Job Description

About Us:

Liberate builds AI agents to automate manual tasks for the $2.7T insurance industry. We started with voice — the hardest and most valuable channel in insurance — and are now expanding into full workflow automation across sales, servicing, and claims. Our long-term vision is to build reasoning agents capable of handling the entire spectrum of insurance carrier and broker operations. We've raised $72M to date, including a $50M Series B in October 2025, backed by top-tier venture firms.

About The Role:

We are seeking an AI Agent Engineer to bridge the gap between our cutting-edge products and our customers' technical needs, ensuring successful deployment and integration. In this role, you will work closely with customer success, sales, product, and engineering teams to deliver AI-driven solutions that drive measurable value for our customers.

*Location: Boston or San Francisco (Berkeley) hybrid role (2 day/week in-office) 

Key Responsibilities:

• Collaborate with the sales team to understand customer requirements and design tailored AI-driven solutions that meet their specific business needs.
• Serve as the technical expert during the post-sales process, providing product demonstrations, technical presentations, and answering detailed customer inquiries.
• Work closely with customers to assess their current systems and workflows, identifying integration points for our AI solutions.
• Develop and deliver customized product configurations and prototypes to demonstrate the value and functionality of our solutions.
• Assist in the implementation process by providing technical guidance, troubleshooting issues, and ensuring seamless integration with customer systems.
• Act as a liaison between customers and the product development team, communicating customer feedback and helping to shape future product features.
• Provide post-sales support to ensure customer satisfaction and continued product success.
• Create and maintain technical documentation, including integration guides, FAQs, and best practices.

Qualifications:

Must have

• 3+ years of experience in a solutions engineering or technical consulting role, preferably within the AI or technology sectors.
• Bachelor's degree in Computer Science, Engineering, or a related field.
• Extreme sense of ownership, urgency, and customer obsession to ensure that you will thrive in our early stage enterprise startup environment
• Experience with programming languages such as Python, Java, or similar, and familiarity with APIs, data integration, and cloud platforms.
• Strong technical background with experience in software development, system integration, and cloud-based solutions.
• Excellent communication and presentation skills, with the ability to clearly explain complex technical concepts to both technical and non-technical audiences.
• Proven ability to manage multiple customer engagements simultaneously, delivering high-quality results under tight deadlines.
• Strong problem-solving skills and a proactive approach to addressing customer challenges.

Nice to have

• Familiarity with AI, machine learning, and data analytics technologies and how they can be applied in enterprise environments.
• Experience in the insurance technology or financial services industries.
• Previous experience working in a startup or high-growth environment.
• Certifications in cloud platforms such as AWS, Google Cloud, or Azure.

Salary Range: $120,000-170,000 

The salary range may be inclusive of several levels that would be applicable to the position. Final salary will be based on a number of factors including, level, relevant prior experience, skills and expertise. This range is only inclusive of base salary, not benefits (more details below) or equity.

Benefits:

• Competitive salary with equity options
• Flexible PTO
• 401(k) plan
• Comprehensive health, dental, and vision insurance
• Flexible work environment 
• Collaborative and innovative company culture

Job Description

About Liberate

Liberate builds AI agents to automate manual work for the $2.7 trillion insurance industry. We started with voice — the hardest and most valuable channel in insurance — and are now expanding into full workflow automation across sales, servicing, and claims. Our long-term vision is to build reasoning agents capable of handling the entire spectrum of insurance 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. We're insurance people building AI, and that operator DNA is why customers trust us with their highest-volume operations.

About the Role

As Liberate scales from early traction into a repeatable, predictable revenue engine, we're looking for a Head of Revenue Operations to build and run the GTM plumbing underneath it. You'll own the entire revenue cycle end-to-end — territory design, pipeline hygiene, forecasting, metrics and KPIs, and the systems and behaviors that keep the whole engine honest.

This is a builder's role, not a caretaker's. You'll design the geo and segment territory model, define the metrics that tell leadership the truth about the business, and put real teeth behind data hygiene — building the rules, automations, and accountability structures that keep the CRM clean at the source rather than inspecting it after the fact. You'll report to the CRO and work directly with Sales, Marketing, and CX leadership.

