Enterprise Sales Director - Chicago
About Giga
Giga has recently raised a $61M Series A and has several paying customers, including DoorDash. We’re building the next generation of customer experience — real-time AI agents that can understand emotion, resolve issues instantly, and scale across the world’s largest enterprises.
It’s an exciting inflection point for the company. While we have been successful, we have larger ambitions. Our goal is to become the go-to AI platform for all enterprise automation, powered by our voice superintelligence.To achieve this, we need more great engineers.
The work affects millions of people every day and our engineers have autonomy and make true impact. This opportunity is unique because we have brilliant founders, have found commercial success, and see a clear path to becoming a generational company. Some further info about us:
Giga builds AI agents trusted by the largest B2C companies in the world. Industry leaders like DoorDash trust Giga with their most complex support and operations workflows across voice, chat, and email. If being a part of this resonates with you, please apply!
About the Role
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.
What You’ll Do
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.
Who You Are
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.
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.
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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.