Sales Manager, Cross-Sell & Expansion

Overview

Squarespace is seeking a Sales Manager to hire, build, and lead a brand-new team of Account Executives focused on driving expansion revenue through the existing Squarespace ecosystem. This is a rare opportunity to be a founding member of a completely new, strategic sales motion designed to unlock the full potential of our customer base by cross-selling and upselling our suite of products.

You will be given the autonomy to help hire the team from scratch and shape the strategy and direction for how Squarespace deepens customer relationships and increases product adoption. We are looking for an extremely hands-on, metrics-driven sales leader who excels at building from the ground up. You thrive in a “player-coach” environment and have a passion for developing talent and creating scalable, repeatable sales processes in a fast-paced, high-growth setting.

This role reports to the VP of Sales.

• Build Your Team: Partner with leadership to recruit, hire, and onboard a high-performing team of Account Executives, establishing a culture of success, accountability, and consultative selling from day one.
• Define the Playbook: Architect and implement the sales strategy and playbook for cross-sell and expansion, including identifying buying signals, developing outreach cadences, and articulating value propositions for our integrated product suite.
• Lead from the Front: Provide daily, hands-on coaching to your reps on the front lines. You will be deep in the details of the business—joining calls to help move deals forward, workshopping deal strategy, and providing real-time feedback to develop your team's skills.
• Drive Expansion Revenue: Lead your team to consistently meet and exceed monthly and quarterly expansion sales targets. You will be responsible for accurate forecasting, meticulous pipeline management, and reporting to sales leadership.
• Collaborate Cross-Functionally: Partner closely with our Customer Success, Marketing, and Product teams to ensure a seamless customer experience, identify expansion opportunities, and provide critical feedback to inform GTM strategy.
• Master the Tools: Champion the use of our sales tech stack to drive efficiency and leverage data for coaching and strategic decision-making.

• 5+ years of experience in B2B SaaS sales, with at least 2-3+ years in a sales management or team lead role. Preferred experience should be in an Account Management, Acquisition sales, or dedicated expansion/cross-sell role within a high-velocity SMB environment.
• Proven track record of success in building and scaling a team that consistently exceeds expansion revenue targets through cross-selling and upselling. You’ve successfully hired and developed top-performing AEs.
• A deep "player-coach" mentality; you’re a leader who is passionate about daily coaching, call reviews, and being actively involved in your team's deals to get them across the finish line.
• Experience in creating sales playbooks, processes, and methodologies from an early stage (i.e. Challenger).
• Expertise in pipeline management, accurate forecasting, and using data to drive team performance.
• Deep proficiency with Salesforce and modern AI-driven sales tools (e.g., Gong, Clay, Momentum, Onum).
• Exceptional communication, leadership, and interpersonal skills. Proven track record of hiring high performers and managing effectively to structure top-performing teams.
• A builder’s mindset—you are comfortable with ambiguity and excited by the challenge of creating something new.

This isn’t a role where you’ll be inheriting a legacy team or process. You will be at the forefront of building a critical new engine for Squarespace’s growth by deepening the value we provide to our customers. If you are a builder who is passionate about creating high-performing sales teams and wants to make a tangible impact on the future of a world-class brand, this is your opportunity to write the playbook and define what expansion sales looks like at Squarespace.

• A choice between medical plans with an option for 100% covered premiums including medical, dental, and vision
• Supplemental Life and Disability…