VP of Product and Technology

Travel Zap•Chicago, IL

27d•$200,000 - $250,000•Remote

About The Position

We are Destify! We focus on our people, our culture, and our technology. 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. Who You Are and What You’ll Do: An experienced VP who will 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 and Design 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. You will apply AI as a pragmatic force multiplier across discovery, delivery, and operations—establishing clear guardrails and ROI criteria so the “latest” tool doesn’t automatically mean “best.”

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.

Responsibilities

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, especially where AI can 10× speed, quality, or personalization. Establish decision rules that “latest ? best”: prefer the simplest tool that meets the outcome; require evaluation and ROI evidence before adopting new models, frameworks, or vendors.
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. Coach teams on AI-assisted workflows (coding, testing, analytics, support) while upholding architecture, security, accessibility, and reliability fundamentals.
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. Enable scalable delivery practices by setting standards, removing blockers, and aligning teams on quality and release expectations; partner with Engineering leadership on systems and process choices that support rapid, reliable iteration. Champion AI-assisted development (e.g., Claude Code or equivalent) through policy, training, and evaluation; align on org-level metrics and reviews to ensure tangible impact—without owning tool implementation. Set expectations for rapid prototyping (e.g., v0 and Figma-to-code tools) to compress concept-to-prototype timelines; ensure outputs inform discovery and are validated before build commitments. Partner with Engineering leadership to mature our LLM/AI platform layer (prompt libraries, evaluation harnesses, guardrails, observability, data/privacy controls) and set the product standards for where and when to apply it.
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. Use experimentation to make “kill or double-down” decisions quickly based on evidence—not novelty.
Cross-Functional Collaboration & Go-to-Market Partner with Marketing, Operations, and Sales to launch new features and enhancements that resonate with couples and partners, including AI-powered experiences where they deliver clear value. Translate technical capabilities into compelling product stories and market advantages —especially communicating AI capabilities, limitations, safety, and value. Gather post-launch insights to continuously improve both the product and underlying systems.