Head of Sales, North America

Jobgether

13h • Remote

About The Position

This role is a senior leadership position responsible for driving revenue growth and scaling enterprise sales across North America. You will combine strategic oversight with hands-on involvement in complex, multi-stakeholder deals, ensuring consistent execution of long sales cycles and high-value account management. The position involves building and mentoring a high-performing team of Enterprise Account Executives, defining market strategies, and partnering with cross-functional teams such as Marketing, Product, and Solutions Engineering. The environment is fast-paced, innovative, and centered on cutting-edge AI and automation technologies, providing opportunities to shape the adoption of transformative solutions in large enterprises. You will be accountable for regional revenue, pipeline development, and team performance while fostering a culture of collaboration, experimentation, and results-driven execution. Remote work is supported, with travel as needed to meet business objectives.

Requirements

• 10+ years of experience in Enterprise SaaS Sales, including 3–5+ years in a leadership role (VP, Head of Sales, or Senior Director).
• Deep knowledge of AI, Machine Learning, Customer Experience (CX), Voice Technology, or related enterprise solutions.
• Proven track record of closing and guiding teams through $250K–$1M+ ARR deals.
• Expertise in sales methodologies such as MEDDIC, Challenger, or Command of the Message.
• Strong leadership, coaching, and team-building skills, with the ability to recruit and develop high-performing sales teams.
• Experience managing long, complex, multi-stakeholder enterprise sales cycles.
• Excellent communication and presentation skills, capable of engaging C-level executives.
• Bachelor’s or Technical degree required; MBA or equivalent preferred.
• Comfortable operating in a fast-paced, remote-first environment with flexibility to travel as needed.

Responsibilities

• Own North American enterprise revenue, forecast, and pipeline strategy, ensuring regional growth targets are achieved.
• Act as a hands-on “player-coach” by participating in complex enterprise deals and guiding the team through multi-stakeholder sales cycles.
• Recruit, train, and retain top-tier Enterprise Account Executives, fostering a high-performance sales culture.
• Define and execute strategic “Land and Expand” initiatives targeting high-value verticals such as Banking, Telecom, Hospitality, and Healthcare.
• Collaborate with Marketing to align outbound strategies, with Product to tailor enterprise solutions, and with Solutions Engineering to secure technical wins.
• Translate complex AI, ML, or automation solutions into clear business value propositions for enterprise clients.
• Establish processes and best practices to maximize team productivity, drive deal velocity, and ensure consistent execution across accounts.

Benefits

• Competitive base salary plus commission and equity opportunities.
• Flexible working hours with a dedicated remote work budget.
• Professional development stipend and education leave.
• Unlimited PTO, paid sick leave, and public holidays.
• Comprehensive health benefits (U.S. only) and 401(k) plan with employer match.
• Company-provided technology, including MacBook and other tools.
• Regular remote team events and annual company-wide offsite.
• Opportunity to lead and shape the growth of a cutting-edge enterprise AI business.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 11-50 employees