Senior Director - Demand Gen & Field Marketing
About the job
- Seven to ten or more years of experience developing and leading demand generation strategies within business-to-business software-as-a-service companies, preferably supporting high-volume and high-velocity sales motions.
- Demonstrated experience owning the strategy, framework, development, and execution of global, multi-channel demand generation programs targeting mid-market companies and delivering measurable pipeline.
- Strong understanding of business-to-business software-as-a-service go-to-market strategy, ideal customer profile development, personas, buying journeys, use cases, pipeline generation, and funnel conversion.
- Strong experience with answer engine optimization, search engine optimization, search engine marketing, paid social, LinkedIn, review sites, intent data, and account-based marketing platforms such as 6sense.
- Demonstrated experience using generative artificial intelligence, artificial intelligence agents, automation, or artificial-intelligence-powered marketing platforms for audience research, campaign ideation, content creation, personalization, prospect intelligence, experimentation, campaign optimization, and performance analysis.
- Competence with marketing automation platforms such as HubSpot, customer relationship management platforms such as Salesforce, Excel, Google Workspace, and marketing analytics and reporting tools.
- Outstanding written and verbal communication and executive presentation skills; a metrics-focused, accountable, results-oriented approach; intellectual curiosity; and comfort challenging traditional approaches.
- Develop and lead the global demand generation strategy aligned to go-to-market priorities, target segments, pipeline goals, and evolving market dynamics.
- Own overall pipeline goals across Marketing, Sales, and sales development representative-generated sources in support of new bookings targets.
- Manage a portfolio of new-logo acquisition campaigns and continually identify opportunities to build awareness, engagement, and pipeline within the addressable market.
- Own the creation and execution of integrated demand generation plans in partnership with Marketing Communications, Product Marketing, Sales, sales development, and Revenue Operations.
- Lead a team of marketing managers and agency partners across email, direct mail, organic digital, paid search, paid social, events, webinars, account-based marketing, and emerging channels.
- Build artificial-intelligence and agentic capabilities into the demand generation operating model by identifying repeatable workflows that can be automated or augmented to increase team productivity, campaign velocity, personalization, and performance.
- Partner with Sales and sales development leadership to develop prospecting and account-engagement programs that uncover new opportunities, improve account penetration, and accelerate deal velocity.
- Explore opportunities to use artificial intelligence and agents to improve prospect research, prioritization, personalization, and follow-up.
- Communicate marketing program strategy, status, performance, insights, and recommendations across the go-to-market organization.
- Participate in quarterly business reviews and executive-level business reviews.
- Partner with Revenue Operations on ideal customer profile and persona segmentation, account prioritization, attribution, funnel measurement, and database strategy.
- Monitor demand funnel performance, conversion rates, pipeline contribution, customer acquisition cost, and channel efficiency using traditional analytics and artificial-intelligence-powered analysis to identify trends, opportunities, and recommended actions.
- Experience developing and leading demand generation strategies within business-to-business software-as-a-service companies supporting high-volume and high-velocity sales motions.
About the company
LinkSquares offers a cloud-based contract lifecycle management platform for in-house legal teams. It helps draft, review, and approve contracts in one system using customizable templates and dynamic workflows. The platform also includes legal project management to track tasks and ownership, accessible to both legal and non-legal users. Its goal is to standardize contract operations, shorten cycle times, and scale with a subscription model.
Company Size
201-500
Company Stage
Series C
Total Funding
$161.5M
Headquarters
Boston, Massachusetts
Founded
2015
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Simplify's Take
What believers are saying
- August 2026 Inc. 5000 recognition for sixth straight year reinforces growth momentum.
- June and August 2026 G2 leader badges show strong customer satisfaction and retention.
- September 2026 Workflow Builder Agent lowers setup friction and widens business-user adoption.
What critics are saying
- Ironclad's March 2026 agents and Deloitte alliance attack LinkSquares' core CLM budget.
- Bill Hewitt became interim CEO on March 10, 2026, signaling leadership instability.
- If agentic promises disappoint, customers can shift contract operations to Ironclad or Icertis.
What makes LinkSquares unique
- May 2026 all-agentic CLM rebuilt LinkAI to draft, redline, and execute contracts.
- June 2026 GA added Legal Front Door, citation-backed research, and governance controls.
- 1,200-plus customers and repeated G2 leadership signal sticky mid-market workflows.
