Tradewind Services Vice President of Technology

Who We Are:

Archipelago Companies a portfolio of highly successful consumer lifestyle brands is seeking a talented and passionate individual with an entrepreneurial mindset to join our team. Our brands including OluKai Kaenon Melin Roark and Tradewind Services are leaders in their respective markets offering high-quality products and authentic marketing stories direct to consumers. At Archipelago Companies we pride ourselves on our commitment to integrity and we strive to create a culture of excellence in everything we do. If you are a driven and innovative individual with a passion for consumer brands we invite you to apply for our open position and become a part of our dynamic and growing team.

About The Role:

The Vice President of Technology is a critical member of the senior leadership team responsible for defining and executing the companys overarching technology and digital product strategy. This executive will oversee the end-to-end delivery of scalable secure and consumer-centric technology platforms across ecommerce and retail channels.

Combining deep technical acumen with a strong business mindset the VP of Technology will lead product development technology infrastructure and innovation initiatives. You will manage high-performing cross-functional teams and play a key role in shaping a seamless omnichannel consumer experience ensuring alignment with business goals and customer needs.

You are entrepreneurial hands-on and thrive in high-growth dynamic environments. You balance strategic foresight with a roll-up-your-sleeves attitude and are passionate about fostering innovation collaboration and agility.

Responsibilities include but are not limited to:

Strategic Leadership & Roadmap Development:

• Develop and execute a comprehensive digital product and technology strategy aligned with business goals and customer expectations.
• Build and manage an integrated roadmap for ecommerce retail and cloud platforms ensuring timely delivery scalability and performance.
• Drive adoption of agile lean and data-informed decision-making practices to optimize team output and product success.
• Discover and implement new technologies that yield a competitive advantage

Technology & Platform Ownership:

• Lead the design development deployment and optimization of the companys technology backbone encompassing cloud infrastructure digital workflows and omnichannel applications.
• Ensure platforms are scalable secure and performant supporting both ecommerce and in-store operations.
• Promote technological innovation and identify opportunities to solve business challenges through tech enablement.
• Contribute directly to codebases or architecture when needed to unblock teams or set best practices.

Team & Talent Development:

• Lead mentor and grow a multidisciplinary team of software engineers digital product managers designers QA engineers and technical staff.
• Foster a culture of innovation experimentation and collaboration.
• Establish and track KPIs to guide team performance consumer experience enhancements and continuous improvement.

Cross-Functional Alignment & Stakeholder Management:

• Collaborate with ecommerce retail IT operations marketing and creative teams to ensure unified execution of the digital and technology roadmap.
• Drive organizational change management and lead the adoption of new technologies and processes.
• Maintain strong relationships with senior leadership third-party vendors and external partners to ensure successful strategy execution.

Executive Communication & Reporting:

• Develop and deliver executive-level presentations updates and strategic insights for leadership and stakeholders.
• Translate technical financial and marketing information into clear actionable business language.

Other responsibilities as assigned.

Qualifications Skills Experience:

• Bachelor Degree in technology related field Masters Degree preferred.
• At least 15 years of direct digital product management experience with a successful track record in the ecommerce and/or retail sectors.
• Minimum of 3 years of leadership experience managing multidisciplinary and distributed teams.
• Strong product management and planning skills with the ability to manage multiple priorities in a fast-paced environment.
• Deep understanding of agile/Scrum methodologies and iterative development cycles.
• Strong business acumen and ability to apply KPI tracking financial metrics and ROI analysis to guide decisions.
• Hands-on experience with Shopify (Required); familiarity with Full Circle (Preferred).
• Strong working knowledge of AI and how to utilize in business.
• Ability to translate complex financial technical and marketing data into actionable product and technology plans.
• Must have experience with international store expansion Shopify Markets and omnichannel orchestration. A deep understanding end to end order flows OMS architecture and ERP is a plus.
• Excellent communication and interpersonal skills with proven ability to build trust and influence stakeholders at all levels.
• Experience leading cross-functional teams across multiple time zones and geographic locations.

What We Offer:

• A high-impact leadership role with strategic influence across the organization.
• Opportunity to lead innovation and shape the future of technology and digital product development.
• A collaborative agile and growth-focused culture that embraces experimentation and bold thinking.

Location & Office Structure: This is an in-office hybrid position mandatory 4 days per week in office in Irvine CA with the option to work from home 1 day per week. On call as needed and subject to change without notice as per company guidelines.

Compensation: The salary range for this position is $200000 to $250000 plus opportunity for annual bonus; salary is based on the experience that you bring to the position.

Benefits and Perks:

• Complimentary chef prepared breakfast and lunch provided Monday - Thursday
• Generous product gift program and all brand discounts
• Growth opportunities within the Archipelago family of brands: OluKai Kaenon Melin Roark
• Company bonus program
• 5 year and 10 year Anniversary gifts to Hawaii and other desirable destinations
• Wellness program including but not limited to in-office gym and group fitness classes
• 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
  

Archipelago Companies values a diverse inclusive and entrepreneurial workforce and culture and we provide equal employment opportunity for all applicants and employees. All qualified applicants for employment will be considered without regard to an individuals race color sex gender identity gender expression religion age national origin or ancestry citizenship physical or mental disability medical condition family care status marital status domestic partner status sexual orientation genetic information military or veteran status or any other basis protected by federal state or local laws. If you are unable to submit your application because of incompatible assistive technology or a disability please contact us at Archipelago will reasonably accommodate qualified individuals with disabilities to the extent required by applicable law.

Required Experience:

Chief