What is an Account Executive?

As an Account Executive at Glean, you are not just selling software; you are evangelizing a fundamental shift in how enterprises access and utilize their own knowledge. Glean’s AI-powered work assistant connects across a company’s entire ecosystem of apps, making you the primary driver for bringing this transformative technology to new customers. You will act as a strategic partner to IT leaders, CIOs, and business executives, helping them solve the critical problem of information fragmentation in the hybrid workplace.

This role places you at the intersection of cutting-edge Generative AI and complex enterprise sales. You will own the full sales cycle—from prospecting and discovery to negotiation and closing—for mid-market or enterprise accounts. Because Glean is a high-growth unicorn, your work directly impacts the company's revenue trajectory and market share. You are expected to navigate complex stakeholder maps, articulate technical value propositions, and manage deal cycles that can span several months.

Successful Account Executives at Glean are resilient, data-driven, and deeply curious. You will be joining a team that values high performance and collaboration, working alongside product and engineering teams to refine the market fit. This is a role for builders who want to define the playbook for selling AI in the enterprise, rather than just following an existing one.

Getting Ready for Your Interviews

Preparing for the Account Executive interview process at Glean requires a shift in mindset. You should view the process not just as a series of questions, but as a simulation of a live deal cycle. The hiring team is looking for consistency, strategic thinking, and the ability to navigate a multi-stage process with various stakeholders.

Key Evaluation Criteria:

• Complex Deal Management – You must demonstrate the ability to manage long, multi-stakeholder sales cycles. Interviewers will look for evidence that you can navigate procurement, legal, and security reviews while keeping deal momentum alive.
• Strategic Account Mapping – A critical part of the evaluation involves how you plan your territory. You need to show how you identify champions, map out decision-makers, and prioritize accounts based on propensity to buy.
• Coachability and Adaptability – Glean is evolving rapidly. You will be evaluated on your ability to take feedback during the interview process (especially during presentation rounds) and incorporate it immediately.
• Past Performance and Metrics – Generalizations will not work here. You need to know your numbers cold—quota attainment, average deal size, conversion rates, and pipeline generation statistics from your previous roles.

Interview Process Overview

The interview process for the Account Executive role at Glean is known to be rigorous and, at times, lengthy. Candidates have reported processes taking anywhere from 4 weeks to several months, involving nearly a dozen touchpoints in extreme cases. The company places a heavy emphasis on consensus, meaning you will likely meet with a wide range of team members, from peers and hiring managers to executive leadership like the VP of Sales or even the CRO.

While the process can sometimes feel unstructured depending on the specific territory or hiring manager, the core philosophy is to test your endurance and your ability to "sell" yourself internally. You should expect a mix of standard behavioral interviews and practical, hands-on simulations. The team is looking for candidates who can maintain professionalism and clarity even when the process becomes arduous or lacks immediate transparency.

The timeline above illustrates a typical flow, moving from initial screening into deep-dive practical rounds. Use this visual to manage your energy; the Account Mapping and Presentation stages are the most resource-intensive and often determine whether you advance to the executive rounds. Be prepared for gaps between stages and stay proactive in your follow-up, just as you would with a prospect.

Deep Dive into Evaluation Areas

To succeed, you must prepare thoroughly for the specific competencies Glean values. Based on candidate experiences, the evaluation is heavily weighted toward practical application of sales skills rather than just theoretical knowledge.

Strategic Account Mapping & Territory Plan

This is often the most critical practical step. You may be asked to walk through how you would attack a new territory or a specific set of named accounts.

• Why it matters: Glean sells a complex solution. Spray-and-pray tactics do not work. They need to see that you have a methodology for breaking into large organizations.
• How it is evaluated: You will likely have a dedicated session where you present a territory plan. Success looks like a detailed, data-backed strategy that identifies ideal customer profiles (ICPs) and entry points.

Be ready to go over:

• Targeting Methodology – How you prioritize accounts based on employee count, tech stack, and industry.
• Stakeholder Analysis – Identifying the Economic Buyer vs. the Technical Champion.
• Outbound Strategy – Your specific plan for generating pipeline (cold calls, emails, social selling) independent of marketing leads.

The "Pitch" and Presentation

You will almost certainly face a presentation round. This is often a mock discovery call or a solution pitch to a panel acting as a customer.

• Why it matters: You are the face of the company. Your ability to articulate the value of AI search clearly and concisely is paramount.
• How it is evaluated: The panel will assess your discovery skills, your ability to handle objections, and your command of the room.

Be ready to go over:

• Value Proposition – explaining "Why Glean?" without getting bogged down in technical jargon.
• Objection Handling – Managing concerns about data privacy, security, and AI hallucinations.
• Closing Skills – Moving the meeting to the next concrete step (e.g., a POV or technical validation).

Past Performance & Deal Autopsy

Expect deep scrutiny of your resume and past deals. This is not just about "what" you sold, but "how" you sold it.

• Why it matters: Past behavior predicts future success. They want to verify that your success was due to your skill, not just a lucky territory or a booming market.
• How it is evaluated: Interviewers, often including the VP or CRO, will drill down into specific deals.

Be ready to go over:

• Deal Deconstruction – Walking through a specific closed-won deal from lead to close.
• Loss Analysis – Discussing a deal you lost, why you lost it, and what you learned.
• Metrics – Exact figures on your quota attainment, year-over-year growth, and pipeline coverage ratios.

The word cloud above highlights the most frequent concepts discussed in Glean interviews. Notice the prominence of "Performance," "Cycle," "SaaS," and "Mapping." This indicates that while culture is important, your technical sales acumen and ability to execute a rigorous sales process are the primary drivers for a hiring decision.

