Business Development Representative (BDR) - Chicago

About the role

Compensation: $60k Base + $24k Variable = $84k OTE
We're hiring a driven, hungry, and personable Outbound Business Development Representative to help us grow Filed's customer base from the ground up.

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

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

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

• 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