Growth Director, Enterprise

ChicagoPeople Manager, Manager, User Acquisition Marketing$130k–$150kPosted Jun 4, 2026
Skai   All Jobs Growth Director, Enterprise 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 Growth Director, Enterprise who will be responsible for retaining and growing a portfolio of strategic enterprise clients, driving net revenue expansion, and leading client conversations at the forefront of AI-powered marketing technology. You will report to and partner with the VP, EGrowth.Duties and ResponsibilitiesClient Growth & RetentionRetain and grow assigned strategic enterprise clients by managing senior-level relationships and owning the overall partnershipDrive net new revenue (NRR) via upsell and cross-sell — including global expansion, product expansion, new lines of business, and custom projectsManage the renewal process end-to-end: identifying opportunities, leading negotiations, and finalizing contracts to deliver NRR growthPipeline development; account planning; forecasting, and proactive management of leads across assigned regional enterprise clientsExecutive Relationship DevelopmentLead account development by establishing and deepening relationships with senior client executives and key decision-makersRepresent Skai at client, industry, and other eventsBe an expert in your clients' industries — understand their business needs and challenges, and exemplify how Skai is their strategic partnerAgentic & AI Product SellingDevelop strong fluency in Skai's agentic product suite — including Celeste AI, Skai MCP, and the upcoming Skai Studio — and translate these capabilities into clear business value for enterprise buyersLead discovery conversations to understand how clients are building internal AI workflows, identify where Skai's tools fit, and partner with product and CS to co-create solutionsStay current on the AI and agentic marketing landscape so you can credibly advise clients on where the market is heading, not just what Skai does todayInternal PartnershipPartner with the Client Success team to ensure a high level of customer satisfaction and ongoing support across assigned clientsBe an expert, both internally and externally, in Skai products and positioning; feed client insight back into product and GTM strategyMaintain rigorous pipeline hygiene in Salesforce and other sales productivity tools Requirements 5–8+ years of sales experience, including selling SaaS-based software and service solutions to enterprise clientsBackground in media planning, digital advertising, ad-tech, or SaaS strongly preferred; agency experience welcomeProven track record of exceeding NRR targets and expanding strategic accountsGenuine curiosity for AI-powered products — you don't need to be an engineer, but you should be able to hold a credible conversation about how agentic workflows create value for marketersExecutive presence and proven ability to manage complex, multi-stakeholder dealsSkilled use of Salesforce and other sales productivity toolsWe 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–$150,000 base plus strong commission plan and equity. The actual salary amount will vary depending on the applicant's experience, skills and abilities as well as internal equity and market data.Equal Opportunity EmployerSkai, 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...

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