The Path to $350,000 in Tech Sales Within Five Years, According to Aaron Reeves

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Aaron Reeves

LinkedIn Author

Helping AEs close 25% more outbound deals. Founder @ Outbound OS. We help AEs earn multi-6-figures by self-sourcing their own deals. Apply to join → theoutboundos.io

In a recent LinkedIn post, Aaron Reeves outlines a clear strategy for achieving a substantial income in tech sales, specifically targeting a $350,000 earning potential within a five-year timeframe. Reeves, who speaks with numerous Account Executives (AEs) weekly from both burgeoning startups and established global corporations, highlights the impressive On-Target Earnings (OTE) that often exceed expectations.

According to Reeves, the earning potential can be broken down by market segment: SMB representatives can earn around $190,000, Mid-Market (MM) reps $260,000, and Enterprise (ENT) reps an estimated $400,000. He points out that many individuals reaching these figures are in their late twenties or early thirties and often have less than five years of experience in tech sales. Reeves states that he has personally coached a dozen individuals to exceed $300,000 in earnings, suggesting the path is more accessible than commonly perceived.

“And the OTEs always blow my mind.”

Key Steps to High Earning Potential in Tech Sales

Reeves details a five-step approach for aspiring sales professionals aiming for high incomes in the tech industry. He emphasizes that these steps, when followed diligently, can lead to significant financial success.

1. Strategic Company Selection

The first crucial step, as outlined by Reeves, is to identify and join a company with strong product-market fit, robust internal coaching programs, and genuine opportunities for career advancement and promotion. He advises against prioritizing frequent job hopping solely for salary increases, suggesting that loyalty and growth within a single organization can be more rewarding long-term.

2. Mastering the SDR Role

Reeves stresses the importance of excelling as a Sales Development Representative (SDR) and developing strong prospecting skills. He argues that this foundational experience is invaluable and will significantly benefit individuals later in their careers when they transition to AE roles.

“Win as an SDR – be willing to learn how to prospect. Don’t try to skip over this because this will serve you later in your career when you’re in AE”

3. Investing in Sales Tools

A practical tip from Reeves involves being willing to invest in personal sales tools to enhance productivity. He specifically mentions FullEnrich as a tool that can dramatically improve connect rates, potentially quadrupling the number of meetings booked.

4. Phased Market Progression

Reeves recommends starting in the Small to Medium Business (SMB) market to learn the fundamentals of transactional sales. From there, he advises a gradual transition into the Mid-Market segment, with the ultimate goal of moving into Enterprise sales.

5. Continuous Learning

The final piece of advice from Aaron Reeves is the necessity of a commitment to lifelong learning. He cautions against complacency, stating that there is always more to learn and improve upon within one’s career.

“Keep learning – never think you’ve understood everything about your career. There’s always something to learn and improve.”

The Appeal of a Tech Sales Career

Reeves also touches upon the broader advantages of a career in tech sales. He highlights that it is one of the most lucrative fields globally, offering significant benefits such as remote work flexibility, the opportunity to sell cutting-edge products, and the chance to engage with major global companies, all without the high-stakes pressure often found in other professions.

“Tech is one of the highest-paying careers on the planet. And when you look at it? We get to work mostly remotely. We get to sell world-class products. We get to work with the biggest companies in the world. All without ever being in life-or-death situations.”

In conclusion, Aaron Reeves presents a structured and achievable roadmap for individuals seeking high financial rewards in tech sales. By focusing on strategic career moves, skill development, and continuous improvement, he suggests that reaching a multi-six-figure income is well within reach for dedicated professionals.

📝 About This Content

This article is based on insights shared by Aaron Reeves on LinkedIn.

📅 Originally posted on September 14, 2026 | View original post on LinkedIn →