Critical MetricsNew ACV bookings (not ARR, not MRR - multi-year annual contract value)Pipeline coverage ratio and stage velocityWin rate on qualified opportunitiesAverage deal size and sales cycle durationADR-sourced meetings that convert to qualified opportunitiesResponsibilitiesTeam Leadership & DevelopmentManage, coach, and develop 4 Account Executives who are selling enterprise transformation, not software featuresCollaborate with Solutions team leadership to refine the unified AE/Solutions sales motion and resolve conflicts over resource allocation, deal prioritization, and technical positioningBuild AE capability in consultative selling: business case development, executive engagement, navigating technical procurement, and managing complex buying committeesDevelop ADRs to balance account intelligence operations with pipeline generation activities—determining the optimal split between deep account research and outbound engagementConduct deal reviews that focus on account strategy, stakeholder mapping, competitive positioning, and technical validation status - not activity metricsSales Execution & StrategyOwn the commercial pipeline: ensure adequate coverage, healthy stage distribution, and accurate forecastingWork with AEs to develop account strategies for 50-75 named Fortune 500 target accountsEnsure AEs and Solutions team members are collaborating effectively on discovery, technical validation, proof-of-value, and commercial negotiationManage complex deal cycles where product co-development and implementation planning are part of the sales processSupport AEs in executive-level conversations, C-suite engagement, and final negotiations on whale dealsEstablish sales methodology and playbooks appropriate for consultative enterprise sellingPipeline Generation & ADR ManagementDefine ADR focus areas between account intelligence/research and direct pipeline generation based on what drives the most qualified opportunitiesPartner with Marketing Lead on account-based marketing campaigns, executive events, and demand generation targeted at named accountsPartner with Partnership Lead on channel strategy, systems integrator relationships, and OEM partnerships as critical pipeline sourcesDevelop processes for ADRs to identify trigger events (leadership changes, funding, strategic initiatives) that create buying windowsEnsure ADRs are generating qualified meetings that convert to opportunities at healthy ratesLeverage referral and partnership channels as primary pipeline sources alongside marketing-generated demand and ADR activitiesCross-Functional CollaborationMaintain tight operational alignment with Solutions team leadership on resource allocation, deal prioritization, and joint account planningWork with Customer Success Lead on handoff processes, implementation scoping during sales cycle, and customer reference developmentCollaborate with Marketing Lead on messaging, positioning, case studies, and demand generation for whale accountsCollaborate with Partnership Lead on channel enablement, partner-sourced pipeline, and joint go-to-market executionInterface with Product and Engineering leadership to communicate market requirements and manage customer expectations around product roadmapParticipate in CRO staff meetings and contribute to overall revenue strategyMust-Have8+ years in enterprise B2B software sales with 4+ years managing quota-carrying AEsDirect experience selling into Fortune 500 accounts with deal sizes $250K+ ACVTrack record managing teams that consistently achieve or exceed $3M-$5M+ annual bookings targetsExperience with consultative, complex sales cycles (6+ months) involving technical validation, procurement, and multi-stakeholder buying committeesDemonstrated ability to coach AEs on business case development, executive engagement, and strategic positioning (not just pipeline management)Strongly PreferredExperience with technical co-selling models where engineers or technical architects participate actively in the sales processBackground selling platform or infrastructure technology that requires customer co-development or heavy implementationFamiliarity with OEM partnerships, channel sales, or selling through systems integrators to enterprise accountsPrior experience in services-heavy or professional services-led sales motionsUnderstanding of edge computing, IoT, distributed systems, or infrastructure software marketsRequired CapabilitiesStrategic account planning: You can develop multi-quarter strategies for penetrating complex enterprise accounts with multiple buying centersSales coaching: You improve AE performance through deal-specific coaching, not generic training programs or activity managementTechnical fluency: You can engage in technical conversations with CTOs, VPs of Engineering, and enterprise architects without relying on your Solutions teamPipeline management: You forecast accurately, identify risk early, and course-correct without surprisesCross-functional influence: You can drive alignment across Product, Engineering, Marketing, Partnerships, and Customer Success without formal authorityOperational discipline: You establish clear processes, cadences, and accountability mechanisms without creating bureaucracyThe Benefits of Building with UsWe offer competitive salaries and meaningful equity. 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.