Essential Work Samples for Hiring Top Enterprise Sales Managers

Enterprise sales management requires a unique blend of leadership, strategic thinking, and sales acumen. The best enterprise sales managers excel at coaching their teams, developing strategic account plans, managing complex sales cycles, and building relationships with key stakeholders at large organizations. However, traditional interviews often fail to reveal whether candidates truly possess these critical capabilities.

Work samples and role plays provide a window into how candidates will actually perform in real-world scenarios they'll face daily. By observing candidates in action, hiring teams can assess their practical skills, problem-solving approaches, and ability to adapt to feedback—all crucial indicators of future success in an enterprise sales management role.

For enterprise sales managers specifically, these exercises help evaluate a candidate's ability to coach representatives effectively, develop strategic account plans, manage complex pipelines, and navigate challenging client situations. These skills are difficult to assess through standard interview questions but become readily apparent when candidates engage in realistic simulations.

Implementing the following work samples will dramatically improve your ability to identify candidates who can truly drive enterprise sales performance. Each exercise is designed to evaluate specific competencies essential for success in enterprise account management, providing a comprehensive assessment of each candidate's capabilities.

Activity #1: Sales Call Coaching Role Play

This exercise evaluates a candidate's ability to provide effective coaching to sales representatives, a critical skill for any sales manager. The best enterprise sales managers can quickly identify areas for improvement in sales calls and provide actionable feedback that helps their team close more deals.

Directions for the Company:

• Prepare a recording of a mock sales call between a sales representative and an enterprise prospect. The call should include both strengths and clear areas for improvement (e.g., failing to uncover business pain, not addressing objections effectively, missing upsell opportunities).
• Share the recording with the candidate 24 hours before the interview, along with context about the deal (prospect company size, industry, current stage in the sales cycle).
• Ask the candidate to prepare to conduct a 15-minute coaching session with the sales representative (role-played by an interviewer).
• Provide a brief on the "sales rep's" personality and experience level to make the role play more realistic.

Directions for the Candidate:

• Review the sales call recording and identify 2-3 key strengths and 2-3 areas for improvement.
• Prepare to conduct a 15-minute coaching session with the sales representative.
• Focus on providing specific, actionable feedback that would help the representative improve future calls.
• Be prepared to demonstrate coaching techniques that would be effective for this particular representative.
• Structure your coaching session as you would in a real work environment.

Feedback Mechanism:

• After the coaching session, the interviewer should provide feedback on one aspect the candidate handled well and one area for improvement.
• Give the candidate 5 minutes to incorporate the feedback and demonstrate how they would adjust their coaching approach based on this input.
• Observe how receptive the candidate is to feedback and how effectively they implement it.

Activity #2: Strategic Account Planning Exercise

This exercise assesses a candidate's ability to develop comprehensive account strategies for enterprise clients—a fundamental responsibility for enterprise sales managers. It reveals their strategic thinking, resource allocation skills, and understanding of enterprise sales dynamics.

Directions for the Company:

• Create a fictional enterprise account profile including company information, current product usage, organizational structure, key stakeholders, and business challenges.
• Include information about the competitive landscape and any existing relationships.
• Provide the candidate with this information 24 hours before the interview.
• Prepare a template for the strategic account plan that aligns with your company's approach.

Directions for the Candidate:

• Review the enterprise account information provided.
• Develop a 12-month strategic account plan that includes:
• Key objectives and growth opportunities
• Stakeholder mapping and engagement strategy
• Potential obstacles and mitigation plans
• Cross-sell/upsell opportunities
• Required resources and timeline
• Prepare a 15-minute presentation of your strategic account plan.
• Be ready to explain your rationale for prioritizing specific opportunities and approaches.

Feedback Mechanism:

• After the presentation, provide feedback on one strength of the strategic plan and one area that could be improved.
• Ask the candidate to spend 5 minutes revising one section of their plan based on the feedback.
• Evaluate how the candidate incorporates the feedback and whether they can quickly adapt their strategic thinking.

Activity #3: Pipeline Review and Forecasting Simulation

This exercise evaluates a candidate's ability to analyze sales data, identify risks and opportunities in the pipeline, and make accurate forecasts—essential skills for enterprise sales managers who must deliver predictable results.

Directions for the Company:

• Create a mock sales pipeline report for an enterprise sales team with 5-7 representatives.
• Include 15-20 opportunities at various stages with details such as deal size, probability, next steps, and close dates.
• Intentionally include some deals with red flags (stalled deals, unrealistic close dates, missing decision makers).
• Provide historical win rate data by stage and representative.
• Share this information with the candidate 24 hours before the interview.

