Director, AI Adoption

About EvenUp

EvenUp is on a mission to close the justice gap using technology and AI. We empower personal injury lawyers and victims to get the justice they deserve. Our products enable law firms to secure faster settlements, higher payouts, and better outcomes for victims injured through no fault of their own in vehicle collisions, accidents, natural disasters, and more.

We are one of the fastest-growing vertical SaaS companies in history, and we are just getting started. EvenUp is backed by top VCs, including Bessemer Venture Partners, Bain Capital Ventures, SignalFire, and Lightspeed.

Director, AI Adoption

We are seeking an experienced Director of AI Adoption to lead the post-sale onboarding experience for newly acquired personal injury firms. This is a senior, client-facing role responsible for ensuring every firm is successfully transitioned, fully operational, and confident in their partnership with us.

The Director of AI Adoption is a customer advocate first, balancing operational rigor with relationship management. You will lead a traveling onboarding team, personally engage with firm leadership, and coordinate closely with Sales, Product, Customer Success, Engineering, Operations, and Finance teams to deliver a seamless onboarding experience; often on site.

The role demands exceptional organizational and coordination skills, including managing complex schedules, aligning diverse stakeholders, and navigating competing expectations. Furthermore, it requires experience instrumenting and managing teams against SaaS and user activation metrics, to ensure "magic moments" and widespread, lasting user adoption. Regular travel is a core component of the position.

What you'll do

• Own the post-sale onboarding experience for new firms, from handoff through successful go-live and stabilization.
• Serve as the primary advocate for newly onboarded firms, ensuring their needs, concerns, and feedback are heard and addressed internally.
• Lead, mentor, and manage an onboarding team that conducts on-site and remote implementations, including travel planning and execution.
• Personally participate in on-site onboarding engagements as needed, particularly for complex or high-priority firms.
• Build and maintain structured onboarding plans, success metrics, timelines, and checklists tailored to each firm.
• Coordinate cross-functionally with Sales, Product, Customer Success, Engineering, Operations, Finance and leadership to ensure alignment and accountability.
• Develop and refine onboarding processes to improve consistency, efficiency, and client satisfaction.
• Manage scheduling across multiple firms, teams, and time zones with precision and flexibility.
• Identify risks or gaps early and proactively escalate or resolve issues before they impact the client experience.
• Create systems to track onboarding progress, outcomes, and performance metrics; report insights and trends to leadership.
• Act as a trusted senior presence for firm owners and leadership during a critical transition period.

What we look for

• 8+ years of experience in onboarding, implementation, client success, operations, or a related leadership role.
• Experience in legal services (preferred), professional services, or similarly complex environments.
• Proven experience managing teams that travel and execute on-site client engagements.
• Strong background in customer advocacy and relationship management, particularly in high-stakes or transition-heavy environments.
• Exceptional organizational and project management skills; comfortable juggling multiple onboarding tracks simultaneously.
• Demonstrated ability to work cross-functionally and influence without direct authority.
• Willingness and ability to travel regularly (including overnight and multi-day site visits).
• Executive-level communication skills with the ability to engage confidently with firm owners and senior leadership.
• Calm, solution-oriented leadership style with a high level of accountability.

What success looks like

• New firms feel supported, confident, and well-prepared from day one.
• Onboarding timelines are met or exceeded without sacrificing quality.
• Internal teams are aligned, informed, and clear on their roles.
• Issues are anticipated and resolved before they become escalations.
• The onboarding team operates efficiently, consistently, and professionally in the field.

Benefits & Perks

• Choice of medical, dental, and vision insurance plans for you and your family.
• Additional insurance coverage options for life, accident, or critical illness.
• Flexible paid time off, sick leave, short-term and long-term disability.
• 10 US observed holidays, and Canadian statutory holidays by province.
• A home office stipend.
• 401(k) for US-based employees and RRSP for Canada-based employees.
• Paid parental leave.
• A local in-person meet-up program.
• Hubs in San Francisco and Toronto.