Business Development Representative (BDR)

Fairway IT Solutions is hiring a 100% outbound-focused Business Development Representative (BDR) to help build the pipeline that powers the sales team. This role centers on prospecting, qualifying top-of-funnel leads, and booking discovery meetings, with clear weekly and monthly activity and pipeline KPIs to track progress.

Based in Chicago, IL and operating on a hybrid schedule, you will support both outbound outreach and inbound lead qualification, ensuring qualified opportunities move forward in the CRM.

What you’ll do

• Prospect into target accounts (typically 20–500 employees) using outbound calling, email sequences, and LinkedIn outreach.
• Qualify inbound leads generated by marketing (web, referrals, events) using an established qualification framework such as BANT or equivalent.
• Research target accounts before outreach, including the current IT environment, pain points, decision-makers, and relevant trigger events (for example, a recent breach, growth, or a compliance deadline).
• Book qualified discovery meetings on the calendar of the Account Executive / Director of Technology.
• Maintain accurate, up-to-date records of activity and lead status in the CRM.
• Meet weekly and monthly activity and pipeline KPIs, including calls, emails, conversations, meetings booked, and opportunities created.
• Build working knowledge of core MSP offerings, including managed IT, cybersecurity, cloud, and compliance, to support credible first conversations and basic objection handling.
• Partner with marketing to refine messaging, target lists, and campaign follow-up.
• Represent Fairway at local networking events, chamber functions, and industry meetups as needed.

What you bring

• 1–3 years of outbound sales, BDR, or SDR experience in a B2B environment (IT services, SaaS, or other technical or professional services background recommended but not required).
• Strong phone presence and written communication, with comfort working high-volume outbound activity and rejection.
• Experience hitting or exceeding activity and pipeline targets.
• CRM proficiency, with HubSpot preferred.
• Self-motivated, coachable, and competitive, with a metrics-driven mindset.
• Comfort learning technical concepts (no IT background required), with genuine curiosity about technology.

Tools and frameworks you’ll use

• HubSpot
• LinkedIn
• BANT

Compensation and benefits

• Salary: USD 45,000 - 65,000 per year
• 401(k)
• 401(k) matching
• Dental insurance
• Health insurance
• Vision insurance
• Flexible schedule
• Paid time off
• Paid training

Work location: Hybrid remote in Chicago, IL 60631.