{"id":1123577,"url":"https://alion.io/job/squarespace-senior-lead-ai-pricing-margin-strategy","title":"Senior Lead, AI Pricing & Margin Strategy","company":{"id":63,"name":"Squarespace","domain":"squarespace.com","url":"https://alion.io/company/squarespace","size_band":null,"is_staffing_agency":false,"employer_type":"direct","is_intermediary":false,"listed_via":null,"ats_vendor":"Greenhouse","truth_index":{"grade":"B","score":80,"open_postings":5,"ghost_share":0,"stale_share":0.8,"repost_share":0,"time_to_fill_p50_days":35,"computed_at":"2026-10-23T05:54:15Z"}},"role":"AI/ML","role_family":"AI/ML","seniority":"lead","employment_type":null,"work_mode":"on_site","remote_scope":null,"remote_scope_basis":null,"remote_working_hours":null,"hiring_geo_confidence":"structured","locations":["New York, United States"],"countries":["US"],"hiring_countries":[],"hiring_countries_total":0,"salary":{"min":125800,"max":170200,"currency":"USD","period":"year","gross":null,"usd_annual":170200},"salary_estimate":null,"experience_years_min":5,"visa_sponsorship":false,"relocation_package":false,"has_equity":false,"technologies":[{"name":"Anthropic","optional":false},{"name":"LLM","optional":false},{"name":"OpenAI","optional":false},{"name":"SQL","optional":false}],"status":"live","first_seen_at":"2026-09-22T18:06:39Z","employer_posted_date":"2026-10-15","last_verified_at":"2026-10-23T09:52:49Z","board_verified":true,"closed_at":null,"days_open":30,"trust":{"level":"ok","repost_count":null,"flags":[],"days_open":30},"description":"Squarespace is looking for an analytical, curious thinker to help build out the economics of our growing AI product portfolio. This role sits at the intersection of commercial strategy and emerging technology - supporting the pricing, margin analysis, and packaging work that shapes how Squarespace monetizes AI-powered features for customers and manages AI costs internally.\nYou will join a centralized Commercial Strategy team that drives revenue growth across the platform by optimizing monetization models and packaging for Squarespace's product suite. The team works across pricing, packaging & promotions, purchase behavior analysis, and feature monetization - aligning price with customer value and unlocking incremental ARPU and retention.\nIn this role, you will support the team's AI pricing and margin workstreams: building financial models, analyzing usage and cost data, researching the competitive AI landscape, and partnering with Product and Billing to bring pricing decisions to life. You will report to Commercial Lead and work from our NYC office 2-3 days per week.\nWhat You'll Do…\nCost & Margin Analysis\nLead margin analysis across AI usage - including API costs, token consumption, and inference spend - to build a clear picture of margin across customer-facing features and internal tooling.\nBuild and maintain financial models that translate AI usage into credit equivalents, helping the team track unit economics across model providers and feature surfaces.\nModel the cost and quality tradeoffs of model routing configurations to inform routing decisions made with Product & Engineering.\nPricing & Packaging Support\nDesign and evaluate customer-facing credit and usage-based pricing models, including tier structures, usage limits, and overage mechanics.\nTranslate pricing strategy into concrete SKU and entitlement definitions, working with Product and Billing to ensure commercial intent is correctly implemented.\nStructure promotional offers and launch incentives for new AI features, modeling expected revenue and margin impact.\nCross-functional Collaboration\nPartner with Finance, Data Science, Product, and Billing teams to gather inputs, align on assumptions, and ensure pricing decisions are grounded in accurate usage and cost data.\nPrepare clear, well-structured analyses and presentations that communicate findings to stakeholders across the business.\nTrack and report on the commercial performance of AI features, flagging margin risks and opportunities as they emerge.\nAI Market Research\nMonitor the AI model landscape - tracking pricing changes, capability updates, and new providers across frontier labs - and surface relevant implications for Squarespace's strategy.\nResearch how competitors are packaging and monetizing AI capabilities to inform our own positioning and pricing decisions.\nWhat We're Looking For…\n5+ years of experience in pricing strategy, commercial analytics, product finance, management consulting, or a related analytical role.\nStrong analytical toolkit: SQL required, financial modeling from scratch, and comfort stress-testing assumptions - you're comfortable querying large-scale usage and cost data directly and presenting findings clearly.\nAn interest in AI and a working familiarity with the LLM provider landscape (e.g., OpenAI, Anthropic, Google); you don't need to be a practitioner, but you should be genuinely curious about how these systems work and how they're priced.\nExperience working cross-functionally with Product, Engineering, or Finance teams, and an ability to navigate ambiguity with structure and clarity.\nStrong written and verbal communication skills; you can synthesize complex information into a clear, decision-ready summary.