Essential Work Sample Exercises for Hiring Top Digital Customer Success Managers

In the competitive landscape of SaaS and technology companies, Digital Customer Success Managers (DCSMs) serve as the critical bridge between your product and your customers' success. These professionals don't just respond to customer needs—they proactively drive adoption, retention, and growth through strategic guidance and relationship management. Finding the right DCSM can dramatically impact your customer satisfaction metrics, renewal rates, and ultimately, your bottom line.

Traditional interviews often fail to reveal how candidates will actually perform in real-world customer success scenarios. While resumes and behavioral questions provide valuable context, they don't demonstrate a candidate's ability to navigate complex customer interactions, analyze usage data, or communicate product value effectively. This is where well-designed work samples become invaluable.

Work samples for DCSM candidates should evaluate their ability to build relationships, demonstrate product expertise, analyze customer health metrics, and identify growth opportunities. By observing candidates in action through realistic scenarios, you gain insight into their communication style, strategic thinking, problem-solving approach, and ability to balance customer advocacy with business objectives.

The following four work sample exercises are specifically designed to assess the core competencies required for Digital Customer Success Manager excellence. Each activity simulates a real-world challenge DCSMs face regularly, allowing you to evaluate candidates based on actual performance rather than self-reported abilities. By incorporating these exercises into your hiring process, you'll be able to identify candidates who not only understand customer success principles but can execute them effectively in your specific business context.

Activity #1: Customer Onboarding Strategy Session

This exercise evaluates a candidate's ability to establish rapport, understand customer needs, and create a strategic plan for successful product adoption. Effective onboarding is crucial for long-term customer success, making this skill essential for any DCSM.

Directions for the Company:

• Create a fictional customer profile including company size, industry, business goals, and specific challenges they hope your product will solve.
• Provide the candidate with basic information about your product's features, benefits, and typical implementation timeline.
• Assign a team member to role-play as the customer's primary point of contact (ideally someone familiar with common customer questions and concerns).
• Allow 20-25 minutes for the exercise, followed by 5-10 minutes for feedback.
• Evaluate the candidate on their ability to ask insightful questions, tailor the onboarding approach to specific needs, and set clear expectations and next steps.

Directions for the Candidate:

• Review the customer profile and product information provided.
• Prepare for and conduct a 20-minute initial onboarding call with the customer.
• Your goals are to:
• Build rapport and establish a foundation for a strong working relationship
• Understand the customer's specific goals and success metrics
• Outline a tailored onboarding plan with clear milestones and timelines
• Address any initial questions or concerns
• Set expectations for ongoing communication and support
• Conclude the call with clear next steps and action items for both parties.

Feedback Mechanism:

• The interviewer should provide specific feedback on one aspect the candidate handled particularly well (e.g., "I appreciated how you connected our product features directly to the customer's stated business goals").
• The interviewer should also provide one piece of constructive feedback (e.g., "You could improve how you set expectations around implementation timeline").
• Give the candidate 2-3 minutes to respond to the feedback and explain how they would adjust their approach based on this input.

Activity #2: Customer Health Analysis and Action Planning

This exercise assesses a candidate's analytical abilities and strategic thinking in identifying at-risk accounts and developing intervention plans. Data-driven customer success management is essential for proactive relationship management and churn prevention.

Directions for the Company:

• Create a mock customer health dashboard for 5-7 accounts showing metrics such as:
• Product usage frequency and depth
• Feature adoption rates
• Support ticket volume and resolution times
• NPS or satisfaction scores
• Days since last login
• Contract renewal date (including some approaching renewal)
• Include a mix of healthy, at-risk, and declining accounts.
• Provide brief context about each customer's industry, size, and initial goals.
• Allow 30 minutes for analysis and action plan development.

Directions for the Candidate:

• Review the customer health dashboard and supporting information.
• Identify which accounts are at risk and why, prioritizing them based on both risk level and strategic importance.
• For the two highest-priority accounts, develop detailed action plans including:
• Specific interventions to address identified issues
• Key stakeholders to engage
• Timeline for implementation
• Success metrics to track improvement
• Prepare a brief (5-minute) presentation of your analysis and recommendations.
• Be prepared to explain your prioritization methodology and rationale for proposed interventions.

Feedback Mechanism:

• The interviewer should highlight one strength in the candidate's analytical approach or strategic recommendations.
• The interviewer should provide one area for improvement regarding either the analysis or action planning.
• Ask the candidate to revise one element of their action plan based on the feedback, allowing 5 minutes for this adjustment.

Activity #3: Escalation Management Role Play

This exercise evaluates a candidate's ability to handle difficult customer situations, demonstrate empathy, and resolve issues while maintaining the relationship. Effective escalation management is critical for customer retention and satisfaction.

