Customer Success Manager

Adaptive is a vertical AI company of 50, building the agentic operating system for the $2 trillion U.S. construction industry. We work with over 1,000 customers, partner with over 50 accounting firms, and have raised $26m from Emergence, a16z, and other top funds.

As a Customer Success Manager at Adaptive, you'll be the primary advocate, technical partner, and growth driver for our customers from Day 1 onward. Reporting to the Manager of Customer Success and collaborating closely with our existing team of CSMs, you'll own the end-to-end onboarding experience, drive ongoing adoption and value realization, and grow each account by expanding the team of AI agents running their accounting.

Adaptive's Project Accounting Agents run construction accounting 24/7, and customers can start with a single agent or hire the full team. A core part of this role is knowing each customer's workflows well enough to spot where an additional agent — a Billings Clerk, an AP Clerk, a WIP and Forecasting Analyst, and beyond — will unlock more value, and then leading that expansion. You'll need to be technical enough to configure agents, guide integrations with customers' PM and ERP systems, and troubleshoot alongside our engineers.

Above all, this role is for someone who builds with AI rather than just talks about it — you'll be hands-on with the agents every day, shaping how they map to real customer workflows. This is an individual contributor role with ample opportunity to shape our customer success practices and grow your career alongside a fast-growing team.

• Lead kickoff calls, discovery sessions, and training to ensure a smooth, efficient product launch.

• Own the technical setup: configure agents, connect and validate integrations with customers' PM/ERP systems, and map each customer's accounting workflows to the right agents.

• Decompose each customer's messy, real-world accounting process into agent logic — defining triggers, tools, approval gates, override paths, and dry-run modes — and decide where automation is safe versus where a human stays in the loop.

• Customize implementation plans to align with each customer's workflows and objectives.

• Develop and maintain onboarding materials: guides, checklists, video tutorials, and FAQs.

• Serve as the day-to-day point of contact and trusted technical advisor.

• Conduct regular business reviews to track adoption metrics, agent performance, usage patterns, and ROI.

• Identify at-risk customers early and execute retention strategies to maximize renewals.

• Own expansion within your book of business: identify where additional agents will drive value and lead the upsell from initial agents to the full team.

• Analyze customer data and agent output to surface concrete upsell and cross-sell opportunities.

• Partner with Sales on expansion plays and with Product on feature requests, and carry expansion targets tied to net revenue retention.

• Champion customer feedback across the organization to inform roadmap priorities.

• Partner with Engineering to diagnose and resolve agent behavior, output quality, and integration issues.

• Tune agent configurations, prompts, and workflows as customer needs evolve, and refine agent logic when edge cases surface.

• Exercise judgment about where automation is performing reliably versus where an output needs human review, and adjust approval gates and override paths accordingly.

• Translate between customer requirements and technical implementation, so customers always understand what their agents are doing and why.

• Continuously refine our success playbooks and workflows for scalability.

• Build with AI to automate repetitive parts of your own workflow, and partner with Engineering to standardize best practices across the team.

• Implement metrics and dashboards to monitor health scores, agent performance, and team performance.

• Work alongside Support and Engineering to resolve complex issues.

• Liaise with Marketing to develop case studies, testimonials, and referenceable success stories.

• Share customer insights in weekly leadership meetings to align on strategy.

• AI fluency. You build with AI, not just talk about it. You have hands-on experience using LLMs as a working instrument — prompt engineering, agent architecture, and skill/workflow design. You know how to decompose a messy human process into agent logic (triggers, tools, approval gates, override paths, dry-run modes), and you have judgment about where automation is reliable versus where it needs a human in the loop.

• 3+ years of SaaS Customer Success, Onboarding, or Enablement experience.

• Demonstrated track record of managing full-lifecycle customer relationships and driving both retention and expansion revenue (upsell/cross-sell).

• Technical aptitude: comfortable configuring software, working with integrations and APIs, reading and interpreting data, and troubleshooting technical issues directly with customers and engineers.

• Exceptional verbal and written communication skills, with an ability to simplify complex technical concepts.

• Data-driven mindset; comfortable using CRMs, reporting tools, and customer health platforms.

• Highly organized, self-starter attitude; thrives in a fast-paced, evolving environment.

• Bonus: experience in construction, real estate, accounting, or related verticals; familiarity with PM/ERP systems (e.g., Procore, Sage, QuickBooks); or a background working with AI/automation products.

This role requires you to work Monday–Thursday in our Boston office located at 10 High Street.