Operations shouldn't depend on heroics.They should depend on systems.
Embedded operational leadership for companies that have outgrown their infrastructure.
The playbook that got you here stopped working. Decisions bottleneck. Good people burn out on coordination instead of output. The business needs operational leadership—but a full-time hire isn't the right move yet.
Part-time presence. Full-time thinking.
Embedded COO isn't consulting. We don't deliver recommendations in a deck and leave you to figure out implementation. We work alongside your team 1–3 days per week, building the systems, developing the people, and driving the projects that turn strategy into execution.
This is for companies that need operational leadership but aren't ready for (or don't need) a full-time executive hire. You get the experience, the pattern recognition, and the execution capacity, without the $300K+ annual commitment.
The goal is building systems that work when we're not there. We succeed when you don't need us anymore.
After 90 Days
Decisions happen without you
Your team has frameworks for the situations that don't need executive input. You hear about outcomes in a weekly summary, not approval requests at 9pm.
Strategic work actually moves
The initiatives that kept getting pushed to "next quarter" are in motion. Important work has protected time, not just whatever's left after the urgent stuff.
The operation runs
Processes are documented. Handoffs don't break. Someone takes a vacation and nothing falls apart. New hires get up to speed in weeks, not months.
Operational Leadership, Not Advice
This isn't consulting. We embed with your team 1–3 days per week, building systems, developing people, and driving the projects that turn strategy into execution.
Strategic Planning & Execution
Annual and quarterly planning. Goals that actually drive behavior. The rhythm of accountability that keeps initiatives on track.
Team Development
Mentoring your operations leaders. Building decision-making capability across the organization. Developing the person who might eventually run this full-time.
Systems & Process
Documented workflows that hold weight. Handoffs that don't break. Infrastructure that scales with the business.
Vendor & Contract Oversight
RFP management. Vendor negotiations. Making sure implementations actually work: not just on the dashboard, but on the floor.
Cross-Functional Alignment
Getting sales, ops, finance, and product working from the same playbook. Breaking down the silos that form as companies grow.
Pattern Recognition
Finding the structural issues hiding behind symptoms. The diagnostic instinct that comes from decades of operational leadership.
How This Works
Diagnose
Weeks 1–4: We go where the work happens. Observe handoffs, sit in real meetings, talk to recent hires. Surface the patterns that have become invisible. Deliver a friction map and recommended priorities.
Build
Months 2–3: Execute on the highest-impact fixes. Document processes. Install decision frameworks. Develop your team's capability to own what we're building together.
Operate
Month 4+: Ongoing operational leadership. Strategic planning. Team development. Continuous improvement. Month-to-month after the initial term; stay as long as it's valuable.
Sustain
The goal isn't permanent engagement. It's building systems and capabilities that outlast the partnership. We succeed when you don't need us anymore.
The $1.2M fix that wasn't.
62%
Rework reduction in 60 days
78% → 97%
Credit accuracy improvement
Zero
Partner escalations after fix
New
First-pass resolution metric
The company had just finished a $1.2M systems overhaul. Dashboards glowed green. But the VP couldn't shake a feeling—operators were still grinding, morale was slipping, and the numbers didn't match what she saw on the floor. Her implementation vendor had moved on to the next project. She called Charter Oak for a second opinion.
Two weeks in, we found the gap. The new system handled 70% of cases beautifully. For the other 30%—high-value partner returns that drove margin—it was nearly impossible. Three-step workarounds on every complex case.
The root causes weren't technical. Operators had to guess disposition codes because correct options didn't exist. Tribal knowledge had vanished in migration. And the dashboard measured tickets closed, not rework created.
We pulled Finance, Operations and IT into one room. Walked through five actual returns. By the third, everyone saw the gap.
Codified the missing codes. Documented what senior operators carried in their heads. Reset the dashboard to measure first-pass resolution.
The fix took two weeks. Not two quarters.
"Every metric said success. But I could see the operators still grinding. Charter Oak found in two weeks what the new dashboards would never have shown us."
Is This Right For You?
This works if...
- +You're between $5M–$30M and feeling the friction of growth
- +Leadership is strong but stretched—there's no capacity for operational projects
- +You need someone who executes, not someone who advises
- +You're ready to act on what surfaces
- +You want systems that outlast the engagement
This isn't the right fit if...
- −You're looking for validation of a decision already made
- −The executive team protects turf over outcomes
- −You want a full-time hire but hope to pay for part-time
- −The real issue is product-market fit, not operations
- −You need a quick fix rather than sustainable change
Your Partner
Colin Darling — 20+ years designing operating models for high-volume, high-standards environments. Architect of Apple's trade-in programs at Phobio. Co-founder of Assembly, a marketplace that surpassed $250M GMV on the strength of its systems, not its story. The through-line: inflection points expose whatever the system can't carry—and most organizations fail not from talent or technology, but from structural debt that compounds faster than they can clear it.
Full backgroundThe Engagement
Commitment
1–3 days/week
Enough presence to see patterns and drive change. Not so much we become overhead. Most engagements settle at two days per week.
Initial Term
3 months
Time to diagnose the real problems, execute the highest-impact fixes, and build your team's capacity to sustain them. After that, month-to-month.
Investment
$12–18K/month
Fixed monthly fee based on days per week and scope. No hourly billing, no surprises. Includes all diagnostic and implementation work.
Guarantee
90-day results
If you don't see measurable operational improvement within the first 90 days, we'll work free until you do or refund your final month.
Not ready for embedded partnership?
Most companies benefit from diagnosis first—or targeted sprints on specific problems. Both create the clarity needed to know if ongoing partnership makes sense.
Diagnose First
Surface the patterns causing friction. Get a friction map and prioritized roadmap before committing to larger engagement.
$8–15K · 2–4 weeks →
Build Specific Systems
Know exactly what's broken? Our focused sprints deliver working solutions in 3–8 weeks. Decision frameworks, knowledge capture, documentation systems.
$7,500–24K · 3–8 weeks →
Let's figure out if this fits.
Every engagement starts with a conversation. We'll talk about where the operation is stuck, what's been tried, and whether embedded leadership makes sense—or if one of our focused engagements is a better starting point.