Jimmy R.

Raleigh, NC, USA

Fractional Head of Product for SaaS and Platform Businesses Navigating Scale and Complexity

I’m a fractional product and technology leader with 20+ years of experience helping SaaS and platform businesses regain clarity when growth, complexity, or change starts to outpace execution. I’ve built products both as a founder and as an executive inside scaling organizations, partnering closely with leadership teams when product direction needs focus, teams need structure, or platforms need to evolve without slowing the business down.

My background spans commerce, payments, customer experience…

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Experience

Self-employed
Fractional Head of Product / Product & Technology Advisor
Jan 2024 - Present
Partnering with founders and executive teams to provide hands-on product leadership across strategy, platform evolution, team structure, and AI-enabled product development. Engagements typically focus on clarifying product direction, modernizing platforms, improving execution, and supporting leadership through periods of scale or transition.
- Led product strategy and roadmap definition for SaaS and platform businesses across commerce, payments, and customer experience
- Advised leadership teams on product org design, operating models, and delivery cadence
- Supported platform modernization initiatives involving APIs, data, and AI-driven capabilities
- Operated in fractional, hands-on roles bridging strategy and execution
Jewelers Mutual Group
VP of Product, Digital Customer Solutions
Dec 2024 - Jan 2026
Built and scaled a modern digital product organization inside a legacy enterprise, launching new customer and partner platforms while establishing product operating models from the ground up.
- Led zero-to-one initiatives including a DTC mobile app and a B2B retailer platform
- Built and led a 40+ person product, design, and engineering organization across multiple domains
- Established product strategy, roadmaps, OKRs, and execution standards to shift from project delivery to outcome-driven product teams
- Introduced AI-assisted discovery and prioritization to improve decision quality and alignment
- Modernized customer-facing platforms across mobile, web, and partner experiences
- Embedding experimentation, behavioral analytics, and AI-powered personalization across customer journeys to drive measurable outcomes.
Gorgias
VP of Product, CX Platform
May 2022 - Dec 2024
Owned and scaled a customer experience platform serving 15,000+ ecommerce brands, focused on self-service, automation, and AI-enabled workflows.
- Led product strategy across onboarding, in-product guidance, automation, analytics, and support workflows
- Built and mentored globally distributed product teams across multiple squads
- Embedded AI and automation into customer workflows to reduce friction and improve time-to-value
- Improved retention and expansion by aligning product investments to activation, engagement, and operational efficiency metrics
- Leading the enterprise-readiness initiative, ensuring the platform could meet the demands of larger, more complex customers.
- Balanced platform scalability with intuitive, human-centered experiences
Shift4 Payments
VP of Product, Commerce
Oct 2020 - Apr 2022
Led commerce and payments product strategy through rapid scale and post-acquisition integration, modernizing platform architecture and onboarding experiences.
- Transformed a monolithic commerce platform into a multi-tenant SaaS architecture
- Led product integration following acquisition, aligning commerce and payments strategies
- Drove significant user growth through improved onboarding and product-led growth initiatives
- Expanded platform integrations across payments, ordering, and inventory systems
- Established core product management practices including roadmaps, discovery, and KPI-driven planning
3dcart
Head of Product (Co-Founder)
Aug 2014 - Nov 2020
Co-founded and scaled an ecommerce SaaS platform from early growth through acquisition, owning long-term product, technology, and business outcomes.
- Defined product strategy and roadmap for a platform serving 25,000+ merchants
- Built and scaled product, engineering, and customer teams to 100+ employees
- Owned end-to-end ecommerce experiences including acquisition, conversion, checkout, and retention
- Built a broad partner ecosystem across payments, shipping, and tax providers
- Led the company through sustained growth and eventual acquisition
3dcart
Head of Product & Engineering (Co-Founder)
May 2004 - Sep 2014
Led early-stage product and engineering execution, designing and building the core platform while scaling the organization and operations.
- Designed the core ecommerce platform architecture and APIs
- Led zero-to-one product development across inventory, SEO, performance, and post-purchase workflows
- Established early engineering practices and delivery rhythms
- Balanced product development with operational and business constraints
Ceramicas Caribe
Senior Business Analyst, Intranet & Data Platforms
Apr 2002 - Apr 2004
- Designed and implemented SQL Server databases to support the intranet.
- Built internal data and reporting platforms to improve operational visibility
- Integrated ERP data into decision-support tools for manufacturing and logistics
- Designed, coded, tested, and documented web and business applications using .NET technologies
ClosetMaid
Technical Implementation Engineer, ERP & Operations
Oct 2000 - Apr 2002
- Implemented ERP systems for manufacturing and warehouse operations
- Used Microsoft SQL Server to manage ERP data, ensuring integrity and accuracy.
- Led process documentation and standardization initiatives