Director of Sales, Ad Agencies

Director of Sales, Ad Agencies Sales Chicago, United States Senior Full-time Description Ready to take your career to the next level? Skai is looking for the best and the brightest to join our rapidly growing team. We're proud of our industry-leading digital marketing software but we're even prouder of the people behind it. That's where you come in! Skai is seeking a Director of Sales for our US Independent Agency Team , who will be responsible for generating new agency accounts, owning the GTM sales process and developing strategic agency partnerships which meet our average tenure. You will report to and partner with the EVP Sales, AMER Independent Agency. Duties and Responsibilities Outwork the competition! Develop relationships both internal and external Own net new revenue, retention, and expansion across a defined book of independent agency accounts: including regional GTM planning that reflects how indy agencies actually buy (no procurement, principal-led decisions, margin-sensitive). Build and maintain a high-quality pipeline through disciplined discovery, active multithreading across agency stakeholders (strategist, data/ops lead, principal), and rigorous account planning — with forecasts grounded in verified buyer intent, not activity. Lead the full sales cycle — from discovery through negotiation, pricing, and contract close: in partnership with the EVP. Apply constructive pressure at key stages to keep deals moving without defaulting to discount. Bring a differentiated commercial point of view into every account: reframing how agencies think about AI-driven optimization and commerce media, not just responding to existing briefs. Develop account-level strategies that create expansion opportunity beyond the initial sale. Collaborate cross-functionally with Industry leads, Client Success, Product, Legal, and EVP to ensure clean handoffs, accurate scoping, and long-term agency partnership health, and feed ground-level agency insight back into product and GTM strategy. Be the CEO of your desk! Manage consistent quality pipeline development, account planning, revenue forecasting and internal resource utilization Drive a regional TAM and GTM strategy in collaboration with your EVP, SDR and Marketing support team Get out there! Develop budgets for client visits and industry events necessary for quota success Know your industry! Know the AdTech, MarTech and Independent Agency landscapes Know your clients! Understand how independent agencies like to do business and make profit Requirements What You'll Bring 5+ years in AdTech, commerce media, or AI/data SaaS sales, with a documented track record of exceeding quota in complex, multi-stakeholder environments. Experience selling into independent agencies specifically is strongly preferred. Passion for your craft! A willingness to learn and develop every day Proven ability to run a full discovery-led sales process: mapping stakeholders, surfacing unconsidered problems, and building consensus across agency principals, strategists, and ops leads simultaneously. You don't wait for a champion to pull you through; you build the map yourself. A proven track record with independent agencies and Founder/C level clients Running a consultative and complex sales cycle for small to large agency organizations A genuine point of view on where AI is (and isn't) delivering for media buyers today. You bring insight into conversations before you're asked for it, and you're comfortable challenging a prospect's assumptions when the data supports it. Collaborative by default, direct when it matters. Strategic and creative commercial thinking: the ability to diagnose an agency's real growth constraints (not just their stated tool needs) and construct partnership structures that create durable value for their business and yours. You think in business outcomes, not feature sets. We are hybrid for the long term - with a great home/ office work mix (three days in office per week), passionate and diverse team members, and a vibrant company culture. The salary range for this position is $130,000 - $135,000 base plus strong commission plan and equity. The actual salary amount will vary depending on the applicants experience, skills and abilities as well as internal equity and market data. Equal Opportunity Employer Skai, Inc. is an Equal Opportunity Employer. At Skai, we believe ensuring a diverse, equitable, and inclusive workplace is not just an ideal to strive for; it is right, necessary, and our responsibility as humans. Our full DE&I commitment and global framework can be viewed on our company website and are aligned to our core values. We strongly encourage and seek applications from women, people of color, and bilingual and bicultural individuals, as well as members of the lesbian, gay, bisexual, and transgender communities. Applicants shall not be discriminated against because of race, religion, sex, national origin, ethnicity, age, disability, political affiliation, sexual orientation, gender identity, color, marital status, medical condition including acquired immune deficiency syndrome (AIDS) and AIDS‑related conditions, or any other protected status. Also pursuant to the San Francisco Fair Chance Ordinance, we encourage and will consider for employment qualified applicants with arrest and conviction records. Applicants with Disabilities Reasonable accommodation will be made so that qualified disabled applicants may participate in the application process. Please advise in writing of special needs at the time of application. Skai is an E-Verify employer #J-18808-Ljbffr