Your SaaS Can’t Scale on Product Alone—Here’s the Real Hidden Engine

Hey 👋

I’ve been sharing a lot recently about scaling SaaS—how we optimize funnels, run experiments, convert deals, and reduce churn.

But if there’s one thing I’ve learned the hard way as a SaaS founder—it’s this:

You can’t scale your company unless you know how to scale trust.
And nothing tests that more than managing independent contractors.

Let’s talk about the part of the business most founders ignore until it’s too late:
Retention—not of users, but of the people doing the actual work.

Over the past few years, we’ve worked with dozens of contractors across 7+ countries—writers, engineers, designers, analysts, data entry specialists, and customer success agents.

And across all those roles, here’s what I’ve noticed:

• The best ones don’t just wait for tasks—they think.

• The reliable ones aren’t necessarily the most experienced—they’re the most plugged in.

• And the ones who stay? They don’t stay because of the pay. They stay because they feel part of something.

That’s not luck.
That’s intentional design.

What Actually Keeps Contractors Around?

Let me break down the systems we’ve implemented to make contractors feel like mission-critical team members (because they are):

1. Onboarding Like They're Full-Time

Whether someone’s working 5 hours or 30 hours a week—how you onboard them sets the tone.

We used to just drop links and logins in Slack.

Now? Every contractor goes through a 3-part onboarding:

• A short video that shares our mission, goals, and product roadmap

• Access to a "Contractor HQ" Notion page with SOPs, communication norms, and tools

• A real-time onboarding call where we walk them through context—not just tasks

That one 30-minute call makes more impact than any Asana checklist ever could.

2. Weekly Syncs & Wins Channel

We run a simple 20-minute weekly sync for key contributors.

No complex updates. Just three prompts:

• What did you work on this week?

• What are you focused on next?

• Anything blocking you?

Then, we shout out wins in a shared channel. Even if someone only touched one part of a project, they see the bigger picture.

And that makes them feel connected to the outcome—not just the input.

3. Defined Roles, Flexible Scope

Here’s what I’ve learned: contractors thrive when their role is clear, but their impact is expandable.

We give every contractor:

• A job scorecard (yes, even for freelancers)

• A “room to grow” list—things they can take on if they want to go beyond scope

• A link to internal projects we’re exploring, so they can self-elect to contribute

This has led to unexpected innovation—from a copywriter rewriting product tours to a QA analyst suggesting a better test automation framework.

4. Performance Reviews Aren’t Just for Payroll

Once a quarter, we do a light-touch check-in with every core contractor.

We ask:

• What’s working for you?

• Where do you feel underused?

• How can we make your work smoother or more valuable?

These reviews have surfaced things I would’ve never caught on my own—like timezone misalignments, platform access frustrations, or blockers in process handoffs.

The ROI of Contractor Retention

Let’s be honest—most people think:
“If they leave, I’ll just hire someone new.”

Sure. You can.
But here’s what that really costs:

• 10–20 hours of context transfer

• 2–3 weeks of lost velocity

• Accumulated tech or process debt from lack of history

• Friction with the rest of your team, who now have to “fill in the blanks”

It’s not just a swap. It’s a rebuild.

Retention isn’t a soft metric. It’s a hard efficiency lever.

Final Thought

There’s a line I remind myself of every month:

| “You don’t scale a SaaS with just product. You scale it with people who care enough to make the product better every week.”

Whether they’re in the office or on another continent, part-time or full-time—your job is to give them a reason to care.

Because when they do, you don’t just get tasks done.
You build something that compounds.

If you’re managing a remote SaaS team or working with independent contractors and want to see the Notion templates, onboarding docs, or job scorecards we use—just reply and I’ll share them.

Talk soon,
Angelo