Geoffrey McCaleb

About

With over 15 years of product management experience, I excel at creating and scaling user-centric products that solve real problems and deliver value. My expertise spans fintech, B2B SAAS, and multi-sided marketplaces, as well as emerging technologies such as AI and DeFi/NFT's. As the Head of Product at CitizenShipper, I led the product development and engineering teams to achieve aggressive platform growth and introduced overall maturity into the product lifecycle. I successfully integrated Stripe Connect and Payouts, and redesigned the UX/UI strategy for this multi-sided marketplace/SaaS platform. I leverage data, empathy, vision, and agile methods to deliver outstanding user experiences that just work.

Experience

• AI Training and Hands-on Building · Independent2025-09-01 –

  AI isn’t a feature or a single layer in the stack. It introduces a fundamentally different process and workflow for product and engineering teams. I took time off to explore this firsthand by building and shipping a full-stack application using multiple LLMs (primarily Claude), with a focus on production-grade workflows, quality controls, and AI-augmented development practices. Infrastructure & DevOps - Docker-based containerization with local, staging, and production environments - CI/CD pipelines using GitHub Actions and self-hosted runners - API-driven infrastructure operations (custom host-ops and debug APIs) - Git workflow hardening with branch protection and automated hooks Testing & Quality - Test-Driven Development with enforced RED → GREEN → REFACTOR discipline - Multi-layer testing strategy: E2E (browser), API, and database assertions - Playwright automation for UI and API coverage - Pre-push verification and automated quality gates Development Workflow - Structured AI collaboration with defined guardrails and human review checkpoints - Workflow state tracking to ensure consistency and traceability - Design-fidelity validation between mockups and implementation - Documentation-driven development with living API contracts and test checklists

• Director of Product Management · BeSmartee2024-02-01 – 2025-06-01

  • Spearheaded the development of a cutting-edge Mortgage SaaS platform, driving innovation in the digital mortgage space. • Integrated AI technologies to streamline end-to-end design and enhance R&D processes, significantly reducing time to market. • Managed a high-performing team of product managers, fostering collaboration to achieve ambitious growth targets. • Expanded a vendor marketplace, improving pricing transparency and operational efficiency across the mortgage industry.

• Head of Product · CitizenShipper2021-08-01 – 2023-11-01

  • Spearheaded a comprehensive redesign of the 6 and 12-month product roadmap for this multi-sided marketplace/B2B SaaS platform. • Successfully launched the migration to end-to-end payments using Stripe and Affirm, enhancing user experience. • Implemented advanced capabilities that reduced fraud usage by 99.4%, improving platform security and trust.

• Director of Product · Surkus2020-01-01 – 2021-07-01

  • Recruited by a Groupon co-founder to spearhead a local-focused SaaS platform for small business discovery. • Led a team of 9 product managers, QA, and UX professionals to enhance user experience and product functionality. • Executed a suite of B2B SaaS tools, optimizing ad budgets and special offers for small businesses. • Expanded the reach and engagement of the multi-platform Native App, increasing revenue by 30%

• Relocation to the USA · Me, Myself, and I2019-11-01 – 2019-12-01

  After 15+ years of living in London, my wife and I decided to start a new chapter of our life in the USA!

• Head of Product (Interim) · Pollinate International2019-01-01 – 2019-09-01

  • Part of the go-to-market & launch management team to deliver a 0-1 merchant acquiring platform for SMB's across the UK and abroad. • Designed and built out a comprehensive B2B SaaS platform designed to help small businesses manage their day to day payment and data/insight operations. • Personally directed a team of 12+ across Product, Project Management, and Business Analysis teams. • MVP launch resulted in a $80M+ fundraise and a successful spinout into a standalone company. • Short term role due to impending relocation to the USA.

• Founder, Head of Product · Join Pinch2018-10-01 – 2019-03-01

  Pinch was a side project to build a compelling private social media platform using Flutter and Elixir. Angel funded.

• Mobile Product Director · Ascential2016-09-01 – 2018-10-01

  • First hire to deliver a suite of native mobile apps (iOS, Android) and e-commerce platforms for two of the largest live events in the world: Cannes Lions (Marketing & Advertising) and Money 20/20 Vegas, EU, and Asia (FinTech). • Drove $1M+ in incremental revenue for Cannes Lions via checkout funnel optimization and platform rationalization. • Developed mobile and desktop product strategies that resulted in trac and NPS increase by 75%. • Designed the strategy and corpus for their Sales AI Chatbot, which leveraged Google's Dialogow and WhatsApp for Business API.

• Activations Product Consultant · Apple2015-08-01 – 2016-07-01

  • Member of the delivery team that integrated both front and backend capabilities of ApplePay with the initial launch partner, Barclays Bank within just 60 days. • Deployed Apple's multi-channel platform to Apple Retail stores spanning from China, Germany, Canada, and the USA to allow customers to purchase a connected iPhone or iPad. • Lead work stream to update payment systems to comply with PCI DSS certication.

• Senior Product Consultant · Three.2014-09-01 – 2015-07-01

  • Re-designed Three’s connected e-commerce sales product strategy while also mentoring up to 12 sprint teams in LEAN (Agile) from their existing Waterfall (Prince2) process. • New tablet strategy led to an overall sales increase of 40% YoY during a key sales period. Strategy later transferred to phones. • Also designed the corpus and strategy for their AI chatbot, built using IBM’s Watson.

Education

• Los Angeles Valley CollegeObject Oriented Programming

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