Director, Enterprise Sales

This is a fully remote position, open to applicants in California, +2 more states.

📋 Description

• Lead, mentor, and develop a team of 4 Account Executives focused on enterprise transformation rather than just software features.

• Partner with the Solutions team leadership to enhance the aligned AE/Solutions sales approach and address conflicts related to resource distribution, deal prioritization, and technical positioning.

• Cultivate AE proficiency in consultative selling, including business case development, executive engagement, navigating technical procurement, and managing intricate buying committees.

• Develop Account Development Representatives (ADRs) to balance account intelligence operations with pipeline generation efforts, determining the ideal split between in-depth account research and outbound outreach.

• Conduct deal reviews centered on account strategy, stakeholder mapping, competitive positioning, and technical validation status rather than solely on activity metrics.

• Oversee the commercial pipeline to ensure sufficient coverage, a healthy distribution of stages, and precise forecasting.

• Collaborate with AEs to craft account strategies for 50-75 designated Fortune 500 target accounts.

• Guarantee effective collaboration between AEs and Solutions team members on discovery, technical validation, proof-of-value, and commercial negotiations.

• Manage intricate deal cycles that incorporate product co-development and implementation planning as essential components of the sales process.

• Assist AEs in high-level discussions, C-suite engagement, and final negotiations on significant deals.

• Establish a sales methodology and playbooks tailored for consultative enterprise selling.

• Define focus areas for ADRs between account intelligence/research and direct pipeline generation based on what leads to the most qualified opportunities.

• Collaborate with the Marketing Lead on account-based marketing initiatives, executive events, and demand generation aimed at named accounts.

• Work with the Partnership Lead on channel strategies, systems integrator relationships, and OEM partnerships as vital sources for pipeline development.

• Create processes for ADRs to identify trigger events (leadership changes, funding, strategic initiatives) that open buying windows.

• Ensure that ADRs are generating qualified meetings that convert to opportunities at healthy rates.

• Utilize referral and partnership channels as primary sources of pipeline alongside marketing-generated demand and ADR efforts.

• Maintain strong operational alignment with Solutions team leadership regarding resource allocation, deal prioritization, and joint account planning.

• Collaborate with the Customer Success Lead on handoff processes, implementation scoping during the sales cycle, and developing customer references.

• Team up with the Marketing Lead on messaging, positioning, case studies, and demand generation for major accounts.

• Collaborate with the Partnership Lead on channel enablement, partner-sourced pipeline, and joint go-to-market strategies.

• Engage with Product and Engineering leadership to convey market requirements and manage customer expectations concerning the product roadmap.

• Participate in CRO staff meetings and contribute to the overall revenue strategy.

⛳️ Requirements

• Over 8 years of experience in enterprise B2B software sales, with at least 4 years of experience managing quota-carrying Account Executives.

• Direct experience selling to Fortune 500 companies with deal sizes of $250K or more in Annual Contract Value (ACV).

• Proven track record of leading teams that consistently meet or surpass annual booking targets of $3M to $5M or more.

• Experience in consultative, complex sales cycles lasting over 6 months, involving technical validation, procurement, and multi-stakeholder buying committees.

• Demonstrated capability to coach Account Executives on business case development, executive engagement, and strategic positioning, beyond just managing the pipeline.

🏝️ Benefits

• Health insurance

• Dental insurance

• Vision insurance

• Life insurance

• Disability insurance

• 401(k)

• Flexible spending accounts

• Flexible time off