Business Development Representative (BDR) - Chicago

Business Development Representative (BDR) - Chicago Join Filed as a BDR in Chicago: own outbound, hunt for new customers, build real relationships, and fast-track to AE with a clear growth path. We usually respond within a week Compensation: $60k Base + $24k Variable = $84k OTE About Filed Filed is redefining how Tax Firms Work. This is a ground-floor opportunity to join a startup that is actively building its go-to-market engine. The sales team is small by design right now, but that's exactly why this role matters so much, and why the upside for you is real. The Role We're hiring a driven, hungry, and personable Outbound Business Development Representative to help us grow Filed's customer base from the ground up. This is a hybrid inside + field sales role, meaning you'll be just as comfortable dialing prospects from your desk as you are walking into a business, introducing yourself, and starting a conversation. You won't just be setting meetings, you'll be the face of Filed in the field, building genuine relationships with decision-makers and helping prospects understand why there's a better way to work. If you thrive on the energy of outbound sales, love the hunt, and want a clear path to closing deals yourself, this is the role for you. What You'll Do Cold call prospects daily with confidence, persistence, and a consultative approach Conduct in-person visits to prospect businesses within your territory to introduce Filed and generate qualified pipeline Research target accounts, identify key decision-makers, and craft personalized outreach via phone, email, and LinkedIn Book qualified discovery meetings for the Account Executive team (and eventually yourself) Maintain accurate activity and pipeline data in CRM, own your numbers Collaborate closely with leadership to refine messaging, targeting, and outreach sequences Represent Filed at local networking events, industry meetups, and in-person prospect visits as well as industry tradeshows or sponsored events. Provide feedback from the field to inform product positioning and go-to-market strategy What We're Looking For Required: 1–3 years of sales, customer-facing, or business development experience (SaaS, tech, or field sales a strong plus) A genuine hunter mentality — you get energized by outbound, not intimidated by it Excellent verbal communication skills; you can hold a room and hold a conversation Comfort with rejection and the resilience to keep dialing Self-starter who can manage their own schedule and territory without micromanagement Valid driver's license and reliable transportation for in-person prospect visits Familiarity with CRM tools (HubSpot, Salesforce, or similar) A Reliable vehicle to conduct onsite visits in your territory Bonus Points: Experience in a BDR, SDR, or inside sales role at a SaaS or tech startup Familiarity with document automation, workflow software, or business process tools Experience using sales engagement tools (Apollo, Outreach, Salesloft, etc.) Proven track record of meeting or exceeding activity and pipeline quotas Career Path This role is intentionally designed as a launchpad. We expect strong performers to step into an Account Executive role within 9–12 months. We're growing fast and we promote from within, the BDRs we hire today are the closers and team leads of tomorrow. You'll get direct exposure to deals from the very beginning. You'll sit in on discovery calls, shadow AEs, and be brought into the full sales motion. By the time you're ready to carry a quota, you'll already know the playbook inside and out. Benefits Health & Wellness Medical insurance (multiple plan options including a low-premium PPO and HDHP) Dental and vision coverage Company contribution toward premiums for employee and dependents Financial 401(k) retirement plan with employer match Mileage and gas reimbursement for all in-person prospect visits (ongoing from Day 1) Time Off Flexible PTO policy Paid company holidays Growth & Culture Annual learning & development stipend for courses, certifications, and events Direct access to founders and senior leadership Regular team off-sites and a culture that actually celebrates wins Equity opportunity as the company scales (to be discussed during offer) The 90-Day Contractor Period — What to Know Your first 90 days will be as a 1099 Independent Contractor. This gives both you and Filed the chance to ensure it's the right fit before converting to full employment. During this period: You'll receive the full base pay and variable structure outlined above You'll be onboarded, trained, and fully supported by the team Mileage and gas reimbursement for prospect visits is active from Day 1 At 90 days, successful contractors convert automatically to W-2 employees with full benefits Why Filed? Best-in-class product — we're not asking you to sell something you'll have to apologize for. Filed genuinely solves real pain for the businesses we work with. Small team, big opportunity — you'll have a seat at the table, not a ticket number Fast track to AE — we're scaling quickly and we'd rather promote internally than hire externally You'll actually be heard — your feedback from the field shapes how we sell, position, and build Department Sales Role Outbound Business Development Representative (BDR) Locations Chicago Remote status Fully Remote Yearly salary $60,000 Employment type Full-time Positions 1 Chicago About Filed Filed is an AI tax preparer that helps firms prep faster, scale smarter, and stay in control without breaking what already works. It’s not a replacement for human judgment. It’s a new kind of leverage for those who carry the weight of tax season year after year.