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

Youll be the architect of a new SDR organization including hiring & developing top talent, designing the systems & playbooks theyll use, & leveraging cutting-edge tools to drive scalable, repeatable growth. 

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

Youll work hybrid from our NYC Headquarters office, report to the VP of Sales, & work closely with leadership across Sales, Marketing, & Revenue Operations to build the foundation of Squarespaces next major growth engine.

Youll Get To

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

Who Were Looking For:

• 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 & innovations in sales outbound as a craft
• Deep experience with modern AI & automation platforms (e.g., Clay, Gong, Onum, Momentum) & a strong perspective on how to deploy them for maximum efficiency.
• Proven success building, scaling, & coaching high-performing SDR teams that consistently exceed targets.
• Expertise in Salesforce hygiene, forecasting, & pipeline management, making data actionable.
• Excellent communication & leadership skills with a passion for developing people & creating a culture of excellence.
• A builders mentality - youre energized by ambiguity & motivated to create structure, process, & results from the ground up.

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums 
• Fertility & 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 & 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 & snacks
• Private rooftop
• Hack week twice per year

Cash Compensation Range: $106,250 - $143,750 USD

The base salary for this position will vary based on job-related criteria including relevant skills, experience, & 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 & businesses online. We empower millions of customers in more than 200 countries & territories with all the tools they need to create an online presence, build an audience, monetize, & scale their business. Our suite of products range from websites, domains, ecommerce, & marketing tools, as well as tools for scheduling with Acuity & creating & managing social media presence with Bio Sites & Unfold. Our team of more than 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, & coworking spaces in the UK, Netherlands, & Australia. For more information about our company culture, visit https://www.squarespace.com/about/careers.

Our Commitment 

Today, more than a million people around the globe use Squarespace to share different perspectives & experiences with the world. Not only do we embrace & 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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