Senior GTM Data Analyst
Job Description
About the company: LinkSquares is a Boston-based, AI-powered CLM SaaS leader trusted by organizations like DraftKings, Manscaped, and Vivid Seats. We automate the contracting process for legal, finance, and HR teams, helping them save time, cut costs, and improve business outcomes. For more information, visit linksquares.com.
About the team: Join our Revenue Operations organization, the central engine of our Revenue Team that sits at the intersection of marketing strategy, sales execution, and AI innovation. We are a detail-oriented and financially driven team dedicated to driving long-term value and growth by transforming internal processes into strategic advantages. We prioritize a “learn and get better” mentality, where you will not only execute proven processes but actively help refine them for the next generation of LinkSquares' growth.
About the role: As the Senior GTM Data Analyst, you will shape how we understand and optimize our growth engine by owning the analytical truth layer across the entire revenue organization. In this high-impact role, you will function as an internal revenue economist and independent partner to the VP of Revenue Operations and GTM executives, answering three critical questions: What is happening? Why is it happening? What should we do about it?
You’ll join a collaborative team where you have the autonomy to evolve an existing foundation while building new, scalable data models, KPI architectures, and executive reporting systems that directly influence strategic decisions. Sitting at the intersection of revenue analytics, analytics engineering, business intelligence, and strategic decision support, this is an ideal role for a strategic thinker who enjoys the balance of technical depth, commercial judgment, and hands-on execution.
Responsibilities:
- Serve as an independent analytical partner to GTM leadership, analyzing performance across the full customer lifecycle (pipeline creation, conversion, bookings, retention, expansion, and churn) to surface emerging trends, quantify business impact, and recommend strategic actions.
- KPI Architecture & Dashboards: Own the Revenue organization's KPI architecture, metric definitions, and calculation logic across Sales, CX, Marketing, Product, and Finance. Rationalize reporting, reduce dashboard sprawl, and create trusted, scalable reporting.
- Planning & Scenario Analytics: Develop models that support revenue planning, pipeline coverage, conversion, velocity, push/slip, and productivity analysis. Model upside/downside scenarios and leading indicators of risk to improve organizational predictability.
- Executive & Board Support: Own the analytical development of recurring executive and Board reporting, ensuring outputs are grounded in reconciled metrics, consistent business logic, and clear, decision-ready frameworks.
- Data Modeling & Architecture: Own, build, and optimize durable transformation and semantic models across the modern data stack for core GTM concepts (accounts, pipeline, bookings, ARR, retention, expansion, churn, and customer lifecycle) while ensuring data quality and lineage.
- Analytics Innovation & AI: Leverage AI tools and automation to accelerate analytical workflows, investigation, documentation, quality assurance, and insight generation while establishing responsible AI governance and patterns.
- Cross-Functional Partnership: Collaborate closely with Revenue Operations, Sales, Marketing, Customer Experience, Product, and Finance to challenge assumptions, guide roadmap prioritization, and act as a trusted advisor on major GTM decisions.
Requirements:
- B2B SaaS Experience: 6+ years supporting a B2B SaaS or recurring-revenue business, with deep fluency in SaaS/GTM economics, unit economics, and full customer lifecycle analysis across Marketing, Sales, and Customer Experience.
- Technical & Modeling Depth: Advanced proficiency in SQL, Snowflake, dbt, Fivetran, Looker (or comparable BI tool), Git, semantic-layer design, ETL/ELT concepts, and data quality monitoring, alongside strong familiarity with Salesforce and GTM data structures.
- AI Integration: Demonstrated proficiency using AI tools to accelerate analytical workflows, documentation, automation, and insight generation, with a strong ability to critically evaluate and validate AI-generated outputs against governed data.
- Analytical & Commercial Mindset: Experience building and governing enterprise KPI frameworks, pipeline/forecasting models, and executive/Board reporting with the ability to translate complex technical findings into actionable commercial insights.
- Collaborative Leadership: A track record of working across departments (Operations, Finance, Sales, CX, Product) to align on metric definitions, establish single-source-of-truth frameworks, and drive consensus.
- Adaptability & Rigor: High standard of intellectual independence and curiosity, with the ability to bring clear recommendations—not just data—in a fast-paced, evolving environment.
