COO · CHRO PARTNERSHIP FOR MISSION-DRIVEN CEOS

I help mission-driven orgs grow without snapping back.

I partner with CEOs on the Operations and People systems that hold an organization together, either stepping into the COO or CHRO seat or working alongside the leaders already in it. Across 20+ years I scaled one organization from $4.5M to $30M as COO and Co-CEO, and I have led others through executive transitions, distributed growth, and operational redesign.

$4.5M→$30M
Scaled as COO/Co-CEO through the entire arc
$1M–$50M
Orgs served as interim or fractional COO/CHRO
40–500 Staff
Team size across engagements
12 States · 6 Countries
Multi-jurisdiction operations built & managed
Tim Cynova, Fractional and Interim COO and CHRO, New York
Where I help

The moments that tend to bring me in.

Senior Leader Departs
Structural gaps the role was quietly holding together surface and the weight shifts onto the CEO. The risk of snapback increases.
Growth Outpaces Infrastructure
Programs and expectations scale faster than the systems meant to support them.
Momentum Stalls
Teams silo. Meetings multiply. Everyone's working hard but the org isn't moving.
Culture Feels Disconnected
Hybrid norms fray, converssations are avoided, and the distance between people widens before anyone names it.
Board Pressure Rises
Big launches, audits, or transitions surface risk, and the cost of being unaligned climbs fast.
Leadership Changes Hands
New or departing leadership needs stable operations underneath it so continuity holds.
What Changes

The goal is a more coherent operating environment, where the chaos stops being the thing everyone manages around.

The leadership team moves in sync instead of reacting in parallel.
Decisions run through clearer channels and stop getting reopened.
Meetings get shorter and sharper, and fewer of them are needed.
Managers have the structures and backup to lead well.
Expectations are clear enough that people stop guessing what matters.
The board sees stability, coherence, and progress it can measure.
How It Works

Every engagement is adaptive.

1
Insight & Clarity
A fast, accurate read of what's happening, surfacing patterns and sketching the 2–3 moves that will shift things fastest.
2
Stabilization
COO or CHRO leadership while things move, or partnership with the leaders already in those roles.
3
Design & Build
Nimble operational scaffolding: decision pathways, goal setting, role clarity, workflows, onboarding systems, and tools for healthy conflict.
4
Momentum & Thrive
Embed habits and systems so progress holds. The shift from crisis-driven execution to structured, sustainable motion.
Starting Point
The Friction Finder
My quick diagnostic that surfaces your human, relational, and operating conditions *plus* the 2–3 specific moves most likely to create momentum.
Areas of Expertise

Across the full operational stack.

Operations & Systems
Operational Scaling Systems Integration OKRs & Execution Cadence Meeting Architecture Distributed Decision Models
HR / People & Culture
Compensation Design Staff Development Planning Core Curriculum Onboarding Labor & Employee Relations Talent Acquisition & Hiring
Finance & Governance
Multi-Scenario Budgeting Financial Infrastructure Board & Funder Relations Audit Readiness Fiscal Sponsorship Models
Technology & AI
HRIS / ATS Implementation AI Workflow Integration Ethics-Guardrailed Automation Digital Capital Projects Data & Reporting Infrastructure
Risk Assessment
Risk Calibration Framework Compliance & Labor Law Multi-Jurisdiction Exposure Org Health Diagnostics Crisis Stabilization
R&D & Innovation
R&D Pipeline Development Acquisition Due Diligence Spin-off & Integration Product Strategy (B2B/B2C) Earned Revenue Ventures
Why CEOs Bring Me In
The pattern behind the work.
I've run organizations, not just advised them.
As COO and then Co-CEO, I helped scale Fractured Atlas from $4.5M to $30M, and led a 50-person team across 12 states and 6 countries. When I recommend a structure, it's one I have operated under pressure.
People and operations are one system, and I hold both.
I work across finance, operations, culture, and staff experience as a single environment, because a compensation model, a decision pathway, and a hard conversation are usually the same challenge through different lenses.
I work in the seat or alongside the leaders already in it.
Some organizations need someone to step into the COO or CHRO role for a season. Others need a partner to build with the strong people already there. I do both.
I build structures that hold after I leave.
I leave behind decision pathways, operating cadences, and tools your team owns, so progress doesn't quietly snap back to the old pattern.
I can move quickly because I've done the read before.
Across 20+ years I have developed and tested 35+ tools for this work. That library lets me get an accurate read in weeks rather than quarters.
In Their Words

What CEOs say.

"Tim creates environments where the CEO can have a high risk tolerance with new initiatives, while guardrails protect the organization."
CEO, Tech Nonprofit
"With Tim you get something rare: insurance for upside, not just mitigation of downside risks."
CEO, Investment fund
"Structure is care. Tim builds the structures that unlock and support people and performance."
COO, Arts Nonprofit
"Tim contributed significantly to making our organization a leader in the nonprofit sector."
Board Chair
"My work with Tim changed the way I think about culture, hiring, and leadership."
CFO, B Corp
"Tim's capacity to engage in this complex work stems from his depth of knowledge — and his kindness, openness, and humor."
CEO, social impact futures

BEST FIT

Who I work with.

Mission-driven nonprofits, public benefit corps, higher education, tech start-ups, and cultural organizations navigating growth, leadership transitions, or structural complexity.

Typically $1M–$50M in revenue, with 40–500 staff often across multiple locations, states, or countries.

Engagements range from a focused 90-day stabilization to an ongoing fractional COO or CHRO relationship.

You lead a mission-driven org and the internal experience feels scattered despite a strong external reputation
Your leadership team is talented but struggles to move in sync
You've inherited complex systems shaped by predecessors, rapid growth, or pandemic-era decisions
You need steadiness and an opening for meaningful transformation, not just crisis management
You want a partner who holds strategy and execution simultaneously, without needing you to manage them
Get In Touch
Let's get this moving.

Growth, a transition, or a leadership gap will eventually test the structure underneath your mission. The work is making sure it holds, and that it keeps holding after I step back.

Start with the Friction Finder for a fast, honest read on where things stand. Or reach out directly, and we will treat the first conversation as exactly that: a first move, and a read on whether we are a fit to make it together.