Enterprise Sales Director - AI Workforce Management Platform (Chicago)

PLEASE CLICK HERE TO SEE *ALL* OF OUR JOB OPENINGS!Enterprise Sales DirectorSeeking an Enterprise Sales Director to bring video measurement and optimization products to market. You'll work directly with the world's largest brands and agencies to help them eliminate waste and drive better outcomes across key media channels. This is a quota-carrying individual contributor role with full ownership of pipeline generation, deal progression, client adoption, and account growth. You'll be responsible for opening new accounts, building pipeline independently, and running a structured sales process from first contact through close. The ideal candidate has a demonstrated track record of meeting and exceeding ARR-based sales targets.Key ResponsibilitiesOwn and achieve an ARR-based sales quota through direct sales to enterprise brands and agencies.Generate and manage a qualified pipeline with strong CRM hygiene, including accurate stage assignments, realistic close timelines, and documented next steps.Lead the full sales cycle independently, from prospecting and discovery through proposal, negotiation, and close, while leveraging internal resources when appropriate.Conduct structured discovery conversations that uncover clients' digital media spend, content quality exposure, and measurement gaps.Deliver compelling product demonstrations that clearly connect the company’s technology and methodology to each client's advertising environment.Maintain a client-first approach throughout the sales process by being responsive, prepared, and focused on delivering business outcomes.Partner with Product and Account Management to ensure smooth client handoffs and successful onboarding.Represent the company at client meetings, agency presentations, industry events, and business reviews.Provide structured market feedback and customer insights to Product and Go-to-Market teams.Qualifications5+ years of digital media or AdTech sales experience with a proven record of meeting or exceeding ARR quotas.Experience selling directly to enterprise brand marketers and agency investment or media teams.Demonstrated sales process discipline with a consistent methodology, accurate CRM management, and strong pipeline forecasting.Excellent communication skills with the ability to translate complex measurement technology into compelling business value for CMOs, VPs of Media, agency executives, and other senior stakeholders.Comfortable operating in an early-stage company where you'll help build the sales playbook while actively selling.Experience selling brand safety, contextual measurement, verification, or related advertising technology solutions is a strong plus.Job-3636543*LI-AD1#LI-Remote