Highlight is seeking a hands-on Director of Sales to lead the Account Executive team and scale the software sales motion. This critical leadership role within the Go-To-Market organization is ideal for someone with deep tech sales experience who thrives in dynamic environments and excels at driving performance through structure, clarity, and enablement. As Director of Sales, you will set the tone, refine the playbook, and help shape the go-to-market strategy as the company grows and evolves its offering.

Responsibilities will include:

• Lead and develop a high-performing team of Account Executives, supporting experienced sellers, setting clear expectations, and driving accountability
• Own new business software sales targets and ensure the team consistently meets or exceeds quota
• Support the CRO in refining sales strategy and infrastructure, including forecasting, SOPs, packaging, pitch language, and sales motion
• Partner with Product, Engineering, and Enablement to align on solutions, roadmap priorities, and customer feedback loops
• Influence revenue planning and translate company priorities into team action
• Monitor and improve team productivity and sales efficiency, identifying process bottlenecks and implementing scalable solutions
• Coach Account Executives on deal strategy, messaging, and execution, with a focus on multithreading and enterprise sales best practices
• Use data to drive decision-making, identify trends, and report on performance across the funnel
• Help define and evolve territory strategy and account allocation to ensure balance and high-impact coverage
• Champion a culture of learning, collaboration, and accountability within the sales team

You’re a great fit if you:

• Have 7+ years of B2B sales experience, with 2+ years in sales leadership roles
• Have experience selling tech/SaaS platforms, ideally subscription-based or software with AI/data components
• Possess a strong understanding of sales processes from pipeline generation to deal close, with a track record of building scalable systems
• Demonstrate the ability and desire to operate in a dynamic startup environment, balancing speed, ownership, and evolving priorities
• Are comfortable managing and motivating teams through ambiguity and change
• Have experience partnering cross-functionally with Product, Marketing, Enablement, and Customer Enablement teams
• Are highly proficient in Salesforce or Hubspot (Hubspot experience preferred)

Total Compensation

The on-target earnings for this position are $240,000 - $280,000, based on experience and skillset.

Additional benefits include:

• Health insurance (medical, dental, vision) with 100% of employee premiums covered
• Unlimited PTO
• Flexible, remote work-from-home culture
• Access to Hearst Tower facilities in NYC (optional)