Open to opportunities

Benjamin Gelb

@benjamingelb

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SaaS AI leader building agentic GenAI products through strategy, architecture, and measurable business outcomes.

Spain

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What I'm looking for

I’m looking to lead AI-native SaaS product teams—translating AI strategy into agentic GenAI systems, measurable quality, and clear business value. I want high-trust, cross-functional collaboration with strong executive alignment and room to scale impact.

I’m Head of SaaS AI, acting as the connective tissue between central AI & Data capabilities and product squads. I design AI solution architectures and agent flow patterns, then help teams judge feasibility, defensibility, and business value.

Most recently, I shipped a conversational AI payments agent for UK sole traders—pairing voice-to-invoice with smart reminders and LLM-based bank feed matching. I defined eval sets, quality benchmarks, failure modes, and human-in-the-loop journeys, making disciplined build vs buy decisions across models and APIs.

Before that, I owned the full roadmap for a mobile-first B2C fintech SaaS at Tymit, driving rapid go-to-market alignment across engineering, design, compliance, and commercial while maintaining brand autonomy. I improved onboarding conversion with landing page optimisation and A/B experimentation.

I’ve led teams from early-stage to scale: at Chessable, I ran a 25+ person product org, rebuilt AI & Data analytics infrastructure, and championed AI & Data upskilling to increase brand self-sufficiency. Earlier roles—from Product Owner through Scrum Master—shaped my focus on cross-functional leadership, OKRs, and execution that turns strategy into measurable outcomes.

Experience

Work history, roles, and key accomplishments

Current

Senior Product Owner

Current

Sage

Dec 2024 - Present (1 year 5 months)

Built a conversational AI payments agent for UK sole traders (voice-to-invoice, smart reminders, LLM-based bank feed matching) and defined eval sets, quality benchmarks, failure modes, and human-in-the-loop journeys. Led the Factory Framework to design AI solution architectures and advise product squads on feasibility, defensibility, and business value.

Agentic AI LLM AI Solution Architecture Eval Sets & Benchmarks Human In The Loop Voice To Invoice

Senior Product Manager

Tymit

May 2023 - Jun 2024 (1 year 1 month)

Owned the full roadmap for a mobile-first B2C fintech SaaS serving SME customers, driving go-to-market alignment across engineering, design, compliance, and commercial teams. Improved onboarding conversion through landing-page optimization and A/B experimentation.

Fintech Product Management Market Alignment Onboarding A B Experimentation Stakeholder Management

VP of Product

Chessable

Jul 2021 - Sep 2022 (1 year 2 months)

Led a 25+ person product organization in a matrixed environment, setting OKRs and rebuilding AI & Data analytics infrastructure. Championed AI & Data upskilling initiatives to increase brand self-sufficiency and drove executive alignment through briefings.

OKRs AI Data Analytics Cross functional Leadership Matrix Environment Brand Self Sufficiency Enablement

Senior Product Manager

Chessable

Jul 2020 - Jul 2021 (1 year)

Scaled a two-sided B2C SaaS marketplace from 0 to 150K mobile users in 9 months, increasing day-30 retention from 4% to 6% (+50%). Drove upsell experimentation to grow MRR from ~€850K to ~€1M and used Offline Mode to deliver a 10% upgrade uplift and €11K MRR in Phase 1.

Two Sided Marketplaces Retention A B Experimentation Upsell Offline Mode Product Strategy

Product Owner

Holded

Nov 2019 - Jul 2020 (8 months)

Joined post-acquisition as Holded integrated into a larger SaaS portfolio, running customer discovery and A/B experimentation to improve B2B onboarding activation for SME customers. Built a data-driven roadmap creating measurable business value across CRM, HR, and payments squads.

Post Merger Integration Customer Discovery A B Experimentation Roadmapping CRM Payments Product

Technical Product Manager

Typeform

Feb 2018 - Nov 2019 (1 year 9 months)

Owned pricing, packaging, and developer experience at a globally recognised B2C SaaS platform. Supported due diligence for third-party AI & Data tools and partnered with Sales, Marketing, and Customer Success across multiple market segments.

Pricing Strategy Packaging Developer Experience Growth Product Management Cross Functional Collaboration Market Segmentation

Co-founder & CEO

Jobgator

Apr 2017 - Feb 2019 (1 year 10 months)

Co-founded and led a B2B SaaS job marketplace serving SME customers, reaching ~200 paying customers. Drove product direction from founding through accelerator participation (MassChallenge finalist).

B2B SaaS Leadership Marketplace Strategy Startup Execution Product Leadership Customer Growth Accelerator Exposure

Product Owner

JRNI

Jul 2016 - Apr 2017 (9 months)

Owned integrations and partner-facing product surface for an enterprise scheduling SaaS. Managed partner product needs to support reliable scheduling workflows.

Product Ownership Integration Partner Facing Product Enterprise SaaS

Scrum Master

State Street Bank

May 2015 - Jul 2016 (1 year 2 months)

Served as Scrum Master and agile delivery lead across cross-functional engineering teams in financial services. Coordinated agile delivery execution in a regulated, financial-services context.

Scrum Master Agile Delivery Cross Functional Execution Financial Services Delivery leadership