Senior Enterprise Account Executive - East

Contentsquare • Boston, MA

4d • $300,000 - $340,000

About The Position

The Senior Enterprise Account Executive will drive Contentsquare’s growth across North America by identifying, developing, and closing strategic enterprise opportunities. The role owns the full sales cycle, from prospecting and pipeline development through negotiation and close, and builds trusted relationships with senior decision-makers and C-suite executives.

This role suits a proven enterprise sales professional who thrives in a competitive, fast-paced environment, takes an entrepreneurial approach to building pipeline, and can translate complex business challenges into compelling solutions. The Account Executive works cross-functionally with Solutions Consulting, Customer Success, Finance, Legal, and other teams to help customers realize the value of Contentsquare and contribute to regional growth.

Requirements

• At least 7 years of successful B2B SaaS sales experience, including a strong track record of acquiring new enterprise customers and driving new revenue.
• Demonstrated success managing complex, consultative enterprise sales cycles from prospecting through contract negotiation and close.
• Experience building and maintaining a healthy pipeline, prioritizing opportunities, and managing multiple deals at different sales stages.
• Proven ability to build relationships with senior executives and C-suite stakeholders, influence buying decisions, and navigate complex organizational structures.
• Strong business acumen and ability to uncover customer challenges, develop compelling value propositions, and connect solutions to measurable business outcomes.
• Excellent communication, presentation, negotiation, and relationship-building skills.
• Entrepreneurial mindset and ability to work independently, take ownership, and adapt in a fast-paced, evolving environment.
• Customer-first approach and genuine interest in building long-term partnerships and driving customer success.

Nice To Haves

• Experience selling MarTech, digital experience, customer experience, analytics, or other technology solutions to enterprise organizations.
• Familiarity with challenges enterprise businesses face when optimizing digital journeys and improving customer experiences.

Responsibilities

• Own the end-to-end sales cycle, from prospecting and qualification through negotiation and close, with a focus on acquiring new enterprise customers.
• Build and manage a pipeline of high-value opportunities through strategic prospecting, territory planning, account research, and engagement with key stakeholders.
• Lead complex, multi-stakeholder enterprise sales cycles and develop business cases connecting Contentsquare’s solutions to customer priorities and measurable outcomes.
• Build credibility and lasting relationships with senior executives, decision-makers, and influencers across target accounts.
• Identify opportunities to expand existing customer relationships through cross-selling, upselling, and strategic account development.
• Communicate Contentsquare’s value proposition and differentiate its platform by connecting customer challenges to tangible business impact.
• Collaborate with Solutions Consulting, Customer Success, Finance, Legal, and other internal teams to deliver a cohesive customer experience and advance opportunities.
• Share customer insights and market feedback with the business to inform product innovation, go-to-market strategy, and continuous improvement.
• Contribute to Contentsquare’s regional growth with an entrepreneurial mindset, strong commercial judgment, and a results-driven approach.

Benefits

• Virtual onboarding, hackathon, and opportunities to interact with team members and global colleagues on and offsite each year.
• Hybrid and remote work policies.
• Generous paid time-off policy, varying by location.
• Lifestyle allowance.
• Country-based Culture Crews that coordinate employee activities and social connection.
• Stock options for every full-time employee.
• Employee Resource Groups that provide spaces for connection, support, and advocacy.
• Other benefits tailored to each country.
• Career development and mentorship.
• Social events and philanthropic activities.
• Competitive benefits.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed