Dmitry Alexenko

Dmitry Alexenko is a Russian-American engineering leader and angel investor. He serves as Head of Enterprise Engineering at Cloudflare (since September 2024), having joined from Stripe where he spent over four years leading billing infrastructure teams. He is active on X as @dalexeenko.

Career

Alexenko began his software career at Google as an engineering intern, then moved to Microsoft where he worked on Outlook and Windows features. He subsequently joined Airbnb as Engineering Manager for the Trust and Safety (anti-fraud) team.

He then spent 4+ years at Stripe, serving as Head of Engineering for both Billing Infrastructure and Invoicing. After Stripe he was Senior Director of Engineering at Checkr.

In September 2024 he joined Cloudflare as Head of Enterprise Engineering. He holds a Master's degree in Computer Science from South Ural State University.

Stripeflare Project

During 2025, Alexenko was building an HTTP-level agent-friendly monetisation layer he referred to as "Stripeflare" — a project combining Cloudflare's infrastructure with Stripe-style payments for easy monetisation of Workers-based applications. He described three pillars: (1) easy monetised apps on Cloudflare, (2) HTTP-level monetisation layer for web publishers, (3) social payments.

This concept overlaps significantly with Jan_Wilmake's sponsorflare project, which also builds a monetisation layer on top of Cloudflare Workers.

Connection to Jan

Dmitry reached out to Jan directly on X following Jan's high-visibility activity in early 2025. The two met to discuss the Stripeflare project and the Cloudflare ecosystem.

See Also

• Jan_Wilmake
• Sunil_Pai
• Ricky_Robinett
• sponsorflare
• Cloudflare