Director, Large Enterprise Sales in United States at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Director, Large Enterprise Sales based in United States.

This leadership opportunity is designed for an accomplished enterprise sales professional who thrives on building high-performing teams and driving strategic growth within complex B2B environments. The role focuses on acquiring and expanding relationships with large enterprise organizations, guiding sophisticated sales cycles that involve multiple stakeholders and long-term decision-making processes. You will play a critical role in shaping sales strategy, coaching top-tier account executives, and fostering a culture of accountability, operational excellence, and customer-centric selling. Working cross-functionally with teams across the business, you will help accelerate growth by delivering compelling value propositions and strengthening executive-level partnerships. This position offers the chance to make a measurable impact while leading a talented remote team in a fast-paced, innovation-driven environment.

• Lead, coach, and develop a team of Large Enterprise Account Executives focused on acquiring new enterprise customers within the 5,000–20,000 employee segment.
• Drive strategic pipeline generation, account planning, and execution across complex enterprise sales cycles involving multiple decision-makers and procurement processes.
• Ensure consistent adoption and execution of enterprise sales methodologies, including MEDDPICC, Sandler, and consultative selling frameworks.
• Conduct regular pipeline reviews, deal inspections, forecasting sessions, and performance evaluations to maintain sales excellence.
• Coach team members on executive engagement, discovery techniques, negotiation strategies, objection handling, and value-based selling.
• Build a high-performance culture centered on accountability, continuous improvement, and achievement of revenue targets.
• Partner with Legal, Security, Finance, Product, Marketing, and Customer Success teams to remove obstacles and accelerate strategic opportunities.
• Strengthen executive-level storytelling capabilities, helping sellers articulate business value, workforce impact, and return on investment.
• Support relationship management within existing enterprise accounts to identify expansion opportunities and reinforce long-term partnerships.
• Monitor sales performance metrics and provide leadership with accurate forecasting and strategic insights.

• 10+ years of experience in enterprise SaaS, fintech, HCM, payroll technology, or related enterprise software sales environments.
• 3–5+ years of experience leading and developing high-performing enterprise sales teams.
• Proven success selling into and managing sales organizations focused on large enterprises with 5,000–20,000 employees.
• Demonstrated ability to navigate complex sales cycles involving executive stakeholders, procurement, legal, security, and cross-functional buying committees.
• Deep expertise in MEDDPICC, Sandler, and consultative sales methodologies, with a track record of improving team performance and execution.
• Strong leadership skills with experience coaching, mentoring, and holding sales professionals accountable to ambitious goals.
• Exceptional communication, presentation, and executive relationship-building abilities.
• Strong business acumen and ability to position solutions through compelling value-based storytelling.
• Experience managing forecasts, pipelines, and sales operations within structured enterprise environments.
• Results-driven mindset with the ability to thrive in fast-paced, growth-oriented organizations.

• Competitive base salary ranging from $163,000 to $250,000 annually, depending on location and experience.
• Performance-based commission opportunities.
• Equity participation opportunity.
• Comprehensive medical, dental, and vision insurance coverage.
• Life insurance and AD&D coverage.
• Short-term and long-term disability benefits.
• Employee Assistance Program (EAP).
• 401(k) retirement plan with company matching contributions.
• Unlimited paid time off.
• Employee Resource Groups and inclusive workplace initiatives.
• Company-sponsored events and team-building activities.
• Fully remote work environment within the United States.
• Career growth opportunities within a high-performing and collaborative culture.