Director of Sales

About Chalk

Chalk (chalk.ai) is the platform for production AI. Trusted by enterprises including Whatnot, Grindr, Mission Lane, Turo, and Apartment List, Chalk brings together context, runtime, and learning for agents and models. Chalk’s Context Engine delivers live context by querying data across warehouses, databases, streams, and APIs, straight from the source. Chalk’s runtime powers agents and models with infrastructure and governed access to LLMs and tools. Together, these capabilities help teams build AI that understands their business, continuously improves, and runs reliably in production. We've recently raised a $50 million Series A, led by Felicis. Learn more at chalk.ai.

The Role

We're hiring a Director of Sales who will grow new business at Chalk. We already have strong Account Executives and Forward Deployed teams that win hard technical evaluations. Our buyers are engineering leaders who test everything we claim. We need someone to build for scale across segments, territories, and products, and to design how we qualify, forecast, price, and hire.

You'll report to our VP Revenue, lead the Account Executive team, and work every day with our founders, the SDR team, our Forward Deployed teams, post-sales, product, and marketing.

We work in person Monday through Friday in our SF and NY offices. We don't currently offer remote or hybrid positions.

What You'll Do

• Own new business and build the org. Drive pipeline and bookings for net-new customers. Build the coverage and hiring plans, then hire the next wave of AEs.
• Lead and develop the team. Coach AEs, set the performance bar, and build onboarding that ramps reps fast on a technical product.
• Design the sales process. Write the stage definitions, qualification criteria, and pricing and discount approvals that hold up as the team grows.
• Turn pilots into commitments. Set the entry criteria, success metrics, and timelines that move pilots into production.
• Run the operating rhythm. Own the weekly forecast and pipeline reporting, and partner with RevOps and finance on quota and comp plans.
• Shape how we go to market. Bring what you learn in deals back to product and pricing, and work with growth to turn product adoption into pipeline.
• Win the biggest deals as a team. Step into strategic opportunities alongside founders and our Forward Deployed teams.
• Partner across GTM. Work with SDRs on meeting quality and handoffs, with post-sales on onboarding and expansion, and with marketing on pipeline targets.

About You

• 7+ years in B2B sales, with 2+ leading a team. You've carried a quota and beaten it consistently. As a leader, you've hired your own reps and gotten them past quota.
• Data-driven, first-principles operator. You've taken an early sales team to a repeatable motion. You think in systems, run the business on data, and would rather design the motion than run one someone else designed.
• A track record selling technical products. Developer tools, data platforms, APIs, cloud, or AI infrastructure, sold to engineering, data, and ML teams. You can go deep with an engineer without calling for backup.
• Closed on consumption. You've structured and won usage-based or committed-spend deals, and you know how to forecast them.
• Fluent in sales-led, product-led, and hybrid motions. You've sold to developers and know how product-led demand becomes an enterprise deal.
• Rigor with judgment. You learned the craft somewhere known for its sales rigor. You know which parts of the motion to harden and where to stay flexible and experiment.
• Candid and hungry. You give direct feedback and expect it back. You move fast and care more about the team's number than your own credit.

Bonus Points

• Experience selling through cloud marketplaces or co-selling with cloud and data platform partners
• Experience designing territory, comp, and forecast plans

What We Offer

• Comprehensive medical, dental, and vision insurance
• FSA, HSA, and expert healthcare guidance
• Retirement savings
• 15 company holidays and 15 days of personal time off each year
• Flex commuter benefits
• Daily lunch and dinner on Chalk, and a ride home if you're staying late