Head of Sales

Summary

Join Ditto's rapidly scaling Go-To-Market team as the Head of Sales, leading a growing team of Account Executives across the US and Canada. Focus on coaching, enablement, and strategic deal execution, not individual sales. You will play a critical role in shaping the sales process, supporting team performance, and building scalable revenue growth. The company has recently achieved product-market fit and is experiencing rapid growth, doubling revenue and headcount in the next year. This is an opportunity to significantly impact a high-growth tech company. The role reports to the VP of Sales.

Requirements

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

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

Preferred Qualifications

• 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

• Health, dental, vision, life, and disability insurance
• 401(k)
• Flexible spending accounts
• Private healthcare through Vitality
• A pension plan
• Flexible time off