Top Senior Customer Success Jobs in Chicago, IL

Owns strategic customer success for enterprise legal management software customers. Develops success plans, drives adoption and value realization, monitors customer health, mitigates renewal risk, leads recovery initiatives, manages executive relationships, and coordinates cross-functional teams. The role conducts business reviews, supports renewals and expansion opportunities, advocates for customer needs, and influences stakeholders without direct authority.

Own strategic relationships with complex enterprise clients, serving as a trusted executive advisor and voice of the customer. Lead migrations from legacy travel-management technology to Navan, including scoping, implementation, go-live, and hypercare. Drive adoption, retention, compliance, training, health checks, business reviews, risk mitigation, and churn prevention. Partner with Product, Engineering, and Sales on feedback, enhancement requests, and escalations while managing stakeholder alignment and change resistance.

Build and lead enablement programs for Customer Success and Implementation teams, including onboarding, product training, continuous learning, playbooks, and AI-enabled workflows. Identify performance gaps, translate product updates into practical training, improve adoption of tools and processes, and establish feedback loops with Product, Support, Customer Education, and Product Marketing. The role supports stronger renewals, expansions, customer outcomes, and operational efficiency in a growing SaaS organization.

Manage end-to-end success for a portfolio of non-enterprise healthcare customers: drive adoption, troubleshoot complex data and platform issues, run trainings and implementations, coordinate cross-functional teams, develop customer roadmaps, and support renewals while ensuring data quality and security compliance.

The role involves leading the Customer Success team, enhancing customer engagement strategies, and driving value realization for mid-market customers while fostering an inclusive team culture.

Lead and coach a Customer Success team to drive renewals, retention, and expansion for enterprise B2B SaaS customers. Own team performance metrics, support strategic escalations, improve CS processes and playbooks, align goals using OKRs, collaborate cross-functionally, and advocate AI adoption. Role requires up to 50% travel and stewardship of hiring, development, and talent decisions.

Manage strategic bank, credit union, and fintech accounts to drive adoption, onboarding, and product-driven fraud mitigation. Provide consultative guidance, set business goals, run trainings, share performance data, collaborate cross-functionally, support renewals, and travel to clients as needed.

Manage relationships for enterprise bank, credit union, and fintech clients. Onboard customers, provide dashboard training, establish business goals, share performance insights, drive renewals, and consult on fraud solutions. Collaborate cross-functionally with Sales, Data Science, Product, and Engineering to maximize customer success and adoption.

Lead the Customer Success team by driving onboarding, engagement, and retention strategies, while managing high-value accounts and collaborating with product and sales.

Own strategic enterprise customer relationships from deployment through adoption, value realization, renewal, and retention. Develop success plans, manage executive stakeholders, monitor customer health and KPIs, facilitate executive business reviews, identify expansion opportunities, handle escalations, and coordinate Sales, Support, Product, Renewals, and Professional Services. Mentor CSM peers and improve scalable customer success processes.

Leads Customer Success Operations by building retention models, digital engagement programs, and scalable operating processes. Owns Customer Success Platform deployment and optimization, including health scoring, workflows, automation, and predictive insights. Develops dashboards, forecasting, capacity models, and performance metrics while driving cross-functional governance and organizational change. Builds and manages the Customer Success Operations team, improving retention, efficiency, adoption, and customer outcomes without proportional cost growth.

The Customer Success Manager enhances customer operations using Samsara's IoT platform, builds relationships with clients, and collaborates cross-functionally for success plans and workshops.

As a Customer Success Engineer, you'll drive adoption and satisfaction for enterprise customers using Deepgram's voice AI technology, fostering strong relationships and aligning technical solutions with business objectives.

Own a portfolio of 8–12 lender accounts, driving adoption, engagement, retention, and measurable customer outcomes after implementation. Serve as the strategic customer partner and escalation point while coordinating Product, Support, Implementation, and Sales. Build Vesta’s Customer Success function from the ground up, including playbooks, engagement models, success metrics, feedback loops, operating cadence, and hiring and managing the first 1–3 team members.

