Senior Sales Executive - Legal Services

Senior Sales Executive - Legal Services

Hot Job

Chicago Office - Chicago, IL 60602

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 growththis 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 applyyou 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 View email address on click.appcast.io.