Compensation for this role includes an annual base salary range between $150,000 to $175,000. The estimated compensation range listed in this job posting reflects base salary only. This role may include additional forms of compensation such as a bonus. LinkSquares takes into consideration a number of factors when determining an employee’s starting salary, including work location, job-related skills, and relevant education, experience and training. The recruiter assigned to this role will share more information about the specific compensation and benefit details associated with this role during the hiring process.
Candidates are eligible to participate in the company’s benefit programs. LinkSquares’ benefits include but are not limited to medical, dental, and vision insurance, 401k retirement plan with a company match, equity awards (a new hire grant, along with opportunities for additional awards throughout your tenure), flexible paid time off, generous parental leave, life and disability insurances and more.
LinkSquares is an Equal Opportunity Employer and does not discriminate based on any legally protected characteristics.
Graphic Designer
Job Description
About the company: LinkSquares is a Boston-based, AI-powered CLM SaaS leader trusted by organizations like DraftKings, Manscaped, and Vivid Seats. We automate the contracting process for legal, finance, and HR teams, helping them save time, cut costs, and improve business outcomes. For more information, visit linksquares.com.
About the team: You’ll join a high-energy Marketing organization that operates at the heart of the business. We are currently building out our award-winning, in-house Creative Team—a group of storytellers, data-enthusiasts, and strategists who believe that our brand and customer experience are our greatest assets. Our team culture is built on transparency, creative problem-solving, and mutual support—we celebrate big wins together and tackle challenges as a unit. You will sit at the strategic intersection of Brand, Content, Demand Generation, and Events, working with teammates who are as committed to your professional growth as they are to elevating our brand visual identity.
About the role: LinkSquares is looking to hire a “swiss-army-knife” Graphic Designer who can take direction and run with it. In this high-impact role, you will be responsible for creating and delivering pixel-perfect design assets for marketing projects across all channels, mediums, and platforms.
You’ll join a collaborative team where you have the autonomy to support both daily design production needs and long-range assignments. This is an ideal role for a creative thinker who enjoys the balance of high-level brainstorming/concepting and hands-on execution across web design, ads, print graphics, pitch decks, social content, event materials, email campaigns, and motion graphics.
Responsibilities:
- Creative Concepting & Strategy: Brainstorm and concept with the creative team to develop innovative ideas, design solutions, and brand identities that elevate LinkSquares across all channels.
- Multi-Channel Execution: Design webpages and produce digital and print marketing assets—including ads, social content, pitch decks, email campaigns, event/conference materials, and motion graphics for video.
- Brand Stewardship: Keep brand design standards at the highest possible level, delivering pixel-perfect, clean, and organized design assets while maintaining the central brand asset library and design system.
- Team Enablement: Create templated assets (e.g., in Canva) to empower internal teams while maintaining brand consistency across all touchpoints.
- Cross-Functional Collaboration: Partner closely with various marketing segments to respond to and provide constructive feedback, taking direction from the Brand Director to refine visual solutions.
- Workflow & Asset Management: Organize, manage, and name files appropriately for team members using project management platforms (ClickUp, Asana, Jira, etc.) to handle incoming creative requests and maintain final production files.
Requirements:
- Professional Design Experience: Bachelor's degree in Graphic Design (or related field) with 3–5 years of professional design experience (or equivalent) in B2B SaaS or fast-paced marketing environments.
- Technical Mastery: Expert user of Adobe Creative Suite, Figma, and Canva, with strong design vision, typography skills, and a commitment to eagle-eye attention to detail.
- Production & Web Knowledge: Strong understanding of modern print and digital design principles, basic UI/UX standards, web responsive design, and delivery of clean, final production files.
- Process & PM Tools: Familiarity with managing creative intake and workflows through project management platforms such as Asana, ClickUp, or Jira.
- Collaborative Mindset: Eager to learn, take direction, incorporate feedback, and operate both independently and as part of a high-energy creative unit.
- Portfolio Requirement: A strong portfolio of work demonstrating end-to-end design capabilities across digital and print mediums is required for consideration.
Compensation for this role includes an annual base salary range between $80,000 to $100,000. The estimated compensation range listed in this job posting reflects base salary only. This role may include additional forms of compensation such as a bonus. LinkSquares takes into consideration a number of factors when determining an employee’s starting salary, including work location, job-related skills, and relevant education, experience and training. The recruiter assigned to this role will share more information about the specific compensation and benefit details associated with this role during the hiring process.
