Principal Customer Success Manager, Enterprise (Chicago)

Fin is the AI Customer Agent company on a mission to help businesses provide perfect customer experiences.Our AI Agent Fin is the highest-performing AI Customer Agent on the market today, enabling businesses to deliver impeccable, always-on customer support across the customer journey – from service, to sales, to ecommerce. Powered by our own AI models, Fin resolves complex customer issues end-to-end across every channel, with minimal set-up and integration. Fin can also be combined with our natively integrated Intercom help desk for one single system that is designed to meet the needs of modern day support teams.Founded in 2011, Fin became one of the fastest growing companies and remains one of the largest private software companies in the world with nearly 30,000 global businesses using our products to transform their customer support. Driven by our core values, we push boundaries, build with speed and intensity, and relentlessly deliver incredible value to our customers.What's the opportunity? 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.This role is an opportunity to shape how the world’s leading companies deploy AI to transform their customer and support operations — and to achieve strategic outcomes aligned to their business goals.What will I be doing? 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.Monitor Fin usage patterns to identify risks, recommend optimizations, and uncover expansion opportunities. 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.Partner with Sales and Renewals to protect GRR, drive growth and progress further exposure of Fin to our customers' challenges. 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.What skills do I need? 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.Benefits We are a well-treated bunch with awesome benefits! If there’s something important to you that’s not on this list, talk to us! Competitive salary and meaningful equityComprehensive medical, dental, and vision coverageRegular 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 policyPaid Parental Leave Program401k plan & matchIn-office bicycle storageFun events for employees, friends, and family!*Proof of eligibility to work in the United States is required.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. All regular employees may also be eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs). #LI-HybridPolicies Fin has 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.We have a radically open and accepting culture at Fin. We avoid spending time on divisive subjects to foster a safe and cohesive work environment for everyone. As an organization, our policy is to not advocate on behalf of the company or our employees on any social or political topics out of our internal or external communications. We respect personal opinion and expression on these topics on personal social platforms on personal time, and do not challenge or confront anyone for their views on non-work related topics. Our goal is to focus on doing incredible work to achieve our goals and unite the company through our core values. Fin values diversity and is committed to a policy of Equal Employment Opportunity. Fin will not discriminate against an applicant or employee on the basis of race, color, religion, creed, national origin, ancestry, sex, gender, age, physical or mental disability, veteran or military status, genetic information, sexual orientation, gender identity, gender expression, marital status, or any other legally recognized protected basis under federal, state, or local law.