Enterprise Sales Director - Chicago
Giga AI, Inc., Chicago, IL, United States
Sales Director
We're looking for a Sales Director to own and expand relationships with Giga's largest and most important enterprise accounts. You'll drive complex, multi-stakeholder sales cycles across Fortune 1000 organizations leading with insight, partnership, and a deep understanding of the customer's business. You'll collaborate directly with Giga's leadership, product, and engineering teams to shape custom solutions and unlock expansion opportunities within existing accounts and large-scale pilots. This is a foundational, high-impact role for someone eager to drive transformational change inside the world's biggest brands. Responsibilities: Develop deep, trusted partnerships with executive stakeholders across CX, Operations, and Product teams. Lead expansion within our largest customers and convert POCs into multi-year, multi-million-dollar partnerships. Manage enterprise negotiations, coordinate technical validation, and align stakeholders from first meeting through close. Build and execute tailored account plans to deepen engagement and expand into new lines of business. Partner with founders, engineering, and deployment teams to deliver customized, high-value solutions. Bring customer insights directly into our product and strategy discussions to shape future capabilities. Qualifications: 5+ years in strategic or enterprise SaaS sales with a strong record of closing and expanding 6 or 7-figure deals. Skilled at navigating large, complex organizations and building executive-level relationships. Thrives in early-stage, fast-paced environments where process and playbooks are still being written. Clear, thoughtful, and able to align internal and external teams around shared outcomes. Nice to Have: Experience selling AI, automation, or CX transformation solutions. Familiarity with large-scale deployments in telecom, logistics, or e-commerce sectors. Early GTM or founding sales experience at a fast-growing startup. Compensation & Benefits: Competitive base + commission + equity Catered lunch daily Dinner stipend $150/month wellness benefit (gym, fitness classes, mental health) 401(k) plan Paid parental leave (12 weeks maternal, 6 weeks paternal) Commuter benefits Medical, dental, and vision coverage Why Giga: At Giga, you'll sell one of the most advanced enterprise AI platforms on the market to the world's most recognized consumer brands. You'll be joining a team that moves fast, builds fearlessly, and values people who take ownership and drive impact. If you're motivated by closing transformative deals and partnering with global enterprises to redefine how they serve their customers, this is your opportunity to make it happen. Giga is an equal opportunity employer. We're committed to providing equal employment opportunities regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.
We're looking for a Sales Director to own and expand relationships with Giga's largest and most important enterprise accounts. You'll drive complex, multi-stakeholder sales cycles across Fortune 1000 organizations leading with insight, partnership, and a deep understanding of the customer's business. You'll collaborate directly with Giga's leadership, product, and engineering teams to shape custom solutions and unlock expansion opportunities within existing accounts and large-scale pilots. This is a foundational, high-impact role for someone eager to drive transformational change inside the world's biggest brands. Responsibilities: Develop deep, trusted partnerships with executive stakeholders across CX, Operations, and Product teams. Lead expansion within our largest customers and convert POCs into multi-year, multi-million-dollar partnerships. Manage enterprise negotiations, coordinate technical validation, and align stakeholders from first meeting through close. Build and execute tailored account plans to deepen engagement and expand into new lines of business. Partner with founders, engineering, and deployment teams to deliver customized, high-value solutions. Bring customer insights directly into our product and strategy discussions to shape future capabilities. Qualifications: 5+ years in strategic or enterprise SaaS sales with a strong record of closing and expanding 6 or 7-figure deals. Skilled at navigating large, complex organizations and building executive-level relationships. Thrives in early-stage, fast-paced environments where process and playbooks are still being written. Clear, thoughtful, and able to align internal and external teams around shared outcomes. Nice to Have: Experience selling AI, automation, or CX transformation solutions. Familiarity with large-scale deployments in telecom, logistics, or e-commerce sectors. Early GTM or founding sales experience at a fast-growing startup. Compensation & Benefits: Competitive base + commission + equity Catered lunch daily Dinner stipend $150/month wellness benefit (gym, fitness classes, mental health) 401(k) plan Paid parental leave (12 weeks maternal, 6 weeks paternal) Commuter benefits Medical, dental, and vision coverage Why Giga: At Giga, you'll sell one of the most advanced enterprise AI platforms on the market to the world's most recognized consumer brands. You'll be joining a team that moves fast, builds fearlessly, and values people who take ownership and drive impact. If you're motivated by closing transformative deals and partnering with global enterprises to redefine how they serve their customers, this is your opportunity to make it happen. Giga is an equal opportunity employer. We're committed to providing equal employment opportunities regardless of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.