What You'll Do

• Own the revenue cycle end-to-end. Territory design, capacity planning, quota setting, forecasting, pipeline management, and comp administration — you're accountable for the full motion from pipeline creation through renewal and expansion.
• Build and maintain geo and segment territories. Design territory and account-scoring models that align coverage with opportunity, and evolve them as the business grows into new geos and segments.
• Define and own the metrics that run the business. Establish a single source of truth for pipeline coverage, conversion by stage, velocity, win rate, ARR/NRR, CAC, and rep productivity — with consistent definitions across Sales, Marketing, and CX.
• Make pipeline hygiene a system, not a task. Build the rules, automations, and accountability structures — in partnership with sales leadership — that keep CRM data clean and trustworthy at the source, and enforce the behaviors that keep it that way.
• Own the GTM plumbing. Administer and evolve the revenue tech stack (CRM, marketing automation, analytics, and AI/automation layers), ensuring clean, synchronized data flows across every system of record.
• Run the executive operating cadence. Forecast calls, pipeline reviews, QBRs, and board-level reporting — with the rigor and consistency that let leadership make fast, confident decisions.
• Default to AI-first workflows. Identify where AI tools can replace manual reporting, forecasting, and analysis work, and build the case for adoption with measurable outcomes — time saved, accuracy improved, pipeline impact — not adoption for its own sake.
• Partner cross-functionally. Work closely with Sales, Marketing, CX, and Finance leadership to drive one shared set of definitions, one operating rhythm, and consistent execution against company objectives.

What We're Looking For

Must Have

• 10+ years in Revenue Operations, Sales Operations, or GTM Strategy, ideally in B2B SaaS, with a track record of building the operating rhythm and data infrastructure for a scaling revenue org.
• Deep, hands-on experience owning the full revenue cycle: territory design, quota setting, forecasting, pipeline management, and compensation administration.
• Proven ability to build and enforce pipeline hygiene and data discipline — you build the guardrails and incentives that keep CRM data clean, not just the dashboards that report on it.
• Hands-on experience with AI-first GTM tools — e.g., Cursor, HubSpot, and Clay for AI-powered enrichment and prospecting — along with general fluency using tools like Claude to automate reporting, analysis, and coaching workflows.
• Strong analytical and storytelling skills — you can turn a messy dataset into a clear, executive-ready narrative.
• Comfortable operating at both altitudes: strategic planning with executives and the board, and detailed, in-the-weeds problem solving with reps and managers.

Nice to Have

• Experience in AI-native or Voice AI companies, or exposure to insurance, fintech, or another regulated industry.
• Background at a high-growth, venture-backed startup where you built process rather than inherited it.

What Success Looks Like

• Leadership and the board trust the numbers because the definitions, the data, and the process behind them are consistent and clean.
• Reps and managers operate inside a clear, enforced operating rhythm — territory, quota, forecast, and pipeline hygiene are systems, not once-a-quarter scrambles.
• AI-first tools are doing the manual reporting and analysis work, freeing the team to focus on judgment and strategy.
• Liberate's GTM engine scales cleanly into new geos, segments, and product lines without the plumbing breaking.

Compensation & Benefits

Target compensation: $200,000 – $220,000 base, plus equity and variable. Final offer depends on level, experience, and location.

• Competitive salary with equity options
• Comprehensive health, dental, and vision insurance
• 401(k) plan
• Flexible PTO
• Flexible, hybrid work environment out of our Bay Area office
• Collaborative, high-ownership company culture

Job Description

About Us:

Liberate builds AI agents to automate manual tasks for the $2.7T insurance industry. We started with voice — the hardest and most valuable channel in insurance — and are now expanding into full workflow automation across sales, servicing, and claims. Our long-term vision is to build reasoning agents capable of handling the entire spectrum of insurance carrier and broker operations. We've raised $72M to date, including a $50M Series B in October 2025, backed by top-tier venture firms.

Location: Boston or Bay Area, hybrid preferred (2x/week in office)

Reporting: VP Engineering, dotted line partnership with CPO, and Customer Success leadership

Mission

Build the secure, reliable infrastructure foundation for Liberate’s agentic platform. You will be a hands-on owner of cloud infrastructure and DevOps while serving as Liberate’s senior technical owner and primary point of contact for product security, cloud security, and compliance.

Make the safest path the fastest path so engineers can ship quickly without normal mistakes becoming outages, security incidents, or compliance failures.

About the role

This is intentionally an infrastructure-heavy security role. You will spend most of your time building and operating production cloud infrastructure, deployment systems, and developer tooling while owning security across the product and platform.

This is not a governance-only CISO role or a corporate IT/help desk role. As Liberate’s first dedicated security engineering leader, you will define the function, use vendors where they create leverage, and have the opportunity to build the team as the company scales.

