Founding Deployment Strategist

Liberate; Boston (MA); Hybrid; USD 140,000 - 200,000; Full time

Benefits offered by this job

Equity options

Health, dental, and vision insurance

Flexible PTO

Hybrid work environment (SF or Boston)

Collaborative culture

Job summary

Liberate is hiring a founding Deployment Strategist to own relationships with our largest customers, defining outcomes and ensuring real value from deployment. You will work across the deployment team, product managers, and engineers to drive value, adoption, and expansion opportunities throughout go-live and beyond.

In this role, you will lead discovery, map workflows, anchor outcomes to business value, and maintain executive-level alignment.

Qualifications

• High EQ and trust-building across all levels of an organization.
• Executive presence with clients and executives.
• Ability to anchor decisions to customer outcomes and quantify value.
• Strong project management across timelines and dependencies.
• Translate business needs into technical possibilities and work with engineers.
• Align stakeholders across product, engineering, and customer teams.
• Experience owning enterprise relationships and outcomes (7+ years).
• Willingness to travel 25–40% to customer sites.

Responsibilities

• Drive value and outcomes; bridge between technical implementation and business adoption.
• Strategic consulting during the sales cycle; map workflows and identify high-value use cases.
• Maintain the primary relationship with C-suite sponsors and end-users; keep org aligned.
• Own change management and drive end-user adoption of the deployed solution.
• Suggest continuous product improvements from field learnings to make deployments repeatable.
• Grow the account by expanding value across lines, functions, and teams.

Skills

High EQ

Executive presence

Value-driven

Project management

Technical acumen

Stakeholder alignment

Enterprise relationships

Travel readiness

Job description

Liberate builds AI agents that automate manual work for the $2.7 trillion insurance industry. We started with voice, the hardest and most valuable channel in insurance, and we're expanding into full workflow automation across sales, servicing, and claims. The long-term goal is reasoning agents that can handle the full range of carrier and broker operations. We've raised $82M to date, including a $50M Series B in October 2025, backed by top-tier venture firms.

Today our agents run millions of automated transactions a month across enterprise carriers, brokers, and agencies, resolving calls, emails, and SMS end-to-end and writing back to the core systems of record. These are not chatbots that deflect, but true AI agents that complete the transaction and hand off to a human with full context when the need arises. We're insurance people building AI, and that operator DNA is why customers trust us with their highest-volume operations.

About the Role

We're hiring a founding Deployment Strategist to own the relationship with our largest customers and make sure they get real value from Liberate. Think of it as a customer success role with a builder's mandate. You'll join during the sales cycle to define the outcomes a customer wants and the value we'll deliver, then stay with them through go-live and beyond, driving continuous value delivery, proving impact, and finding the next place we can help. You will collaborate closely with our deployment team, our Agent Product Managers and AI Agent Engineers, who build and ship the AI agents. You own the "why" and the "what" and the customer relationship; they own the "how."

Our deployment organization has three roles that work as a unit on every enterprise account. Agent Product Managers scope and design the agent workflows. AI Agent Engineers build the agents and integrate them with the customer's systems. The Deployment Strategist collaborates closely with both, owning the customer relationship end-to-end: defining the value up front, keeping the deployment pointed at the outcomes that matter, ensuring continuous value delivery once it's live, and finding the next opportunity to expand.

Key Responsibilities

• Drive value and outcomes. Own the bridge between technical implementation and business adoption. You're accountable for the customer achieving the outcomes they signed up for, not just a successful go-live.
• Strategic consulting. Join during the sales cycle to define what we'll deliver and the desired customer outcomes. Lead discovery sessions to map workflows and identify high-value use cases before the deployment team is committed. You determine what Liberate needs to build; the deployment team scopes and builds it.
• Relationship building. Act as the primary bridge between C-suite sponsors, frontline end-users, and our deployment team. Keep every level of the customer's organization aligned on what's being built, why, and what good looks like.
• Own change management and adoption. Train end-users and build internal champions so the software actively solves the business problem and the customer achieves their desired outcomes.
• Drive continuous product improvement. Feed what you learn in the field back to Product and Engineering so it makes its way into the core product. Every deployment should make the platform stronger and more repeatable.
• Grow the account. Map the customer's organization to find where we can deliver more value, and turn proven results into expansion across lines, functions, and teams.

Qualifications

Must Have

• High EQ. You read people and rooms well, and you build trust quickly at every level of an organization.
• Presence with clients and real relationship acumen. Executives take your calls and frontline teams want to work with you.
• Value-oriented. You anchor everything to the outcome the customer is trying to reach and can quantify it.
• Strong project management skills. You can execute, manage timelines and dependencies, and drive steady progress across teams.
• Technical acumen. You can translate between business needs and what's technically possible, and hold your own with engineers.
• Strong at stakeholder alignment, internal and external. You keep customers, product, and engineering pointed in the same direction.
• Experience: 7+ years in customer-facing roles (customer success, solutions, implementation, consulting, or product), including time owning enterprise relationships and outcomes.
• Willing to travel to customer sites as engagements require (roughly 25–40%).
• Bonus: insurance, fintech, or another regulated industry, or experience with AI-native or enterprise SaaS deployments.

What Success Looks Like

• Customers reach time-to-value fast and expand Liberate across lines, functions, and teams.
• Liberate becomes mission-critical to how customers handle their sales, servicing, and claims.
• You're the trusted advisor bridging customers, product, engineering, and growth.
• You help define how Liberate runs customer relationships and deployment engagements as we scale across the industry.
• Competitive salary with equity options
• Comprehensive health, dental, and vision insurance
• Flexible PTO
• Flexible, hybrid work environment out of our San Francisco or Boston office
• Collaborative, high-ownership company culture