Reign is the Autonomous Commerce Platform for DTC founders. We unify storefronts, checkout, payments, and operations into one AI-native platform where agents handle the operational grind and merchants focus on growth: making the most money, with the least headache, on their own terms.

We set out to build the "Shopify of Direct Response," and along the way we recognized something bigger. Direct response is roughly a third of all ecommerce transactions, a trillion-dollar market chronically overlooked by Silicon Valley. The merchants who run it are obsessive about tooling. They live and die by velocity, conversion, and margin. They have no brand moats, so they compete purely on operations, which is exactly what makes them the earliest and fastest adopters of AI agents in commerce.

This is a category-defining bet, and we are running at it from a position of strength.

Where We Are Today

8-figure ARR, growing 100%+ YoY (top 0.5% of all startups launched in 2024), and we do it with capital efficiency: there is a real chance we finish the year with more cash on our balance sheet than we have ever raised
Rapid merchant adoption and expanding market presence
On track to beat our budgeted sales target by 100%+
Industry-leading NPS score
70% of our new deals come as referrals from existing merchants
Venture-backed by a multi-billionaire ex-founder and direct response industry leaders
An executive team that has done this before: multiple leaders who have scaled a company from zero to unicorn status
A founder who builds from domain expertise: he bootstrapped $200M+ in DTC revenue as a direct response merchant before starting Reign, and is building the platform he always wanted as a merchant

Why Now

This is a rare opportunity for a technical leader to step into a company with proven revenue, product-market fit, an established team, and a large market opportunity.

Three things make this an inflection point:

Product-market fit is established. Demand continues to grow, merchant adoption is accelerating, and Reign is outperforming expectations.
There is an opportunity to define a category. While many companies are building AI tools for commerce, few are focused on helping sophisticated DTC operators automate revenue-generating decisions at scale.
Our customers are AI-ready. They adopt technology quickly when it drives measurable business outcomes, creating an ideal environment for agentic products.

The Role

You will own all of technology and engineering at Reign. Strategy, architecture, execution, hiring, culture, AI roadmap, platform reliability, payments infrastructure, and merchant-facing product engineering all sit with you.

You will inherit a strong engineering foundation, experienced technical leaders, and a talented team with deep domain expertise. This role is focused on scaling the organization, driving technical strategy, and leading Reign through its next phase of growth.

What You'll Own

Technical Vision and Strategy

Define and execute the long-term technical roadmap for an AI-native commerce platform
Architect for an agent-first future
Drive platform scalability across checkout, subscriptions, payments, merchant tooling, and storefronts
Represent Reign's technical vision to investors, partners, and the broader market

Engineering Leadership

Build and lead a high-performing engineering organization
Set and maintain a high bar for engineering excellence, velocity, and accountability
Mentor engineering leaders and senior ICs
Attract and retain exceptional technical talent

AI and Automation

Own the company's AI strategy and roadmap
Drive the development of AI agents that make production-grade decisions on real merchant outcomes
Operationalize AI-assisted software development practices throughout the organization

Product and Cross-Functional Partnership

Drive AI adoption through the product
Partner with leadership to identify opportunities for AI internally across the business
Translate business priorities into technical execution
Work closely with Product, Payments, Operations, and Customer Success

Engineering Organization Health

Own hiring, performance management, and culture within engineering
Build and maintain a high-performance organization
Create an environment where top engineers can do the best work of their careers

Executive Leadership

Serve on the executive leadership team
Participate in strategic planning, budgeting, and organizational design
Communicate technical vision to investors and partners
Be a key decision-maker on company-wide initiatives

What We're Looking For

Required

8+ years of software engineering experience and 5+ years leading engineering organizations
Experience as a CTO, VP Engineering, or senior technical leader in a high-growth environment
Startup experience required
Demonstrated success scaling teams, systems, and products
Experience building platform products serving business customers
Strong interest in AI and emerging technologies
Deep architectural and systems design expertise
Experience operating reliable, high-scale systems

Preferred

DTC commerce technology experience
Payments or fintech infrastructure experience
Hands-on AI/LLM product development
B2B or B2B2C platform experience

Our Values

We are a value-driven company. These aren't words that we just put on a wall. They dictate how we hire, fire, and promote.

All In to Win. Operate with urgency and a relentless focus on excellence.

A Players Only. Build and maintain exceptional talent density. Pure meritocracy.

Merchant First. Every decision is measured by merchant impact.

Entrepreneurial Spirit. Move quickly, stay resourceful, and take ownership.

No Ego. The best ideas win regardless of title or tenure. No BS politics.

**Reign is mission-first and performance-driven. We operate with urgency, give direct feedback, and expect high ownership. If you thrive under pressure and love building in fast-moving environments, you'll do great here. If you strongly prioritize predictability, comfort, and work/life separation, this 100% isn't the right role.**

We operate as a flat, high talent density, meritocratic organization.

Chief Technology Officer