Jeff Sheldon

I'm a technology and engineering executive who has spent the last decade-plus helping companies scale through their hardest growth phases. As Chief Architect at Recurly, I set enterprise AI strategy, lead technical due diligence on acquisitions, and advise the board on technology direction. Before that, as SVP of Engineering, I owned all of engineering through Recurly's biggest growth years — scaling the team to 100+ and sustaining 99.99%+ availability on a PCI DSS Level 1 payments platform processing billions in annual volume. Across my career I've led engineering at high-growth companies including Coupa (pre-IPO), Life360 (scaled 15 to 60+ engineers, 1B+ API requests/day), and StumbleUpon. I've built incident response programs, led zero-downtime cloud migrations, established AI build/buy/orchestrate frameworks, and developed leaders from individual contributors into VPs. What I love most is helping founders and engineering leaders think clearly about hard problems: scaling teams without losing velocity, setting technical and AI strategy, navigating payments and compliance, evaluating M&A, and building a leadership bench. Whether you're a founder figuring out your first engineering hires or a leader navigating hypergrowth, I'm happy to be a sounding board. I'm always glad to connect with founders, operators, and investors. If you're looking for an experienced executive perspective — or exploring whether I'd be a fit as an advisor to your company — let's book a call and talk through what you're working on.

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  Advice on funding

  My funding-side experience comes from the deal and board perspective. At Recurly I led technical due diligence on two acquisitions — assessing codebase, team, security, and scalability — and shaped deal structure and the integration thesis. I brief the board on technology strategy and M&A posture. I'm most useful to founders preparing for diligence (what acquirers and investors actually probe technically), evaluating build-vs-buy-vs-acquire, and strengthening the technical story behind a raise.

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  Building a team

  Building and scaling engineering teams is what I'm known for. I've grown orgs from 15 to 100+ engineers through hypergrowth (Recurly, Life360) without losing velocity, established leveling, career ladders, and title structures, and built executive leadership benches — promoting individual contributors to VP. I introduced Agile/Scrum operating models across globally distributed teams. I help founders and leaders hire their first engineers, structure teams, and develop leaders.

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  Data science

  My data and ML background runs deep. At EmSense I led data strategy for a system handling 1.5+ TB/day of biometric and EEG sensor data, delivering a 4x cost-efficiency gain through a three-tier architecture. At Recurly I built the data infrastructure, ML tooling, and partnerships that enabled our AI roadmap, and set the build/buy/orchestrate framework guiding AI investment. I help founders and leaders think pragmatically about data, ML tooling, and where AI creates a real moat versus hype.

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  Go to market strategy

  I've worked GTM from the engineering and executive side of the table. At Recurly I partnered with Sales, Product, and Customer Success on multi-year platform commercialization, closed enterprise deals as executive sponsor on strategic accounts, and ran our London sales office as interim leader during a transition. I help founders and technical leaders align product and engineering with go-to-market: positioning, enterprise readiness, and landing and expanding strategic accounts.

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  Technology and tools

  I've spent 15+ years choosing, integrating, and scaling technology stacks for high-growth SaaS. At Recurly I set the enterprise AI build/buy/orchestrate framework, led a zero-downtime migration to Google Cloud on Kubernetes, and ran a PCI DSS Level 1 platform at 99.99%+ uptime. I help founders and leaders make pragmatic decisions about architecture, cloud infrastructure, data tooling, and AI adoption — choosing what to build versus buy and avoiding costly over-engineering.

• https://www.sheldon.nyc/articles/your-ai-strategy-needs-a-home
• https://www.sheldon.nyc/articles/the-next-phase-of-work-is-agentic
• https://www.sheldon.nyc/articles/the-velocity-trap
• https://www.sheldon.nyc/articles/the-measurement-crisis-behind-the-ai-roi-debate