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Customer Success Associate Director - Healthcare SaaS

Wolters Kluwer · Chicago, IL · $122,300–$218,550 a year · Full time

Posted Sep 15, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you built a relationship with a health system executive, like a CMIO or CNO, that changed the account.

What they are checking: Whether they have real executive presence and healthcare relationships, which the posting leans on heavily.

Tell me about a time you were the customer's advocate inside your own company and had to push for something.

What they are checking: Whether they can represent customer needs internally with credibility and without burning bridges.

How do you stay current on what's happening in health systems, and how does it change your conversations with customers?

What they are checking: Whether their healthcare industry knowledge is current enough to make them a trusted advisor.

How do you manage your time across a portfolio of large, complex accounts that all need attention?

What they are checking: Whether they can prioritize by risk and value, and keep many senior relationships healthy at once.

What would you do

A major customer's adoption of Lexidrug is low a year into the contract. What would you do?

What they are checking: Whether they can diagnose adoption barriers and drive a plan instead of just reporting the gap.

Sales wants to pitch an expansion, but you know the customer is unhappy with support. How do you handle it?

What they are checking: Whether they put long-term partnership ahead of short-term sales while staying a good teammate to Sales.

A health system merges with another that uses a competitor's product. What's your plan?

What they are checking: Whether they can think strategically about risk and opportunity in a changing customer landscape.

About the work

How would you build a strategic success plan for a large health system that uses UpToDate, Lexidrug and Patient Engagement?

What they are checking: Whether they can tie products to the customer's own clinical, operational and financial goals in a real plan.

How do you show a health system measurable outcomes from clinical decision support?

What they are checking: Whether they can talk value in terms that matter to clinical and financial leaders, not just usage counts.

How would you run an executive business review so the customer leaves with decisions, not just slides?

What they are checking: Whether they can lead high-level meetings that produce action and deepen the partnership.

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The full job description

As published by Wolters Kluwer.

