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Our client is a family-owned leader in court reporting and litigation technology, trusted by law firms, corporations, and government agencies to support high-stakes matters across the U.S. and internationally. Since opening its doors more than a decade ago, the company has posted record growth by pairing skilled court reporters with technology that helps legal teams work faster and smarter, including digital reporting, secure virtual depositions, and AI-powered tools. Free of private equity ownership, the company is known for a close-knit culture, strong employee tenure, and the urgency and personal attention clients rely on around the clock. As it continues to expand its presence in key markets, the company is seeking an Account Executive in Chicago to help grow one of its most important metros.

Position Overview

This is a rare opportunity to build a long-term client portfolio in one of the company’s highest priority markets, backed by an established reputation and close support from sales leadership. First, the clients you win stay with you, so the relationships you build in year one carry forward and keep growing in the years that follow. Second, Chicago is a market where the company sees significant untapped opportunity, giving you room to grow and a highly visible role in expanding its local presence. Third, you will bring a technology-forward offering to law firms, including digital court reporting and AI-powered litigation tools, with short sales cycles and repeat work that reward consistent effort. For a relationship-driven seller with legal industry experience, this role offers the chance to build a lasting business within a stable company focused on long-term growth.

Position Responsibilities

  • Win new law firm clients across the Chicago market, targeting firms of every size that handle litigation, with roughly half of new revenue expected to come from new client relationships.
  • Turn opposing counsel on active matters into new clients, using every case the company supports as an introduction to another firm.
  • Expand existing accounts by building relationships with additional attorneys, practice groups, and offices, increasing the company’s share of work within each firm.
  • Retain and strengthen client relationships through consultative selling and fast, reliable follow-through, which keeps clients coming back for repeat work.
  • Educate attorneys and litigation teams on digital court reporting and the company’s technology platform, including AI-powered tools, showing how these solutions improve coverage, efficiency, and flexibility.
  • Spend at least three days per week in the field, keeping a weekly rhythm of roughly 15 in-person client visits and 75 proactive outreach touches by phone and email to maintain a healthy pipeline.
  • Plan each day with structure and discipline, prioritizing the opportunities with the highest potential return.
  • Keep Salesforce accurate and current by logging all calls, emails, and meetings within 24 hours, giving you and sales leadership clear visibility into pipeline and client activity.
  • Partner closely with scheduling, client services, pricing, marketing, and sales support teams to deliver a smooth experience on every matter.

Position Qualifications

Required:

  • A proven track record of meeting or exceeding sales targets, supported by specific results such as quota attainment, team ranking, and new client wins.
  • A minimum of 3 years of quota-carrying B2B sales experience, including selling products or services to law firms or other legal industry buyers.
  • Demonstrated ability to build pipeline from scratch through a consistent, structured prospecting approach.
  • Strong CRM habits and comfort managing pipeline and activity in Salesforce or a similar platform.
  • Based in the Chicago area and able to meet with clients in person at least three days per week.

Preferred:

  • Background in court reporting, eDiscovery, legal research, or legal technology sales, with existing relationships among Chicago law firms.
  • A relationship-first approach and a reputation for exceptional responsiveness, with a history of building client relationships that last for years.
  • Motivated to build a long-term career and grow a client portfolio over many years with a company committed to growth.

If you’re ready to build something lasting in one of the country’s busiest legal markets, apply now and a member of Talentfoot’s recruitment team will be in touch should your track record of success, experience, skills and qualifications match our client’s requirements.

Talentfoot Overview

Talentfoot Executive Search specializes in future proofing organizations by securing forward-thinking leaders across sales, marketing, eCommerce, product, data, operations, finance, and technology with a track record of accelerating growth, innovation, and profitability. Since 2010, we’ve partnered with more than 2,500 companies and lead the industry with a 98% client success rate. Learn more at Talentfoot.com

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