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Benefits
Stock options
Medical and dental plans with flex spending and dependent care
Matching 401k plan
Unlimited vacation
Health & wellness programs
Paid parental leave
Growth & Insights and Company News
6 month growth
0%1 year growth
1%2 year growth
0%LinkSquares has introduced Workflow Builder Agent and Workflow Blueprints to its contract lifecycle management platform. The new capabilities allow legal and business teams to create contract workflows using plain language rather than technical configuration. Workflow Builder Agent translates business requirements described in plain English into operational workflows with appropriate steps, sequencing, and routing. Teams can modify workflows through continued conversation as policies evolve. Workflow Blueprints provide pre-built templates for common pre- and post-signature processes across buy-side and sell-side contracting. Users can customize these foundations to match their organisation's specific policies and approval requirements. The platform maintains human oversight, allowing teams to review and refine configurations before publishing. LinkSquares serves more than 1,200 customers including DraftKings, ProPharma, and TIME.
LinkSquares names Lyle McCutcheon-Schour SVP of Revenue to drive Agentic CLM growth. Veteran LinkSquares leader brings a decade of industry experience and revenue growth track record to new role. LinkSquares, the leading Agentic contract lifecycle management (CLM) platform, proudly announces the appointment of Lyle McCutcheon-Schour as Senior Vice President of Revenue. McCutcheon-Schour has spent over a decade at LinkSquares in various customer-facing roles. Most recently, McCutcheon-Schour served as Vice President of Account Management for LinkSquares, where he led significant revenue growth. "Lyle was here at the beginning of LinkSquares and bleeds orange," says Bill Hewitt, CEO of LinkSquares. "Starting as a Business Development Representative ten years ago and rising through the ranks, he brings passion, knowledge, and desire to the job. His leadership will continue to fuel our success as the only fully-Agentic CLM solution available today." LinkSquares' new agentic platform is the first of its kind. Designed to act on contracts by handling repetitive tasks automatically, the LinkSquares platform keeps legal teams in full control of review and strategic decision-making. Agents draft, redline, research and generate communications in minutes, while contract data automatically triggers workflows, tracks obligations and connects insight to execution in a single flow. Non-legal teams can use the platform within legal guardrails, accelerating deal cycles without introducing risk. And with citation-backed research, structured data and built-in governance, organizations can trust every output. "I am thrilled to be stepping into this new role at LinkSquares at such an exciting time in our history," said McCutcheon-Schour. "As employee #1, I've seen how our platform has delivered significant value for our customers, their businesses, and the market. I'm excited to be at the forefront of driving this next phase of strategic growth with such a dedicated and talented team." LinkSquares has recently been named to the Inc. 5000 list of fastest-growing private companies in America for the sixth straight year. This recognition highlights the company's commitment to growth and delivering value to customers.
LinkSquares ranks on the 2026 Inc. 5000 List of America's fastest-growing private companies for 6th straight year. This recognition solidifies LinkSquares' position as a leading performer in one of the economy's most rapidly evolving sectors LinkSquares has been ranked No.2532 on the 2026 Inc. 5000 list, the annual list of the fastest-growing private companies in America. As the leading AI-powered contract lifecycle management platform, LinkSquares earns its place on the Inc. 5000 for the 6th consecutive year. The list is the most prestigious ranking of the nation's most successful independent and entrepreneurial businesses, recognizing companies that have achieved remarkable growth while driving innovation, creating jobs, and shaping the future of the economy. Past honorees include companies such as Microsoft, Meta, Chobani, Oracle, and Patagonia. "Being recognized on the Inc. 5000 for the sixth straight year reflects more than our growth - it reflects the transformation happening across the legal technology market," said Bill Hewitt, CEO of LinkSquares. "Organizations are moving beyond systems that simply manage contracts to AI that actively executes work to deliver business outcomes. At LinkSquares, we're proud to be leading that shift with our all-agentic AI platform. We're grateful to our customers, partners, and employees for making this milestone possible, and we're just getting started." This year's Inc. 5000 recognizes a new class of companies redefining what growth looks like. From AI and advanced manufacturing to healthcare, consumer products, and professional services, these businesses are expanding their impact, creating jobs and proving that entrepreneurial ambition continues to fuel the U.S. economy. Among the 5,000 companies on the list, the median three-year revenue growth rate was 130%, and those companies have collectively added more than 627,208 jobs to the U.S. economy over the past three years. "Every company on the Inc. 5000 has a story of perseverance, smart decision making, and a refusal to sit still," says Mike Hofman, editor-in-chief of Inc. "Their growth reflects more than strong financial performance-it reflects creativity, resilience, and the customer focus required to build companies that make a lasting impact. We congratulate all honorees on this significant achievement." For the full Inc. 5000 list, honoree company profiles, and a searchable database by industry and location, please visit: www.inc.com/inc5000. Inc. 5000 List Methodology Companies on the 2026 Inc. 5000 are ranked according to percentage revenue growth from 2022 to 2025. To qualify, companies must have been founded and generating revenue by March 31, 2022. They must be U.S.-based, privately held, for-profit, and independent - not subsidiaries or divisions of other companies - as of December 31, 2025. (Since then, some on the list may have gone public or been acquired.) The minimum revenue required for 2022 is $100,000; the minimum for 2025 is $2 million. As always, Inc. reserves the right to decline applicants for subjective reasons. About Inc. Inc. is the leading media brand and playbook for the entrepreneurs and business leaders shaping its future. Through its journalism, Inc. aims to inform, educate, and elevate the profile of its community: the risk-takers, the innovators, and the ultra-driven go-getters who are creating the future of business. Inc. is published by Mansueto Ventures LLC, along with fellow leading business publication Fast Company. For more information, visit www.inc.com. Justin McGetrick is a Sr. Marketing Campaign Associate at LinkSquares.
