MediumUpwork Has Changed: How to Leverage It for Your Startup in 2025 | by Jovan Cicmil | Entrepreneurship Handbook
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Entrepreneurship Handbook is a carefully selected collection of stories featuring real expertise, insight, opinion, and passion focused on innovation, entrepreneurship, and tech.

Upwork Has Changed: How to Leverage It for Your Startup in 2025

Hiring the right freelancers to propel your startup forward

5 min readJun 2, 2025

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In its early years, Upwork was the digital Wild West. Anyone with a keyboard could create a profile, apply to gigs, and — if they were fast, cheap, or lucky — win projects. It was chaotic, noisy, and unpredictable. I loved it and made good money on the platform.

Back then, Upwork was a goldmine of talent for cash-strapped startups.

Today, it’s a very different place.

It’s slicker, more polished, but harder to use effectively. Not because of bugs or poor design, but because the platform’s incentives have shifted. Fees have increased, membership tiers now favor long-time freelancers, and Upwork’s algorithm tends to prioritize those who already have traction, reviews, and earnings.

That’s good for experienced freelancers. It’s harder for newcomers.

For startup founders it absolutely sucks.

Unless you know how to shift your approach.

The New Upwork Landscape

Before we talk tactics, let’s understand what’s changed:

1. Membership Model Favors Veterans

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Entrepreneurship Handbook is a carefully selected collection of stories featuring real expertise, insight, opinion, and passion focused on innovation, entrepreneurship, and tech.