VP of Product and Engineering

At Destify, we're reimagining the destination wedding experience — simplifying the complex, celebrating the meaningful, and building technology that connects thousands of couples to their dream celebrations. Destify is seeking an experienced VP to lead the vision, strategy, and execution of our technology and product platforms, shaping the future of destination weddings. You'll sit on the company leadership team while overseeing both the Product and Engineering functions, ensuring seamless collaboration, innovation, and delivery.

In this role, you'll be responsible not only for innovating new capabilities but also for strengthening and evolving our existing product stack. Improving performance, scalability, and reliability as we prepare to scale Destify's platform and accelerate our growth. Here's what you will do:

• Product & Technology Strategy
• Define and own the product and technology vision aligned with Destify's business strategy.
• Translate company goals and customer needs into a clear, actionable roadmap.
• Identify market trends, technical opportunities, and user insights that drive innovation and competitive advantage.
• Leadership & Team Development
• Lead, mentor, and grow cross-functional teams across Product, Engineering, and Design.
• Foster a culture of ownership, accountability, and collaboration.
• Set clear objectives and create pathways for professional development across both disciplines.
• Execution & Delivery
• Oversee the full product lifecycle — from discovery and design to development, testing, and release.
• Partner with company leadership to prioritize initiatives that drive business growth and operational efficiency.
• Ensure timely, high-quality delivery.
• Implement scalable systems, tools, and processes to support rapid product iteration and reliability.
• User Experience & Data-Driven Optimization
• Champion a user-first mindset across all product and engineering initiatives.
• Leverage analytics, A/B testing, and customer feedback to inform decision-making.
• Collaborate with business stakeholders to align the product experience with revenue, engagement, and retention goals.
• Cross-Functional Collaboration & Go-to-Market
• Partner with Marketing, Operations, and Sales to launch new features and enhancements that resonate with couples and partners.
• Translate technical capabilities into compelling product stories and market advantages.
• Gather post-launch insights to continuously improve both the product and underlying systems.

Requirements:

• 10+ years of progressive experience in product management or combined product/technology roles within a high-growth consumer tech environment — ideally in travel, marketplace, or mobile apps.
• Proven track record of leading teams through rapid scale and delivering measurable business outcomes (e.g., $10M ? $50M+ growth).
• Deep understanding of both product strategy and technical execution — you can think like a founder, act like an operator, and communicate like a product storyteller.
• Strong intuition for great UX combined with analytical rigor.
• Expert at defining and tracking metrics, running A/B tests, and making data-driven prioritization decisions.
• Excellent communicator and motivator who thrives in a fast-paced, entrepreneurial environment.
• Bachelor's degree or equivalent experience in computer science, design, business, or related field.

We Offer:

• Salary from $200,000-250,000
• Flexible Paid Time Off and Paid Parental Leave
• Caribbean travel perks to reward high performers
• Fully remote work environment
• Comprehensive benefits – Medical, Dental, and Vision
• 401(k) with company match

Employment Notes:

Candidates should be authorized to accept employment in the US from any employer, should be willing to start within three weeks of accepting an offer, and should be able to work the same daily working hours as our Chicago office.

Destify is committed to providing equal employment opportunities regardless of sex, age, race, color, national origin, religion, marital status, pregnancy, sexual orientation, gender identity, disability, citizenship, veteran or military status, and other legally protected characteristics.

AI use disclaimer:

Please be advised that Destify utilizes artificial intelligence tools to assist in the initial review of resumes. This technology is used to enhance our recruitment process by analyzing key qualifications and skills. However, interviewing decisions are made by our human resources team based on a comprehensive evaluation of each candidate's qualifications and experience. If you have any concerns about the use of AI in our hiring process, please feel free to contact our HR department, at for clarification.