Director of Marketing, B2B

Squarespace is looking for a highly strategic and entrepreneurial Director of B2B Marketing to define and lead our go-to-market engine for the upmarket SMB segment. This is a senior leadership role for a marketing executive who understands how to reach, engage, and convert larger SMB merchants at scale using modern B2B marketing tactics.

You will be responsible for building a world-class demand engine that drives qualified pipeline, fuels outbound sales motions, and strengthens our brand presence across key verticals. With ownership across media spend, demand generation, account-based programs, and sales partnership, this role is a chance to architect and scale a marketing function from the ground up.

Reporting to the SVP of Commercial, you will work cross-functionally with Sales, Product Marketing, and RevOps. You’ll also have the opportunity to build and lead your own team, shaping the future of B2B marketing at Squarespace. This role will work hybrid from our NYC Headquarters.

You’ll Get To...

Define & Own the B2B GTM Strategy

• Develop and own a unified marketing strategy for acquiring and growing larger SMB merchants, deeply aligned with Sales and Customer Success.

• Translate growth objectives into a roadmap of integrated campaigns across paid media, brand, content, ABM, lifecycle marketing, and outbound sales support.

• Work to refine the Ideal Customer Profile to ensure long-term retention. Build verticalized playbooks, narratives, and ICP definitions that resonate with merchants across industries.

• Develop a position on the market, defining messaging architecture and key value propositions. Build a long-term brand that is focused on providing value and avoids transactional interactions

Build & Scale a Demand Generation Engine

• Stand up a new Demand Generation team with expertise in media, inbound lead generation, outbound, and full-funnel execution. Have a deep analytical understanding of demand gen channels and understand capital allocation to double down on winners and starve losers all while preserving the ability to test.

• Drive high-impact paid media programs while balancing cost efficiency and scale, with a particular focus on generating marketing qualified leads that convert to closed sales.

• Partner with Sales leadership to orchestrate joint demand plays that accelerate outbound pipeline creation.

• Leverage AI-powered tools (e.g., for lead scoring, personalization, content optimization, and conversational outreach) to increase efficiency and impact.

Drive Sales Alignment & Enablement

• Collaborate with Sales Enablement to ensure campaigns directly translate to opportunities and closed revenue.

• Equip outbound sales teams with campaigns, messaging, and content tailored to merchant pain points and buying journeys.

• Partner with RevOps to optimize lead routing, scoring, and funnel conversion.

Refine the Infrastructure for Scale

• Refine the marketing tech stack to support advanced targeting, personalization, attribution, and reporting (e.g., HubSpot, 6sense, Marketo, Clearbit, Gong, Drift).

• Integrate AI and predictive analytics into campaign targeting, pipeline forecasting, and marketing mix optimization.

• Establish measurement frameworks for CAC, pipeline contribution, and ROI at the campaign and segment level.

• Create dashboards and reporting systems shared across Sales and Marketing leadership, ensuring a real-time, data-driven operating rhythm.

• Instill a culture of test-and-learn experimentation across channels, leveraging data and automation to continuously optimize.

Who We’re Looking For

• 12-15+ years of experience in B2B marketing, demand generation, or revenue marketing, ideally in high-growth SaaS, commerce tech, or PLG environments.

• 5+ years in senior leadership, with a proven ability to design and execute large-scale GTM strategies across media, ABM, demand gen, and outbound.

• Proven track record building and scaling high-performing marketing teams.

• Deep expertise in modern B2B marketing channels and tactics—from performance media and demand gen to outbound orchestration and ABM.

• Strong understanding of merchant buyer journeys and experience engaging SMBs with higher ACVs.

• Hands-on with data and tooling: comfortable evaluating, implementing, and refining modern martech and AI platforms; able to connect strategy with technical execution.

• Data-driven operator with experience forecasting pipeline, aligning attribution, and reporting on ROI.

• Strong cross-functional leader who thrives in partnership with Sales, RevOps, Product Marketing, FP&A, Product and Analytics.

• Bonus: Experience marketing to service providers, agencies, or commerce-driven SMB ecosystems.

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums

• Fertility and adoption benefits

• Access to supplemental insurance plans for additional coverage

• 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: $211,600 - $340,860 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 1,700 is headquartered in New York City, with offices in Dublin, Ireland, and Aveiro, Portugal. For more information about our company, 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 customer base, but we also strive for 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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