity, impact, and executive readiness.
  
  
  

Highly preferred candidates also have:

• Experience within the property and casualty insurance industry (preferred).
• 5 years of experience managing strategic, cross-functional projects.
• Knowledge of methodologies like Lean, Six Sigma, or Agile for optimizing processes.
• Previous experience working in a geographically dispersed team.
  
  
  

About SageSure:

Named among the Best Places to Work in Insurance by Business Insurance for four years in a row (2020-2023), SageSure is one of the largest managing general underwriters (MGU) focused on catastrophe-exposed markets in the US. Since its founding in 2009, SageSure has experienced exceptional growth while generating underwriting profits for carrier partners through hurricanes, wildfires, and hail. Available in 16 states, SageSure offers more than 50 competitively priced home, flood, earthquake, and commercial products on behalf of its highly rated carrier partners. Today, SageSure manages more than $1.9 billion of inforce premium and helps protect 640,000 policyholders.

SageSure has more than 1000 employees working remotely or in-office across nine offices: Cheshire, Connecticut; Chicago, Illinois; Cincinnati, Ohio; Houston, Texas; Jersey City, New Jersey; Mountain View, California; Marlton, New Jersey; Tallahassee, Florida; and Seattle, Washington.

SageSure offers generous health benefits and perks, including tuition reimbursement, wellness allowance, paid volunteer time off, a matching 401K plan, and more.

SageSure is a proud Equal Opportunity Employer committed to building a workforce that reflects the spectrum of perspectives, experiences, and abilities of the world we live in. We recognize that our differences make us strong, and we actively seek out diverse candidates through partnerships with organizations, institutions and communities that represent various backgrounds. We champion belonging and inclusion for all identities, including, but not limited to, race, ethnicity, religion, sexual orientation, age, veteran status, ability status, gender, and country of origin, striving to create a culture where all individuals feel valued, respected, and empowered to bring their authentic selves to work.

Our nimble, highly responsive culture nurtures critical thinkers who run toward problems and engineer solutions. We relentlessly pursue better outcomes by investing in the technology, talent, and tools that position us to succeed in demanding markets. Come join our team! Visit sagesure.com/careers to find a position for you.