Lead Deployment Strategist

About the Role

Axle is the AI-native clearinghouse for insurance. Our infrastructure and AI agents automate complex insurance workflows for Fortune 500 businesses like Rocket Mortgage, Avis, and Experian. Speed up shared workflows like verification, monitoring, and policy updates by 20x while recovering more than $200M in losses.

Axle’s Deployment Strategists own enterprise client engagements and deployments. As our first Lead Deployment Strategist (i.e., Engagement Manager), you’ll be the strategic client partner responsible for helping our most important clients successfully deploy our clearinghouse, convert pilot engagements into long-term contracts, and drive expansion into deeper and broader deployments.

Your primary KPI is Net Dollar Retention. You'll own client outcomes across the full post-sales lifecycle: designing deployments around each client's business objectives, converting pilots into long-term contracts, and identifying expansion opportunities across new use cases and agent touch points.

You'll work directly with Fortune 500 companies, collaborating closely with Technical Account Managers, Product Managers, Engineering, and Sales to drive adoption and unlock new revenue within accounts. We’ve already grown enterprise deployments from $100K to $1M, and you’ll have the chance to take them to $10M+.

This is a senior, high-leverage role for someone who has led complex enterprise engagements/deployments and has the strategic instincts to identify expansion opportunities within accounts. We're looking for a hands-on operator who can own client outcomes today and grow into a leadership role as we scale the deployment function.

Why you should consider joining

• Trusted by leading Fortune 500 companies and top brands like Rocket Mortgage, Hertz, Avis, Sixt, and Experian - with more joining every month.
• Mid 7-figures ARR with 160%+ Net Dollar Retention and clear signs of PMF
• Backed by world-class investors including Gradient (Google’s AI Fund), Y Combinator, and the founding team of Plaid
• Join a tight-knit team where everyone drives real impact we have top-tier customer and revenue metrics with half the team size of typical startups.
• Work on genuinely hard, unsolved problems at the intersection of agentic AI, complex data structuring, and financial risk.
• We care deeply about our team and provide great compensation and equity, full benefits, unlimited time-off, and plan an annual team offsite!

We're a lean team, and our customer base is growing too quickly for us to keep up. We're looking for talented team members to join our early team and execute on an ambitious roadmap.

What You'll Do

You will successfully deploy Axle with new clients, convert them to long term engagements, and grow revenue through deeper penetration into existing agent deployments and new use case adoption.

• Deployment: Work with enterprise clients to understand their business objectives, design the pilot or initial deployment around them, and partner with Technical Account Managers and Product Managers to ensure successful launch and rapid time-to-value.

• Pilot Conversion: Define what must be true to convert a pilot into a full long-term contract or achieve full share of business for the initial use case. Own the outcome - work with client leadership to hit those milestones and close the conversion.

• Expansion: Partner with client leadership and Axle's Product Managers to identify additional initiatives and use cases for deploying Axle agents. Prioritize expansion opportunities, build business cases, and reduce time-to-value for each new deployment.

• Client Management: you’ll build deep relationships with clients across their organization. From technical team members writing the code to the Presidents and CEO’s of their business. You’ll chart their organization and build real, fulfilling relationships.

• Run executive steering and QBRs: drive regular cadence with client senior leadership - align on objectives, review deployment progress against success metrics, surface risks early with options, and ensure rapid decision-making.

• Codify the playbook: build reusable deployment and growth accelerators - implementation frameworks, onboarding templates, stakeholder communication plans - that improve speed and quality as we scale across new clients.

What Success Looks Like

• Pilots convert to long-term contracts consistently - you've built a repeatable motion for defining success criteria, hitting milestones, and closing the conversion.
• Net Dollar Retention grows quarter over quarter - existing accounts expand into deeper volume penetration and new agent use cases under your leadership.
• New deployments launch on time with rapid time-to-value - clients see measurable business outcomes against baselines established pre-deployment.
• Executive trust earned - steering forums and QBRs run to cadence, risks surface early with options, and client stakeholders describe the engagement as well-managed and high-impact.
• The playbook scales beyond you - deployment frameworks, onboarding templates, and best practices are codified and reusable, enabling the next hire to ramp faster and deliver at the same bar.
• Product gets sharper because of you - your field insights translate into crisp product requirements that ship, and you close the loop by validating that shipped capabilities deliver real customer value.

What We’re Looking For

• 8+ years of experience in fast-paced client-facing strategic roles: strategy consulting, investment banking, Chief of Staff, founding experience, and product or business operations
• Expert at building client relationships at all levels - from day-to-day operators to C-suite - and driving outcomes from point A to point B across complex enterprise organizations.
• Ability to parachute into a new client and get up to speed quickly on their product, business model, and technology stack - then translate that understanding into a deployment strategy.
• Experience leading complex enterprise implementations or deployments - managing cross-functional stakeholders, timelines, and deliverables to drive projects to successful completion.
• Excellent communication skills with the ability to translate complex technical concepts for diverse audiences - from engineering teams to business leadership.
• Strong strategic instincts - you can identify expansion opportunities within accounts, build business cases, and prioritize where to focus for maximum impact.
• Comfortable with technical concepts - solid understanding of APIs, integrations, and modern software architectures (you don't need to code, but you need to speak the language).
• Self-motivated, adaptable, and thrives in a fast-paced startup environment where you'll wear many hats and build the plane while flying it.

We’ve found the best Deployment Strategists have the highest raw horsepower - they’re intensely curious, thrive in ambiguity, enjoy teaching themselves new things, and crave ownership.

What would be even better?

• Experience building or scaling a post-sales, solutions, or deployment function - you've defined processes, built playbooks, and laid operational foundations for a growing team.
• Experience in insurance, insurtech, or adjacent financial services industries - you understand the ecosystem, the players, and the pain points.
• Experience managing pilot-to-contract conversions or land-and-expand motions within large enterprise accounts.
• Background in API-first or infrastructure companies where deployment complexity and integration depth are key to customer success.
• Ability to write code or build their own tools