---
title: Dmitry Alexenko
description: Head of Enterprise Engineering at Cloudflare; formerly Head of Billing Engineering at Stripe
category: People
---

# Dmitry Alexenko

![Dmitry Alexenko](https://github.com/dalexeenko.png)

**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](https://x.com/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]]