Sales Director (Chicago)

Giga builds AI agents trusted by the world’s leading B2C companies. Industry leaders like DoorDash rely on Giga to automate their most complex support and operations workflows across voice, chat, and email.

Our mission is to help enterprises deliver faster, smarter, and more human customer experiences at scale — powered by AI that actually works in production.

We operate with speed, precision, and a deep sense of ownership. Backed by top-tier investors and operators, Giga is scaling rapidly across some of the most recognizable consumer brands in the world.

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.

• Own strategic relationships: Develop deep, trusted partnerships with executive stakeholders across CX, Operations, and Product teams.

• Drive growth across key logos: Lead expansion within our largest customers and convert POCs into multi-year, multi-million-dollar partnerships.

• Lead complex deal cycles: Manage enterprise negotiations, coordinate technical validation, and align stakeholders from first meeting through close.

• Develop account strategy: Build and execute tailored account plans to deepen engagement and expand into new lines of business.

• Collaborate cross-functionally: Partner with founders, engineering, and deployment teams to deliver customized, high-value solutions.

• Influence Giga’s roadmap: Bring customer insights directly into our product and strategy discussions to shape future capabilities.

• Experienced enterprise seller: 5+ years in strategic or enterprise SaaS sales with a strong record of closing and expanding 6 or 7-figure deals.

• Trusted partner: Skilled at navigating large, complex organizations and building executive-level relationships.

• Builder mindset: Thrives in early-stage, fast-paced environments where process and playbooks are still being written.

• Collaborative communicator: Clear, thoughtful, and able to align internal and external teams around shared outcomes.

• 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.

• Competitive base + commission + equity

• Full health, dental, and vision coverage

• Daily lunches, snacks, and coffee

• Gym membership and Uber rides home after work

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.