Jobs › Nexstar Media

Director, Legal Sales Strategy

Nexstar Media · Chicago, IL · Full time

Posted May 29, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a sales playbook you built. How did you get sellers to actually use it?

What they are checking: Whether they can enable sales teams and drive adoption across many markets.

Tell me about a time you grew revenue in a category or vertical. What did you change?

What they are checking: Whether they have a track record of driving revenue at a strategic level.

What would you do

A law firm says TV is too expensive and they only want digital. How do you respond?

What they are checking: Whether they can make a fair, data-driven case for the right mix rather than just pushing one product.

Local sellers in different markets approach legal clients in different ways. How would you create consistency without losing local knowledge?

What they are checking: Whether they can lead nationally while respecting local relationships.

A major legal client's results drop mid-campaign. What do you do?

What they are checking: Whether they can diagnose performance and protect the relationship.

About the work

How do the marketing needs of a personal injury firm differ from a family law practice, and how would you sell to each?

What they are checking: Whether they understand the legal vertical well enough to own category strategy.

Walk me through how you'd build an integrated campaign for a mass tort firm using linear, OTT/CTV, search and first-party data.

What they are checking: Whether they can design solution selling across Nexstar's full suite.

How would you measure ROI for a law firm in terms they care about, like case volume and cost per signed case?

What they are checking: Whether they connect media spend to the client's real business outcomes.

What advertising rules and ethics concerns apply to legal advertising, and how do they affect your recommendations?

What they are checking: Whether they know attorney advertising rules vary by state and plan around them.

What trends in legal marketing do you think will matter most over the next couple of years?

What they are checking: Whether they think ahead as the national subject matter expert.

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The full job description

As published by Nexstar Media.

Position Overview Nexstar Media Group, the nation’s largest local broadcasting company and a leading digital media organization, is seeking a strategic, results-driven Director, Legal Sales Strategy to lead growth initiatives within the Legal & Professional Services vertical . This role is responsible for driving revenue by positioning Nexstar’s full suite of advertising, marketing, and data-driven solutions—across digital, linear, and advanced AdTech platforms—to law firms and legal service providers nationwide. This leader will define and execute a best-in-class go-to-market strategy, enable and elevate sales teams, and deliver high-impact solutions aligned to the unique client acquisition challenges of the legal industry. Key Responsibilities • Category Ownership: Serve as the national subject matter expert for the Legal vertical, owning category strategy, sales execution, and revenue performance across key legal segments (e.g., personal injury, mass tort, family law, and local practice areas). • Solution Selling: Position Nexstar’s integrated suite of AdTech and marketing solutions—including programmatic, OTT/CTV, search, social, and first-party data activation—to drive client acquisition, case volume, and ROI for law firms. • Sales Enablement: Develop and deploy vertical-specific playbooks, messaging frameworks, and sales tools tailored to legal marketing use cases (e.g., lead generation, call conversion, brand authority, geographic targeting). • Coaching & Development: Provide ongoing coaching, joint client engagement, and pipeline oversight to improve seller effectiveness, accelerate deal cycles, and increase close rates within the legal category. • Positioning & Messaging: Craft compelling, insight-driven narratives aligned with legal advertiser priorities, including cost per case, qualified lead generation, intake efficiency, and competitive conquesting . • Revenue Growth: Drive measurable revenue expansion within the Legal vertical through both direct account engagement and scalable enablement of local and regional sales teams. • Partnership Management: Collaborate with internal product teams, data providers, and external partners to enhance Nexstar’s legal-specific offerings, including attribution solutions, call tracking, and lead verification tools. • Market Intelligence: Stay ahead of key industry dynamics, including legal advertising regulations, competitive spend trends, consumer search behavior, and emerging client acquisition channels. Required Qualifications • 7+ years of experience in digital media, AdTech, or SaaS sales, with at least 3 years focused on the legal or professional services vertical . • Deep understanding of law firm marketing strategies , including lead generation, intake optimization, and compliant advertising practices. • Proven track record of sales leadership in a matrixed, multi-market environment. • Demonstrated success in sales enablement, go-to-market strategy, and team coaching . • Strong analytical skills with the ability to translate campaign data into actionable insights and performance improvements. • Excellent communication, presentation, and client-facing skills, with experience engaging senior stakeholders. • Willingness to travel up to 50-75% to support key markets and client relationships. Preferred Qualifications • Experience selling into personal injury, mass tort, or high-volume consumer legal categories . • Familiarity with legal marketing tools and platforms (e.g., call tracking, case management integrations, lead attribution systems). • Understanding of legal advertising compliance and regulatory considerations (e.g., state bar guidelines). • Proficiency with Salesforce or similar CRM systems. Salary Range - $200-250K

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