Director of Sales & GTM Operations
Director of Sales & GTM Operations
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Job Description
Squarespace is seeking a Director of Sales & GTM Operations to be the chief architect of the systems and intelligence that will power our new B2B upmarket growth engine. This is a unique opportunity for a systems-first leader who thrives in creating order from ambiguity and is passionate about building a truly modern AI-native revenue infrastructure from the ground up.
You will play a pivotal role in shaping our entire GTM strategy laying a scalable foundation for rapid growth across Sales Agency Partnerships and Customer Success. We are looking for a strategic builder who can architect a well-oiled intelligent revenue machine. You have the vision to design what a next-generation AI-powered GTM motion looks like and the technical-mindedness to roll up your sleeves and build it.
This role reports to the VP of Sales and is based out of Squarespaces NYC Headquarters (hybrid).
Youll Get To...
- Architect an Intelligent GTM Future: Design and implement a scalable end-to-end GTM systems architecture. Your primary focus will be on building a tech stack that is not only integrated and usable but is infused with AI and automation to create a competitive advantage.
- Build a Predictive Engine from Day One:Establish and scale core RevOps functions including predictive forecasting dynamic pipeline management data-driven compensation design and optimized territory planning. You will ensure every GTM touchpoint is measurable actionable and informs our strategy.
- Lead with an Engineering Mindset:Own the GTM technology stack as if it were a product. You will drive the roadmap evaluation implementation and optimization of our tools. This includes leveraging AI-native platforms for conversation and deal intelligence process automation predictive scoring and data integration to maximize rep productivity and deal velocity.
- Champion AI-Driven Insights:Move beyond traditional reporting. You will lead the charge on data governance and hygiene to create a pristine data foundation enabling the use of AI for predictive analytics lead scoring and identifying new revenue opportunities. You will own the strategy for data enrichment and the generation of high-intent target accounts.
- Drive Strategic & Operational Cadence:Partner with GTM leadership to establish and run the operating rhythms of the business including QBRs performance tracking and strategic planning. You will ensure these forums are grounded in data and forward-looking insights.
- Innovate and Automate:Constantly seek out opportunities to streamline processes and automate workflows across the customer lifecycle. You will be expected to reduce friction for our sales and success teams allowing them to focus on high-value activities.
Who Were Looking For
- 12-15 years in Revenue or Sales Operations with at least 5 years in a leadership roleideally in a high-growth B2B SaaS environment.
- A Proven Builder Track Record: You have successfully built and scaled a modern RevOps function for a large organization demonstrating your ability to design systems and processes from scratch.
- Deep AI & GTM Tech Stack Expertise: You are a power user of Salesforce and possess a strong opinionated view on the modern GTM technology landscape. You have hands-on experience implementing and optimizing AI-driven tools for conversation intelligence predictive forecasting and workflow automation.
- An Engineering and Systems Mindset: You are a strategic thinker with a bias for execution. You naturally gravitate towards systems-thinking automation and applying engineering principles to solve operational challenges and ensure data integrity.
- Data-First and Analytically Rigorous: You have a proven ability to translate complex data into actionable business insights and strategic recommendations. Experience with BI tools (e.g. Tableau Looker) and a fundamental understanding of data warehousing concepts is essential.
- Cross-Functional Leadership: You excel at managing complex cross-functional initiatives and building strong relationships with senior leaders in Sales Marketing Finance and Product to drive unified revenue-focused outcomes.
- A passion for simplification elegant system design and achieving measurable impact in a fast-paced environment structure and driving measurable business outcomes.
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
- 20 weeks for parental leave and up to 12 weeks to care for an ill family member
- 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: $203500 - $327750 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 on-target commissions or overtime pay) Squarespace employees are eligible to be granted an option to purchase our common stock.
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 1500 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 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. #LI-Hybrid Thank you in advance for providing the following details about your work history from your resume! This helps us ensure that your candidate information is accurate and consistent during the hiring process. Squarespace will never solicit your personal banking information or ask you to transfer money in connection with a job offer or interview. We also will not reach out to you via phone or SMS without your permission or knowledge.
Required Experience:
Director
Employment Type
Full Time
