Senior Sales Executive - Legal Services

Posted Yesterday
Be an Early Applicant
60602, Chicago, IL, USA
In-Office
150K-250K Annually
Senior level
Legal Tech • Professional Services
The Role
Drive new revenue and expand enterprise law firm and corporate legal accounts through full-cycle consultative selling. Manage pipeline, forecast in Salesforce/NetSuite, lead strategic reviews, attend client events, and meet quota and retention goals.
Summary Generated by Built In
Close Deals. Grow Enterprise Accounts. Own Your Sales Territory.

If you’re a consultative seller who thrives on building long-term relationships, expanding enterprise accounts, and driving measurable revenue growth—this is your seat at the table. Base Pay + Uncapped Commission (On-Target Earnings (OTE): $150,000–$250,000, with uncapped earning potential for top performers).

Why Choose Esquire?

Esquire is a leader in legal support services, known for innovation, professionalism, and delivering exceptional quality. As part of our team, you’ll receive comprehensive training, competitive benefits, and the opportunity to grow within a people-first culture. At Esquire, we are focused on Getting it Right for our clients, our partners, and our employees. We understand that the client experience begins with us, and we’re committed to empowering our teams to continually innovate and earn clients for life.

About the Role

You’ll partner with top law firms and corporate legal teams. You are a high-performing Senior Sales Executive driving new revenue, expanding strategic accounts, and strengthening our footprint in key markets.

This is a true revenue-generating role with autonomy, executive-level client exposure, and meaningful earning potential.

Key Responsibilities
  • Drive revenue growth across assigned law firms and zero-based firms (ZBFs)
  • Prospect, penetrate, and expand key accounts
  • Run full-cycle sales from outreach to discovery, proposal, close, and renewal
  • Lead consultative conversations that uncover client challenges and align tailored deposition solutions
  • Forecast accurately and manage pipeline using Salesforce and NetSuite
  • Lead QBRs and strategic business reviews for enterprise accounts
  • Develop recovery plans for underperforming accounts
  • Represent Esquire at industry events and networking engagements
What You’ll Need
  • Skills: Strong communication, presentation, and consultative selling skills; team-oriented with a client-first mindset
  • Experience: 5+ years of B2B or professional services sales experience; legal industry experience preferred
  • Technical: Proficiency in Salesforce, NetSuite, Microsoft Office; comfortable with digital research tools
  • Education: Associate’s degree in Business Administration or equivalent preferred
  • Attributes: High-energy, self-directed, organized, adaptable, and results-focused
What Success Looks Like
  • Consistent attainment of sales quotas and KPIs
  • Expanded market share and client base in assigned territories
  • Effective growth and retention of enterprise-level accounts
  • Active contributions to team goals and collaborative wins
We offer a comprehensive benefits package including
  • Insurance: Medical, dental, vision, short- and long-term disability insurance, basic life insurance, and supplemental insurance for employees and their dependents
  • Retirement: Eligibility to enroll in the company’s 401(k) plan with match contribution
  • Paid Time Off: Employees receive two weeks of vacation leave per year, or 80 hours annually
  • Holidays: 10 paid holidays per year and 2 paid floating holidays per year
  • Sick Leave: 5 paid sick days per year
  • Tuition Reimbursement: Financial assistance to support your career development
Work Environment

This is a remote-based role with virtual collaboration across internal teams, travel to client sites, and attendance at client-facing events. You’ll thrive in a culture that values teamwork, growth, and winning with integrity.

💬 Don’t meet every single requirement?

We’re committed to building a diverse and inclusive workplace. If you’re excited about this role but your experience doesn’t align perfectly, we still encourage you to apply—you may be just the right person for this or other opportunities.

Equal Opportunity & Accommodations:

Esquire Deposition Solutions policy is to provide equal employment opportunities to all applicants and employees without regard to race, color, religion, creed, gender, gender identity or expression, age, national origin or ancestry, citizenship, disability, sexual orientation, marital status, pregnancy, veteran status, membership in the uniformed services, genetic information, or any other basis protected by applicable law.

Esquire Deposition Solutions is committed to fair hiring practices. Qualified applicants with criminal histories will be considered for employment in a manner consistent with applicable laws, including but not limited to the California Fair Chance Act, the Los Angeles Fair Chance Initiative for Hiring Ordinance, and the Los Angeles County Fair Chance Ordinance. We also comply with similar laws in other jurisdictions where we operate.

If you are a qualified individual with a disability or a disabled veteran and require support throughout the application and/or recruitment process as a result of your disability, you have the right to request reasonable accommodation. You can submit your request to [email protected].

Skills Required

  • 5+ years of B2B or professional services sales experience
  • Legal industry sales experience
  • Proficiency in Salesforce
  • Proficiency in NetSuite
  • Proficiency in Microsoft Office
  • Comfortable using digital research tools
  • Strong communication, presentation, and consultative selling skills
  • Team-oriented with a client-first mindset and results-focused attitude
  • Associate's degree in Business Administration or equivalent
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The Company
876 Employees

What We Do

Esquire Deposition Solutions is a national provider of remote and in-person deposition management solutions, court reporting services, and technology. They offer comprehensive litigation support, including court reporting, video, and interpreting, for law firms, insurance carriers, and corporate legal departments. Operating 49 offices nationwide, they support over 300,000 depositions annually using state-of-the-art technology to ensure seamless and secure legal proceedings.

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