Deployment Strategist

Deployment Strategist

Location: Onsite – San Francisco, CA
Compensation: $140,000 – $170,000 base salary
Additional Compensation: Equity
Work Authorization: Must be authorized to work in the U.S. — no visa sponsorship

The Opportunity

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.

What You'll Do

Candidates will be considered for interview based on demonstrated ability to perform the following 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

Technology Environment

• Asana, Jira

• API integrations and data mapping

• SFTP and ETL pipelines

• AWS-based infrastructure

Required Qualifications (Non-Negotiable)

These qualifications are mandatory. Candidates who do not meet all requirements will not be considered for interview.

• 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

Preferred Qualifications (Strong Differentiators)

Candidates with the following background will be viewed as standout applicants:

• 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

Who Thrives in This Role

• Operators who enjoy owning outcomes, not just frameworks

• Strategists who are equally comfortable in executive conversations and technical implementation details

• Professionals energized by deploying AI in real-world, regulated industries

• Leaders who can balance structure with adaptability in a startup environment

Why This Role Matters

The Deployment Strategist directly shapes how enterprise customers experience and adopt the platform. Your work will influence customer success, product evolution, and the broader modernization of the workers compensation ecosystem. The impact is immediate, measurable, and visible across the organization.

HireNow Staffing Disclaimer

HireNow Staffing is acting as a direct placement partner for this role. All candidate information is handled confidentially and evaluated against defined requirements. This job description outlines the general scope of responsibilities and qualifications. Duties may evolve based on client needs and business growth. Only candidates meeting the core qualifications will be considered for interview.

https://www.careers-page.com/hirenow-staffing-inc/job/X96568V3