Director, Enterprise Sales

Director Of Enterprise Sales

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.

Critical Metrics

• 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

Responsibilities

Team Leadership & Development

• 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

Sales Execution & Strategy

• 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

Pipeline Generation & ADR Management

• 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 (leadership changes, funding, strategic initiatives) that create buying windows
• Ensure ADRs are generating qualified meetings that convert to opportunities at healthy rates
• Leverage referral and partnership channels as primary pipeline sources alongside marketing-generated demand and ADR activities

Cross-Functional Collaboration

• Maintain tight operational alignment with Solutions team leadership on resource allocation, deal prioritization, and joint account planning
• Work with Customer Success Lead on handoff processes, implementation scoping during sales cycle, and customer reference development
• Collaborate with Marketing Lead on messaging, positioning, case studies, and demand generation for whale accounts
• Collaborate with Partnership Lead on channel enablement, partner-sourced pipeline, and joint go-to-market execution
• Interface with Product and Engineering leadership to communicate market requirements and manage customer expectations around product roadmap
• Participate in CRO staff meetings and contribute to overall revenue strategy

Must-Have

• 8+ years in enterprise B2B software sales with 4+ years managing quota-carrying AEs
• Direct experience selling into Fortune 500 accounts with deal sizes $250K+ ACV
• Track record managing teams that consistently achieve or exceed $3M-$5M+ annual bookings targets
• Experience with consultative, complex sales cycles (6+ months) involving technical validation, procurement, and multi-stakeholder buying committees
• Demonstrated ability to coach AEs on business case development, executive engagement, and strategic positioning (not just pipeline management)

Strongly Preferred

• Experience with technical co-selling models where engineers or technical architects participate actively in the sales process
• Background selling platform or infrastructure technology that requires customer co-development or heavy implementation
• Familiarity with OEM partnerships, channel sales, or selling through systems integrators to enterprise accounts
• Prior experience in services-heavy or professional services-led sales motions
• Understanding of edge computing, IoT, distributed systems, or infrastructure software markets

Required Capabilities

• Strategic account planning: You can develop multi-quarter strategies for penetrating complex enterprise accounts with multiple buying centers
• Sales coaching: You improve AE performance through deal-specific coaching, not generic training programs or activity management
• Technical fluency: You can engage in technical conversations with CTOs, VPs of Engineering, and enterprise architects without relying on your Solutions team
• Pipeline management: You forecast accurately, identify risk early, and course-correct without surprises
• Cross-functional influence: You can drive alignment across Product, Engineering, Marketing, Partnerships, and Customer Success without formal authority

Operational discipline: You establish clear processes, cadences, and accountability mechanisms without creating bureaucracy

The 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. In the US, that includes health, dental, vision, life, and disability insurance, plus a 401(k) and flexible spending accounts.

Regardless of where you live, everyone at Ditto can utilize flexible time off. And 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 know game-changers don't always come wrapped in a "perfect" resume. Years of experience? Every single bullet point checked? Meh. That's not what drives us.

What does matter?

• Grit.
• Curiosity.
• Adaptability.
• And a genuine spark for what we're building.

So if you're fired up about our mission but not sure you tick every box - hit that apply button anyway. Use your application to show us how you'll make an impact here.

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