Principal Customer Success Manager, Enterprise

About the role

As an Enterprise CSM, you’ll partner with our largest and most complex enterprise customers to help them succeed in the new era of AI-driven customer service. You’ll work with C-suite leaders and their teams to guide them through their AI Agent transformation with Fin — as both a Customer Agent and a Service Agent — from early project scoping and requirements gathering, to measurable adoption, to industry-best automation rates and business outcomes.

Responsibilities

• Develop trusted advisor relationships with customers (from c-suite stakeholders to individual contributors across a focused portfolio of high-value enterprise accounts).
• Facilitate requirements gathering and process mapping for the customer’s standard operating procedures; document in clear, precise, and actionable terms.
• Act as a transformation architect influencing customer strategy at the highest levels and defining automation and AI maturity roadmaps that drive structural cost reduction, CX innovation, or both.
• Collaborate with engineers to translate customer requirements into Fin solution designs, guiding the customer on configuration best practices and prompt strategy.
• Maintain deep product knowledge of Fin’s fast-expanding capabilities; remain market aware of the fast evolving AI-agent industry.
• Lead Success Plans, QBRs/EBRs, and strategic planning sessions with executive stakeholders hold yourself and your customers accountable to clearly defined milestones and measurable outcomes.
• Quantify and communicate customer value through ROI metrics, outcome narratives, and executive briefings — building compelling business cases for continued and expanded investment.
• Prioritize competing demands to drive the highest-value outcomes across your customer portfolio.
• Be the Voice of the Customer internally, advocating for customers’ needs and shaping our solutions strategy.

Requirements

8+ years of customer-facing experience in management consulting, strategy, advisory, or enterprise SaaS CSM roles.

Experience with business process mapping, requirements analysis, and solution design at enterprise scale.

Strong technical acumen and genuine passion for AI — comfortable engaging with technical concepts and holding meaningful conversations with engineering and product teams (coding not required).

Ability to evaluate AI performance data — automation rate, resolution rate, CSAT deflection — and translate metrics into compelling business outcomes.

Strong commercial instincts: understands enterprise procurement cycles and how to frame value for CFO and CX executive audiences.

Ability to simplify and communicate complex problems clearly across audiences — from technical teams to boards.

Experience leading large-scale enterprise transformation programmes involving AI, automation, or modern customer service platforms.

Ability to apply a deep understanding of product roadmap to enhance customers’ automation strategies and deliver measurable outcomes.

Proven ability to manage multi-threaded Success Plans across complex enterprise accounts, aligning multiple stakeholders and workstreams to drive coordinated outcomes.

Self-motivated, adaptable, and intellectually curious — a leader among peers with a high level of self-efficacy.

Qualifications

Master’s degree in Business Administration, Computer Science, or a related field.

Proven track record of success in managing and driving transformation initiatives in large enterprises.

Experience with AI and machine learning technologies.

Excellent communication and interpersonal skills.

Ability to work independently and as part of a team.

Passion for customer success and a commitment to excellence.

Skills

• Customer relationship management
• Business process mapping
• Requirements analysis
• Solution design
• AI and machine learning
• Commercial acumen
• Strategic planning
• Project management
• Leadership

Benefits

• Competitive salary and meaningful equity
• Comprehensive medical, dental, and vision coverage
• Regular compensation reviews - great work is rewarded!
• Unlimited access to Claude Code and best-in-class AI tools; experimentation & building is encouraged & celebrated.
• Flexible paid time off policy
• Paid Parental Leave Program
• 401k plan & match
• In-office bicycle storage
• Fun events for employees, friends, and family!

Pay

The OTE range for candidates within the Greater Chicago Area is $200,100 - $238,950. Actual base pay will depend on a variety of factors such as education, skills, experience, location, etc. The base pay range is subject to change and may be modified in the future.

Schedule

We have a hybrid working policy. We believe that working in person helps us stay connected, collaborate easier and create a great culture while still providing flexibility to work from home. We expect employees to be in the office at least three days per week.