How to Get Promoted Into a $300K+ Tech Sales Role

INTRO

Most reps don’t realize how close they are to $300K+ roles. You don’t need 20 years of experience—you need a different skillset. In this post, we break down the real shifts it takes to go from SMB or mid-market AE to full-cycle Enterprise AE. It’s a deep dive conversation between Eric Finch and Connor Murray—two enterprise AEs who’ve sold into the Fortune 500 and trained reps across every segment.

If you’re 2–5 years into your sales career and starting to eye bigger opportunities, this post is for you.

WHAT YOU’LL LEARN

• Why Enterprise deals require a totally different motion than SMB
• How to avoid getting blindsided by complex buying groups
• The mistakes most reps make when they "level up"
• What it takes to be seen as credible with execs—and win trust internally

CONTEXT: WHY THIS MATTERS

There’s a reason most AEs plateau around $150K.

SMB and mid-market deals reward speed. Get in, get the buyer excited, close fast. But once you step into Enterprise? That approach gets you burned. Sales cycles stretch to 12–18 months, buying committees balloon, and your product is now a small piece in a much larger transformation.

Enterprise AE is where the big money lives. It’s not uncommon to make $300K+ within 4–6 years of entering tech sales. But you need a new playbook—one built on access to power, multi-threading, political acumen, and implementation foresight. This blog breaks down what changes and how to prepare.

SHIFT #1: ACCESS TO POWER IS 10X HARDER

In SMB, you’re used to getting the decision-maker on call #1. The CEO of a 20-person startup might book a demo themselves. That luxury disappears in Enterprise.

At the Enterprise level:

• The real decision-maker often doesn’t show up until ~month 4
• Stakeholders are risk-averse and slow to move
• People you’re talking to may have zero authority

You can’t rely on charisma or excitement to drive momentum. You need to proactively map the org, identify true economic buyers, and build a step-by-step plan to get to power. If you're not building in multi-threading as part of your sales motion—you're setting yourself up to be blindsided.

SHIFT #2: CHAMPIONS CAN’T BE TRUSTED BY DEFAULT

You’ll meet smart, ambitious people in these accounts who love your product. But if they’ve never bought software before, they might unknowingly tank the deal.

On the Higher Levels Podcast, Connor shared a story about a promising IT contact who raved about Oracle’s solution. Weekly calls, strong alignment—then radio silence. What he didn’t know? Finance, the actual decision-maker, had already implemented a competitor in the past and wasn’t even in the loop. They had been in conversation for several months with Oracle's competitor. Connor wasn't even aware that this was taking place.

If you're single-threaded and your champion goes dark, you have no one else to call. While this applies to any deal cycle including SMB, it is EXTREMELY prevalent in the Enterprise space.

How to avoid it:

• Ask your champion who else has bought similar tools before
• Clarify the buying process early—don’t wait until the deal stalls
• Set the expectation that demos or trials require broader buy-in first

SHIFT #3: POLITICS AND INTERNAL RISK MATTER MORE THAN ROI

In SMB, a clean ROI case and a fast implementation can be enough to win. Not in the Enterprise.

Your product could be 3x better and 50% cheaper, and you’ll still lose the deal. Why? Because a VP of IT who built their career on an on-premise system may see your cloud-based solution as a personal threat. Even if it’s the right move for the company (this is just one example of many that was discussed)

Enterprise buyers aren’t just looking for upside—they’re avoiding risk. The bigger the deal, the more your solution becomes a political chess piece inside the org.

That’s why discovery isn't just about pain points for one person or team—it’s about power dynamics, agendas, and internal career and organizational incentives. We could spend hours discussing this alone.

SHIFT #4: IMPLEMENTATION REALITY WILL KILL A GOOD DEAL

In SMB, most teams can turn on a tool and start using it. In Enterprise, adoption takes time, budget, headcount, and leadership alignment.

Eric gave the example of selling into a Fortune 100 engineering org. Sure, the team wanted to go cloud-native. But the engineers had been working with on-prem tools since 2004. The skill gap alone made implementation nearly impossible in the timeline desired.

AEs need to forecast not just the sale—but the rollout. That means:

• Validating internal resource availability
• Validating who will purchase and what would define success such that they would move forward
• Often not providing any trial or free usage until all teams are in alignment
• Involving implementation teams early
• Setting realistic timelines and success criteria

SHIFT #5: ENTERPRISE PROSPECTING REQUIRES STRATEGY, NOT SPRAY-AND-PRAY

In mid-market, you might have 1,000+ accounts. In Enterprise? You might have 50 (in many cases 20 or less).

That means every touchpoint matters. Your prospecting has to be tailored, strategic, and multi-threaded from the beginning. You’re not just booking meetings—you’re planting seeds across complex orgs with long sales cycles.

As one example of many from Connor:

You prospect subsidiaries and parent companies differently. You use events, referrals, and even implementation partners as part of your outreach motion.

This is pipeline generation at the highest level. And it’s where many reps stall when making the leap.

SHIFT #6: YOU NEED INTERNAL CREDIBILITY TO WIN SUPPORT

In SMB, you can work a deal solo or with a very scrappy Sales Engineer. In Enterprise, you’re part of a village: SEs, architects, consultants, exec sponsors, partners.

If you blow a deal because you didn’t qualify it properly, you don’t just lose commission—you lose internal trust.

Both Eric and Connor talk about deals where they pulled in multiple teams, burned calendar time and resources… only to lose because they never got to power or didn’t vet the buying process. That hurts your internal brand and makes it harder to get executive support and engineering coverage on future deals.

Build your reputation as a rep who:

• Pre-qualifies hard
• Respects the team’s time
• Follows through with process disciplineFAQ

Q: How much can Enterprise AEs actually earn?
A: Most earn between $250K–$400K, with some hitting $500K+ in top years thanks to uncapped commission and accelerators.

Q: How is Enterprise sales different from SMB?
A: Enterprise deals are longer, more political, and involve many more stakeholders. Access to power, internal credibility, and implementation planning matter much more.

Q: What if I only have SMB experience—how do I get promoted?
A: Start building Enterprise habits and connections now: multi-thread every deal, practice deep discovery, and work with SEs and cross-functional teams. Your deal reviews will start to reflect Enterprise readiness, and your internal brand will become more prominent when leadership is discussing potential promotions.

Q: What's the fastest path to an Enterprise AE role?
A: Become a top performer in mid-market, work closely with your SE and CS teams, and/or look for internal openings or external Enterprise Account Executive roles that promote AE's to that level with an external hire.

AE Mastery

→ If you’re ready to make the leap to Enterprise sales, join AE Mastery. This is our most advanced program—designed specifically for reps buidling their career to $300K+ roles. You’ll learn how to win complex deals, avoid landmines, and build pipeline that closes.

Students like Ben increased their salary by 50%, and Mike closed more in Q1 of 2025 than he did in all of 2024.

‍The program gave me the clarity and structure I needed to actually execute—and now I’m outperforming my entire last year’s sales in just Q1.

TL;DR

• Enterprise sales requires a different playbook than SMB or mid-market
  
• Access to power is harder—you must multi-thread and map orgs
  
• Implementation, politics, and risk aversion kill deals—even with a strong ROI
  
• Internal credibility is critical for pulling in SEs and getting support
  
• $300K+ roles are real—but only if you learn the Enterprise motion