Josh Chapman
I'm COO at Aeropay, building pay-by-bank payment infrastructure for gaming and cannabis businesses, industries most payment processors won't touch. Before stepping into the COO seat, I built Aeropay's financial model as CFO, so when I run the operating plan today, it's the same plan I built: no gap between the numbers and the reality.
That work sits on top of 31 years of operating and executive leadership, including CEO of a 50-person Series A startup (GiveForward), VP of Operations for a company that sold for $3 billion (Cars.com), and COO roles across healthcare, marketplace, and wholesale/logistics businesses.
Also: raised over $100 million in capital from angels, VCs, and strategics; turned an underperforming company from burning $100K/month to profitable in 14 months; and led an operating business through the onset of COVID-19 without disruption to customers or team (LandscapeHub).
The Core Sample
Granite forms in layers, under pressure, over time. So does an operator. Read from the bedrock up.
Aeropay: CFO → COO
Built the financial model, then took ownership of running against it.
Postindustria: Fractional CRO
Rebuilt the revenue org and systems ahead of a $5M → $25–30M growth target.
Hunt Club: SVP
Scaled the search function from 20 to 100 people in 9 months.
LandscapeHub: COO
Owned all functions outside Product, Tech, and Sales, including operations through the onset of COVID-19.
MATTER: COO & Treasurer
Operating leader for a 200-startup healthcare innovation collaborative.
GiveForward: CEO
Led a pivot beyond crowdfunding; closed two financing rounds; sold to a top competitor.
Cars.com: VP of Operations
Senior leadership through the company's $3B exit.
Xerox, StarTek, Allianz Global Assistance
Bedrock years: full P&L ownership, site turnarounds, and scaling operations from the ground up.
The most common question I get isn't "what do you do." It's "will you join full-time?"
Over the past 8 years I've advised dozens of start-ups and mid-market companies. The two questions I hear most:
1. Will you join our company as COO? The honest answer is usually no, not because I wouldn't want to, but because you're often not ready for a full-time COO, and don't need one yet. I've been the COO hired too early in a company's trajectory, and I help others avoid that mistake.
2. Do I need a COO? That takes a real conversation with the leadership team. Being fractional lets me help you answer that before you make a long-term commitment.
Fintech & Payments · SaaS · Marketplace · Media · Auto · Professional Services · Specialty Insurance · Healthcare · Retail · Crowdfunding · Co-working · Events
- Board Member: La Rabida Children's Hospital
- Board Member: Park Ridge Baseball Softball
- Mentor: Junto Institute