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Squarespace · 2 days ago

Senior Team Lead, Sales Development Representatives

New York, NY

Full-time

Hybrid

Mid, Senior Level

$106K/yr - $144K/yr

5+ years exp

Squarespace is looking for a Senior Team Lead, Sales Development Representatives to build and scale their next-generation outbound engine. The role involves creating a world-class pipeline generation function for SMB sales, recruiting and developing a high-performing SDR team, and collaborating with various departments to drive predictable business growth.

Developer ToolsE-Commerce PlatformsPublishingSoftwareWeb Design

Comp. & Benefits

Responsibilities

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

Qualification

B2B SaaS experienceSDR managementAIAutomation platformsSalesforce expertiseGTM engineering mindsetData-driven strategyCoaching skillsCommunication skillsLeadership skills

Required

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