Director of PMO & Technology Delivery - REMOTE

K2 Security Insurance•San Diego, CA

10d•$150,000•Remote

About The Position

K2 IT, a division of K2 Insurance Services, LLC, is seeking a full-time Director of PMO & Technology Delivery to join its growing technology leadership team. K2 Insurance, through its affiliated insurance companies and agencies, continues to expand its technology capabilities and enterprise initiatives by developing innovative insurance programs, implementing scalable systems, and strengthening its project management and IT delivery functions across multiple business units. Job Summary: The Director of PMO & Technology Delivery is a high-impact leadership role responsible for the end-to-end orchestration of the enterprise’s most critical technology and business initiatives. You are not just a manager of projects, but a builder of functions - responsible for establishing a centralized Project Management Office (PMO) that will eventually scale to include a team of Project Managers under your leadership. Operating in a high-growth environment with 30+ distinct business units, you will lead with an enterprise scale, boutique feel approach. You will be a versatile leader capable of pivoting between complex Policy Administration System (PAS) implementations, cross-functional technology projects, technical/API integrations, and critical IT Infrastructure or Security initiatives. You deeply understand insurance technology and the MGA/Program Administrator ecosystem, ensuring that every project enhances our scalability and competitive edge.

Requirements

Insurance Expertise: 10+ years in Insurance Technology, with a deep understanding of the MGA/Program Administrator model and P&C insurance lifecycle.
Technical Versatility: Proven success leading PAS implementations, API/integration projects, and IT Infrastructure/Security initiatives.
PMO Experience: Demonstrated ability to build or mature a PMO function in a high-growth, multi-business unit environment.
Education: Bachelor’s degree in Business or IT.

Nice To Haves

PMP and CPCU (or similar insurance designations) are strongly preferred.
Mindset: A Service-Leader who thrives on complexity but maintains the high-touch, responsive communication style of a boutique partner.

Responsibilities

PMO Leadership & Scaling
Founding the PMO: Design and implement the organizational framework for a centralized PMO. This includes establishing standardized project management methodologies, reporting dashboards, and governance protocols.
Team Building: Act as a player-coach in the short term, with the long-term mandate to hire, mentor, and lead a team of Project Managers as the organization grows.
Strategic Prioritization: Manage the "front door" for all technology requests, ensuring resource allocation aligns strictly with executive priorities and long-term ROI.
Enterprise Governance & Technical Stewardship
Holistic Delivery: Provide oversight for the full technical stack, from API integrations and PAS configurations to Infrastructure, Security, and Cloud initiatives.
Security & Regulatory Stewardship: Serve as a key steward of system integrity, ensuring that all technology delivery is filtered through a rigorous lens of security and compliance to protect the enterprise, our carriers, and our agents from day one of any initiative.
Operational Composure: Act as the operational anchor, identifying bottlenecks before they become crises and managing resolutions with a steadfast demeanor.
MGA Strategy & Relationship Advocacy
Frictionless Experience Mandate: Evaluate and execute projects through the lens of the agent/broker and carrier experience to ensure our technology reduces friction and drives loyalty.
Carrier & Agent Liaison: Understand the technical and data requirements of carrier partners, ensuring systems facilitate seamless reporting and underwriting authority.
Vendor & Roadmap Sync: Masterfully synchronize internal roadmaps with 3rd-party vendor delivery schedules to maximize the velocity of external implementations.
Ecosystem Integrity & Quality
Technical Translation: Ensure complex business requirements are translated into precise technical specifications.
Impact Analysis: Conduct rigorous upstream/downstream analysis for tech changes, ensuring data integrity across the insurance lifecycle.
Value Protection: Manage scope creep by anchoring every decision in the project’s original business intent and the company’s competitive positioning.