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trusted operator academy
You have the right person. The role just grew faster than the support did.
You've watched them step up every time you needed them to. You know what they're capable of. You're just waiting for the role and the person to finally catch up to each other.
Five full days over five months. Six to eight seats per cohort.
THE PROBLEM NOBODY NAMES
There is someone in your business you trust. You have trusted them for a while now.
They know the work. They show up when it matters. And somewhere in the last year or two, the gap between what you need from them and what they can currently give you has gotten harder to ignore.
They are capable. The role got bigger than the support did.
You have probably said some version of: I need you to be more strategic. Or: I need you to stop solving things personally and start building systems. Or you’ve said nothing, because you’re not sure how to say it without making them feel like they’re failing.
Nothing is wrong with them. They are doing a job most businesses never give anyone structured support for.
That is the gap TOA closes.
WHAT MAKES THIS DIFFERENT
Most training takes people out of their work. Case studies. Cohorts in conference rooms. Frameworks that have nothing to do with the actual business sitting in front of them.
Your operator comes back more informed. The business is exactly the same.
In the Trusted Operator Academy, your operator builds the structure inside your organization, on your real problems, alongside a small cohort of peers navigating the same terrain. The learning happens in the work itself.
Five full days. One a month, over five months. A more capable operator, a clearer picture of what the business needs, and the momentum to build it.
The Program
The Trusted Operator Academy is a cohort experience for the key leaders and operators in founder-led businesses, the people in COO-adjacent roles who are ready to lead at the level the role requires.
Five full-day sessions, one a month for five months. A one-hour accountability session sits mid-month between each day. Six to eight seats per cohort, so the room stays small and the work stays real.
Every day ends with something to apply. The operator takes it back to your business, works it over the next month, and brings what happened to the next day.
$6,500 CAD per seat.
Sponsored by the founder on behalf of their operator.
How the Five Days Build
Five days, one a month. Each one building on the last.
Day 1: Who You Are
Your operator gets clear on the role and builds the working relationship with you.
Taught: how values show up in decisions under pressure, what the role asks of an operator, where an operator’s time builds trust and where it only fills gaps, responsibility versus authority versus accountability, and the trust equation.
Built: a Communication Contract between you and your operator, started in a first real conversation.
For you: an operator who tells you how to bring them something important, and a clear way of working together.
Day 2: How You See and Structure operations
Your operator maps how work really moves, then assigns who owns what inside it.
Taught: mapping the business as a system, where work waits and changes hands, accountability charts, decision rights (who is responsible, accountable, consulted and informed), and making decisions at the right altitude.
Built: a map of your business drawn in the room, an accountability chart with one name per seat, and decision rights for five recurring decisions, shared with the people they affect.
For you: fewer decisions that bounce back to your desk because nobody knew who owned them.
Day 3: How You Hold It
Your operator learns to spot strain early and keep the business’s capacity and priorities honest.
Taught: operational load, friction and flow, the constraint that sets the pace for everything else, and priority integrity. Operational health signals: leading versus lagging, drift versus crisis, and which signals AI can help monitor.
Built: a friction map of your business with its costliest friction named in one sentence, a stated-versus-actual view of where the team’s hours go, a four-field habit for saying what moves when something new lands, and health signals applied to your own business.
For you: an operator who reads the business’s health signals before anything breaks, and can tell a business running well from one running quietly toward a wall.
Day 4: How You Build and Lead the Team
Your operator builds the team and leads it through change.
Taught: building the team and hiring, leading the team and performance conversations, and leading change and working across functions.
Built: a plan for one real team need in your business, such as a hire, a performance conversation or a change.
For you: hiring and performance conversations that happen instead of waiting another quarter.
Day 5: Who You and the Business Are Becoming
Your operator leaves with the numbers, the rhythm and the plan to run the business without you holding it together.