\nA proactive, self-starter mindset - you're comfortable asking the right questions, defining scope, and driving work forward with limited direction.\nBenefits & Perks\nA choice between medical plans with an option for 100% covered premiums including medical, dental, and vision\nSupplemental Life and Disability Insurance plans\nFertility and adoption benefits\nHeadspace mindfulness app subscription\nGlobal Employee Assistance Program\nRetirement benefits with employer match\nFlexible paid time off\n12 weeks paid parental leave and family care leave\nPretax commuter benefit\nEducation reimbursement\nEmployee donation match to community organizations\n7 Global Employee Resource Groups (ERGs)\nDog-friendly workplace\nFree lunch and snacks\nPrivate rooftop\nHack week twice per year\nUS Cash Compensation Range\nCash Compensation Range: $125,800 - $170,200 USD\nThe base salary for this position will vary based on job-related criteria including relevant skills, experience, and location, among other factors.\nIn 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.\nAbout Squarespace\nSquarespace 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. \nOur Commitment \nToday, 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.\n\nThank 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.\nSquarespace 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.\nIf you plan to use AI in any capacity during your candidate journey, please review our Candidate AI Policy.","description_format":"text","description_chars":6957,"description_truncated":false,"requirements":{"experience_years_min":5,"management_years_min":null,"team_size_min":null,"manages_managers":false,"education":null,"security_clearance":false,"languages":[]},"benefits":["Parental leave"],"hiring_locations":[],"hiring_excludes":[],"relocation_offered":false,"industries":["Domain Registrars & Registries","E-commerce Platforms","Website Builders"],"lifecycle":[{"event":"open","at":"2026-09-22T20:07:42Z"}],"visa":[{"country":"US","licensed_sponsor":true,"evidence":"H-1B filings in 12 months: 20 · green card filings: 6","filings_12m":20,"filings_prev_12m":20,"green_card_filings_12m":6,"median_offered_wage_usd":176731,"route":null,"cap_exempt":false,"checked_at":"2026-10-15T11:24:14+00:00","sources":["US Department of Labor: LCA disclosure data (H-1B, H-1B1, E-3)","US Department of Labor: PERM disclosure data (green cards)"],"filings_for_role_12m":11}],"liveness":{"score":55,"band":"ok","label":"Likely open","p_open":1,"p_active":0.733,"p_room":0.75,"age_days":30,"expected_fill_days":35,"reasons":["conf:0","win:late"],"computed_at":"2026-10-23T05:54:15Z"},"pay":{"stated_usd_annual":170200,"is_top_pay":false},"html_url":"https://alion.io/job/squarespace-senior-lead-ai-pricing-margin-strategy","json_url":"https://alion.io/job/squarespace-senior-lead-ai-pricing-margin-strategy.json","meta":{"generated_at":"2026-10-23T13:14:16Z","cache_seconds":300,"methodology":"https://alion.io/methodology","terms":"https://alion.io/terms","contact":"https://alion.io/contact","api":"https://alion.io/developers","about":"Alion is a live layer of people, companies and AI agents: who they are, whether they are real and active right now, what they do and how to work with them, readable by people and by agents and paid per call.","catalog":"https://alion.io/catalog.json","usage":{"tier":"crawler_verified","counted_by":"address","units_charged":1,"used_today":19710,"day_limit":null,"remaining_today":null,"minute_limit":300,"resets_at":"2026-10-24T00:00:00Z"}},"offers":[{"id":"company.slices","title":"One company in depth, by slice","status":"live","price":{"credits":0.02,"usd":0.002,"plus_per_slice":{"credits":0.05,"usd":0.005}},"unit":"per company, plus each slice with data","note":"the employer in depth","call":{"mcp_tool":"get_company","arguments":{"id":63},"rest":"https://alion.io/mcp/rest/get_company?id=63"},"human":"https://alion.io/catalog?offer=company.slices&for=job%2Fsquarespace-senior-lead-ai-pricing-margin-strategy"},{"id":"market.stats","title":"A market slice: pay, demand and time to fill","status":"live","price":{"credits":1,"usd":0.1},"unit":"per slice","note":"pay, demand and time to fill for this role and place","call":{"mcp_tool":"market_stats"},"human":"https://alion.io/catalog?offer=market.stats&for=job%2Fsquarespace-senior-lead-ai-pricing-margin-strategy"},{"id":"job.search","title":"Open jobs by role, technology, place, pay and visa","status":"live","price":{"credits":0.02,"usd":0.002},"unit":"per posting in a list","note":"similar open postings","call":{"mcp_tool":"search_jobs"},"human":"https://alion.io/catalog?offer=job.search&for=job%2Fsquarespace-senior-lead-ai-pricing-margin-strategy"},{"id":"company.verify","title":"Is this company real and active right now","status":"pilot","price":null,"unit":"per company","request":{"url":"https://alion.io/catalog/request","method":"POST","body":"{\"offer\": \"company.verify\", \"for\": \"job/squarespace-senior-lead-ai-pricing-margin-strategy\", \"note\": \"what you need it for\"}"},"human":"https://alion.io/catalog?offer=company.verify&for=job%2Fsquarespace-senior-lead-ai-pricing-margin-strategy"}]}