Director of Sales

Chalk • San Francisco, CA

1d • Onsite

About The Position

Chalk is hiring a Director of Sales to grow new business and build a scalable sales organization across segments, territories, and products. The role leads the Account Executive team and owns the design of sales qualification, forecasting, pricing, hiring, and related processes. The Director works closely with the VP of Revenue, founders, SDRs, Forward Deployed teams, post-sales, product, marketing, RevOps, and finance. The position is in person Monday through Friday at Chalk’s San Francisco or New York offices; remote and hybrid work are not offered.

The role is responsible for driving pipeline and bookings from net-new customers, hiring and developing Account Executives, establishing a repeatable sales motion, and helping turn product pilots into production commitments. It also includes leading the sales operating rhythm, supporting strategic deals, and using customer and deal insights to inform product, pricing, and go-to-market strategy.

Requirements

• At least 7 years of B2B sales experience, including at least 2 years leading a team.
• A history of carrying a quota and consistently exceeding it.
• Experience hiring sales representatives and helping them exceed quota.
• Experience taking an early sales team to a repeatable sales motion.
• Data-driven, first-principles approach to operating and designing sales systems.
• Track record selling technical products such as developer tools, data platforms, APIs, cloud, or AI infrastructure to engineering, data, and machine learning teams.
• Ability to discuss technical products in depth with engineers.
• Experience structuring and winning usage-based or committed-spend deals and forecasting them.
• Experience with sales-led, product-led, and hybrid motions, including turning developer product-led demand into enterprise deals.
• Sales rigor and judgment about which parts of a sales motion to standardize and where to experiment.

Nice To Haves

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

Responsibilities

• Drive pipeline and bookings for net-new customers.
• Build sales coverage and hiring plans, and hire additional Account Executives.
• Coach and develop Account Executives, establish performance expectations, and build onboarding that helps representatives ramp on a technical product.
• Define sales stages, qualification criteria, and pricing and discount approval processes.
• Set pilot entry criteria, success metrics, and timelines to convert pilots into production commitments.
• Own weekly forecasting and pipeline reporting, and partner with RevOps and finance on quota and compensation plans.
• Share deal learnings with product and pricing teams, and work with growth to turn product adoption into pipeline.
• Participate in strategic opportunities with founders and Forward Deployed teams.
• Partner with SDRs on meeting quality and handoffs, post-sales on onboarding and expansion, and marketing on pipeline targets.

Benefits

• Comprehensive medical, dental, and vision insurance.
• Flexible spending account (FSA) and health savings account (HSA), plus expert healthcare guidance.
• Retirement savings.
• 15 company holidays and 15 days of personal time off each year.
• Flexible commuter benefits.
• Daily lunch and dinner at Chalk, and a ride home when staying late.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed