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The Navigator Retainer

You know you can’t keep being the person everything runs through.

You’re just not sure what or who comes next.

The Navigator Retainer is ongoing operations strategy and implementation for the founder who needs more than another pair of hands.

Whether you’re building your first team, working with a VA who’s tapped out, or leading a small contractor team that still routes every decision through you, I step in to help own the operational decisions, projects, and systems that keep the business moving.

You keep CEO ownership. The Navigator takes operational ownership.

So more of your attention can go where only you can put it: serving clients, selling, leading the vision, or creating enough white space to enjoy the life your business is supposed to support.

Book My Fit Call Custom-scoped retainers starting at $1,300/month · 3-month minimum
Not another task list

Most operational help stops at the task list. This doesn’t.

You probably don’t need another person waiting for you to tell them what to do. You need someone who can see what’s slowing everyone down, decide what needs attention next, and keep it moving without routing every decision back through you.

Here’s what that can look like:

Catching the missing handoffbefore it delays a launch.
Getting the right contractors talkinginstead of waiting for you to connect them.
Fixing the process everyone keeps working aroundinstead of adding another workaround.
Keeping the project movingwhen Plan A changes halfway through.
Flagging the number that needs attentionand helping decide what happens next.

The real shift happens when you’re no longer required to personally connect every dot.

“Cass’s problem-solving skills have been the best leverage in my business. I have been able to save hours of time and peace of mind.”
Latrice Prater Founder, Digital Solutions Team
Sound familiar?

Which version of “I can’t keep doing this” are you in?

01

You’re still the whole team.

You know you can’t keep carrying everything alone. But hire who? A VA? An ops person? A specialist? What should you hand off first without creating a mess you’ll have to untangle later?

The Navigator helps you build the sequence intentionally: what to hire for, when, and what needs to exist before another person enters the business.

The order you build your team matters as much as who’s on it.

02

You have a VA, but she’s tapped out.

Your VA is good at what you hired her to do. The problem? You now need someone thinking above the task list — what’s next, what’s about to break, who needs to be involved, what changes when Plan A doesn’t work.

The Navigator sits at that layer. I’m not there to replace your VA or hover over her work. I’m there to bring the operational judgment your growing business needs next.

A task taker completes what you assign. An owner keeps going when the checklist stops being enough.

03

You built a team, and somehow you’re still the glue.

You’ve got contractors doing good work, but every decision still funnels through you. The designer needs an answer from the copywriter, so you make the introduction. Nobody knows who owns the loose end, so it lands on your desk.

You’re still the operating system connecting all of them. That’s where I come in — I clarify who owns what, connect the moving pieces, and keep work moving when something changes.

Delegating the work only gets you so far when you still have to coordinate all of it.

Growth has a way of breaking what used to work.

Processes collect workarounds. Projects get more complicated. New people need context that still lives in your head. Eventually, working harder stops solving it.

That’s an operations problem.

And it’s exactly the kind of problem the Navigator is built to step into.

Scope

So, what exactly does a Navigator do?

Every retainer is custom-scoped because a solo founder making her first hire does not need the same support as a founder coordinating five contractors. Depending on your scope, I may:

Turn a quarterly goal into an operating planSTRATEGY — with priorities, owners, and next steps.
Build or repair the process your team keeps working aroundSYSTEMS
Drive a launch or project timelinePROJECTS — so you’re not chasing every handoff yourself.
Create the infrastructure for hiring, onboarding, and offboarding.TEAM — gets a new contractor up to speed without everything living in your head.
Coordinate across specialistsPROJECTS — when copy, design, tech, client experience, and timelines all need to work together.
Keep a pulse on key numbersANALYTICS — so something important doesn’t sit unnoticed until the end of the quarter.
“Cass is always ten steps ahead and can see the fire coming from miles away before it even starts.”
Anna Ancheta The Organized Monday

You’re not buying a bucket of hours.
You’re buying back CEO capacity.

Not so you can disappear from your business. So you can stop spending your best thinking on work that doesn’t require the CEO to be the person doing the thinking. The goal is simple:

Your business keeps moving without requiring your fingerprints on every operational decision.

“She created a maternity leave plan that let me fully step away and actually be present with my family.”
Leah Neaderthal Founder, Smart Gets Paid

That leaves more capacity for client delivery, sales, relationships, creative direction, vision, or simply closing the laptop without wondering what stopped moving while you were gone.

Book My Fit Call Retainers start at $1,300/month with a 3-month minimum
Process

Here’s how it works.

01

Start with a Fit Call.

We’ll talk through where the business is now, where things keep bottlenecking, and what you need someone else to own. We’re both deciding whether the fit makes sense. If it does, I’ll recommend a scope and investment based on what your business actually needs.

02

I learn the parts of your business I’m stepping in to own.

Once the scope is agreed on, I get the context I need to make good decisions inside it — relevant processes, the tools we’ll use, who owns what, the people I’ll work alongside, and current priorities. This isn’t a full-business audit tucked into your retainer. It’s focused onboarding for the scope we’ve already agreed on.

