Head of Sales

About Ditto

Ditto is redefining how data moves at the edge. Our mission is to make it seamless for developers to build resilient, real-time applications, regardless of network conditions. Whether you're in a stadium, airplane, or remote military base, Ditto's peer-to-peer sync engine ensures devices stay connected and data stays consistent, even without internet.

With more than $145 million in funding and trusted by organizations like Chick-fil-A, Delta Airlines, and the U.S. military, Ditto powers mission-critical experiences across aviation, retail, travel, hospitality, defense, and more. As a globally distributed, fast-growing startup, we’re committed to building a diverse and inclusive team that reflects the wide range of perspectives needed to solve the world’s hardest connectivity problems.

About the Role

Ditto is seeking a Head of Sales to join our rapidly scaling Go-To-Market team. In this role, you'll lead a growing team of Account Executives across the US and Canada, focusing on coaching, enablement, and strategic deal execution, not carrying a bag yourself. Reporting to the VP of Sales, you'll play a critical role in shaping our sales process, supporting our team’s performance, and laying the foundation for scalable revenue growth.

We’ve recently hit product-market fit, signed household-name enterprise customers like Delta and Chick-fil-A, and are doubling revenue and headcount over the next 12 months. If you're energized by helping teams sell better, faster, and more confidently in a technical environment, this is your chance to make a big impact.

Responsibilities

• Lead a team of Account Executives (early career to senior) on strategic account planning, discovery, and deal execution.
• Jump into deals when needed to support coaching, strategy, or executive alignment.
• Partner with the VP of Sales to improve forecasting, qualification frameworks, and quarterly planning.
• Drive rigor and consistency in the sales cycle - from outbound to close - by refining how we qualify, position, and forecast.
• Build out onboarding, playbooks, and training rituals to help us scale a high-performing AE team quickly and consistently.
• Collaborate with Marketing, Product, and Solutions Engineering on messaging, content, and feedback loops.
• Develop and maintain clean sales performance reporting to spot trends, diagnose issues, and track improvement.
• Partner with sales enablement, marketing, and product to improve messaging, surface new insights, and unlock new channels or segments.

Requirements

• Experience leading high-performing sales teams selling complex technical solutions.
• High tolerance for ambiguity and evolving processes.
• Strong internal stakeholder collaboration strategies.

Nice to Have

• Experience scaling a sales team in an early-stage startup.
• Familiarity with developer tooling, infrastructure, or edge computing platforms.
• Exposure to distributed systems, mobile SDKs, or real-time data platforms.

Benefits of Building with Us

We offer competitive salaries and meaningful equity. We believe everyone on the team should have a stake in what we’re building. Benefits vary by region to make sure you're covered in the ways that matter most.

• US Benefits: Health, dental, vision, life, and disability insurance, plus a 401(k) and flexible spending accounts.
• UK Benefits: Private healthcare through Vitality, a pension plan, and region-specific coverage.
• Global Benefits: Equitable benefits and coverage through our global employer platform.

Regardless of where you live, everyone at Ditto can utilize flexible time off. While we work remotely, our Atlanta and San Francisco offices are open if you ever want a place to work or meet up with teammates.

Apply Anyway

At Ditto, we believe success isn’t defined by a flawless resume, a set number of years of experience, or checking every box in a job description. What matters most to us are qualities like grit, resilience, and a passion for solving complex problems.