Candidates are eligible to participate in the company’s benefit programs. LinkSquares’ benefits include but are not limited to medical, dental, and vision insurance, 401k retirement plan with a company match, equity awards (a new hire grant, along with opportunities for additional awards throughout your tenure), flexible paid time off, generous parental leave, life and disability insurances and more.
LinkSquares is an Equal Opportunity Employer and does not discriminate based on any legally protected characteristics.
Sr. Director, Demand Gen & Field Marketing
Job Description
About the company: LinkSquares is a Boston-based, AI-powered CLM SaaS leader trusted by organizations like DraftKings, Manscaped, and Vivid Seats. We automate the contracting process for legal, finance, and HR teams, helping them save time, cut costs, and improve business outcomes. For more information, visit linksquares.com.
About the team: You’ll join a high-energy Marketing organization that operates at the heart of the business. We are a group of storytellers, data-enthusiasts, and strategists who believe in driving rapid, efficient growth across our target markets. Our team culture is built on transparency, creative problem-solving, and mutual support—we celebrate big wins together and tackle challenges as a unit. You will sit at the strategic intersection of Product Marketing, Sales, SDR, Marcom, and Revenue Operations, working with teammates who are as committed to your professional growth as they are to hitting our collective pipeline and new bookings goals.
About the role: The Sr. Director, Demand Generation & Field Marketing will be the primary architect of building, filling, and accelerating our new business funnel across target markets, developing and optimizing integrated demand generation programs across organic and paid channels. You’ll join a collaborative team where you have the autonomy to evolve an existing foundation while building a modern, AI-first demand generation engine. A critical part of this role will be leveraging AI, automation, and AI agents to transform how demand generation operates—identifying opportunities to improve audience identification, campaign development, personalization, experimentation, prospect engagement, optimization, and reporting to deliver exceptional business outcomes.
Responsibilities:
- Strategy & Pipeline: Develop and lead the global demand generation strategy aligned to LinkSquares’ GTM priorities, target segments, pipeline goals, and evolving market dynamics. Own overall pipeline goals across Marketing, Sales, and SDR-generated sources in support of new bookings targets.
- Campaign Management: Manage a portfolio of new-logo acquisition campaigns and continually identify new opportunities to build awareness, engagement, and pipeline within our addressable market.
- Integrated Execution: Own the creation and execution of integrated demand generation plans in partnership with Marcom, Product Marketing, Sales, SDR, and Revenue Operations. Lead a team of marketing managers and agency partners across email, direct mail, organic digital, paid search, paid social, events, webinars, ABM, and emerging channels.
- AI & Agentic Operations: Build AI and agentic capabilities into the demand generation operating model, identifying repeatable workflows that can be automated or augmented to increase team productivity, campaign velocity, personalization, and performance.
- Sales & SDR Alignment: Partner with Sales and SDR leadership to develop prospecting and account-engagement programs that uncover new opportunities, improve account penetration, and accelerate deal velocity. Explore opportunities to use AI and agents to improve prospect research, prioritization, personalization, and follow-up.
- Cross-Functional Communication: Communicate marketing program strategy, status, performance, insights, and recommendations across the GTM organization. Participate in Quarterly Business Reviews and executive-level business reviews.
- Operations & Database Strategy: Partner closely with Revenue Operations on ICP and persona segmentation, account prioritization, attribution, funnel measurement, and database strategy.
- Funnel Optimization: Monitor demand funnel performance, conversion rates, pipeline contribution, CAC, and channel efficiency, using both traditional analytics and AI-powered analysis to identify trends, opportunities, and recommended actions.
Requirements:
- B2B SaaS Experience: 7–10+ years of experience developing and leading demand generation strategies within B2B SaaS companies, preferably supporting high-volume and high-velocity sales motions.
- Multi-Channel Expertise: Demonstrated experience owning the strategy, framework, development, and execution of global, multi-channel demand generation programs targeting mid-market companies and delivering measurable pipeline.
- GTM & Funnel Fluency: Strong understanding of B2B SaaS GTM strategy, ICP development, personas, buying journeys, use cases, pipeline generation, and funnel conversion.
