Outside Sales Representative

Location: Chicago, IL Workplace: hybrid 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 Here's the honest pitch: field sales is a brand-new motion at Filevine, and we're looking for the person who builds it. Not runs a proven playbook — writes it. You'll be the first Filevine salesperson to plant a flag in your territory, and everything you learn on the ground becomes the blueprint for the reps who come after you. If "figure it out and build it from scratch" makes you lean in rather than flinch, keep reading. 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, working 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 win by showing up — consistently, professionally, and with something useful to say every time. You'll also need range: the ability to build rapport in the reception area and get your foot in the door with a paralegal, and the sophistication to sit across from a managing partner and hold your own on price, value, and strategy. This is a premium-priced product in a market full of commodity providers — so you have to be able to sell the difference, not just the service. 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 your own small business, you'll thrive here. There is no ceiling on your earnings What You'll Do Build the playbook. As the first rep in your territory, you'll test what works, document it, and help shape the model Filevine scales from. Your wins and your lessons both matter. 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. Get your foot in the door at every level: earn trust with paralegals and legal staff, then work your way up to the conversations with managing partners and firm administrators who sign off on the deal. Sell Filevine's full deposition stack — court reporting, remote depositions, and AI-powered products including Depo CoPilot — as a premium offering in a commodity market. You'll own the "why we're worth it" story. Drive initial customer enablement, training, and product adoption — get new firms up and running, walk them through their first depositions, and make sure they're confident with the product. (A dedicated in-house team handles full, ongoing trainings; your job 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 builder's mindset — you're energized by white space, ambiguity, and being the one who figures out what works before there's a manual for it. A proven track record of building a book of business from in-person relationships — not inbound leads. The range to connect with anyone in the building: warm and credible with a paralegal, sharp and strategic with a managing partner. Demonstrated ability to learn a new industry quickly and translate insights to subject-matter experts (in this case, litigators). Comfort selling a premium product against cheaper alternatives — you know how to make value the conversation instead of price. 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. 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. 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: $100,000 - $140,000 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. Work Location Expectation: Most roles for candidates in or near these metro areas (San Francisco, Salt Lake City, Chicago, or New York) are fully onsite. Some roles offer a hybrid schedule of 2–3 days in-office per week     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.