The Profile / Strategy & Operations
Madeleine
Ormond
The strategist who turns big plans into working businesses - and built a firm to prove consulting can do the same.
The strategist who turns big plans into working businesses - and built a firm to prove consulting can do the same.
Madeleine Ormond spends her days on the least glamorous and most decisive part of business: the handoff between a good idea and a working operation. As co-founder and chief strategist of The Backflip Group, a boutique firm she helped launch in New York, she works with growing technology companies on the mechanics of getting from a plan to something real - the financial model, the product roadmap, the go-to-market motion, the pricing.
The firm's promise is deliberately blunt. It calls itself "a new kind of consulting designed to get you from strategy to reality." For Ormond, that phrase is less a tagline than a critique of the industry she works in. Traditional consulting tends to end where the hard part begins - a polished recommendation, a thick deck, and a client left to build it alone. The Backflip Group is structured to carry the work further, embedding with clients to test ideas, incubate proof-of-concepts, and put scalable systems in place.
She and co-founder Ceylan Conger split the work along complementary lines. Conger leads on customer-driven growth strategy and operations; Ormond leads on product, business, and financial planning. Together they describe their approach as looking at a business through a wide-angle lens - the discipline of examining product, finance, operations, and market all at once rather than solving for one and breaking another.
What makes that possible is a decade spent inside technology companies before she ever hung out a shingle. Ormond worked in-house at both emerging startups and established tech enterprises, leading cross-functional teams through the kind of strategic initiatives meant to accelerate growth and efficiency. That vantage point - having lived on the client's side of the table - shapes how she works now.
Ormond's work sits at the intersection of numbers and product. These are the disciplines she leans on most - a spread that explains why clients bring her the problems that do not fit neatly into one department.
Rather than betting a company on a sweeping transformation, she favors low-risk testing and incubation - small experiments that reveal whether an idea holds up before real money is committed.
A financial model is not just a forecast. For Ormond it is a way to pressure-test a strategy early, surfacing the assumptions that would otherwise only fail in production.
The point is not the recommendation - it is the working system left behind. She builds toward scalable operations and solid foundations, not one-off answers.
Her route into strategy ran through the inside of tech companies, not a consulting firm's analyst program - which is part of why her practice looks different from the ones she competes with.
The Backflip Group's third "team member" is a dog named Sgt. Pepper, listed as Chief Motivational Officer - a small sign of a small, personable firm.
Her whole philosophy fits in the firm's tagline: strategy to reality.
She works across product, finance, operations, and go-to-market instead of specializing in a single lane - the wide-angle lens in practice.