Taught: financial fluency, covering fixed and variable costs, the four levers, and reading the whole P&L. Operational rhythm, covering the daily, weekly, monthly and quarterly cadences that align priorities and decisions. Strategic thinking for a functional leader: stewarding outcomes, presenting options and trade-offs, and thinking across time horizons.
Built: a founder-ready case on one P&L line, a meeting rhythm your operator agrees with you, and a closing commitment the operator brings back to you.
For you: an operator who leaves with clarity on what changed in the business, what they are now capable of, and what comes next.
Is this right for you?
The right founder has someone in the business already. Trusted, stretched, carrying more than is sustainable. They are not looking to fix their operator. They are ready to invest in developing them.
The right operator is already in the role, or is stepping into it and ready to grow into what it demands. Ready to build. Not waiting to be ready.
If that is not where you are, this is not the right moment. If it is, this is the right way in.
Still not sure?
Find Out for Yourself
for the operator
Trusted with the role. Ready to lead it.
The expectations are real. The responsibility is real. The gap between where you are and where the role needs you to be is a development gap. Most businesses don't have a way to close it.
This program was built for the operator or key leader inside a founder-led business who is already trusted, whether already in the role or stepping into it, and ready to build.
Six to eight seats per cohort.
Ask your founder to sponsor your seat.
Frequently Asked Questions
The Trusted Operator Academy is a cohort program for operators in founder-led businesses. These are the people in COO-adjacent roles, already in the role or stepping into it, who keep execution moving as the organization grows.
The program runs as five full-day sessions over five months. Each day is applied to real work inside the participant’s actual organization, alongside a small cohort of peers navigating the same terrain.
It is a structured development experience that produces a stronger leader and a more functional organization at the same time.
The founder (business) sponsors the seat on behalf of their operator. The program is designed for founders who have someone in the business they trust, a right hand, a director of operations, a general manager, an operations manager or lead who has never had structured support for leading at this level. The founder invests in their operator's development. The operator does the work.
Most operations training happens away from the work, through case studies, frameworks, and content that has nothing to do with the business in front of the learner. In The Trusted Operator Academy, the operator builds operational structure inside their actual organization. They map how work moves, assign decision ownership, read the financials, manage capacity, and set the rhythm the business runs on. Each of the five days is instructor-led and ends with work to apply over the following month. The result is a more functional organization, improved by the person who will own it when the program ends.
The right operator is already in the role, or stepping into it, trusted and carrying more responsibility than they have ever had structured support for. They do not need to have everything figured out. They need to be ready to give one full day a month and to do real work in between, applying what they learn inside their actual organization. If your operator is someone you trust and you have been waiting for them to build the structure the business needs, they are ready.
Coaching gives an operator insight into how they lead. The Academy gives them instruction and a place to build from it: five full days led by an instructor, a small cohort of peers, and real operational work inside their own business over the month between sessions. Coaching opens something up. TOA builds something that stays.
The return is an operator who executes faster, carries more of the business without you, and creates fewer dropped initiatives along the way. Fewer questions land back on your desk, because the person answering them now has the judgment and authority to decide. The team trusts the structure underneath them instead of waiting on you to hold it together.
Each day ends with work to apply over the following month, so the return starts showing up while the program is still running.
The effects don’t stay contained to one role. A team working inside clearer structure makes fewer dropped-ball mistakes. Projects move without you needing to catch what’s slipping. Hiring and performance conversations happen instead of getting deferred another quarter.
Most founders feel it first as space: decisions that used to sit on their desk now move without them. Over time, that space becomes room to lead the business instead of run it.
The Trusted Operator Academy is a SOLVED Collective program.
Learn more about Lindsay Sheldrake and SOLVED Collective.
START with TRUST
Most engagements begin with a conversation. Book a discovery call and we'll look at where your business is, where trust is breaking down, and what would help most.
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Fractional executive support for founders of growing service businesses. We build the operational structure that makes trust possible and stepping back safe.
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