Enterprise Deployment Strategist - AI Insurance

Liberate Inc.; Boston (MA); Hybrid; USD 120,000 - 170,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

Equity opportunities

Flexible PTO

Hybrid work environment (SF or Boston)

Job summary

Liberate Inc. is hiring a founding Deployment Strategist to own enterprise customer relationships and ensure value delivery from go-live onward.

You’ll define outcomes with customers during the sales cycle and guide adoption through deployment, collaborating with product managers and AI engineers to keep initiatives on track. You will drive strategic consulting, manage stakeholder alignment, and grow accounts by expanding value across lines and teams, in a role blending customer success with

Qualifications

• 7+ years in customer-facing roles owning enterprise relationships and outcomes.
• Willing to travel to customer sites roughly 25–40%.
• High EQ with ability to build trust at all levels of an organization.
• Translate business needs to technical solutions and collaborate with engineers.
• Experience with AI-native or enterprise SaaS deployments in regulated industries is a bonus.

Responsibilities

• Drive value and outcomes by bridging technical implementation and business adoption.
• Join during the sales cycle to define deliverables and desired outcomes; map workflows pre-deployment.
• Act as the primary bridge between executives, end-users, and the deployment team; ensure alignment.
• Own change management and adoption by training end-users and building internal champions.
• Provide feedback to Product/Engineering to improve the core product across deployments.
• Grow the account by expanding value across lines, functions, and teams.

Skills

High EQ

Relationship building

Strategic consulting

Project management

Technical acumen

Stakeholder alignment

Travel readiness

Industry knowledge (insurance/fintech)

Job description

Liberate Inc. is hiring a founding Deployment Strategist to own enterprise customer relationships and ensure value delivery from go-live onward.

You’ll define outcomes with customers during the sales cycle and guide adoption through deployment, collaborating with product managers and AI engineers to keep initiatives on track. You will drive strategic consulting, manage stakeholder alignment, and grow accounts by expanding value across lines and teams, in a role blending customer success with