Strategic Planning Director

Who We Are

At Olu Kai, we build premium products for the ocean lifestyle. Our footwear is created using the highest quality materials and crafted into beautiful, functional and incredibly comfortable designs that reflect the spirit of the ocean lifestyle we all enjoy.

At Olu Kai, we build premium products for the ocean lifestyle. Our footwear is created using the highest quality materials and crafted into beautiful, functional and incredibly comfortable designs that reflect the spirit of the ocean lifestyle we all enjoy.

We are committed to creating quality products for our customers while leaving the smallest footprint possible on the planet. Our company philosophy is to be environmentally responsible as manufacturers and to pledge Olu Kai to actively support and work for a clean environment and a better quality of life.

Our customers and staff embody the connection that exists between people and the ocean, it is our Culture. We want to build a team of individuals who embrace this culture and have a passion for providing premium products and service to our customers.

Olu Kai is seeking a Strategic Planning Director to shape the long‑term vision and strategic priorities that drive our continued growth. Reporting directly to the Chief of Staff, this highly visible role sits at the intersection of strategy and execution, translating ambitious business objectives into clear, actionable plans across the organization.

The ideal candidate is an influential thinker and trusted partner who can navigate complex decisions, align cross‑functional teams, and bring clarity to competing priorities. Working closely with Product, Creative, Marketing, Sales, and leadership teams, you will help define where we are headed, ensure strategic alignment, and create the focus and accountability needed to turn vision into results. This role will play a critical part in how Olu Kai plans, prioritizes, and scales for the future.

• Lead the development of Olu Kai’s multi‑year brand and business strategy, translating consumer insight, market dynamics, and financial realities into a clear set of priorities and growth bets.
• Build and maintain long‑range plans and roadmaps that stay grounded in what the business can realistically execute, season over season.
• Structure and facilitate the strategic planning cadence — annual planning, quarterly check‑ins, milestone reviews — so prioritization and decision‑making stay disciplined as Olu Kai scales.
• Bring planning frameworks, tools, and a consistent strategic vocabulary to the organization so other teams can plan and prioritize more effectively on their own.

• Partner day‑to‑day with Product, Creative, Marketing, and Sales leadership to shape roadmaps, align go‑to‑market plans, and make sure strategic priorities show up in what each team actually builds and sells.
• Act as a close thought partner to the Chief of Staff, helping frame key decisions, prepare leadership discussions, and keep enterprise priorities moving in step with one another.
• Spot interdependencies and risks across Product, Creative, Marketing and Sales early, and help resolve them before they become roadblocks to execution.
• Drive alignment across stakeholders; act as the connective tissue between long‑term strategy and the day‑to‑day decisions each function is making.
• Partner closely with the Tradewind Services finance team to align strategic plans with budgeting, forecasting, and financial reporting cycles, ensuring priorities are grounded in financial reality.

• Turn consumer research, sell‑through data, competitive intelligence, and market trends into recommendations — challenging assumptions and surfacing opportunities the business might otherwise miss.
• Maintain a rigorous, evidence‑based approach to prioritization, so resourcing and investment decisions are grounded in the strongest available data.

• Develop the strategic narrative and materials — leadership readouts, long‑range plans, business cases — that get executives and cross‑functional teams aligned and moving in the…