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.
