Senior Sales Executive - Legal Services

This Is a True Hunter Role.

We want to be upfront so you can decide if this is the right fit: this position does not come with an existing book of business. You'll build your territory from the ground up by prospecting, opening doors, and winning new clients. If you love the thrill of landing new logos and want your earnings to reflect the accounts you personally bring in, you'll feel right at home here. Ideally, we are looking for people who live in the Washington D.C and New York City markets.

Win New Business. Grow Client Relationships. Support Cases from Deposition to Verdict.

If you’re a consultative seller who builds lasting relationships with litigators, opens new doors, and grows accounts as cases grow — this is your seat at the table. Base Pay + Uncapped Commission (On-Target Earnings (OTE): $120,000–$220,000, with uncapped earning potential for top performers).

Why Choose DEG? (A Subsidiary Brand of Esquire Deposition Solutions)

Digital Evidence Group (DEG) is growing fast. We work with leading law firms and corporate legal teams on complex litigation, providing court reporting, deposition services, trial preparation, legal graphics, trial presentation, and in-court technology support. What makes DEG different is the breadth of our work: we support clients from their first deposition through discovery, trial preparation, and courtroom presentation, all the way to verdict.

At DEG, you’ll make a visible impact. We have the close relationships and quick decisions of a smaller company, with the resources and backing of Esquire behind us.

About the Role

You’ll own and grow a territory of law firm and corporate legal clients. As a Senior Sales Executive, you’ll develop new business, expand existing relationships, and work closely with DEG’s operations and trial teams to deliver for clients across the life of a case.

This is a remote, full-time role reporting to the Vice President of Sales, with real autonomy, senior-level client exposure, and the chance to help shape DEG’s next stage of growth.

Key Responsibilities

• Build relationships with litigators, litigation support teams, and corporate legal departments
• Win new clients and grow business within existing accounts
• Run full-cycle sales: first conversation → proposal → close → ongoing account growth
• Understand what clients need at each stage of litigation and connect them with the right DEG services and people
• Identify opportunities to support clients as matters move from depositions and discovery into trial preparation and presentation
• Partner with operations and trial teams to deliver a strong client experience, resolve issues promptly, and support clients after the sale
• Maintain an accurate pipeline and forecast in Salesforce, including pricing and RFP support
• Respond proactively to client questions about services, pricing, and solutions
• Gather and share market intelligence, and partner with marketing on lead generation and marketing programs
• Represent DEG at client meetings, industry events, and networking opportunities

What You’ll Need

• Skills: Strong written, verbal, and presentation skills, with the curiosity and confidence to engage senior legal professionals; a strong ability to network and build lasting client relationships
• Experience: 5+ years of B2B or professional services sales experience, with a record of developing new business, growing client relationships, and meeting or exceeding performance-based metrics; legal services or litigation support experience preferred
• Technical: Familiarity with Salesforce and Microsoft Office
• Education: Bachelor’s degree or equivalent experience preferred
• Attributes: Self-directed, proactive, organized, and process-oriented, with a sense of urgency, adaptability, solid business acumen, and a collaborative approach across teams

What Success Looks Like

• Consistent attainment of monthly, quarterly, and annual sales quotas
• New client acquisition and growth within existing accounts
• An accurate pipeline and forecast in Salesforce
• Meeting or exceeding sales activity metrics

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 position. You’ll work primarily from a home office, with travel for client meetings, industry events, and networking opportunities. You’ll thrive in a culture that values close client relationships, quick decisions, and teamwork across sales, operations, and trial teams.

💬 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].