LinkSquares advances Contract Intelligence with rebuilt Smart OCR engine. Jul 21, 2026, 11:24 ET Improved document understanding helps organizations turn agreements into reliable business intelligence that supports stronger decisions, relationships, and outcomes BOSTON, July 21, 2026 /PRNewswire/ - LinkSquares, the leading AI-powered contract lifecycle management platform, today announced a rebuilt Smart Optical Character Recognition (OCR) engine designed to strengthen the foundation of Contract Intelligence. Every agreement represents an active business relationship, but organizations can only act on it when the contract is transformed into reliable data. As companies invest more heavily in AI, the quality of the outcome depends on how accurately that technology can read, interpret, and understand the agreements behind the business. LinkSquares rebuilt Smart OCR to produce cleaner, more structured contract text for AI, search, and data extraction. By preserving more of the context, hierarchy, and relationships within complex documents, the new engine helps organizations turn contract data into actionable intelligence, manage commitments, make better decisions, and keep business moving. "Contracts are more than documents. They are the foundation of relationships between businesses," said Andrew Leverone, Chief Product Officer at LinkSquares. "Rebuilding Smart OCR strengthens that foundation enabling more accurate search, more reliable data extraction and more meaningful contract intelligence." The rebuilt Smart OCR engine improves the quality of the contract data that powers LinkSquares' Contract Intelligence. With a clearer understanding of each agreement, organizations can better manage current commitments and relationships, then apply those insights to improve future decisions, workflows, and contract terms. The rebuilt Smart OCR engine is now available as part of the LinkSquares platform. To learn more about LinkSquares Contract Intelligence and its all-agentic AI platform, visit the LinkSquares' website. About LinkSquares LinkSquares is the leading AI-powered contract lifecycle management platform, trusted by more than 1,200 customers, including DraftKings, ProPharma, and TIME. Built on more than a decade of experience partnering with general counsel and legal operations leaders, LinkSquares' all-agentic AI platform sets a new standard for how AI operates across the contract lifecycle. LinkSquares revolutionizes contract management by transforming them from static documents into dynamic, AI-driven business assets - delivering deeper insights and analytics, minimizing organizational risk, unlocking greater efficiency and reliability, and driving more strategic value for teams across the business. SOURCE LinkSquares, Inc.
LinkSquares advances Contract Intelligence with rebuilt Smart OCR engine. Improved document understanding helps organizations turn agreements into reliable business intelligence that supports stronger decisions, relationships, and outcomes LinkSquares, the leading AI-powered contract lifecycle management platform, today announced a rebuilt Smart Optical Character Recognition (OCR) engine designed to strengthen the foundation of Contract Intelligence. Every agreement represents an active business relationship, but organizations can only act on it when the contract is transformed into reliable data. As companies invest more heavily in AI, the quality of the outcome depends on how accurately that technology can read, interpret, and understand the agreements behind the business. LinkSquares rebuilt Smart OCR to produce cleaner, more structured contract text for AI, search, and data extraction. By preserving more of the context, hierarchy, and relationships within complex documents, the new engine helps organizations turn contract data into actionable intelligence, manage commitments, make better decisions, and keep business moving. "Contracts are more than documents. They are the foundation of relationships between businesses," said Andrew Leverone, Chief Product Officer at LinkSquares. "Rebuilding Smart OCR strengthens that foundation enabling more accurate search, more reliable data extraction and more meaningful contract intelligence." The rebuilt Smart OCR engine improves the quality of the contract data that powers LinkSquares' Contract Intelligence. With a clearer understanding of each agreement, organizations can better manage current commitments and relationships, then apply those insights to improve future decisions, workflows, and contract terms. The rebuilt Smart OCR engine is now available as part of the LinkSquares platform. To learn more about LinkSquares Contract Intelligence and its all-agentic AI platform, visit the LinkSquares' website.