Vice President of Sales

Vice President of Sales — Chicago

AdMedia | Full time | In office

AdMedia is seeking a hands-on Vice President of Sales who can win new business, develop salespeople, and build a disciplined team that consistently delivers results. This role is based in our Chicago office and requires full-time, in-person attendance.

You will personally prospect and close advertiser and agency business while leading sales execution, training, and team performance. We want a leader who earns trust, sets clear expectations, stays calm under pressure, and leads by example.

What you will do

• Own the team’s new-business strategy and revenue performance while carrying a personal sales target.
• Hunt for new business through targeted research, outbound calls, email, referrals, and relationships with advertisers and agencies.
• Lead discovery meetings, presentations, proposals, negotiations, and closing conversations with senior decision-makers.
• Recruit, onboard, train, and manage sellers as the team grows.
• Coach salespeople through prospecting, qualification, objection handling, negotiation, and closing.
• Establish consistent one-to-one meetings, call reviews, pipeline reviews, and clear performance expectations.
• Build practical sales playbooks that help the team repeat successful approaches.
• Maintain accurate CRM records and forecasts, with clear ownership and next steps for every opportunity.
• Partner with campaign, account management, and operations teams to deliver on client commitments and grow lasting relationships.

What you bring

• Seven or more years of successful digital advertising, search, performance media, or related enterprise sales experience.
• Three or more years directly managing salespeople, with examples of improving individual and team performance.
• A demonstrated record of personally originating and closing new business.
• Experience selling to advertisers and agencies and navigating complex sales cycles.
• Strong understanding of advertising performance, measurement, and return on ad spend.
• Clear communication, sound judgment, disciplined follow-through, and the ability to hold people accountable while helping them improve.
• Ability to work full time in person at our Chicago office.

Preferred leadership experience

Prior U.S. Marine Corps service with experience leading and developing people is strongly preferred. We also welcome candidates with comparable leadership experience from other military branches or civilian careers.

Experience building a sales team, establishing training programs, and developing agency or advertiser relationships is especially valuable.

Your first 90 days

Assess the team and pipeline, establish clear sales and coaching routines, build and advance personally sourced opportunities, and present a practical plan for improving team performance.

Compensation: Open.

Benefits and perks

• Medical insurance with 100% of employee premiums covered
• 401(k)
• 10 paid company holidays and paid time off
• Company-sponsored gym membership
• Half-day Fridays
• Employee referral programs
• Training and certification opportunities
• A friendly and supportive culture

If you can show both business you personally won and salespeople you helped succeed, we would like to hear from you.