Working with a Freelance Developer: What Founders Should Expect

The Agency vs. Freelance Decision

59% of websites are developed by external agencies or freelancers. For startups and small businesses, this often makes more sense than building an in-house team-you get specialized expertise without ongoing salary commitments.

But working with a freelancer is different from working with an agency. Understanding those differences helps you get better results.

What You're Actually Getting

Direct Communication

No account managers, no telephone game. When you work with a freelancer, you talk to the person doing the work. Questions get answered faster, and there's no message distortion between you and the developer.

Flexibility

Freelancers can often accommodate timeline changes, scope adjustments, and pivot requests more easily than agencies with rigid project management processes.

Lower Overhead

You're not paying for office space, middle management, or large team coordination. That typically translates to better value for the same quality of work.

What to Look For

Portfolio Relevance

Has the freelancer built something similar to what you need? Experience with your industry or problem space reduces the learning curve significantly.

Communication Style

During initial conversations, notice:

• Do they ask clarifying questions?
• Do they push back on unrealistic requirements?
• Can they explain technical concepts clearly?

A freelancer who says "yes" to everything often delivers disappointment.

Technical Judgment

Good developers will suggest simpler solutions when appropriate. If a freelancer never questions your requirements or suggests alternatives, that's a red flag.

Setting Up for Success

Define Success Clearly

Before starting, agree on:

• What "done" looks like (specific deliverables)
• Timeline with milestones
• What's in scope (and what's not)
• How changes will be handled

Establish Communication Rhythms

Weekly check-ins work well for most projects. Agree on:

• Preferred communication channels
• Expected response times
• How to handle urgent issues

Plan for Feedback

Build review points into the timeline. Waiting until the end to provide feedback creates expensive rework.

Red Flags to Watch For

• No questions asked: Complex projects always have ambiguity
• Unrealistic timelines: If it sounds too fast, it probably is
• No portfolio or references: Experience matters
• Resistance to milestones: Good developers welcome structured progress checks
• Vague pricing: You should understand what you're paying for

The Payment Question

Standard practice is 50% deposit, 50% on completion. For larger projects, milestone-based payments (e.g., 30% start, 40% at midpoint, 30% on completion) give both parties security.

Be wary of freelancers who want full payment upfront, but also respect that asking for no deposit shows desperation.

After Launch

Discuss maintenance and support before the project ends:

• How will bugs be handled?
• What about small changes and updates?
• Is there a retainer option for ongoing work?

A good working relationship doesn't end at launch-it evolves into a partnership that supports your growth.