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 Global Employee Resource Groups (ERGs)

• Dog-friendly workplace

• Free lunch and snacks

• Private rooftop

• Hack week twice per year

Cash Compensation Range: $85,000 - $115,000 USD

The base salary for this position will vary based on job-related criteria including relevant skills, experience, and location, among other factors.

In addition to the cash compensation above (which includes base salary and, where applicable for eligible roles, may include overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock. Sales positions generally offer a competitive On Target Earnings (OTE) incentive structure in addition to base salary.

About Squarespace

Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, visit https://www.squarespace.com/about/careers.

Our Commitment

Today, more than a million people around the globe use Squarespace to share different perspectives and experiences with the world. Not only do we embrace and celebrate the diversity of our customer base, but we also strive for the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

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