LOCATION: Hybrid – 8 days a month in the office (Chicago, Dallas, Indianapolis, Waltham, Philadelphia, Kennesaw) OVERVIEW The Customer Success AD is a senior individual contributor responsible for driving customer outcomes, value realization, and strategic partnership across a portfolio of Wolters Kluwer Health's largest, most complex, and highest-priority health system customers. Serving as a trusted advisor to executive, clinical, operational, and digital leaders, this role ensures customers maximize the value of their investments across the UpToDate portfolio, including UpToDate, Lexidrug, Patient Engagement solutions, and future products and capabilities. The Customer Success AD develops and executes strategic success plans, leads executive-level engagement, and serves as the primary advocate for customer needs while helping customers achieve measurable clinical, operational, financial, and patient experience outcomes. Working in close partnership with Sales, Account Management, Product Management, Clinical teams, and Support, the Customer Success AD acts as the central orchestrator of the customer experience for assigned accounts. This role leverages deep healthcare industry knowledge, strong executive presence, and customer success expertise to strengthen strategic partnerships, drive portfolio adoption, identify opportunities for expanded value, and ensure long-term customer success. In addition, the Customer Success AD serves as a mentor and thought leader within the Customer Success organization, contributing best practices and helping advance the organization's customer-centric culture and capabilities. RESPONSIBILITIES Strategic Health System Partnership & Executive Engagement • Serve as the primary Customer Success leader for an assigned portfolio of the organization's largest, most strategic, and most complex health system customers. • Develop trusted relationships with executive, clinical, pharmacy, nursing, digital, operational, and administrative stakeholders across customer organizations. • Establish a deep understanding of each customer's strategic priorities, organizational goals, operational challenges, and clinical initiatives. • Lead executive business reviews, strategic planning sessions, and value realization discussions with senior customer stakeholders. • Act as a trusted advisor, helping customers leverage CDSP solutions to achieve meaningful clinical, financial, and patient experience outcomes. Portfolio Adoption & Value Realization • Drive adoption, utilization, and value realization across the full UpToDate portfolio, including UpToDate, Lexidrug, Patient Engagement solutions, and future products, packages, and capabilities. • Develop and execute comprehensive customer success plans aligned to customer goals and organizational priorities. • Identify opportunities to increase awareness, adoption, workflow integration, and strategic use of portfolio capabilities across the health system. • Partner with customer stakeholders to establish success metrics, monitor progress, and demonstrate measurable outcomes. • Proactively identify risks to adoption, engagement, customer outcomes, or long-term partnership success and develop mitigation strategies. Strategic Account Planning & Customer Success Execution • Develop and maintain detailed account strategies, stakeholder maps, success plans, and engagement plans for assigned health systems. • Coordinate customer success activities across multiple facilities, service lines, departments, and stakeholder groups within complex healthcare organizations. • Ensure customer objectives, risks, opportunities, and outcomes are documented and actively managed. • Leverage customer data, utilization trends, and health indicators to inform engagement strategies and recommendations. • Drive accountability for achieving customer-defined success outcomes and maximizing customer value. Commercial Partnership & Growth Enablement • Partner closely with Sales counterparts to support retention, renewal, and expansion opportunities within assigned accounts. • Provide strategic customer insights, adoption trends, executive relationship intelligence, and value realization metrics to inform account planning. • Collaborate on customer engagement strategies, executive meetings, and renewal preparation activities. • Identify opportunities for broader portfolio adoption and communicate customer needs and priorities to commercial partners. • Support account growth objectives by ensuring customers understand and realize value from current and emerging CDSP capabilities. Cross-Functional Leadership & Customer Advocacy • Serve as the voice of the customer by communicating customer priorities, challenges, feedback, and market trends to internal stakeholders. • Partner with Product Management, Clinical teams, Support, Marketing, and other functions to address customer needs and improve customer outcomes. • Lead coordination of resources and stakeholders necessary to support complex customer initiatives, escalations, and strategic opportunities. • Advocate for product enhancements, service improvements, and innovations that address customer challenges and advance customer success. • Support adoption of new products, capabilities, and strategic initiatives across assigned accounts. Thought Leadership & Organizational Influence • Serve as a subject matter expert and mentor within the Customer Success organization, sharing best practices and expertise related to strategic account management and customer value realization. • Contribute to the development of customer success methodologies, tools, processes, and engagement strategies. • Support onboarding and development of Customer Success Managers and Senior Customer Success Managers through coaching and knowledge sharing. • Participate in strategic initiatives that advance Customer Success capabilities and organizational objectives. • Represent Customer Success in cross-functional projects, customer advisory activities, and strategic business initiatives as appropriate. QUALIFICATIONS Education: Bachelor’s degree in related field, specialized training, or equivalent work experience. Experience: 6+ years of experience in Customer Success, Account Management, Product Marketing, or a related customer-facing role Other Knowledge, Skills, Abilities or Certifications: • Proven track record of influencing cross-functional partners (Sales, Product) without direct authority • Strong ability to engage directly with customers to understand workflows, challenges, and adoption behavior • Exceptional written and verbal communication skills, with the ability to: present to senior stakeholders; facilitate cross-functional alignment; clearly articulate tradeoffs and recommendations • Provider/healthcare segment expertise strongly preferred TRAVEL: Up to 40% of travel; as needed based on customer needs #LI-Hybrid Our Interview Practices To maintain a fair and genuine hiring process, we kindly ask that all candidates participate in interviews without the assistance of AI tools or external prompts. Our interview process is designed to assess your individual skills, experiences, and communication style. We value authenticity and want to ensure we’re getting to know you—not a digital assistant. To help maintain this integrity, we ask to remove virtual backgrounds and include in-person interviews in our hiring process. Please note that use of AI-generated responses or third-party support during interviews will be grounds for disqualification from the recruitment process. Applicants may be required to appear onsite at a Wolters Kluwer office as part of the recruitment process. Compensation: $122,300.00 - $218,550.00 USD This role is eligible for Bonus. Compensation range listed is based on primary location of the position. Actual base salary offer is influenced by a wide array of factors including but not limited to skills, experience and actual hiring location. Your recruiter can share more information about the specific offer for the job location during the hiring process. Additional Information : Wolters Kluwer offers a wide variety of competitive benefits and programs to help meet your needs and balance your work and personal life, including but not limited to: Medical, Dental, & Vision Plans, 401(k), FSA/HSA, Commuter Benefits, Tuition Assistance Plan, Vacation and Sick Time, and Paid Parental Leave. Full details of our benefits are available upon request.

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