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.
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.
We’re always on the lookout for exceptional humans who want to grow, stretch, and build something meaningful with us.
Equal Opportunity Employer
Ditto is proud to be an equal-opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristics. Ditto is committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, please let us know.