RVP, Enterprise Sales

Contentsquare • Boston, MA

1d • $185,000 - $215,000 • Remote

About The Position

The RVP of Enterprise Sales will lead Contentsquare's North American enterprise sales growth. The role is responsible for leading, developing, and scaling a high-performing team of Enterprise Account Executives; setting regional sales strategy; and driving new customer acquisition, pipeline generation, and revenue growth across strategic enterprise accounts. This hands-on leadership position combines strategic direction with direct involvement in deal strategy, pipeline development, and coaching.

Reporting to the VP of Sales, the RVP is a member of Contentsquare's US Sales Leadership team and partners with senior leaders and teams across Sales, Marketing, Solutions Consulting, and Customer Success to accelerate regional growth, strengthen market presence, and deliver long-term customer value.

Requirements

• 7+ years of successful B2B SaaS sales experience, with a strong record of acquiring new enterprise customers and driving significant revenue growth.
• 2+ years of 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 and ability to coach teams in strategic prospecting, executive engagement, negotiation, and deal execution.
• Ability to recruit, develop, and retain top sales talent and build a collaborative, high-performance team environment.
• Strong business acumen and analytical skills, including the ability to use sales metrics, pipeline reporting, and forecasting to guide decisions.
• Exceptional executive presence and communication skills, with the ability to build credibility and influence across customer organizations and internal leadership teams.
• Hands-on, entrepreneurial mindset and ability to balance strategic leadership with direct business involvement.
• Experience working cross-functionally in a fast-paced, evolving technology environment.
• Bachelor's degree or equivalent practical experience.

Nice To Haves

• Experience selling MarTech, digital experience, customer experience, analytics, or other technology solutions to enterprise organizations.
• Familiarity with enterprise challenges in 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.

Responsibilities

• Own Enterprise team revenue performance and drive achievement of individual, team, and regional targets while fostering accountability, high performance, and continuous improvement.
• Recruit, hire, develop, coach, mentor, and retain enterprise sales talent, including supporting career development and building a leadership pipeline.
• Develop and execute regional sales strategy to expand Contentsquare's enterprise footprint, penetrate strategic accounts, and accelerate new business acquisition.
• Build a predictable pipeline through territory planning, strategic prospecting, account prioritization, and collaboration with SDR and Marketing teams.
• Coach Account Executives on strategic opportunities, deal strategy, executive engagement, competitive positioning, negotiation, and closing complex enterprise agreements.
• Use pipeline reporting, forecasting, dashboards, and performance metrics to evaluate business health, identify opportunities and risks, and maintain accurate revenue forecasts.
• Partner with Solutions Consulting, Marketing, SDR, Customer Success, Finance, Legal, and other internal teams on go-to-market efforts and customer experience.
• Build relationships with senior customer stakeholders and executive decision-makers, act as executive sponsor on strategic opportunities, and help navigate complex enterprise organizations.
• Represent Contentsquare at industry events, executive engagements, and customer meetings, strengthening the company's regional market presence.
• Share customer insights, competitive intelligence, and market feedback with internal stakeholders to inform go-to-market strategy, product direction, and continuous improvement.

Benefits

• Career development and mentorship.
• Social events and philanthropic activities.
• Competitive benefits.
• Virtual onboarding, hackathon, and opportunities to interact with team members and global colleagues on- and offsite.
• Hybrid and remote work policies.
• Generous paid time off, varying by location.
• Lifestyle allowance.
• Culture Crew activities in each country where Contentsquare operates.
• Stock options for every full-time employee.
• Employee Resource Groups.

What This Job Offers

• Job Type: Full-time
• Career Level: Director