OluKai Strategic Planning Director

Archipelago Companies • Irvine, CA

4d • $150,000 - $170,000 • Hybrid

About The Position

OluKai 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 OluKai plans, prioritizes, and scales for the future.

Requirements

• Bachelor’s degree in Business, Strategy, Finance, Marketing, or equivalent experience
• Minimum of 10 years of experience in strategy, strategic planning, management consulting, corporate development, or brand strategy.
• Track record of building long-range plans and prioritization frameworks that held up under real business pressure.
• Strong command of consumer insight, market analytics, and competitive intelligence, and the ability to turn them into a clear strategic point of view.
• Proven experience aligning cross-functional partners — particularly Product, Creative, Marketing, and Sales — around a shared go-to-market direction.
• Exceptional executive communication and presentation skills, with experience building materials for boards or senior leadership.
• Comfortable navigating ambiguity and bringing structure to a fast-moving and brand-driven environment.

Responsibilities

• Lead the development of OluKai’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 OluKai 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 same direction.
• Present strategic recommendations clearly and persuasively to senior leadership, translating complex business challenges into focused decisions and actionable direction.

Benefits

• Complimentary chef prepared breakfast and lunch provided Monday - Thursday
• Generous product gift program and all brand discounts
• Company bonus program
• 5 year and 10 year Anniversary gifts to Hawaii and other desirable destinations
• Medical, Dental, Vision insurance in accordance with plan guidelines
• Company paid life insurance
• 401k with employer match in accordance with plan guidelines
• 15 Days of PTO plus one additional day of PTO every year on your anniversary and 3 Floating Holidays per year
• Paid beach and giveback days, bi annual team building events and other in person celebrations
• Work with talented and great people who share a love of the ocean lifestyle
• OluKai is a Certified B Corporation with paid company service days
• Dog friendly office

What This Job Offers

• Job Type: Full-time
• Career Level: Director