Director, Enterprise 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.

The Director of Enterprise Sales leads Ditto's commercial sales execution, managing a team of Account Executives and Account Development Representatives focused on Fortune 500 enterprise customers. This role architects the right playbooks and motions in favor of consultative, high-value selling that positions Ditto as a strategic co-development partner rather than a software vendor.

Your team will work closely with the Solutions team—Solution Architects and Sales Engineers who serve as valuable technical partners throughout the sales process. Your AEs must be capable of managing 6-9 month enterprise sales cycles with heavy technical validation requirements, navigating complex procurement processes, and closing $250K-$10M+ ACV deals towards larger deal sizes.

This is a role for someone who understands that selling to whales requires rigorous account strategies, stakeholder mapping, buying committee orchestration, and the ability to position complex technical capabilities as business transformation. The metrics that this leader designs should align towards these goals.

• New ACV bookings (not ARR, not MRR - multi-year annual contract value)

• Pipeline coverage ratio and stage velocity

• Win rate on qualified opportunities

• Average deal size and sales cycle duration

• ADR-sourced meetings that convert to qualified opportunities

• Manage, coach, and develop 4 Account Executives who are selling enterprise transformation, not software features

• Collaborate with Solutions team leadership to refine the unified AE/Solutions sales motion and resolve conflicts over resource allocation, deal prioritization, and technical positioning

• Build AE capability in consultative selling: business case development, executive engagement, navigating technical procurement, and managing complex buying committees

• Develop ADRs to balance account intelligence operations with pipeline generation activities—determining the optimal split between deep account research and outbound engagement

• Conduct deal reviews that focus on account strategy, stakeholder mapping, competitive positioning, and technical validation status - not activity metrics

• Own the commercial pipeline: ensure adequate coverage, healthy stage distribution, and accurate forecasting

• Work with AEs to develop account strategies for 50-75 named Fortune 500 target accounts

• Ensure AEs and Solutions team members are collaborating effectively on discovery, technical validation, proof-of-value, and commercial negotiation

• Manage complex deal cycles where product co-development and implementation planning are part of the sales process

• Support AEs in executive-level conversations, C-suite engagement, and final negotiations on whale deals

• Establish sales methodology and playbooks appropriate for consultative enterprise selling

• Define ADR focus areas between account intelligence/research and direct pipeline generation based on what drives the most qualified opportunities

• Partner with Marketing Lead on account-based marketing campaigns, executive events, and demand generation targeted at named accounts

• Partner with Partnership Lead on channel strategy, systems integrator relationships, and OEM partnerships as critical pipeline sources

• Develop processes for ADRs to identify trigger events…