How I Doubled My Freelance Income by Targeting the Right Decision-Makers
How I Doubled My Freelance Income by Pitching the "Wrong" People CTOs are the worst people to pitch if you want to make actual money. For 18 months, I thought I was doing everything right. I built a slick personal website, spent hours polishing my GitHub repositories, and sent 317 hyper-personalized outreach emails to CTOs, Tech Leads, and VPs of Engineering. The result? A grueling average of…
The author doubled their freelance income by pitching the wrong people. Initially, they targeted CTOs, Tech Leads, and VPs of Engineering, sending 317 personalized emails but only earning $3,210 a month. After 18 months, they realized this approach was ineffective.
The key insight was that CTOs and Engineering Managers are risk-averse. They view external contractors as an expensive cost center, potentially undermining their team's perceived capability. When quoting a flat fee, they often compare it to the salary of an internal senior developer and engage in technical debates about implementation details.
Recognizing this, the author shifted focus to targeting non-technical executives such as VPs of Product, Heads of Growth, and Operations Directors. These individuals think differently—they care about solving business problems rather than technical challenges. For example, a VP of Product may be concerned about mobile checkout drop-offs costing $62,000 in lost revenue every quarter, while a CTO would focus on the technical implementation.
To transition from engineering jobs to high-value project contracts, the author employed a three-step approach. First, identify the "pain owner" – the person whose performance is directly tied to fixing the specific issue. In the example, this would be the Head of Growth for mobile checkout issues. Second, focus outreach on these bottlenecks rather than technical skills or portfolio links.
The author used a concise template highlighting the metric issue and offering a video demonstration. Finally, when discussing pricing, quote on business risk rather than hourly rates. By fixing the onboarding issue for $14,800, the client could recover $45,000 monthly in lost revenue. This approach changed the author's revenue from $3,210 to $14,830 per month within 87 days.
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