Directions for the Company:

• Create a scenario involving a frustrated customer experiencing a significant issue with your product (e.g., unexpected downtime, missing functionality, or implementation challenges).
• Provide context about the customer's history, importance to your business, and specific complaint.
• Assign a team member to role-play as the frustrated customer, with clear guidance on their specific concerns and emotional state.
• Allow 15-20 minutes for the role play, followed by 10 minutes for discussion and feedback.
• Evaluate the candidate on their ability to demonstrate empathy, take ownership, propose solutions, and maintain a professional demeanor under pressure.

Directions for the Candidate:

• Review the customer situation and any relevant background information.
• Conduct a call with the frustrated customer with the goals of:
• Acknowledging their concerns and demonstrating genuine empathy
• Gathering any additional information needed to understand the full scope of the issue
• Taking ownership of the problem and providing clear next steps
• De-escalating the situation while maintaining a professional relationship
• Setting appropriate expectations for resolution
• Be prepared to handle unexpected objections or emotional responses during the conversation.

Feedback Mechanism:

• The interviewer should provide specific feedback on one aspect the candidate handled effectively (e.g., "Your empathetic response to the customer's frustration helped de-escalate the situation").
• The interviewer should also provide one piece of constructive feedback (e.g., "You could have been more specific about the timeline for resolution").
• Give the candidate an opportunity to respond to a follow-up question from the customer based on the feedback received, demonstrating how they would incorporate the guidance.

Activity #4: Expansion Opportunity Identification and Presentation

This exercise assesses a candidate's ability to identify upsell/cross-sell opportunities and effectively communicate additional value to customers. Driving revenue growth through existing accounts is a key responsibility for DCSMs.

Directions for the Company:

• Create a profile of an existing customer including:
• Current product usage and adoption metrics
• Business goals and challenges
• Organizational structure and key stakeholders
• Current contract details (products purchased, pricing tier, etc.)
• Provide information about your full product suite, including features/modules not currently utilized by this customer.
• Allow 30 minutes for preparation and 15 minutes for the presentation.
• Assign team members to role-play as customer stakeholders who will ask questions following the presentation.

Directions for the Candidate:

• Review the customer profile and product information provided.
• Identify 2-3 expansion opportunities (upsell, cross-sell, or additional user licenses) that align with the customer's business goals.
• Prepare a 10-minute presentation for the customer that:
• Demonstrates understanding of their current situation and challenges
• Clearly articulates the value proposition of the additional products/services
• Provides specific examples of how these additions will address their needs
• Includes implementation considerations and timeline
• Presents a clear ROI case for the investment
• Deliver your presentation and be prepared to answer questions from the customer stakeholders.

Feedback Mechanism:

• The interviewer should highlight one strength in the candidate's value proposition or presentation approach.
• The interviewer should provide one piece of constructive feedback regarding either the opportunity identification or communication of value.
• Ask the candidate to revise their ROI justification based on the feedback, allowing 5 minutes to strengthen this aspect of their presentation.

Frequently Asked Questions

How long should we allocate for these work sample exercises?

Each exercise requires approximately 45-60 minutes total, including preparation, execution, and feedback. We recommend conducting no more than two exercises in a single interview session to prevent candidate fatigue. For senior DCSM roles, you might consider spreading the exercises across multiple interview stages.

Should we use our actual product for these exercises?

While using your actual product creates the most realistic scenario, it may not be necessary or practical. You can create simplified versions of your product information or use generic SaaS product descriptions. The key is ensuring the exercises assess the core competencies required for success in your specific DCSM role.

How should we evaluate candidates who have limited experience with our specific industry?

Focus on transferable skills rather than industry-specific knowledge. A strong candidate should demonstrate excellent communication, analytical thinking, and customer relationship management regardless of their industry background. Technical product knowledge can be taught, but core customer success competencies are harder to develop.

Can these exercises be conducted remotely?

Yes, all of these exercises can be adapted for remote interviews using video conferencing tools. For the data analysis exercise, you can share documents in advance or use screen sharing. Role plays work effectively via video call, often closely mimicking how DCSMs actually interact with customers in today's digital environment.

How should we weight these exercises compared to traditional interview questions?

Work samples typically provide more predictive insights into job performance than traditional interviews alone. We recommend giving these exercises significant weight (40-60%) in your overall evaluation, complemented by behavioral interviews that assess cultural fit and past experiences.

Should we provide feedback during the actual interview process?

Yes, the feedback component is crucial for assessing a candidate's coachability and adaptability. However, keep the feedback constructive and focused on one specific area for improvement rather than providing a comprehensive critique during the interview.

Finding the right Digital Customer Success Manager requires evaluating both technical skills and interpersonal abilities in realistic scenarios. By incorporating these work samples into your hiring process, you'll gain deeper insights into how candidates will actually perform in this critical customer-facing role. Remember that the best DCSMs combine analytical thinking with exceptional communication skills and a genuine passion for customer success.

For more resources to enhance your hiring process, check out Yardstick's AI Job Description Generator, AI Interview Question Generator, and AI Interview Guide Generator. You can also view the complete Digital Customer Success Manager job description that inspired these work samples.

Ready to build a complete interview guide for this role? Sign up for a free Yardstick account