What you should know about Enterprise Sales
+AEs talking about how they use ChatGPT
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One of the first internal conversations I had was with a veteran enterprise AE (account executive). I was a new SDR and was curious what it was like being an AE. I will never forget what he told me; it shocked me.
He said, “If I were to do it all over again, I’d be a commercial account executive.” I was confused by his answer. I thought the high salary, the title, and the role were something to aspire to, but after talking with him, he shared that it might not be all that it seemed.
As a former enterprise sales development representative (SDR) and now in a role that supports enterprise account executives (AEs), I can say that there are several key considerations to keep in mind before pursuing this AE role over another. That high salary may not be as worth it as it seems.
We will examine the key differences between commercial, mid-market, and enterprise account executives.
I’m glad I spoke to this peer, and I remember what he said, more importantly, why he said it. This is not meant to deter you from becoming an enterprise Account Executive (AE), but rather to provide a realistic view of what to expect and what it takes to succeed in that role compared to other AE roles.
You might find that a commercial or mid-market AE role is better suited for your temperament, and it may put you in a better position to hit your quota consistently.
1. Core Responsibilities of an Enterprise Account Executive
Longer Sales Cycles
Deals often take 6–18 months to close.
You'll have to manage more complex buying groups with multiple stakeholders (often 6–10+ people).
Larger Deal Sizes
Average contract values (ACV) often range from $100K to multi-million dollars.
Pricing is usually custom and negotiated (not fixed packages).
Account Strategy & Planning
Enterprise AEs often own a few strategic accounts rather than many accounts.
You’ll create deep account plans and multi-thread relationships within organizations.
Cross-Functional Collaboration
Regularly work with Sales Engineers (SEs), Customer Success Managers (CSMs), Product Managers, Legal, and Finance.
You will often align internal teams to support large, strategic deals.
Executive Presence & Communication
You’ll be expected to sell to senior decision-makers (CIOs, CROs, CFOs, VPs).
You’ll need to be able to present business cases, articulate ROI, and handle high-level objections is crucial.
2. Key Differences: Enterprise AE vs. Commercial / Mid-Market AE
3. Skills You Need to Succeed in Enterprise Sales
I’ve learned enterprise deals aren’t won just because you’re likable or good at demos. What really moves the needle is your ability to think strategically. You need to see the bigger picture. That means mapping out accounts, identifying all the key players, and building relationships on multiple levels.
Your discovery game has to be top tier. You’re not just asking surface-level questions, you’re digging deep to uncover pain across different departments and aligning your solution to multiple agendas. Frameworks like MEDDICC or the Challenger Sale aren’t just buzzwords here; they’re essential tools in your kit.
Business acumen is huge, too. Can you have a real conversation with a CFO about ROI or total cost of ownership? Can you position your solution as a business case, not just a tech purchase?
And then there’s the politics. Large enterprises come with layers of decision-makers, influencers, and blockers. You need to be able to navigate all of that, keep momentum going, and build consensus across the board.
Enterprise sales is a thinking person’s game. It’s less about being fast and flashy, and more about being deliberate, credible, and ridiculously well-prepared.
4. How to Prepare for an Enterprise AE Role
Work your way up from SMB or Mid-Market AE roles.
Get experience with longer deal cycles and complex stakeholders.
Master discovery, executive communication, and value selling.
Study sales methodologies like MEDDICC or Challenger.
Understand industry-specific challenges in your territory (e.g., selling to banks is very different from retail).
As a high achiever and former athlete, my desire is to be the best at what I do and give it my all. If you played sports, you might relate. In tech sales, that’s leadership or an enterprise AE, so I thought. However, after that conversation, I mentioned it got me thinking about what was important to me.
Some key questions to ask yourself as you are mapping out your career in tech sales:
How comfortable am I with long sales cycles?
How comfortable am I with delayed gratification?
How well am I at quarterbacking a deal?
Do I enjoy complexity and problem-solving?
How is my business acumen, not just my product knowledge?
Do I enjoy cross-functional collaboration?
Am I ok with fewer, bigger deals?
How much autonomy do I want in my role?
Do you prefer a high-touch team environment or a more lone-wolf?
Make sure to consider what you want, your personality, and your peace as you pave your career path. Be open to pivoting and change. Talk to others and network internally.
There are often more people than you think willing to share their experiences with you.
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Until next time,
Tajh
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Account Executive (SaaS), GeneMetrics, Inc
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