Account Executive, Acquisition

Squarespace is looking for an Account Executive to join our New Business Acquisition team. This is a new, strategic sales motion, focused on acquiring net new SMB customers. You’d be part of a founding team, building a critical new growth engine for a globally recognized, design-led technology brand. 

As an Account Executive on this team, you’ll be on the front lines of Squarespace’s proactive sales efforts, identifying, engaging, and converting high-potential businesses that can benefit from our best-in-class platform. You’ll play a key role in helping us refine how we bring Squarespace’s value to life for SMBs through a structured, data-driven, and high-velocity sales motion.

This role is ideal for someone who loves building relationships, thrives in a fast-paced sales environment, and is excited to be a part of establishing a new sales playbook from the ground up.

You’ll report to the Sales Manager, Acquisition, and work hybrid from our NYC Headquarter Office. 

You'll Get To... 

• Drive New Business Growth: Own the full sales cycle, from prospecting and discovery through demo, negotiation, and close, to acquire new SMB customers across target industries.
• Outbound Prospecting: Proactively source new opportunities through a mix of personalized outreach, social selling, and working inbound leads in partnership with Marketing. You’ll be expected to build and maintain a healthy top-of-funnel.
• Consultative Selling: Conduct discovery to deeply understand business challenges and tailor Squarespace’s solutions — spanning websites, commerce, and marketing tools — to meet each client’s goals.
• Achieve and Exceed Targets: Consistently hit and exceed monthly and quarterly new business quotas by effectively managing your pipeline and maintaining high activity levels.
• Collaborate and Build: Work closely with leadership to refine messaging, processes, and playbooks as we evolve our SMB sales approach. Your feedback from the field will directly shape our GTM motion.
• Data-Driven Execution: Leverage tools like Salesforce, Gong, and Clay to track activity, manage pipeline health, and forecast accurately. Use performance insights to continuously improve outreach and conversion metrics.
• Champion the Brand: Represent Squarespace’s mission and value proposition with clarity and enthusiasm, helping SMB owners see how our tools can simplify and scale their online presence.

Who We’re Looking For

• 5+ years of B2B SaaS sales experience, ideally within a high-velocity, SMB-focused motion.
• A track record of meeting and exceeding sales quotas through disciplined prospecting, pipeline management, and consultative closing.
• Strong outbound sales skills. You’re comfortable generating your own pipeline and managing multiple deals simultaneously in a fast-paced environment.
• Strong understanding of SMB buyer dynamics and how to sell value to time-constrained, resource-limited business owners and operators.
• Proficiency in Salesforce, Gong, and modern AI-driven sales tools for tracking, engagement, and forecasting.
• Excellent communication, presentation, and storytelling abilities. You know how to simplify complex concepts and connect with decision-makers quickly.
• A builder’s mindset. You’re energized by ambiguity and excited to help shape a new motion within a growing, product-led organization.
• Experience having sold website building, scheduling, payments, or adjacent supporting web systems a plus. 

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums 
• Fertility and adoption benefits
• Access to supplemental insurance plans for additional coverage
• Headspace mindfulness app subscription
• Global Employee Assistance Program
• Retirement benefits with employer match
• Flexible paid time off
• 12 weeks paid parental leave and family care leave
• Pretax commuter benefit
• Education reimbursement
• Employee donation match to community organizations
• 7 Globa