How to Get Your First 5 Retainer Clients (With Scripts)

Most advice on landing fractional clients sounds like wishful thinking.

“Tell your story.”
“Build a personal brand.”
“Start posting.”

Some of that helps. Most of it skips the part where real retainers actually come from.

You don’t need a funnel to land five solid clients.
You need a clear offer, a few honest asks, and some repeatable moves.

This isn’t the only way to do it.
It’s one reliable path I’ve seen work for relationship-driven, retainer-based fractional work.

Below is what tends to help at each stage, from zero to five, plus language you can actually use without feeling awkward or salesy.

Before you begin: the quiet prerequisite

This assumes you have some network to start from.

If you don’t, maybe you changed industries or you’ve been heads down for years, spend a few weeks reconnecting before you “launch.”

Reach out privately.
Ask what’s changed since you last worked together.

You’re not selling.
You’re re-establishing relevance.

When you have 15 to 20 people who’ve seen you work and still respond, you’re ready.

0 → 1: your first client

Goal: validate your offer and language privately before going public.

Start private, then go public.

Before posting anything, DM 15 to 20 warm contacts. Former bosses, teammates, investors, vendors. People who already know how you work.

Ask for short intro chats to test your framing, not to pitch.

Keep the ask small.
Cap calls at 15 minutes.

The goal is to sharpen language and earn a couple of intros.

Then make one simple announcement post:

• What you do
• Who you help
• How to start a conversation

No manifesto.

Pricing as a starting point

Take your last full-time monthly comp, divide by three, then add about 25 percent.

This is a floor, not a ceiling.

It anchors you safely, not optimally. If the problem you’re solving has outsized leverage, price accordingly.

Positioning sanity check script

Use this privately before you go public.

Hey [Name]. I’m testing some positioning around fractional [role] work.

I help [type of company] do [specific outcome] without adding headcount.

I’m not looking for work here. I just want to sanity check whether this lands and who it makes you think of.

If it resonates, I may ask for an intro or two. Would you be open to 15 minutes?

Fifteen minutes means fifteen minutes.

1 → 2: pilot before retainer

Goal: turn interest into proof.

Instead of selling a retainer, sell a path.

Diagnostic.
Pilot.
Then retainer, if it earns its place.

Most people don’t want to commit long-term before they’ve seen value.

Diagnostic proposal language

Based on our chat, here’s what I’m seeing: [2–3 specific observations].

I’d suggest a three-step path:

Diagnostic (3 weeks, $X): map the gaps and build a 90-day plan you can execute with or without me.

Pilot (6–8 weeks, $Y): fix the highest-leverage problem from that plan.

Partnership: if the pilot works, we move to a monthly retainer.

Each step is a decision point. Nothing is locked in. Does that feel reasonable?

Lower pressure. Higher trust.

2 → 3: get referable

People don’t refer “talented generalists.”

They refer something specific.

“A fractional CMO for Series A SaaS companies that just let go of their head of marketing.”

The clearer people can describe you, the easier referrals become.

Being referable also means being willing to say no to work that quietly turns you into full-time execution or blurs your role.

Cold outreach can work here too, if it’s brief and human.

Compliment.
Commonality.
Question.

3 → 4: the capacity test

Goal: add structure, not hours.

Four clients is where things often get hard.

What usually helps:

• Weekly updates with the same format
• Clear calendar blocks per client
• Naming scope early and repeating it

This isn’t rigidity.
It’s how momentum stays intact.

This is also where systems start to matter.

Around four clients, I realized I was running a mini CRM in my head. Action items, follow ups, who said what, which client it belonged to. It worked until it didn’t.

I didn’t want another tool to maintain. I wanted meetings to turn into tasks automatically, without me cleaning things up later. That’s why we started building Juggle.

I just talk in meetings. Everything stays organized by client, with clear ownership and next steps. Nothing slips through, and nothing lives only in my head.

4 → 5: the steady state

Five retainers is sustainable for most fractionals, but not for the same reason.

What actually caps people isn’t client count. It’s where they sit in the work.

If you’re still the execution layer, five clients will feel impossible.
If you’ve moved into the decision layer, five is often manageable.

The shift from doing to deciding is what makes the model hold.

At this stage, the work changes:

Less constant execution.
More judgment, review, and targeted pushes.

You’ve proven value. Now you protect it.

A few patterns that matter at every stage

• Price systems, not promises you don’t control
• Define success early and revisit it
• Monthly beats hourly once trust is there
• Clear boundaries are a kindness

Personal brand helps, but it’s infrastructure, not the product.

Make your profile easy to understand.
Then share useful, specific things consistently.

A simple cadence that tends to work

This isn’t mandatory. It’s one pattern that works for many people.

• Daily: one small value add
• Weekly: a handful of warm touches or intros
• Monthly: one longer post showing how you think

Done consistently, client flow usually stops feeling mysterious.

Thanks for reading.
Gev

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