Senior AI‑Driven Enterprise CSM

Robin; Boston (MA); Hybrid; USD 100,000 - 195,000; Full time

Benefits offered by this job

Medical & Dental Insurance

Vision Insurance

Short & Long Term Disability Insurance

Paid Parental Leave

Incentive Stock Options

401(k) with company match

Flexible vacation policy

12 company holidays

AI Tools Stipend

Referral Bonus Program

In-Office Commuter Stipend

Job summary

Robin in Boston is reimagining workplace operations as a strategic function, powered by AI. The Senior Customer Success Manager will own the full customer lifecycle end-to-end for our larger, more complex customers, from onboarding to renewal and expansion.

You’ll lead executive reviews, build multi-stakeholder plans, mentor teammates, and translate product roadmaps into customer value while leveraging AI tools to accelerate insights and outcomes.

Qualifications

• 4+ years in a customer success or account management role at a SaaS or B2B technology company.
• Consistent track record of meeting or exceeding NRR/GRR targets across a growing book of business.
• Comfortable acting as an informal mentor to peers and contributing to team processes, even without formal management responsibility.

Responsibilities

• Own a book of Robin's larger, more complex customers end-to-end, from onboarding through renewal and expansion, with Net Revenue Retention as the core measure of success.
• Independently manage multi-stakeholder accounts, building account plans that weigh ARR, customer health, renewal timing, expansion potential, and churn risk.
• Lead executive business reviews (EBRs/QBRs) and drive data-backed conversations about ROI and adoption with senior customer stakeholders.
• Build and mobilize Robin champions into advocates, partnering with Marketing on case studies, testimonials, and references.
• Serve as a point of escalation for at-risk accounts within the team, partnering with Support, Product, and Engineering to resolve complex issues.
• Mentor CSMs informally — sharing account planning techniques, coaching on difficult conversations, and modeling best practices.
• Contribute to the evolution of team playbooks, health-scoring criteria, and lifecycle processes based on patterns observed across accounts.
• Stay closely aligned to the product roadmap, proactively translating releases into customer value and surfacing structured feedback to Product.
• Actively uses AI tools to accelerate account research, prep, and internal reporting; adapts quickly as new AI workflows are introduced.

Job description

Robin in Boston is reimagining workplace operations as a strategic function, powered by AI. The Senior Customer Success Manager will own the full customer lifecycle end-to-end for our larger, more complex customers, from onboarding to renewal and expansion.

You’ll lead executive reviews, build multi-stakeholder plans, mentor teammates, and translate product roadmaps into customer value while leveraging AI tools to accelerate insights and outcomes.