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Squarespace · 1 day ago

Sales Manager, Cross-Sell & Expansion

New York City

Full-time

Hybrid

Senior Level

$200K/yr - $300K/yr

5+ years exp

Squarespace is seeking a Sales Manager to build and lead a new team of Account Executives focused on driving expansion revenue. The role involves hiring talent, defining sales strategies, and collaborating cross-functionally to enhance customer relationships and product adoption.

Developer ToolsE-Commerce PlatformsPublishingSoftwareWeb Design

Comp. & Benefits

Responsibilities

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 frontlines. 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

Qualification

B2B SaaS salesSales managementPipeline managementSalesforceCross-sellingUpsellingSales playbooksCoachingLeadershipInterpersonal skills

Required

5+ years of experience in B2B SaaS sales, with at least 2-3+ years in a sales management or team lead role

Proven track record of success in building and scaling a team that consistently exceeds expansion revenue targets through cross-selling and upselling

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

Preferred

Preferred experience should be in an Account Management, Acquisition sales, or dedicated expansion/cross-sell role within a high-velocity SMB environment