Senior Team Lead, Sales Development Representatives

Squarespace is looking for a Senior Team Lead, Sales Development Representatives to build and scale our next-generation outbound engine. This is a new, strategic initiative focused on creating a world-class pipeline generation function for SMB sales. You’ll be part of a founding team defining how Squarespace brings its value to life for small businesses through a modern, AI-powered, and data-driven outbound motion.

You’ll be the architect of a new SDR organization including hiring and developing top talent, designing the systems and playbooks they’ll use, and leveraging cutting-edge tools to drive scalable, repeatable growth. 

If you thrive in fast-paced environments, love blending human creativity with technology, and are passionate about using AI to redefine the future of sales, this is your chance to build something transformative.

You’ll work hybrid from our NYC Headquarters office, report to the VP of Sales, and work closely with leadership across Sales, Marketing, and Revenue Operations to build the foundation of Squarespace’s next major growth engine.

• Build a World-Class Team: Recruit, hire, and onboard a high-performing SDR team that combines creativity, curiosity, and technical fluency. Foster a culture rooted in experimentation, accountability, and continuous improvement.
• Design and Operate an AI-Powered Engine: Partner with Sales Operations and Marketing to develop a sophisticated AI-native tech stack for pipeline generation. Architect automated workflows between tools, streamline data flow, and continuously refine how your team engages prospects.
• Drive Predictable New Business Growth:Own SDR pipeline generation targets and ensure consistent delivery of high-quality opportunities to the New Business Acquisition (AE) team. Collaborate closely with Account Executives to optimize lead flow, feedback loops, and conversion efficiency.
• Develop and Optimize Playbooks: Create and execute a data-driven outbound strategy, combining automation, personalization, and creativity to break through noise and engage high-potential SMB prospects across industries. Continuously refine messaging and multi-channel sequences using insights from tools like Gong, Clay, and Momentum.
• Lead from the Front: Coach daily on fundamentals of prospecting, messaging, and qualification while teaching your team how to fully leverage AI and automation to amplify output. Use performance data to guide 1:1s, identify skill gaps, and celebrate wins.
• Collaborate and Shape Strategy: Work cross-functionally with Marketing, Enablement, and RevOps to refine targeting, campaign strategy, and reporting. Your insights from the field will directly influence how we scale our SMB sales motion.
• Innovate Relentlessly: Keep Squarespace’s outbound strategy at the forefront of the industry by testing new tools, tactics, and channels. Be a champion of experimentation, learning, and intelligent risk-taking.

• 5+ years of experience in B2B SaaS, including 1-3+ years in SDR or BDR management.
• A GTM engineering mindset, you design systems, not one-off processes. You are also love to study the latest cutting edge tactics and innovations in sales outbound as a craft
• Deep experience with modern AI and automation platforms (e.g., Clay, Gong, Onum, Momentum) and a strong perspective on how to deploy them for maximum efficiency.
• Proven success building, scaling, and coaching high-performing SDR teams that consistently exceed targets.
• Expertise in Salesforce hygiene, forecasting, and pipeline management, making data actionable.
• Excellent communication and leadership skills with a passion for developing people and creating a culture of excellence.
• A builder’s mentality - you’re energized by ambiguity and motivated to create structure, process, and results from the ground up.

• 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
• 8 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch and snacks
• Private rooftop
• Hack week twice per year

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.

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.

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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