ditto - Director, Enterprise Sales
Requirements
• 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
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 • 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
Benefits
• Estimated Base Salary $197K – $247K • Pay Transparency at Ditto • Ditto uses a location-based compensation model. This means pay ranges for the same role may vary depending on where you live, based on cost of living and market data.The ranges you see on our job postings represent the full span of target compensation across all markets where we hire. Within that range, actual offers are determined by a candidate’s skills and experience. This ensures we remain competitive with local markets while also maintaining internal consistency and fairness in real spending power across locations. • Upload your resume here to autofill key application fields. • Drop your resume here! • Parsing your resume. Autofilling key fields... • or drag and drop here • Decline to self-identify • Hispanic or Latino - A person of Cuban, Mexican, Puerto Rican, South or Central American, or other Spanish culture or origin regardless of race. • Hispanic or Latino • White (Not Hispanic or Latino) - A person having origins in any of the original peoples of Europe, the Middle East, or North Africa. • White • Black or African American (Not Hispanic or Latino) - A person having origins in any of the black racial groups of Africa. • Black or African American • Native Hawaiian or Other Pacific Islander (Not Hispanic or Latino) - A person having origins in any of the peoples of Hawaii, Guam, Samoa, or other Pacific Islands. • Native Hawaiian or Other Pacific Islander • Asian (Not Hispanic or Latino) - A person having origins in any of the original peoples of the Far East, Southeast Asia, or the Indian Subcontinent, including, for example, Cambodia, China, India, Japan, Korea, Malaysia, Pakistan, the Philippine Islands, Thailand, and Vietnam. • Asian • American Indian or Alaska Native (Not Hispanic or Latino) - A person having origins in any of the original peoples of North and South America (including Central America), and who maintain tribal affiliation or community attachment. • American Indian or Alaska Native • Two or More Races (Not Hispanic or Latino) - All persons who identify with more than one of the above five races. • Two or More Races • Hispanic or Latino • White (Not Hispanic or Latino) • Black or African American (Not Hispanic or Latino) • Native Hawaiian or Other Pacific Islander (Not Hispanic or Latino) • Asian (Not Hispanic or Latino) • American Indian or Alaska Native (Not Hispanic or Latino) • Two or More Races (Not Hispanic or Latino) • I identify as one or more of the classifications of protected veteran listed above • I am not a protected veteran
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