Chief Revenue Officer

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:

1. Product-market fit is established. Demand continues to grow, merchant adoption is accelerating, and Phoenix is outperforming expectations.

2. 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.

3. Our customers are AI-ready. They adopt technology quickly when it drives measurable business outcomes, creating an ideal environment for agentic products.

The Role

We are hiring a Chief Revenue Officer to build and scale the commercial engine behind Reign's AI-native commerce platform.

This role is responsible for defining and executing the company's go-to-market strategy across Marketing, Sales, Partnerships, and Revenue Operations—turning strong product-market fit into a repeatable, scalable revenue engine that accelerates Reign's next phase of growth.

You will own:

• Revenue growth across existing and new markets

• GTM strategy and commercial execution

• Marketing, Sales, Partnerships, and Revenue Operations

• Expansion into adjacent merchant segments

• Commercial forecasting, operating cadence, and organizational design

This is not a traditional sales leadership role. This is company-building.

You will partner directly with the Founder & CEO, President, and executive team to shape how Reign wins in one of the fastest-growing segments of ecommerce. You'll influence product strategy, pricing, partnerships, and organizational design while building the commercial infrastructure required to scale from a high-growth Series A company into the category leader for AI-native commerce.

This role sits at the intersection of product, payments, AI, and go-to-market—defining how Reign acquires merchants, expands into new markets, and builds a commercial organization capable of scaling a generational company.

What You'll Own

Build the Revenue Engine

Design and scale a world-class go-to-market organization spanning Marketing, Sales, Partnerships, and Revenue Operations. Establish the people, processes, and operating cadence required to deliver predictable, repeatable revenue growth while maintaining a high-performance culture.

Define GTM Strategy

Own Reign's commercial strategy across existing and emerging markets. Develop segmentation, positioning, pricing, packaging, and go-to-market motions that accelerate merchant acquisition, expansion, and long-term customer value.

Lead Commercial Execution

Own company revenue performance, including pipeline health, forecasting, conversion, customer retention, and expansion. Build a data-driven operating system that enables accurate forecasting, rapid decision-making, and continuous optimization.

Expand Into New Markets

Identify and validate adjacent merchant segments, develop expansion strategies, and launch new commercial motions. Partner closely with Product to ensure roadmap investments align with customer demand and market opportunity.

Build Strategic Partnerships

Develop and execute Reign's partnership strategy across technology partners, payment providers, agencies, and channel relationships. Build scalable partnership programs that accelerate customer acquisition and strengthen the company's competitive position.

Drive Cross-Functional Growth

Partner closely with Product, Engineering, AI, Payments, Finance, and Customer Success to align commercial strategy with product development and operational execution. Translate merchant feedback and market insights into company priorities that improve revenue, retention, and long-term growth.

What We're Looking For

Required

• 12+ years of progressive commercial leadership experience across high-growth B2B SaaS, ecommerce, fintech, or payments companies.

• Experience owning a company-wide revenue number as a CRO, VP of Revenue, General Manager, or equivalent executive leader.

• Demonstrated success building and scaling GTM organizations across Sales, Marketing, Partnerships, and Revenue Operations.

• Experience designing GTM strategy, pricing, segmentation, forecasting, and commercial operating cadence.

• Proven track record scaling early-stage or growth-stage startups through periods of rapid revenue growth.

• Strong understanding of ecommerce, payments, merchant operations, subscriptions, checkout optimization, or adjacent commerce infrastructure.

• Experience partnering cross-functionally with Product and Engineering to influence roadmap and bring new products or markets to life.

• Strong executive communication skills with experience working alongside founders, executive teams, and boards.

• High ownership mindset with the ability to operate effectively in ambiguous, fast-moving environments.

Preferred

• Founder or early executive at a high-growth startup.

• Experience scaling revenue from Series A/B through later-stage growth.

• Experience expanding into new customer segments or launching new product lines.

• Deep relationships across the ecommerce, payments, or commerce technology ecosystem.

• Experience building AI-enabled or AI-native GTM organizations.

• Background in high-growth ecommerce, merchant infrastructure, payment processing, checkout, subscriptions, or creator economy platforms.

• Passion for building organizations, developing leaders, and creating repeatable systems that scale.

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.com 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.