Advertising Account Executive Jobs in Chicago, IL

Start Date: 10/27/2025

Location: Remote Monday and Friday. Onsite Tuesday, Wednesday, and Thursday from 9:00 am - 5:00 pm CST at 120 N Racine Ave #100, Chicago, IL 60607. 

Ability to graduate to fully remote after 12-months if in good standing.

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.

ShipBob is proud to be named on the Chicago Tribune's list of Top Workplaces: https://www.chicagotribune.com/2024/11/15/top-workplaces-2024-chicago-winners/. 

• 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 LinkedIn, 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 
• Paid Maternity/Parental Leave Program 
• Flexible Time Off Program 
• Paid Sick Leave  
• Floating Holidays (2 days/year) 
• Wellness Days (1 day/quarter) 
• 401K Match  
• Comprehensive Benefits Package >>> https://www.shipbob.com/careers/ 
• See Our High-Performing Culture >>>Check us out on Instagram (@lifeatshipbob)

 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.

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