Head of Enterprise Sales: Scale Complex, High-Value Deals

Juicebox; San Francisco (CA); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Top-of-market compensation

Comprehensive healthcare

Wellness stipend

Daily meals provided

Commuting stipend

Job summary

Juicebox, based in San Francisco, is seeking a founding member of the Sales Leadership team to oversee the Enterprise Account Executives and steer strategy for large, strategic opportunities. You will own pipeline generation, forecasting, and deal execution, coach reps through complex multi-threaded cycles, and partner with founders to scale Juicebox's enterprise GTM motion.

This role blends hands-on deal work with long-term planning, shaping the sales organization as Juicebox grows toward its

Qualifications

• 7+ years in B2B SaaS sales environments with 3+ years leading Enterprise sales teams.
• Proven track record closing complex, high-value enterprise software deals.
• Deep experience coaching enterprise sellers across account strategy, executive discovery, multi-threading, business-case development, negotiation, and closing.
• Experience building predictable enterprise pipeline and forecasting accurately across longer, less linear sales cycles.
• Strong executive presence engaging VP- and C-level buyers.

Responsibilities

• Lead and develop a team of Enterprise Account Executives in our San Francisco headquarters.
• Own pipeline generation, forecasting, deal execution, and team performance.
• Coach and participate in high-stakes enterprise opportunities, navigating committees, stakeholders, and complex negotiations.
• Build executive relationships with senior customer stakeholders to accelerate deals.
• Develop rigorous account planning, territory strategy, pipeline creation, and whitespace identification for top prospects.
• Establish a cadence of 1:1s, team meetings, deal reviews, and development activities.
• Evolve the enterprise sales motion with product, marketing, and leadership to improve positioning and GTM strategy.

Skills

B2B SaaS sales

Enterprise sales leadership

Executive engagement

Forecasting

Pipeline development

Negotiation

Strategic account planning

Coaching

Cross-functional collaboration

Ambiguity tolerance

AI fluency

People leadership

Job description

Juicebox, based in San Francisco, is seeking a founding member of the Sales Leadership team to oversee the Enterprise Account Executives and steer strategy for large, strategic opportunities. You will own pipeline generation, forecasting, and deal execution, coach reps through complex multi-threaded cycles, and partner with founders to scale Juicebox's enterprise GTM motion.

This role blends hands-on deal work with long-term planning, shaping the sales organization as Juicebox grows toward its