Advertising Sales Representative in Chicago: Drive Revenue & Build Elite Client Partnerships

Are you a hunter with a passion for media and a knack for closing deals? We are seeking a dynamic Advertising Sales Representative to join our Chicago team and champion our award-winning advertising portfolios. This isn’t just a sales job; it’s a career-defining opportunity to shape the marketing strategies of top-tier brands while earning uncapped commissions in a high-growth environment.

About the Role & Our Mission

You will be the frontline of our revenue engine, responsible for prospecting, presenting, and selling integrated advertising solutions to new and existing clients across key verticals. Your mission is to understand client business objectives and architect custom ad campaigns that deliver measurable ROI, fostering long-term partnerships that fuel our collective success. We invest heavily in training and provide a robust CRM and proprietary tech stack to empower your sales process.

What You’ll Do: Key Responsibilities

• New Business Development: Aggressively prospect and qualify leads through cold calling, networking, and inbound lead follow-up to build a robust sales pipeline.
• Solution Selling: Conduct compelling needs analyses and deliver persuasive presentations that translate client goals into strategic, multi-platform advertising plans (digital, print, experiential).
• Relationship Management: Nurture and expand accounts by becoming a trusted marketing advisor, identifying upsell and cross-sell opportunities.
• Proposal & Negotiation: Craft winning proposals, expertly negotiate terms, and close contracts with a focus on margin and client satisfaction.
• Market Intelligence: Stay ahead of industry trends, competitor activity, and local market dynamics to inform strategy and value propositions.
• Reporting: Meticulously track activities, pipeline, and forecasts in our CRM; analyze campaign performance data with clients post-sale.

Who You Are: Requirements

Essential Experience & Skills

• 3+ years of B2B sales experience, preferably in media, advertising, digital marketing, or SaaS. A proven track record of exceeding quota is non-negotiable.
• Expert-level communication, presentation, and negotiation skills. You can command a room and articulate complex ideas simply.
• Self-starter mentality with exceptional time management, organization, and resilience. You thrive on autonomy and competition.
• Tech-savvy with proficiency in CRM software (Salesforce, HubSpot), Microsoft Office Suite, and a quick learner of new platforms.
• Bachelor’s degree in Business, Marketing, Communications, or a related field preferred.

Desirable Attributes

• Existing network or relationships within the Chicago business community.
• Understanding of digital advertising metrics (CPM, CTR, impressions) and analytics.
• Experience selling integrated campaigns across multiple channels.

Compensation & Benefits

We believe in rewarding excellence generously. Your compensation is designed to maximize your earning potential and recognize your contributions.

Salary Range & Commission

Base Salary: $45,000 – $65,000 USD/year, commensurate with experience.

On-Target Earnings (OTE): $85,000 – $120,000+ USD/year. This includes a robust, uncapped commission plan (typically 8-12% of revenue) with accelerators for overachievement, quarterly bonuses, and annual profit-sharing potential. Top performers routinely earn well into the six figures.

Comprehensive Benefits Package

• Health & Wellness: 100% employer-paid medical, dental, and vision insurance for employees; generous options for families.
• Financial Security: 401(k) with company match, life insurance, and short/long-term disability.
• Time Off: Flexible PTO policy, plus 10 paid holidays and your birthday off.
• Growth & Development: $2,000 annual professional development stipend for conferences, courses, and certifications.
• Perks: Monthly cell phone and wellness stipend, casual dress policy, and a collaborative, dog-friendly Chicago office with snacks and drinks.

Why Join Our Team?

You will become part of a collaborative, supportive, and fiercely competitive sales culture that celebrates wins daily. We provide the cutting-edge tools, premium inventory, and strategic backing from our award-winning creative and operations teams. This is a role with a clear path to advancement—our Sales Representatives frequently grow into Sales Managers, Account Directors, and leadership positions. If you are ready to be recognized for your results, control your income, and make a tangible impact, we want to hear from you.