Business Development Representative - Mid Market

Business Development Representative - Mid Market

As a member of the Ship Bob Team, you will...

• Grow with an Ownership Mindset
  :
  We champion continuous learning and proactive innovation. Team members are encouraged to identify challenges and take ownership of initiatives that drive merchant, company and personal growth. By tackling complex problems and exploring creative solutions, you won’t just follow a playbook, you’ll be actively building the future of Ship Bob.
• Collaborate with Peers and Leaders Alike: Ship Bob values collaboration and support, where team members and leaders alike are committed to helping each other succeed. We all set high standards and understand the importance of transparency at all levels. We’ve created an environment where trust, open communication, and mutual respect motivate our teams to reach new heights.
• Experience a High-Performance Culture and Clear
  
  Purpose:
  
  Our commitment to delivering results creates a goal-driven, high-performance culture where everyone is empowered to contribute to our mission with a clear understanding of their direct impact and accountability. We measure success in tangible ways, allowing each team member to see the positive outcomes of their work and celebrate shared victories.

Start Date: 3/23/2026

Location: Remote Monday and Friday. Onsite Tuesday, Wednesday, and Thursday at 120 N Racine Ave #100, Chicago, IL 60607. Ability to graduate to fully remote after 12-months if in good standing.

Role

Description:

Are you a strategic thinker with a passion for uncovering opportunities and driving growth? Join our Mid-Market Sales team as a Business Development Representative and play a vital role in helping businesses solve their logistical challenges with our full suite of services.

In this high-impact role, you'll be the first point of contact for mid-market prospects, building meaningful connections and fueling the sales pipeline. Your mission: craft thoughtful, targeted outreach to set high-quality meetings that turn into closed deals for our Mid-Market Account Executives.

• Drive Growth: Identify, research, and qualify new enterprise leads—adding 10+ high-potential prospects to your pipeline daily.
• Proactive Outreach: Execute a high-volume, multi-channel outreach strategy (cold calls, emails, and social selling) including 40+ dials, 5+ quality connections, and 20+ minutes of call time per day.
• Strategic Prospecting: Leverage platforms like Linked In, CRM tools, and industry databases to identify and target ideal customer profiles.
• Engage Decision-Makers: Connect with key stakeholders at target companies to understand their current operations and determine alignment with our solutions.
• Advocate & Advise: Use sound judgment to identify non-traditional opportunities that may fall outside the typical scope and make thoughtful recommendations to leadership.
• Collaborate for Success: Schedule qualified demos for Account Executives and help drive deals forward through strategic collaboration.
• Own the Metrics: Meet and exceed daily activity benchmarks and contribute consistently to monthly and annual revenue goals.
• Stay Ahead: Keep a pulse on industry trends, competitive movements, and evolving enterprise needs to inform outreach strategy and messaging.

What you’ll bring to the table:

• Minimum 1 year of demonstrated success in a sales environment required.
• Experience using ABM strategies.
• Experience selling over the phone and smart calling various types of businesses or merchants.
• Demonstrate a high degree of diligence and accountability.
• Comfortable in a competitive environment, with evidence of personal ambition.
• Relentless persistence in the face of daily rejection and delays from potential merchants.
• An aptitude for research and understanding data.
• Medical, Dental, Vision & Basic Life Insurance

In addition to base salary, the role includes the opportunity to receive and/or earn sales incentives based on Company’s plans and in accordance with Company’s policies.

We recognize that people come with a wealth of experience and talent beyond just the technical requirements of a job. If your experience is close to what you see listed here, please still consider applying. Diversity…