Where stalled
becomes unstoppable.
We work with owner-led roofing and exteriors companies, HVAC and home service contractors, and independent insurance agencies to find where time and money are leaking, build the frameworks to stop it, and stay in the work until results follow.
You can feel it. The phones are ringing and the team is selling, but growth has flattened and margins keep getting thinner. Decisions that used to be clear now sit on your desk for weeks.
Usually it is not a lead problem. The money is slipping out after the sale: in pricing, in comp plans, in rework, in renewals, in work that falls through the cracks.
That is not a motivation problem. It is an operations problem. And it is fixable.
Three industries. We know where they leak.
We focus on owner-led businesses with steady demand, a sales team paid on production, and margins that keep getting thinner. That focus is why we find the leaks fast.
Roofing & Home Exteriors
Demand is there. The margin is not. Jobs install weeks after the sale while material costs climb, scope gets added on a handshake, subbed work comes back as callbacks, and reps earn the same whether they hold price or give it away.
- Margin erosion on late installs
- Unsigned change orders
- Callbacks and rework
- Subcontractor cost and compliance
- Sales comp that rewards discounting
HVAC & Home Services
Flat demand and rising labor costs squeeze every truck roll. The leaks hide in comfort advisor close rates, membership programs that stall, technician time, and lead spend nobody can trace to a sold job.
- Close rates and discounting
- Membership and maintenance revenue
- Truck roll cost and tech productivity
- Lead spend with no attribution
- Callbacks and warranty work
Independent Insurance Agencies
For years, rising rates did much of the growing. As that tailwind fades, the gaps show up in retention, producer economics, carrier mix, and the service work quietly eating your team's time.
- Retention and renewal leakage
- Producer comp and validation
- Carrier and commission economics
- Service workload per account
- Cross-sell and account rounding
How we work.
No discovery decks. No frameworks pulled from textbooks. We work the problem from the inside, the way an owner would.
Get inside the business.
Real conversations with you and your team. Real time inside the operation. A clear-eyed look at where the work actually breaks down.
Name the real problem.
Most operational issues are not what they look like on the surface. We tell you what we see, plainly, and where the highest leverage actually lives.
Build the frameworks.
Systems, accountability structures, and operational rhythms that fit how your business actually runs. Not theory. Tools your team will use.
Stay in the work.
Fractional means embedded, not occasional. We are in it with you, week to week, until the results show up and stick.
Three services. One standard.
We do three things, and we do them with the depth of someone who has been in the seat.
The Business Diagnostic
$7,500 · One Time · 14 DaysA complete teardown of your business, built for owner-led companies with a sales team paid on production: roofing and home exteriors companies, HVAC and home service contractors, and independent insurance agencies.
In 14 days we tear down your financials, marketing spend and return, lead quality, close rates, pricing and discounting, sales comp, job costing or book economics, backlog, callbacks, renewals and retention, crews and subcontractors, operations, team, and compliance exposure.
- A written report of 15 to 25 pages with a graded scorecard
- Every leak we find, with what it is costing you each year
- Quick wins you can act on within two weeks, with no new hires or spend
- A prioritized 90-day roadmap to fix the rest
- A 2-hour readout call where we walk all of it together
This is not a discovery call in disguise. It is the most thorough review your business has ever had, and it stands on its own whether or not we ever work together again.
There is a dedicated advisory practice for established brokerage owners: a complete business diagnostic, an ongoing deal desk, and a syndication masterclass, taught from the funding side of the table. Ten advisory seats, maximum.
Fractional COO & Operational Advisory
We embed into your organization to run operations alongside you. We find where time and money are leaking, build the systems to stop it, and create real cost savings without hiring a full-time executive.
- Operational audits that name the actual problem
- Process and workflow design that your team will actually use
- Financial visibility into where margin is being lost
- Accountability structures that turn meetings into movement
- Hands-on leadership inside the business, week to week
Anyone can save a company money by cutting payroll. We do it differently. We have helped multiple companies across lending, retail, and medical save tens of millions in operating expenses without a single layoff.
The approach starts in the weeds. We learn what each person and department actually does, and why. We find redundancy, the tasks being done that should not be, the important work being skipped. We move people into the right seats. We shift work between teams so the process flows instead of stalls.
Layoffs cost money, time, loyalty, and quality assets. Used well, every hour of payroll returns more than it costs. That is the standard we work to.
Executive Coaching
Running a business is unlike anything else. The decisions are lonelier, the pressure is heavier, and most advice comes from people who have never actually done it.
We bring operational expertise, financial acumen, and real experience as a business owner to help executives push through the decisions, mindset shifts, and challenges that conventional advisors are not equipped to handle.
This is for you if you are carrying weight you cannot fully share with your team, your board, or anyone who has not run a business themselves.
Built by an operator. Not a consultant.
Dooley Advisory was founded on a simple idea: business owners deserve advisors who have actually done the work. Too much of the advisory world runs on theory. Frameworks pulled from textbooks. Decks built by people who have never made a payroll call. Consultants who deliver a presentation and disappear before the work begins.
Derek Dooley has spent over twenty years in business and more than fifteen of those in operations and lending leadership. As co-founder and COO, he helped build a lending organization from zero to over $100 million per month in volume in under four years. The growth was engineered through pipeline management, operational discipline, layered accountability, recruiting, and deep industry expertise applied to every layer of the business.
He has also helped companies across lending, retail, and medical save tens of millions of dollars in operating expenses without laying off a single employee. The approach is not cost cutting. It is operational redesign. Getting in the weeds, finding the redundancies, repositioning the right people into the right seats, eliminating low-value work, and protecting the high-value work that gets overlooked.
He started Dooley Advisory after years of being told the same thing by colleagues and clients: he sees what needs to change and makes it happen without damaging reputations, without losing good people, and without burning the place down to fix it. He built Dooley Advisory to do that work for many companies instead of one at a time.
What people who have worked with him say first: honest to a fault, operates with integrity. He will tell clients the truth, even when it is uncomfortable. He will always do what is right for the client, even when it is not what is easiest for him.
Bachelor of Accounting & Finance
15+ in operations & lending leadership
Five convictions that drive the work.
The real issue is almost always one or two layers deeper than where it shows up. Our job is to find it and name it.
The fastest way to lose credibility with a business owner is to talk like someone who has never run one. We do not.
Layoffs are almost always avoidable when leadership knows the business well enough. Cutting payroll is the lazy answer. Used well, every hour of payroll returns more than it costs.
Most operational problems get worse when the solution is complicated. We build simple, durable structures the team will actually use.
Advice without execution is decoration. We stay embedded until results show up and hold.
The fit matters.
The work requires trust from day one and the willingness to back the changes that come out of it. Without that backing, change does not stick. Without change, the business does not grow.
The right fit
- Owners of roofing and exteriors companies, HVAC and home service contractors, and independent insurance agencies
- Businesses with steady demand and a sales team paid on production, where growth has flattened and margins keep tightening
- Owners who suspect pricing, comp, callbacks, or renewals are leaking money
- Leaders who will trust the process and back the changes with their team
- Founders ready to professionalize how the business actually runs
Not the fit
- Leaders who cannot extend trust to an outside advisor from day one
- Owners who want validation more than honest assessment
- Executives unwilling to back the changes in front of their employees
- Anyone looking for a deck and a quick exit instead of real, embedded work
Ready to stop spinning?
Book a thirty minute discovery call. Tell us where the business is stuck, what you have already tried, and what you want the next twelve months to look like.
There is no pitch deck on the other side. Just a real conversation about whether we are the right fit.