Sr. Director, Demand Gen & Field Marketing

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 support…