Head of technology and systems

Head of Technology & Systems
Brooklyn, NY
$125,000 – $150,000
Full-Time

Overview

We’re hiring a technology leader to run and own a major, cross-functional technology build and integration project while also managing day-to-day technology operations.
This role will manage our outsourced IT partner, hire and oversee outside development firms, and serve as the internal owner responsible for driving the program from discovery through rollout.
Insurance knowledge is not required, but is preferred. The right person is extremely organized, can juggle many workstreams at once, and is strong at translating business needs into clear execution plans for technical vendors.

Core Responsibilities

• Own the end-to-end delivery of a large technology initiative across multiple departments

• Build and maintain the roadmap, timeline, milestones, dependencies, and success metrics

• Run weekly status meetings, track action items, manage risks, and keep stakeholders aligned

• Create structure around requirements, prioritization, testing, rollout, and adoption

• Learn how each department operates and document workflows and pain points

• Translate business needs into clear deliverables for dev firms (user stories, acceptance criteria, etc.)

• Maintain a prioritized backlog and make tradeoffs with leadership

• Source, evaluate, and hire outside development firms and specialist vendors

• Own statements of work (SOWs), deliverables, timelines, and budgets

• Ensure quality through testing plans, staging, acceptance criteria, and go-live readiness

• Hold vendors accountable and prevent scope creep

• Serve as primary point of contact for outsourced IT

• Oversee provisioning/offboarding, permissions, security best practices, devices, and network needs

• Improve internal tech SOPs and reduce recurring issues

• Coordinate training, documentation, and rollout plans across teams

• Communicate clearly to leadership and staff on progress, decisions, risks, and timelines

• Drive adoption and ensure new systems are used correctly

Required Qualifications

• Proven experience leading complex software, workflow, or integration projects

• Strong program and project management capabilities

• Excellent communication with executives, department heads, and technical vendors

• Demonstrated ability to juggle many priorities without losing details

• Vendor management experience (preferred: dev firms, implementation partners)

• High ownership mindset and ability to operate in a fast-paced environment

• Organized and decisive with excellent follow-through

• Calm under pressure and capable of managing many moving parts at once

• Strong at translating between business and technical teams

• Comfortable pushing for clarity, setting priorities, and enforcing accountability

Preferred Qualifications

• Insurance brokerage or financial services experience (helpful, not required)

• Exposure to CRM/workflows, data dashboards, portals, or automation tools

• Experience with SOWs, budgets, or multi-vendor implementations

What Success Looks Like (First 6–12 Months)

• Department workflows and needs clearly documented

• Prioritized requirements backlog established

• Realistic roadmap approved and milestones tracked consistently

• Outside dev partner(s) hired with clear scope, timelines, and accountability

• Reduced operational friction — smoother IT support and cleaner access/permissions

Email resumes to [email protected]