Squarespace is seeking a Sales Manager to hire, build, & 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 & upselling our suite of products.

You will be given the autonomy to help hire the team from scratch & shape the strategy & direction for how Squarespace deepens customer relationships & 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 & have a passion for developing talent & creating scalable, repeatable sales processes in a fast-paced, high-growth setting. This role reports to the VP of Sales.

Who We're Looking For...

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

You'll Get To... 

• 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 & scaling a team that consistently exceeds expansion revenue targets through cross-selling & upselling. Youve successfully hired & developed top-performing AEs.
• A deep "player-coach" mentality; youre a leader who is passionate about daily coaching, call reviews, & being actively involved in your team's deals to get them across the finish line.
• Experience in creating sales playbooks, processes, & methodologies from an early stage (i.e. Challenger).
• Expertise in pipeline management, accurate forecasting, & using data to drive team performance.
• Deep proficiency with Salesforce & modern AI-driven sales tools (e.g., Gong, Clay, Momentum, Onum).
• Exceptional communication, leadership, & interpersonal skills. Proven track record of hiring high performers & managing effectively to structure top-performing teams.
• A builders mindsetyou are comfortable with ambiguity & excited by the challenge of creating something new.

Why This Role at Squarespace

This isnt a role where youll be inheriting a legacy team or process. You will be at the forefront of building a critical new engine for Squarespaces growth by deepening the value we provide to our customers. If you are a builder who is passionate about creating high-performing sales teams & wants to make a tangible impact on the future of a world-class brand, this is your opportunity to write the playbook & define what expansion sales looks like at Squarespace.

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
• Retirement benefits with employer match
• Flexible paid time off
• 12 to 20 weeks of paid family leave
• Equity plan for all employees
• Pretax commuter benefit
• Education reimbursement
• Employee donation match to community organizations
• 6 Global Employee Resource Groups (ERGs)
• Dog-friendly workplace
• Free lunch & snacks
• Private rooftop

Cash Compensation Range: $200,000 - $300,000 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 on-target commissions or overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock. 

About Squarespace

Squarespace (NYSE: SQSP) 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, & hospitality business management via Tock. Our team of more than 1,700 is headquartered in bustling New York City, with offices in Chicago, Dublin, Ireland, Aveiro, Portugal, & coworking spaces in the UK, Netherlands, & Australia. For more information about our company culture, visit 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 customers, but we also work toward 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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