Demo

Outside Sales Representative

Filevine
Chicago, IL Full Time
POSTED ON 8/3/2026
AVAILABLE BEFORE 10/2/2026

Filevine is a Legal AI company delivering Legal Operating Intelligence for the future of legal work. Grounded in a singular system of truth, Filevine brings together data, documents, workflows, and teams into one unified platform—where modern legal work happens with clarity and consistency.

 

Powered by LOIS, the Legal Operating Intelligence System, Filevine connects context across every matter to transform legal operations from reactive to proactive. LOIS reads, understands, and reasons across your data to surface insight, automate complexity, and give professionals the clarity and confidence to see more, know more, and do more. Fueled by a team of exceptional collaborators and innovators, Filevine’s rapid growth has earned AI awards and recognition from Deloitte and Inc. as one of the most innovative and fastest-growing technology companies in the country.


About the Role

This is a true outside sales role. You'll be in the field at least four days a week, walking into law firms, meeting paralegals and attorneys face-to-face, attending bar association events, and becoming the most familiar name in your territory for deposition services.

This isn't an email job. It's not a Zoom job. You will win by showing up — consistently, professionally, and with something useful to say. If you love the rhythm of door-to-door selling, can navigate a downtown legal corridor, and have the discipline to run a territory like a small business, you'll thrive here. There is no ceiling on your earnings.

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What You'll Do
  • Own a defined geographic territory and build a daily route plan that maximizes face-to-face time with litigation attorneys, paralegals, legal assistants, and firm administrators.

  • Spend at least four days per week in the field — walking into firms, dropping by reception, scheduling lunches, and turning every visit into a relationship.

  • Sell Filevine's full deposition stack: court reporting, remote depositions, and AI-powered products including Depo CoPilot.

  • Drive initial customer enablement, training, and product adoption — get new firms up and running, walk them through their first depositions, and ensure they're confident with the product. (A dedicated in-house team handles full, ongoing trainings; your role is to spark and seed adoption.)

  • Attend local and regional industry events: bar association meetings, CLEs, paralegal association mixers, and trial lawyer chapters. Be the visible Filevine presence in your market.

  • Run disciplined prospecting: outbound calls, drop-bys, follow-ups, and a tight cadence on every account.

  • Maintain accurate, up-to-date records of every visit, conversation, and opportunity in CRM (Salesforce). Forecast projected targets and deals

  • Partner closely with Operations, Scheduling, and Client Success to deliver a seamless deposition experience.


You'll Crush This Role If You Have
  • 3–5 years of outside sales experience, ideally B2B and in a field/territory model.

  • A proven track record of building a book of business from in-person relationships — not inbound leads.

  • Demonstrated ability to learn a new industry quickly and translate insights to subject-matter experts (in this case, litigators).

  • High activity, high agency: you build your own pipeline, run your own day, and don't wait for marketing to hand you names.

  • Comfort walking into a law firm cold, navigating gatekeepers, and earning a first conversation.

  • Experience with CRM tools (Salesforce, HubSpot, or similar) and the discipline to keep records clean.

  • Excellent verbal, written, and presentation skills — including in-person demos and virtual meetings.

  • A valid driver's license and reliable transportation; you live in or near your assigned territory.


Nice to Have
  • Prior experience selling into law firms or to attorneys — court reporting, legal videography, e-discovery, medical records retrieval, or legal tech.

  • An existing network in the local legal community.

  • A referral network of attorneys, court reporters, videographers, and adjacent service providers.

  • Familiarity with deposition workflows, litigation timelines, and how legal services are purchased


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$80,000 - $90,000 a year
$80-90K commission, on-target earnings of $30K.
 
Final compensation will depend on experience, territory potential, and qualifications. 
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Why Filevine

  • A real territory you can grow into a business.

  • Best-in-class deposition product, including AI tools that no traditional provider can match.

  • Marketing, ops, and client success teams built to make field reps successful.

  • Career path into senior sales, leadership, or strategic account roles as Filevine Depositions scales.

  • Comprehensive benefits, including [Medical / Dental / Vision / 401(k) / PTO / etc.].

 

Compensation Information: $80,000 - $90,000 base commission

 

The base salary range represents the low and high end of the salary range for this position. The total compensation package for this position will be determined by each individual’s location, qualifications, education, work experience, skills and performance. We believe in the importance of pay equity - the range listed is just one component of Filevine’s total compensation package for employees. This position is also eligible for a paid time off policy, as well as a comprehensive benefits package.


Filevine is an Equal Opportunity Employer. Qualifications for employment, promotion and other terms and conditions of employment are based upon the ability to perform the job. Equal-employment opportunities are provided to all applicants and employees without regard to race, creed, religion, color, age, national origin, sex, disability, veteran status, or other legally protected class. Filevine is committed to providing reasonable accommodations for qualified individuals with disabilities. If you need assistance or accommodation due to disability, or if you have concerns related to Filevine’s equal employment opportunities, you may contact us at legal@filevine.com

 

Cool Company Benefits:

- A dynamic, rapidly growing company, focused on helping organizations thrive 

- Medical, Dental, & Vision Insurance (for full-time employees)

- Competitive & Fair Pay

- Maternity & paternity leave (for full-time employees)

- Short & long-term disability

- Opportunity to learn from a dedicated leadership team

- Top-of-the-line company swag

 

Privacy Policy Notice

Filevine will handle your personal information according to what’s outlined in our Privacy Policy.

 

Communication about this opportunity, or any open role at Filevine, will only come from representatives with email addresses using "filevine.com". Other addresses reaching out are not affiliated with Filevine and should not be responded to.

 

Salary : $80,000 - $90,000

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