Customer Implementation Lead - AI Tax Software Onboarding

Cranston AI; San Francisco, Northern (CA, KY); Hybrid; USD 120,000 - 160,000; Full time

Benefits offered by this job

Health, dental, and vision benefits

Job summary

Cranston AI in San Francisco or US-based remote is seeking a Customer Implementation Lead to own the customer journey from contract to go-live and adoption. You will lead discovery, define milestones, coordinate multi-team efforts, train customers, and ensure a smooth handoff to customer success, with occasional travel.

You will work closely with Forward Deployed Accountants when deeper accounting judgment is needed, and you will help scale onboarding through playbooks and templates.

Qualifications

• 3+ years of experience in implementation, onboarding, customer success, professional services, consulting, operations, or project management for B2B software.
• Ability to manage several customer projects at once without dropping details or losing momentum.
• Clear, thoughtful communicator who can work with executives, operators, and technical teammates.
• Comfortable learning software quickly and turning an unfamiliar workflow into a simple plan.
• Strong teaching ability and the knack to help others move forward without leaving them behind.
• High ownership, strong follow-through, and judgment to escalate risks early.
• Curiosity about accounting and finance, even if you have not worked in the profession before.
• Willingness to work in person in San Francisco and travel occasionally when required.

Responsibilities

• Own onboarding for new accounting-firm customers, from discovery and kickoff through go-live and early adoption.
• Run discovery sessions, define scope, map milestones, assign owners, and set clear success measures.
• Build practical implementation plans that keep customer and Cranston teams moving together.
• Coordinate configuration, data collection, testing, training, and launch readiness across multiple concurrent projects.
• Lead customer kickoffs, working sessions, status updates, and training for partners, managers, preparers, bookkeepers, and administrative staff.
• Track risks, dependencies, and open questions. Surface problems early and drive them to resolution.
• Work inside the product with customers. Diagnose workflow issues, find practical workarounds, and coordinate with product and engineering when the product needs to improve.
• Create onboarding playbooks, templates, training materials, and repeatable operating rhythms as we scale.
• Bring the customer's voice to product and engineering with specific examples, patterns, and recommendations.
• Support a smooth transition from onboarding into ongoing customer success, adoption, and expansion.
• Travel occasionally when being in the room will make customer work better.

Skills

Implementation leadership

Onboarding

Project management

Customer success

Cross-functional collaboration

Accountability

Job description

Cranston AI in San Francisco or US-based remote is seeking a Customer Implementation Lead to own the customer journey from contract to go-live and adoption. You will lead discovery, define milestones, coordinate multi-team efforts, train customers, and ensure a smooth handoff to customer success, with occasional travel.

You will work closely with Forward Deployed Accountants when deeper accounting judgment is needed, and you will help scale onboarding through playbooks and templates.