Directions for the Candidate:

• Review the pipeline data provided.
• Prepare a 15-minute pipeline review meeting as if you were meeting with your sales leadership.
• Your presentation should include:
• An assessment of the overall pipeline health
• A forecast for the current quarter with confidence level
• Identification of 3-5 key deals that need attention
• Specific actions you would take to improve pipeline health
• Recommendations for individual representatives based on their performance data
• Be prepared to explain your forecasting methodology and how you identified risks.

Feedback Mechanism:

• After the presentation, provide feedback on one aspect the candidate handled well and one area for improvement.
• Ask the candidate to spend 5 minutes adjusting their forecast or risk mitigation plan based on the feedback.
• Evaluate how the candidate incorporates new perspectives and whether they can defend or adapt their analysis appropriately.

Activity #4: Enterprise Client Escalation Role Play

This exercise assesses a candidate's ability to handle complex client situations and navigate challenging conversations—critical skills for enterprise sales managers who often need to step in to resolve issues with high-value accounts.

Directions for the Company:

• Create a scenario involving an escalation from a significant enterprise client (e.g., implementation delays, product issues, or misaligned expectations).
• Provide background information including the client's history, the specific issue, stakeholders involved, and business impact.
• Include any relevant internal complications (e.g., resource constraints, competing priorities).
• Share this information with the candidate 24 hours before the interview.
• Select an interviewer to play the role of the frustrated client executive.

Directions for the Candidate:

• Review the client escalation scenario provided.
• Prepare for a 15-minute call with the client executive to address their concerns.
• Develop a plan that includes:
• How you'll approach the conversation
• Key questions you need to ask
• Potential solutions you might propose
• Next steps to resolve the situation
• During the role play, demonstrate your ability to listen effectively, show empathy, maintain the relationship, and work toward a resolution.

Feedback Mechanism:

• After the role play, provide feedback on one aspect the candidate handled well and one area for improvement.
• Give the candidate 5 minutes to reflect on how they would adjust their approach based on the feedback.
• Ask them to briefly demonstrate how they would handle a specific part of the conversation differently.
• Evaluate their receptiveness to feedback and ability to adapt their communication style.

Frequently Asked Questions

How long should we allocate for each work sample exercise?

Each exercise should be allocated approximately 30 minutes: 15 minutes for the candidate's presentation or role play, 5 minutes for feedback, 5 minutes for the candidate to incorporate feedback, and 5 minutes for wrap-up discussion. This timeframe allows for a thorough assessment while respecting everyone's time.

Should we conduct all four exercises with every candidate?

While using all four exercises provides the most comprehensive assessment, you can select the 2-3 most relevant to your specific needs if time is limited. The coaching role play and strategic account planning exercises are particularly revealing for enterprise sales management roles and should be prioritized.

How should we evaluate candidates across multiple exercises?

Create a scorecard that breaks down each exercise into specific competencies (e.g., strategic thinking, coaching ability, analytical skills). Have interviewers score candidates on each competency immediately after the exercise, before discussing with others, to avoid groupthink and recency bias.

What if a candidate has limited experience with our specific industry?

Focus your evaluation on the candidate's approach and process rather than industry-specific knowledge. Strong enterprise sales managers can apply their skills across industries. You can provide additional industry context in the pre-exercise materials to level the playing field.

How much preparation time should we give candidates?

Providing materials 24 hours in advance is recommended for these exercises. This allows candidates to prepare thoughtfully while still demonstrating their ability to analyze information and develop strategies efficiently—skills they'll need in the role.

Can these exercises be conducted virtually?

Yes, all of these exercises can be adapted for virtual interviews. For role plays, use video conferencing. For presentations and planning exercises, have candidates share their screen. Virtual formats may actually better reflect the remote selling environment many enterprise sales managers now operate in.

Implementing these work samples will significantly improve your ability to identify sales managers who can drive enterprise account growth and develop high-performing teams. By observing candidates in action through these realistic scenarios, you'll gain insights that traditional interviews simply cannot provide.

For more resources to enhance your hiring process, explore Yardstick's comprehensive tools for creating AI-powered job descriptions, generating targeted interview questions, and developing complete interview guides. These resources can help you build a systematic approach to identifying and hiring exceptional enterprise sales management talent.

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