Director, Enterprise Sales

Ditto•Austin, TX

1d•$197,000 - $247,000•Remote

About The Position

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.

Requirements

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)
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

Nice To Haves

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

Responsibilities

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 (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
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