Regional Vice President of Enterprise Sales (North America) - Contentsquare

Contentsquare is the all-in-one experience intelligence platform designed to help organizations understand their customers’ digital journeys.

As the RVP of Enterprise Sales, you will play a critical leadership role in driving Contentsquare's growth across North America. You will lead, develop, and scale a high-performing team of Enterprise Account Executives, establishing the regional sales strategy and driving new customer acquisition, pipeline generation, and revenue growth across strategic enterprise accounts.

About the Role

This is an opportunity for an experienced sales leader who combines a strong track record of enterprise SaaS sales success with a passion for building and developing exceptional teams. You'll bring a hands-on, entrepreneurial approach to leadership, balancing strategic direction with active involvement in deal strategy, pipeline development, and coaching to help your team consistently deliver results.

Reporting to the VP of Sales, you will be a key member of Contentsquare's US Sales Leadership team, partnering closely with senior leadership and cross-functional teams across Sales, Marketing, Solutions Consulting, and Customer Success to accelerate regional growth, strengthen our market presence, and deliver long-term customer value.

What You'll Do

• Lead regional sales performance: Own the Enterprise team's revenue performance, driving the achievement of individual, team, and regional targets while establishing a culture of accountability, high performance, and continuous improvement.
• Build and develop a high-performing team: Recruit, hire, develop, and retain top enterprise sales talent. Provide ongoing coaching, mentorship, and career development to strengthen individual performance and build a strong leadership pipeline.
• Drive regional strategy and growth: Develop and execute the regional sales strategy, identifying opportunities to expand Contentsquare's enterprise footprint, penetrate strategic accounts, and accelerate new business acquisition.
• Build a predictable pipeline: Establish a strong pipeline generation culture across the team, driving effective territory planning, strategic prospecting, account prioritization, and collaboration with SDR and Marketing teams to maximize pipeline creation.
• Coach and accelerate deal execution: Partner with Account Executives on strategic opportunities, providing guidance on deal strategy, executive engagement, competitive positioning, negotiation, and closing complex enterprise agreements.
• Drive operational excellence: Leverage pipeline reporting, forecasting, dashboards, and performance metrics to assess business health, identify opportunities and risks, and maintain accurate revenue forecasts.
• Strengthen cross-functional partnerships: Collaborate with Solutions Consulting, Marketing, SDR, Customer Success, Finance, Legal, and other internal teams to create a cohesive go-to-market approach and deliver an exceptional customer experience.
• Build executive relationships: Develop relationships with senior customer stakeholders and executive decision-makers, serving as an executive sponsor on strategic opportunities and helping the team navigate complex enterprise organizations.
• Represent Contentsquare in the market: Act as a senior ambassador for Contentsquare, representing the company at industry events, executive engagements, and customer meetings while strengthening our regional market presence.
• Champion the customer: Bring customer insights, competitive intelligence, and market feedback to internal stakeholders to help inform go-to-market strategy, product direction, and continuous improvement.

What You'll Bring

• 7+ years of successful B2B SaaS sales experience, with a strong track record of acquiring new enterprise customers and driving significant revenue growth.
• 2+ years of demonstrated experience leading, coaching, and developing high-performing enterprise sales teams within a technology company.
• Proven success driving enterprise sales performance, consistently achieving revenue targets, and building a culture of accountability and results.
• Experience developing and executing regional sales strategies, including territory planning, pipeline generation, and new business acquisition.
• Strong understanding of complex enterprise sales cycles, with the ability to coach teams through strategic prospecting, executive engagement, negotiation, and deal execution.
• Demonstrated ability to recruit, develop, and retain top sales talent while building a collaborative, high-performance team environment.
• Strong business acumen and analytical skills, with the ability to leverage sales metrics, pipeline reporting, and forecasting to drive informed business decisions.
• Exceptional executive presence and communication skills, with the ability to build credibility and influence across customer organizations and internal leadership teams.
• A hands-on, entrepreneurial mindset with the ability to balance strategic leadership with direct involvement in the business.
• Experience working cross-functionally in a fast-paced, evolving technology environment.
• A bachelor's degree or equivalent practical experience.

Nice to Have

• Experience selling MarTech, digital experience, customer experience, analytics, or other technology solutions to enterprise organizations.
• Familiarity with the challenges enterprise businesses face when optimizing digital journeys, understanding customer behavior, and improving digital experiences.
• Experience scaling enterprise sales teams and expanding market presence within a high-growth SaaS organization.