Head of Sales, North America

Job Description

Topsort is seeking a Head of Sales for North America to lead regional sales efforts. This role is based in Boston or New York and involves driving pipeline growth, managing a team of 30+ sales professionals, and converting strategic opportunities into long-term partnerships. The ideal candidate will possess deep knowledge of the North American market and strong team leadership skills.Responsibilities:

• Lead commercial execution for the North American market.
• Manage and scale a high-performing regional sales team.
• Drive complex, high-value deals by understanding client needs.
• Collaborate with Marketing, Product, and Customer Experience teams.
• Optimize sales operations across the region.
• Set and exceed aggressive sales targets.
• Act as the focal point for North America, ensuring regional feedback informs broader company decisions.

Requirements:

• 8+ years in enterprise B2B sales leadership.
• Deep understanding of the North American sales landscape.
• Proven track record of building pipeline and mapping key accounts.
• Experience leading teams of 20–30+ across various sales roles.
• Ability to uncover client needs and craft compelling value propositions.
• Familiarity with CRM tools and sales operations.
• Comfortable working with cross-functional teams.
• Resourcefulness in achieving goals with limited resources.

Benefits:

• Direct feedback and rapid growth opportunities.
• Collaborative and competitive team environment.
• Remote-working options with coworking memberships.
• Company offsite events and industry exposure.
• Flexible PTO schedule with floating holidays.
• Working equipment of your choice and surprise swags.
• Meditation app access, birthday and anniversary celebrations.