North America Enterprise Sales Leader

Heap; New York (NY); Hybrid; USD 185,000 - 215,000; Full time

Benefits offered by this job

Stock options

Work flexibility: hybrid and remote

Generous paid time-off

Lifestyle allowance

Culture Crew in each country

Employee Resource Groups

Job summary

Contentsquare is seeking a strategic, hands-on RVP of Enterprise Sales to lead, develop, and scale a high-performing Enterprise Account Executive team across North America. You will drive regional strategy, revenue growth, and new customer acquisition while partnering with cross-functional teams to accelerate deals and deliver long-term customer value.

You will report to the VP of Sales and shape the regional go-to-market approach, balancing strategic direction with active involvement in deal

Qualifications

• 7+ years of successful B2B SaaS sales experience with enterprise customers.
• 2+ years leading, coaching, and developing enterprise sales teams in a tech company.
• Proven success in driving enterprise sales performance and revenue growth.
• Experience developing regional sales strategies, territory planning, and new business acquisition.
• Strong understanding of complex enterprise sales cycles; coach teams through strategic prospecting and negotiations.
• Proven ability to recruit, develop, and retain top sales talent and build a high-performing team.
• Strong business acuity, analytics, pipeline forecasting for decision-making.
• Exceptional executive presence and communication; capable of influencing at senior levels.
• Hands-on, entrepreneurial mindset balancing strategy with direct deal involvement.
• Experience working cross-functionally in fast-paced tech environments.
• Bachelor’s degree or equivalent practical experience.

Responsibilities

• Lead regional sales performance and revenue targets for the Enterprise team.
• Recruit, hire, develop, and retain top enterprise sales talent with coaching and mentorship.
• Develop and execute the regional sales strategy to expand enterprise footprint.
• Build a predictable pipeline through territory planning and strategic prospecting.
• Coach Account Executives on deal strategy, executive engagement, and negotiations.
• Maintain pipeline visibility with forecasting dashboards and performance metrics.
• Collaborate with Solutions Consulting, Marketing, SDR, Customer Success, Finance and Legal.
• Develop executive relationships with senior customer stakeholders.
• Represent Contentsquare at industry events and customer meetings.
• Champion customer insights to inform go-to-market strategy and product direction.

Skills

B2B SaaS sales

Enterprise sales leadership

Coaching & development

Strategic planning

Executive engagement

Forecasting & analytics

Cross-functional collaboration

Bachelor's degree or equivalent

Education

Bachelor's degree or equivalent practical experience

Job description

Contentsquare is seeking a strategic, hands-on RVP of Enterprise Sales to lead, develop, and scale a high-performing Enterprise Account Executive team across North America. You will drive regional strategy, revenue growth, and new customer acquisition while partnering with cross-functional teams to accelerate deals and deliver long-term customer value.

You will report to the VP of Sales and shape the regional go-to-market approach, balancing strategic direction with active involvement in deal