Betts Recruiting

Dive into our latest 2025 Enterprise Compensation Guide.

BLOG

Key Questions to Ask When Hiring an Enterprise Account Executive

The Betts Team
June 20, 2025

Finding the right Enterprise Account Executive (EAE) is a major step for tech companies looking to sell to larger clients. Compared to standard Account Executives (AEs), EAEs typically have both more and much more specific types of experience that make them a better fit for the challenges of selling into enterprise-sized accounts. However, this also makes it more difficult to source and hire unicorn candidates in a competitive market, where such talent is limited and in high demand among SaaS startups and enterprises alike. 

In this blog, we will explore the essential questions to ask when interviewing EAE candidates, divided into two categories: questions about past job experience and responsibilities, and situational questions that reveal how candidates think and operate when faced with complex enterprise sales challenges.

What is an Enterprise Account Executive?

Enterprise Account Executives are senior-level professionals with typically at least 4 years of experience in sales, with significant knowledge and expertise earned through speaking directly to decision-makers in larger companies. They know how to speak the language of the C-suite, cutting through noise to bridge the gap between operational and technical value for SaaS solutions. Collaborating with Sales Engineers (SEs) and product teams, EAEs work to build lasting relationships with enterprise leaders and managers that enable them to quickly spot key pain points and provide resolution for these challenges.

You should consider hiring an Enterprise Account Executive when:

  • Your company is ready to target larger accounts with deal sizes of $250K+
  • Your sales cycle has become more complex and involves multiple stakeholders
  • You need someone who can effectively engage with executive-level decision-makers
  • Your product requires a more consultative, solution-based selling approach
  • You’re looking to establish a strategic enterprise presence in your market

To learn more about enterprise-specific go-to-market (GTM) roles and see our top talent acquisition recommendations for sourcing your best-fit candidates, check out our new Betts Enterprise Compensation Guide.

Questions About Past Experience and Responsibilities

These questions help you assess the candidate’s experience with enterprise-level sales and their ability to manage the responsibilities specific to the EAE role:

  1. Enterprise Sales Experience: Ask the candidate to describe their sales experience in the enterprise market in detail. Have them outline the industries they have worked with, typical company sizes and annual revenue ranges. Inquire about how many enterprise-size accounts they managed simultaneously and the depth of relationships they built. 
  2. C-Suite Engagement: Explore the candidate’s experience with C-level executives and their approach to these high-stakes interactions. Have them walk through their preparation process, conversation strategies and follow-up protocols. Ask for specific examples of C-suite meetings they have led and what outcomes they achieved. 
  3. Enterprise Deal Structure: Probe into the complexity and size of deals the candidate has managed. Have them describe their largest closed enterprise deal, including the financial details, number of stakeholders involved and the approval process they navigated. Ask about the typical contract terms they have negotiated and any custom elements they have incorporated for enterprise clients. 
  4. Long-Term Sales: Enterprise sales cycles often extend 6 to 18 months, so understanding how candidates manage these lengthy processes is crucial. Ask about their strategies for maintaining momentum, establishing milestones and keeping stakeholders engaged throughout extended sales cycles. Inquire about specific tools or processes they use to track long-term opportunities. 
  5. Technical Team Collaboration: Learn how the candidate partners with other GTM teams, including Sales Engineers or Enterprise Customer Success Managers (ECSMs). Have them describe their collaborative approach, how they align support resources with customer needs, and their process for managing pre-sales technical validation. Ask for examples of complex deals where they successfully orchestrated cross-departmental support. 
  6. Enterprise Territory Strategy: Explore how the candidate approaches enterprise territory development and account selection. Ask them to outline their research methods, prioritization criteria, and strategic planning process for territory management. Inquire about how they balance account expansion with new logo acquisition. 
  7. Technical Depth Application: While EAEs do not need the same knowledge as Sales Engineers, they do need sufficient technical understanding to be credible with enterprise-level buyers. Ask the candidate to explain how they have developed their product knowledge, and how they have applied it towards enterprise sales specifically. Have them describe a scenario where their technical understanding was critical to winning a deal. 
  8. Stakeholder Management: Enterprise deals typically involve numerous decision-makers across different departments. Ask the candidate how they identify key stakeholders, map their influence and manage conflicting priorities. Have them share examples of deals where they successfully aligned diverse stakeholders with different objectives. 

Situational Questions

These questions present scenarios specific to enterprise sales to evaluate how candidates would respond to challenges they are likely to encounter as an EAE:

  1. First Hire Scenario: Present a scenario where the candidate would be the company’s first enterprise sales hire, transitioning from a primarily mid-market focus. Ask them to outline their 90-day plan for establishing enterprise selling processes, developing necessary collateral, and setting realistic pipeline expectations when no enterprise foundation exists.
  2. Account Scaling: Present a scenario where the candidate has just closed an initial enterprise deal with significant expansion potential. Ask them to outline their approach to developing and executing an account growth strategy, including how they would identify expansion opportunities, build additional relationships, and create a multi-year account plan. 
  3. Security Concerns: Maintaining security and compliance often become major concerns in enterprise-level SaaS deals. Ask the candidate to describe how they would handle pushback from a prospect’s IT team, including how they would involve technical support, what documentation they would prepare and how they would address cybersecurity requirements. 
  4. Competitive Displacement: Inquire about the candidate’s approach to displacing entrenched competitors in enterprise accounts. Have them outline their competitive strategy, including how they would identify points of dissatisfaction, position your solution’s advantages and overcome the inherent risk aversion that favors incumbents. 
  5. Industry-Specific Compliance: Describe a situation selling to a highly regulated industry (healthcare, financial services, etc.) where the prospect has extensive compliance requirements not yet addressed in your documentation. Have the candidate explain how they would collaborate with product, legal, and security teams to overcome these barriers while maintaining deal momentum.
  6. Deal Revival: Present a scenario where a promising enterprise deal has stalled after months of work. Ask the candidate to walk through their diagnostic process for understanding the blockage, their strategy for re-engaging decision-makers and their approach to getting the opportunity back on track. 
  7. Procurement Navigation: Ask the candidate to outline their approach to navigating complex procurement processes typical of large enterprises. Have them describe strategies for maintaining deal momentum through legal review, mitigating discount pressure from procurement, and securing favorable terms. 
  8. Post-Sale Engagement: Inquire about the candidate’s approach to post-sale customer engagement. Have them outline their 90-day plan following a major enterprise deal closure, including how they would ensure implementation success, identify expansion opportunities, and build additional relationships. 

Finding Your Next Enterprise Account Executive with Betts

An Enterprise Account Executive is a critical addition to your GTM team when you are looking to target enterprise-level clients, but hiring your right-fit candidate is its own challenge. Betts Recruiting will help you track down your unicorn EAE leveraging our experience and expertise in tech talent acquisition, allowing you to source as many new hires as you need at scale.
Contact Betts here to learn how we can help you find the Enterprise Account Executive who will drive your enterprise sales strategy forward.