Deployment Strategist

HireNow Staffing • San Francisco, CA

6d • $140,000 - $170,000 • Onsite

About The Position

HireNow Staffing is partnering with a fast-growing insurance AI startup seeking a Deployment Strategist to lead complex enterprise implementations that are modernizing the workers compensation ecosystem. This role sits at the intersection of technology, operations, and client delivery . The Deployment Strategist will own high-stakes implementations for enterprise customers, serving as the connective tissue between client stakeholders, technical teams, and product leadership. Success in this role requires both strategic rigor and hands-on execution—translating real-world insurance workflows into scalable, production-ready deployments. This is a high-visibility, high-ownership role for someone who thrives in complex environments and enjoys being accountable for outcomes, not just plans.

Requirements

• 4+ years of experience in implementation management, solutions consulting, or strategy consulting with direct ownership of deployments
• Experience delivering complex enterprise B2B SaaS implementations involving multiple systems and data flows
• Strong technical acumen, including the ability to discuss API integrations, data mapping, and cloud-based architectures with confidence
• Demonstrated experience managing data-intensive implementations from planning through go-live
• Bachelor's degree from a top-tier university , with strong academic performance
• Proven ability to operate onsite in San Francisco and collaborate closely with cross-functional teams
• Clear evidence of role longevity and sustained impact in prior positions

Nice To Haves

• Background in top-tier strategy consulting (MBB or equivalent) with hands-on implementation projects
• Experience working in or with early-stage startups following consulting or enterprise roles
• Familiarity with the insurance industry , particularly P&C or workers compensation claims workflows
• Experience partnering with enterprise customers in regulated or operationally complex environments
• High emotional intelligence with the ability to build credibility with C-suite and VP-level stakeholders while earning trust with frontline users
• Low-ego, collaborative mindset with strong intellectual curiosity

Responsibilities

• Lead end-to-end deployments of an AI-powered enterprise claims platform for strategic customers
• Own implementation strategy, including project plans, timelines, dependencies, and milestone tracking
• Manage data ingestion and system integrations , partnering closely with engineering on API connections, SFTP workflows, ETL pipelines, and data mapping
• Serve as the primary point of contact for client stakeholders, ensuring clear communication, expectation-setting, and execution throughout the rollout
• Drive customer adoption through onboarding sessions, workshops, webinars, and targeted training
• Translate customer requirements and implementation learnings into structured feedback that informs product roadmap and platform improvements
• Balance enterprise-level rigor with startup speed, adapting quickly as requirements evolve

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level