- Channel Mastery: Strong experience with AEO, SEO, SEM, paid social, LinkedIn, review sites, intent data, and ABM platforms such as 6sense.
- AI-First Mindset: Demonstrated experience using generative AI, AI agents, automation, or AI-powered marketing platforms for audience research, campaign ideation, content creation, personalization, prospect intelligence, experimentation, campaign optimization, and performance analysis.
- Tech Stack Proficiency: Competent user of marketing automation platforms such as HubSpot, CRM platforms such as Salesforce, Excel, Google Workspace, and marketing analytics/reporting tools.
- Communication & Drive: Outstanding written, verbal communication, and executive presentation skills. Metrics-focused, highly accountable, results-oriented, high energy, intellectually curious, and comfortable challenging traditional approaches.
Compensation for this role includes an annual base salary between $180,000 to $220,000. The estimated compensation range listed in this job posting reflects base salary only. This role may include additional forms of compensation such as a bonus. LinkSquares takes into consideration a number of factors when determining an employee’s starting salary, including work location, job-related skills, and relevant education, experience and training. The recruiter assigned to this role will share more information about the specific compensation and benefit details associated with this role during the hiring process.
Candidates are eligible to participate in the company’s benefit programs. LinkSquares’ benefits include but are not limited to medical, dental, and vision insurance, 401k retirement plan with a company match, equity awards (a new hire grant, along with opportunities for additional awards throughout your tenure), flexible paid time off, generous parental leave, life and disability insurances and more.
LinkSquares is an Equal Opportunity Employer and does not discriminate based on any legally protected characteristics.
Accounting Associate
Job Description
About the company:
LinkSquares is a Boston-based, AI-powered CLM SaaS leader trusted by organizations like DraftKings, Manscaped, and Vivid Seats. We automate the contracting process for legal, finance, and HR teams, helping them save time, cut costs, and improve business outcomes. For more information, visit linksquares.com.
About the team:
Our Accounting & Finance organization is a detail-oriented, commercially driven group that turns transactional data into actionable business insight. We sit at the heart of LinkSquares’ financial integrity, partnering closely with Revenue Operations, Sales, and senior leadership. We value a culture of continuous improvement, where we tackle compliance and optimize systems to build a scalable foundation for a rapidly growing AI-powered company.
About the Role
LinkSquares is seeking an enthusiastic, organized, and detail-driven Accounting Associate with a strong background in Accounts Receivable to join our Finance team. In this role, you will take ownership of the full invoice-to-cash cycle while supporting generalist accounting operations, month-end close activities, and audit processes. You will serve as the primary contact for our customers on all billing matters while gaining broad exposure to GAAP principles and operational accounting in a high-growth environment. This is a role for someone who wants to grow and build on their existing knowledge base.
Responsibilities
- Lead the end-to-end invoice-to-cash workflow—generating and reviewing customer invoices, applying payments (ACH, Wire, Credit Card, Checks), and maintaining accurate data in NetSuite.
- Monitor outstanding balances, drive the dunning process, and partner with Sales, Legal, and Finance leadership to resolve complex invoice disputes with a high degree of professionalism.
- Serve as the primary point of contact for customer billing inquiries, resolving payment portal issues and providing balance summaries to ensure a seamless client experience.
- Own AR-related journal entries, prepare balance sheet reconciliations, and assist with general P&L accounting tasks to support a timely and accurate month-end close.
- Assist with annual financial audits by preparing schedules, maintaining documentation consistent with US GAAP, and working directly with external auditors.
- Assist in broader operational finance functions, including AP support, process documentation and systems integration checks (e.g., NetSuite, Bill.com).
Requirements
- 1+ years of proven accounting experience, with direct background in accounts receivable, billing, or collections (B2B SaaS experience is a plus).
- Bachelor’s degree (BSc/BA) in Accounting, Finance, or a related field.
- Solid understanding of US GAAP principles, financial reporting, and month-end close processes.
- Strong proficiency in Microsoft Excel and general comfort with financial software. Experience with NetSuite, Carta, or Bill.com is highly preferred.
- Exceptional written and verbal communication skills with a natural eye for detail, accuracy, and strong organizing abilities.
- Interest in leveraging automation, AI, and modern software tools to optimize manual processes and scale workflow.
