Head of Innovation

The Company

Glassbox's mission is to reveal the insights that empower organizations to deliver exceptional digital customer experiences.

Glassbox is a leading force in shaping digital experiences. It helps organizations uncover digital issues, boost conversion rates, enhance accessibility, prevent fraud, and more. Leveraging AI-driven customer intelligence, Glassbox enables enterprises to deliver secure, proactive, and preventative digital experiences. Its solutions are trusted by highly regulated organizations, including SoFi, Cal, and many others. We are growing and have been recognized by G2 as one of 2024's Top 50 Software Companies in the world.

Head of Innovation (Product & Technology)

About Glassbox

Glassbox is a leading digital experience analytics platform that empowers organizations to understand and optimize customer journeys. We combine advanced analytics, session replay, and AI-driven insights to help enterprises make smarter decisions and deliver better digital experiences.

About the Role

We are looking for a Head of Innovation (Product & Technology) to lead our innovation domain and drive the next generation of Glassbox products and capabilities.

This role is responsible for owning the full innovation lifecycle—from identifying opportunities based on market trends and customer needs, through ideation and validation, to full end-to-end delivery.

You will lead a small, high-impact team of engineers and operate at the intersection of product strategy, technology, and execution. This role is ideal for former CPTOs / CTOs / CPOs in smaller companies who are passionate about building, experimenting, and delivering real impact.

What You Will Do

Innovation Strategy & Vision

• Define and lead Glassbox's innovation strategy, aligned with company goals and market opportunities
• Identify new product opportunities based on market research, competitors, and emerging technologies
• Build and maintain a forward-looking innovation roadmap
  
  

• Own the full lifecycle of innovation initiatives: idea → validation → MVP → production
• Translate ideas into scalable product capabilities and technical solutions
• Drive rapid experimentation and iteration, including PoCs and pilots
• Ensure successful handoff or integration into core product teams
  
  

• Lead and grow a team of engineers focused on innovation initiatives
• Foster a culture of creativity, ownership, and fast execution
• Mentor engineers and promote cross-functional collaboration
  
  

• Work closely with Product, R&D, GTM, and leadership
• Act as a bridge between business needs and technical execution
• Collaborate with external partners where relevant
  
  

• Stay ahead of industry trends, technologies, and competitive landscape
• Evaluate new tools, frameworks, and architectures
• Drive adoption of cutting-edge technologies (AI, data, etc.)
  
  

• Former CPTO / CTO / CPO / Head of Product or Engineering in a startup or small company
• 8+ years of experience in product and/or engineering leadership
• Proven track record of building and launching innovative products end-to-end
• Experience leading small, high-performing teams
  
  

• Strong ability to combine product thinking with deep technical understanding
• Hands-on approach with a bias toward execution and delivery
• Deep understanding of product lifecycle, architecture, and scalability
• Excellent analytical and market-driven decision-making skills
• Ability to operate in ambiguity and fast-changing environments
  
  

• Builder mentality – from idea to production
• Passion for innovation, experimentation, and impact
• Comfortable being both strategic and hands-on
• Strong ownership and accountability
  
  

• Lead and shape Glassbox's innovation engine
• High visibility and direct impact on company growth
• Work on cutting-edge technologies and products
• Build and lead a focused, high-impact team