Key Responsibilities

As an Account Executive, your daily work revolves around driving revenue through strategic hunting and consultative selling. You are responsible for building your own pipeline, meaning you cannot rely solely on inbound leads. You will spend a significant portion of your time prospecting, conducting high-level discovery calls, and demonstrating the Glean platform to diverse audiences ranging from IT Directors to C-level executives.

Collaboration is central to this role. You will work closely with Sales Engineering to manage technical validations and security reviews, which are major hurdles in the enterprise AI sales cycle. You will also interface with the Product team to relay customer feedback and with Marketing to refine messaging. You are expected to manage the entire commercial negotiation process, including pricing, contract terms, and procurement navigation, ensuring deals close within forecasted timelines.

Role Requirements & Qualifications

To be competitive for this position, you need a specific blend of experience and soft skills. Glean targets top-tier talent who can operate autonomously.

Must-Have Qualifications:

• Proven SaaS Sales Experience: Typically 4+ years of closing experience, specifically in B2B SaaS. Experience selling to IT or Engineering stakeholders is highly preferred.
• Full Cycle Management: Demonstrated ability to source, manage, and close complex deals with average contract values (ACV) in the mid-market to enterprise range.
• Track Record of Success: Consistent over-achievement of quota (e.g., President’s Club, top 10% rankings).
• Strategic Thinking: Experience with territory planning, account mapping, and "land and expand" strategies.

Nice-to-Have Skills:

• Domain Knowledge: Familiarity with Enterprise Search, Knowledge Management, or Generative AI landscapes.
• Start-up Experience: Previous success in a high-growth, Series B-D environment where processes were still being defined.
• Technical Aptitude: Ability to understand and explain complex API integrations or security architectures at a high level.

Common Interview Questions

The following questions are representative of what you might face. They are designed to test your sales methodology, resilience, and cultural alignment.

Sales Acumen & Strategy

• "Walk me through the most complex deal you have ever closed. What were the hurdles, and how did you overcome them?"
• "How do you approach a brand new territory where nobody knows who you are?"
• "Describe your process for account mapping. How do you identify the economic buyer?"
• "If you are behind on your quarterly number with one month to go, what is your recovery plan?"

Behavioral & Culture

• "Tell me about a time you had a conflict with a Sales Engineer or Product Manager. How did you resolve it?"
• "Glean is growing fast and things change quickly. Give me an example of how you adapted to a sudden change in strategy at your last company."
• "Why do you want to sell this specific product? Why Glean?"

Practical Scenarios

• "Pitch Glean to me as if I am a CIO who is skeptical about AI security."
• "Here is a list of target accounts. Which one do you call first and why?"
• "You have a champion who loves the product, but the CFO has frozen the budget. How do you unblock this deal?"

These questions are based on real interview experiences from candidates who interviewed at this company. You can practice answering them interactively on Dataford to better prepare for your interview.

Frequently Asked Questions

Q: How long does the interview process typically take? The process can be lengthy, often spanning 4 to 6 weeks, and sometimes longer if scheduling with executive leadership is difficult. Candidates have reported gaps between rounds, so patience and persistent (but professional) follow-up are key.

Q: Is this role remote or hybrid? Expectations vary by location, but Glean generally values in-person collaboration. For hubs like Toronto or Sydney, there is often a hybrid expectation. You should clarify the specific in-office requirements for your target location during the recruiter screen.

Q: How technical do I need to be? You do not need to be an engineer, but you must be "technically fluent." You are selling an AI product to IT leaders; you need to be comfortable discussing concepts like data privacy, integrations, and the general architecture of enterprise search.

Q: What is the culture of the sales team? The culture is described as high-performance and collaborative but intense. It is a team of "builders" who are expected to figure things out without a perfect playbook.

Q: Is the compensation competitive? While Glean is a top-tier unicorn, some candidates have reported offers coming in lower than expected or "under-market" relative to the rigorous interview process. Be prepared to negotiate and have clear data on your market value.

Other General Tips

• Be the "CEO" of your Interview Process: Given reports of a sometimes unstructured or "confusing" process, take ownership. Ask for next steps at the end of every call, and send high-quality follow-up emails that summarize value and address any concerns.
• Know Your "Why": You will likely speak to the VP or CRO. They want to know why you are passionate about Glean specifically. Generic answers about "liking AI" won't cut it. Connect your personal career goals to Glean's mission.
• Prepare for the Long Haul: Do not get discouraged if the process drags on. Use the time to build rapport with your recruiter, who can be your internal champion.
• Quantify Everything: When discussing past performance, avoid vague terms like "great year." Use percentages, dollar amounts, and specific timelines.

Summary & Next Steps

The Account Executive role at Glean represents a career-defining opportunity to sell one of the most relevant technologies of our time. You will be challenged to sell strategically, think critically, and operate at a high velocity. While the interview process is rigorous and demands significant preparation, it is designed to ensure that you have the resilience and skill set to thrive in a complex enterprise environment.

To succeed, focus your preparation on account mapping, deal mechanics, and value selling. Treat every interview step as a sales meeting where you are the product. Demonstrate that you can navigate ambiguity, manage multiple stakeholders, and close the deal—starting with your own job offer.

When reviewing compensation data, remember that Glean is a pre-IPO unicorn. Equity is a significant component of the total package. While base salary is important, evaluate the potential upside of the stock options, as this is often where the long-term value lies in a role of this caliber. Negotiate based on the total compensation value, not just the cash component.