Controller, AI-Enabled Finance Operations

Lovingly is an AI-driven emotional commerce platform serving around 1,000 independent florists across the U.S. and Canada. We provide platformed websites, point-of-sale, and digital marketing services that help local florists win in their local markets while building a consumer brand that customers return to.

We operate at the intersection of local commerce, technology, and emotionally meaningful moments. Our partners are florists — and the work we do for them shows up at weddings, funerals, birthdays, and every moment in between.

We're a B2B technology platform. We build systems, not one-off campaigns, and we use AI as a core part of how we operate, not as a buzzword. In finance, that means taking our operations from chaos to clarity — systems that just run.

About the Role We're hiring a hands-on Controller to own the accuracy, integrity, controls, timeliness, continuity, and daily operation of our finance function.

This is not a traditional Controller role built around managing a large accounting department or reviewing work from a distance. It's a working finance-leadership role for someone who can personally own the accounting function, directly manage a Senior Accountant, and progressively operate finance through Claire — our AI finance operator — and modern financial systems.

You remain accountable for the finance outcome whether the underlying work is done by you, your Senior Accountant, Claire, an outside provider, or another system. The initial mix is roughly 75% finance stabilization and control, 25% systems, automation, and Claire development, shifting after stabilization to roughly 65% finance reliability and control, 35% systems, automation, team development, and leverage creation.

The Operating Model We're building a finance function where routine work is increasingly performed through intelligent systems, while human expertise concentrates on financial truth, judgment, controls, exceptions, analysis, compliance, and business de