Own strategy, renewals, expansion, and executive relationships for 10–12 strategic enterprise restaurant accounts. Lead cross-functional teams across Sales, Support, Product, Engineering, and Finance; develop champions, identify growth opportunities, and direct account plans. Use AI daily for account planning, health monitoring, communications, and renewal preparation while building reusable tools for the broader customer success team. The role is fully remote in the US or Canada with 10–15% travel.

Manage client relationships throughout the partnership lifecycle, driving engagement, retention, renewals, account growth, and program adoption. Responsibilities include contract and financial coordination, client reporting, KPI analysis, executive communications, onboarding, training, strategic meetings, and cross-functional collaboration. The role translates performance data into recommendations, addresses client feedback, and supports expansions and seasonal program launches.

Leads Strategic and Growth Customer Success teams serving post-acute and outpatient facilities. Responsibilities include improving retention, reducing churn, driving expansion, developing account strategies and playbooks, coaching CSMs, forecasting capacity, analyzing customer health and market data, managing escalations, and representing customer insights to Product and executive leadership. The role is fully remote with occasional local and overnight travel.

Leads Customer Success Managers responsible for customer retention, adoption, renewals, growth, and churn mitigation. Develops retention strategies, forecasts renewal risk, monitors revenue risks, supports executive account engagements, partners cross-functionally to improve the post-sale experience, and drives customer lifecycle improvements. Requires substantial SaaS customer success leadership, commercial contract experience, analytical skills, and executive communication.

Own a portfolio of government regulatory boards and state agencies, building executive relationships and aligning SaaS solutions with agency mandates. Develop success plans, lead regulatory training, monitor platform engagement, provide agency insights, resolve complex account issues, and conduct strategic business reviews. The role focuses on retention, compliance outcomes, value realization, and long-term customer partnerships across public-sector healthcare and licensing organizations.

Manage strategic telecommunications enterprise accounts as the primary post-sale contact. Drive onboarding, adoption, value realization, retention, renewals, and expansion of Redis solutions. Build relationships with DevOps, engineering, and executive stakeholders, deliver business reviews, develop success plans, mitigate churn risks, and advocate for customer needs internally. Collaborate with Sales, Product, Support, Engineering, and Solutions Architecture while providing technically fluent guidance on cloud, data platforms, and telecom use cases.

Own strategic customer relationships across Axway’s managed cloud and SaaS business, driving adoption, retention, expansion, upsells, and cross-sells. Develop customer success plans, monitor revenue and satisfaction KPIs, lead business reviews, document account activity, and collaborate with sales, product, engineering, marketing, and professional services teams. The role requires executive-level communication, strong organization, problem-solving, and experience managing complex technology customers.

Owns customer outcomes, retention, referenceability, and expansion across enterprise healthcare accounts. The Senior Customer Success Executive develops success plans, manages account health and recovery programs, coordinates cross-functional delivery, identifies expansion opportunities, maintains accurate CRM and reporting data, and communicates with customer executives. The role requires deep health-plan operations knowledge, enterprise payer-platform experience, commercial fluency, and the ability to drive results through teams without direct authority.

Manage enterprise Salesforce Commerce Cloud customers as a trusted advisor and single point of accountability. Orchestrate Signature Success deliverables, renewals, expansions, feature adoption, platform optimization, and incident resolution. Build executive stakeholder relationships, translate technical concepts into business outcomes, coordinate cross-functional teams, and guide customers through Salesforce releases. Occasional customer-site travel and after-hours or weekend coverage may be required.

Manage a portfolio of programmatic accounts end-to-end: own campaign execution, client communications, optimization, reporting, troubleshooting, and growth (upsell/renewals). Partner cross-functionally with Sales, Analytics, and Operations to drive performance and ensure client satisfaction.

Build and lead the Customer Success function for a new SaaS business line while managing early customer relationships. Own onboarding, implementation, data cleanup, training, adoption, customer health, business reviews, renewals, expansion, escalations, and advocacy. Create lifecycle processes, playbooks, KPI reporting, HubSpot workflows, documentation, and a Voice of Customer program. Partner with Product, Sales, Marketing, Operations, Finance, and leadership, while translating AI model outputs for law firm executives and preparing for future Customer Success hiring.