Compensation for this role includes an annual base salary between $60,000 to $80,000. The estimated compensation range listed in this job posting reflects base salary only. This role may include additional forms of compensation such as a bonus. LinkSquares takes into consideration a number of factors when determining an employee’s starting salary, including work location, job-related skills, and relevant education, experience and training. The recruiter assigned to this role will share more information about the specific compensation and benefit details associated with this role during the hiring process.
Candidates are eligible to participate in the company’s benefit programs. LinkSquares’ benefits include but are not limited to medical, dental, and vision insurance, 401k retirement plan with a company match, equity awards (a new hire grant, along with opportunities for additional awards throughout your tenure), flexible paid time off, generous parental leave, life and disability insurances and more.
LinkSquares is an Equal Opportunity Employer and does not discriminate based on any legally protected characteristics.
Sales Development Representative (SDR)
Job Description
LinkSquares is the leading contract lifecycle management company in the legal industry, named a Strong Performer in The Forrester Wave™: Contract Lifecycle Management (CLM).
Businesses run on contracts—they drive revenue, manage obligations, enable financing, and support reporting activities. Our AI-powered CLM SaaS product suite delivers end-to-end solutions trusted by some of the world’s most respected organizations, including DraftKings, Wayfair, TIME, and the Boston Celtics. We are proud to support our customers in achieving their goals, and remain dedicated to delivering value and innovation to meet their needs.
We ranked #174 on Deloitte’s Fastest-Growing Companies in North America, named “Contract Management Solution Provider Of The Year” by LegalTech Breakthrough Awards, and has been named to the Inc. 5000 list for the fifth consecutive year, ranking among the fastest-growing private companies in America!
At LinkSquares, our AI-powered, end-to-end contract management and analytics platform takes the manual, time-consuming, tedious tasks out of the contracting process. With LinkSquares, legal, finance, HR, and procurement teams save time, cut costs, and improve business outcomes. We are a 200+ person company headquartered in downtown Boston.
Sales Development Representative (SDR) will be a critical member of our Revenue Team. Successful SDRs will identify & generate new business opportunities by following proven processes and by developing their own prospecting best practices through hands-on experience. You’ll learn how to identify, research & target lists companies to target, and how to develop 360 degree campaigns to generate new business opportunities. You’ll also learn what works best and continuously improve the SDR process for future team members.
Responsibilities:
- Strategize with teammates to identify and target key prospects
- Learn and execute proven processes to generate new sales opportunities
- Grow, manage and maintain top of the funnel pipeline
- Orchestrate discussions with senior execs around their business needs
- Research, profile & map key accounts to support “wider & deeper”, mid funnel sales
Additional Qualifications:
- Desire to learn and succeed in enterprise-level SaaS sales
- Preferably 1 year experience in sales development role in a SaaS environment
- Strong written and verbal skills with an ability to convey complex ideas simply
- Ability to work in a fast-paced, open floor and competitive environment
- Prior successful cold calling or SDR experience in a quota achieving role preferred
- Boston based / hybrid (expectations of 3 days per week in offices)
- Salesforce.com proficiency preferred
Previous sales experience in technology is helpful but it isn’t a requirement.
About LinkSquares
Founded in 2015 with headquarters in Boston, we offer a comprehensive and competitive benefits package that includes medical, dental and vision plans for employees and their families, health and wellness programs, a 401(k) plan, unlimited vacation, paid parental leave and more. Learn more here: https://linksquares.com/careers/
For legal teams needing to move their business forward faster, LinkSquares provides a contracting platform for writing better contracts, analyzing what’s in existing contracts, and working better with their team. It differs from other tools on the market with its powerful AI insights, speed to providing tangible results, and ability to help the entire company collaborate better. LinkSquares saves companies hundreds of hours and thousands of dollars by eliminating manual contract processes and reducing the need for outside counsel. For more information, visit https://linksquares.com/.
LinkSquares is an Equal Opportunity Employer and does not discriminate on the basis of an individual's sex, age, race, color, creed, national origin, alienage, religion, marital status, pregnancy, sexual orientation or affectional preference, gender identity and expression, disability, genetic trait or predisposition, carrier status, citizenship, veteran or military status and other personal characteristics protected by law. All applications will receive consideration for employment without regard to legally protected characteristics.
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