Sales Manager, Cross-Sell & Expansion

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.

You'll Get To...

• 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.

Who We're Looking For...

• 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.

Why This Role at Squarespace

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.

Benefits & Perks

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

• Supplemental Life and Disability Insurance plans

• Fertility and adoption benefits

• Headspace mindfulness app subscription

• Global Employee Assistance Program

• Retirement benefits with employer match

• Flexible paid time off

• 12 weeks paid parental leave and 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 and snacks

• Private rooftop

• Hack week twice per year

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, and 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 and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, and coworking spaces in the UK, Netherlands, and 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 and experiences with the world. Not only do we embrace and 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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