Enterprise Sales Manager Interview Questions

Introduction

Hiring the right Enterprise Sales Manager in the Sales industry is critical: they drive high-value deals, build strategic accounts, and lead cross-functional collaboration. A structured interview process helps identify candidates who can grow revenue, manage complex sales cycles, and develop enterprise relationships.

This guide includes role-specific basic, intermediate, and advanced interview questions plus five targeted pre-screening one-way video prompts designed to help hiring teams screen efficiently and consistently.

Enterprise Sales Manager Interview Questions

Basic Enterprise Sales Manager Interview Questions

1. Describe your experience managing enterprise accounts. What industries and deal sizes have you handled?
2. Explain a typical enterprise sales cycle you’ve managed from lead to close.
3. How do you prioritize and manage your sales pipeline to meet quarterly quotas?
4. Which CRM and sales tools have you used and how do you use them to track opportunities?
5. Give an example of a time you turned around a stalled deal. What steps did you take?
6. How do you approach stakeholder mapping and identifying decision-makers in an organization?
7. Describe a negotiation you led. How did you balance price, terms, and value?
8. What metrics do you review weekly and monthly to assess territory performance?

Intermediate Enterprise Sales Manager Interview Questions

1. Walk me through your process for building a territory plan and setting realistic targets.
2. How do you forecast revenue for enterprise deals with long sales cycles?
3. Describe a time you collaborated with product or customer success to close a strategic account.
4. How do you qualify enterprise opportunities differently than mid-market or SMB deals?
5. Explain how you handle procurement or legal pushback during contract negotiations.
6. Tell me about a time you lost a key account. What did you learn and how did you respond?
7. How do you price value-based proposals for complex solutions?
8. Describe your approach to building and coaching a team of account executives or sales engineers.
9. How do you maintain executive-level relationships and secure executive sponsorship in target accounts?
10. What methods do you use to identify upsell and cross-sell opportunities within existing enterprise accounts?

Advanced Enterprise Sales Manager Interview Questions

1. Outline a go-to-market strategy you developed for entering a new vertical with enterprise offerings.
2. Describe a multi-million dollar deal you closed: what was your role, strategy, and the timeline?
3. How do you build financial models to evaluate deal structure, discounts, and long-term ARR impact?
4. Explain how you align sales, marketing, product, and customer success for a complex enterprise opportunity.
5. Describe a time you influenced pricing policy or contract terms at the company level to win enterprise business.
6. How do you manage global or multi-region accounts with differing procurement and regulatory requirements?
7. Walk through your approach to negotiating with procurement teams and managing compliance hurdles.
8. How do you scale enterprise sales processes while maintaining personalized selling for strategic accounts?
9. Explain how you measure and improve win rates across different segments and buyer personas.
10. Describe an innovative sales tactic you deployed to outmaneuver a larger competitor on a strategic deal.

Pre-Screening Video Interview Questions for Enterprise Sales Manager

Use these one-way video prompts to quickly evaluate communication, strategic thinking, and cultural fit. Each prompt is designed for a short recorded response and provides a clear evaluation focus for reviewers.

1. Question: Introduce yourself and summarize your most significant enterprise sales achievement in under 90 seconds.
   Evaluation: Look for clarity, concise achievement metrics (ARR, deal size), and the candidate’s ability to prioritize highlights.
2. Question: Describe a complex negotiation you led and the approach you used to reach agreement in 60–90 seconds.
   Evaluation: Assess negotiation framework, use of stakeholders, and evidence of value-based concessions rather than arbitrary discounting.
3. Question: Explain how you would approach selling our solution to a C-level executive at a Fortune 500 company in 60 seconds.
   Evaluation: Evaluate executive-level messaging, focus on business outcomes, and understanding of strategic value.
4. Question: Share how you coach or mentor a struggling account executive to improve performance in 60–90 seconds.
   Evaluation: Look for leadership style, measurable coaching actions, and emphasis on development and accountability.
5. Question: Provide a brief example of a time you used cross-functional influence to rescue or accelerate a deal (60–90 seconds).
   Evaluation: Assess collaboration skills, ability to marshal resources, and clarity on outcomes achieved.

Conclusion

This guide helps hiring teams evaluate Enterprise Sales Manager candidates across basic, intermediate, and advanced skills while enabling consistent screening decisions. Structured questions and targeted pre-screening prompts streamline assessment of sales experience, strategic thinking, and leadership.

ScreeningHive supports faster, more objective hiring with one-way video interviews, enabling teams to screen more candidates quickly and maintain standardised evaluations across hiring panels.