What you will do

Cloud infrastructure and DevOps

• Own and evolve Liberate’s production cloud foundation across AWS, Kubernetes/EKS, networking, compute, storage, data services, environment isolation, and production access.
• Build reusable Terraform modules, CI/CD pipelines, deployment automation, configuration standards, and self-service paths that make environments repeatable and safe.
• Improve reliability and operability through observability, alerting, SLOs, capacity and cost management, backup and recovery, disaster recovery, and production-readiness standards.
• Participate in the engineering on-call model, lead infrastructure incidents when needed, and convert incidents and operational toil into durable platform improvements.
• Partner with Platform and product engineering teams on architecture and rollout patterns, reducing manual work and broad privileges through automation and secure defaults.

Security engineering and architecture

• Serve as Liberate’s senior technical security owner and escalation point, leading threat modeling and secure design reviews for agent capabilities, tool execution, memory, integrations, multi-tenant services, and sensitive data flows.
• Build a secure SDLC engineers actually follow, including requirements, code, dependency, container, and infrastructure-as-code scanning, CI gates, security tests, and paved-road defaults.
• Own identity, authorization, secrets, key management, encryption, network boundaries, audit trails, production access, and tenant and data-isolation patterns.
• Establish practical controls for agentic AI risks, including scoped tool access, credential handling, data exfiltration, prompt injection, model and vendor risk, and traceable actions.
• Run vulnerability management end to end, including prioritization, remediation, penetration tests, and third-party reviews.
• Build useful security telemetry, detection, playbooks, and tabletop exercises, then lead calm, accountable response and durable follow-through when incidents occur.

Compliance and customer trust

• Own SOC 2 and related compliance programs end to end: control design, technical implementation, evidence quality, audit readiness, and continuous effectiveness.
• Translate compliance requirements into automated technical controls and operational practices rather than manual checklists.
• Lead audits, penetration tests, customer security reviews, questionnaires, and technical conversations with enterprise customers, partners, and auditors.
• Maintain a clear risk and security roadmap, frame tradeoffs in business terms, and drive concrete mitigations with accountable owners.
• Use tools such as Vanta, security vendors, and external specialists as leverage while retaining internal technical ownership.

What we are looking for

• You are a senior infrastructure, platform, or DevOps engineer with real security depth, or a security engineer who has personally built and operated production cloud infrastructure.
• You write code and infrastructure as code, debug production systems, review architecture, and take changes from design through rollout and operation.
• You think in systems: identity, authorization, tenant boundaries, failure domains, blast radius, recovery, and the incentives that make secure behavior the default.
• You are pragmatic about when to build, buy, automate, delegate, or accept risk, and you right-size controls to the stage of the company.
• You lead through influence without becoming a gatekeeper or creating a separate security lane.
• You are a calm incident operator and a crisp communicator with engineers, executives, customers, auditors, and vendors, and you are energized by building a function from the ground up.

Experience

• 8+ years across infrastructure engineering, platform engineering, SRE, DevOps, cloud security, or security engineering.
• 4+ years with meaningful ownership of security architecture or security programs for a production SaaS platform.
• Deep hands-on experience with AWS, Kubernetes/EKS, Terraform or equivalent infrastructure as code, CI/CD, observability, and production incident response.
• Strong working knowledge of IAM, network security, secrets and key management, vulnerability management, secure software delivery, and multi-tenant cloud architecture.
• Demonstrated ownership of SOC 2 or a comparable compliance program in a fast-moving environment.
• Proficiency in a programming or automation language such as Python, Go, or TypeScript, plus experience in an early-stage or high-growth company where systems had to be built, not inherited.

Helpful, not required

• Experience securing LLM-based or agentic systems, including tool use, model integrations, prompt injection, or data-leakage risks.
• Experience in insurance, financial services, healthcare, or another regulated industry.
• Experience designing disaster recovery, multi-account cloud foundations, regional or tenant-isolation strategies, or managing security and incident-response vendors.

Success looks like

• Production infrastructure is reliable, observable, recoverable, and increasingly defined and enforced through code.
• Engineers ship faster through safe, self-service paths rather than ticket queues, one-off access, or manual deployment work.
• Broad access, secrets exposure, tenant-boundary risk, and preventable security failures are materially reduced. When issues occur, blast radius is smaller and response is faster.
• SOC 2 and customer security work run predictably with strong evidence and minimal fire drills.
• Liberate has one trusted technical owner for security, clear expectations embedded in architecture and CI/CD, and a function that can scale with the business.

Compensation: 

Boston; $180,000-$240,000 + equity

San Francisco; $190,000 – $250,000 + equity