PetFriendly: Chief of Staff
Chief of Staff at a subscription pet wellness startup, 2022 to 2024. Company strategy, OKRs across every department, a 23-person product org across three countries, and the budget behind it.
The Mandate
I joined PetFriendly in February 2022 as Chief of Staff, second in command to the CEO, and stayed through March 2024. The official remit was growth, process, brand, and product launch, which in practice meant whatever the company had not yet built.
The job covered day-to-day operations and chairing the leadership meetings. It also came with standing authority to decide in the CEO's absence, and interim executive duty on business inquiries and high-level decisions when he was out.
Company Strategy
The company-wide strategy spanned four areas: brand, customer experience, technology, and leadership. Building it meant setting the direction each function worked toward, then keeping those directions from pulling against each other, which is most of the job at a company this size.
The data strategy and the process around it came out of the same stretch. Before that, reporting was assembled by hand whenever someone asked a question. Afterwards there was a defined source of truth and a routine for keeping it current, so leadership arguments could be about the decision rather than about whose number was right.
OKRs Across Every Department
OKRs ran across the whole company, not one function. Every department set objectives through the same process, on the same cadence, and reviewed them in the same forum. The value was less in the framework than in the cadence: a standing rhythm where teams said out loud what they intended to do and then reported honestly on what happened.
Coming from agile coaching, I had already spent years watching this go wrong. The failure mode is treating OKRs as a reporting tax instead of a prioritization tool, so I kept the set small and made it acceptable to miss one and say why.
A Product Org Across Three Countries
At its widest the group ran to 23 people. Eleven were in-house product and engineering: backend, frontend, a VP of Technology, plus design and data. Twelve were contracted, eight Laravel engineers in Canada, two in the United States, and two in the Philippines. Alongside that we ran a year-long agency engagement.
Spread across those time zones, the coordination is the work. I owned scope, schedule, and the handoffs between groups, which is where distributed builds usually fail. The practical version was making sure a decision taken in Omaha on Tuesday afternoon reached Manila before it blocked anyone, and that no group was waiting on an answer nobody had been asked for.
Twelve contractors on three continents cannot be supervised, so they were not. Each group decided inside its own scope and was told plainly where the edges were. Freedom with responsibility attached costs less than oversight and it survives a nine-hour time difference, which supervision does not.
Tripling the Product
PetFriendly grew from a single product into a multi-product platform. We tripled the product offering. That meant spotting market opportunities, prioritizing features from customer feedback, and coordinating engineering, design, and marketing to ship on time.
The Headless Commerce Build
The largest objective on the company roadmap was a custom headless commerce platform, built from the ground up for subscription products instead of bolted onto a template. I led it to delivery.
Subscription is the hard part. A standard storefront assumes a one-time cart, so recurring billing, plan changes, skips, and swaps all have to be designed, not configured, and every one of them touches fulfillment for a physical product that ships on a schedule.
Building the Team
I ran hiring and onboarding together with the people team. My focus was team structure, the skills we needed, and the people we brought on, along with the routines a small startup needs to stay organized as it grows.
Onboarding mattered more than usual here. With contractors joining from three countries, anything that lived only in someone's head was a single point of failure, so it had to be written down.
Budget and Vendor Accountability
I held budget and cost-control accountability for the technology program: in-house engineering, two contractor teams, the agency, and the replatform. It was a multi-million-dollar program, and I partnered with the CFO on spend, forecasting, and the trade-off calls underneath it.
Managing a premium agency's scope against an in-house timeline was the real work. An outside shop works to its own delivery window, and keeping that honest against what the internal team could absorb is a different skill from writing the contract.