03

We confirm priorities.

We confirm what I’m owning, what stays with you, where I’ll interface with your team, and what we’re tackling first. Clear ownership. Clear priorities. Clear next moves.

04

Then we work the plan.

We establish our cadence and start moving priorities forward. Not just talking about what needs to happen. Actually making it happen.

The relationship

Three months gets us started. The value compounds from there.

The Navigator has a three-month minimum because good operational decisions require context. But this isn’t designed as a three-month cleanup and goodbye.

Many of my client relationships span 3–5 years.

As your business changes, the work changes with it. And the longer I know the business, the less context you have to rebuild every time something changes.

Already completed a Clarity Compass Audit?
You already know what’s happening. The Navigator is what happens next. Instead of another list for you to execute alone, I stay involved to help drive the changes forward. Diagnosis without a driver just becomes another list you don’t have time for.
Cassandra LeRoy
Why me
18 Years in ops & PM
12 Years corporate PM
6 Years running M+M

I know the difference between someone who completes what you tell them to do and someone who can see the roadblock, make the judgment call, pull in the right person, and keep things moving without needing you to map every step first. I’m not interested in becoming another person waiting for your task list.

I want to become the person your team can bring a roadblock to without knowing it’ll land back on your desk five minutes later.

“She consistently brings a level of strategic thinking, organization, and creativity that sets her apart. She has an incredible ability to see solutions and opportunities that others might miss, while keeping projects moving forward with clarity and confidence.”
Nadia Gabriel Northlight Admin
Before you book

A few things you might be wondering...

There’s overlap. You may have been searching for a chief of staff, OBM, fractional ops director, or operations strategist. The title matters less than the gap: you need someone who can think with you, then keep the operational work moving without waiting for your next instruction.

Possibly. The Navigator usually isn’t replacing her. A VA typically works within a defined scope. The Navigator helps make the decisions around that work: what happens next, what’s getting stuck, how the pieces connect, and who needs to handle it. For many clients, the two roles work side by side.

Not if you know you can’t keep carrying everything yourself. If you’re stuck on who to hire first, what to hand off, or what needs to exist before you hire, this can be exactly the right stage to bring me in.

Not in the traditional middle-management sense. I typically work alongside 1099 contractors, freelancers, and consultants, helping clarify ownership, coordinate the moving pieces, and keep everyone working toward the same priorities.

We’ll typically have a weekly call to stay aligned on priorities and decisions. For solo clients, that’s usually 30 minutes. For clients with teams, it’s typically 60 minutes. You’ll also have one primary communication channel, usually Slack, email, or Voxer, where you and the team members I’m working alongside can reach me. I’m not interested in becoming another gatekeeper your team has to work around. If collaborating directly with the right person gets something unstuck faster, I want us talking. Messages received during my working day are acknowledged by the end of the business day, with a response within one business day.

AI is a powerful operational tool. I use it too, and I have experience building AI-enabled systems for small businesses. But an LLM isn’t a replacement for human judgment or business relationships. It can document a process, analyze information, or automate part of a workflow. It can’t navigate a frustrated team member, understand the history behind a client relationship, or decide when the “efficient” answer is the wrong one for your business. Good operations means knowing what to automate, what needs human judgment, and how the two should work together.

Metrics Maestro builds the dashboard. Navigator helps you act on what the numbers are telling us. Navigator can include light analytics review alongside operations, systems, projects, and team infrastructure. A custom dashboard build is a separate Metrics Maestro engagement.

Three months. That gives me enough time to learn the relevant parts of the business, establish our working rhythm, and make informed decisions instead of guessing from the outside.

If the partnership is still useful, we keep going. Many of my client relationships span 3–5 years, and my longest is approaching six. As your business changes, the scope can evolve with it.

“Cass has a natural ability to meet people where they are. Her warm, grounded communication style creates an environment where people feel safe being honest, asking hard questions, and doing the work it takes to grow.”
Becky Brunner Choose Happy Assisting, LLC
Honest fit check

The Navigator probably isn’t the right fit if...

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You need a task-taker.If you know exactly what needs to happen and simply need someone to knock out the list, hire a great VA.
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You’re not ready to share the real business.This work requires access to the decisions, systems, and numbers relevant to our scope.
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You need an emergency fix by next Friday.Navigator is an ongoing operational partnership, not a rescue mission.
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You want to completely hand over the business.The goal is CEO-led, not CEO-absent.

You still own the vision and the decisions that belong to you. You just stop being the only person who can connect every dot.

You can keep being the person holding all the pieces.

Or you can finally have someone helping you carry the operational ones. If your business has outgrown “just hire another VA,” but you’re not looking for a full-time operations hire, let’s talk.

Book My Fit Call Custom retainers start at $1,300/month · 3-month minimum
No hard pitch, no predetermined package to squeeze you into.
Book My Fit Call