Director of Sales

Chalk•San Francisco, CA
•$350,000 - $450,000•Onsite

About The Position

Chalk is hiring a Director of Sales to grow new business and scale its sales organization. The company has Account Executives and Forward Deployed teams that handle technical evaluations, and its buyers are engineering leaders. The Director will develop sales practices across segments, territories, and products, including qualification, forecasting, pricing, and hiring. The role reports to the VP Revenue and leads the Account Executive team, collaborating closely with founders, SDRs, Forward Deployed teams, post-sales, product, and marketing. The position is in person Monday through Friday at Chalk's San Francisco or New York offices; remote and hybrid positions are not offered. The ideal candidate has a record of exceeding quota, hiring and developing successful sales representatives, and building repeatable sales motions for technical products. They are comfortable selling to engineering, data, and machine-learning teams; managing usage-based or committed-spend deals; and working across sales-led, product-led, and hybrid motions.

Requirements

  • At least 7 years of B2B sales experience, including at least 2 years leading a team.
  • A record of carrying a quota and exceeding it consistently.
  • Experience hiring sales representatives and helping them exceed quota.
  • Experience taking an early sales team to a repeatable sales motion.
  • A data-driven, first-principles approach to operating and designing sales systems.
  • A 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 engage deeply with engineers about technical products.
  • Experience structuring and winning usage-based or committed-spend deals and forecasting them.
  • Experience with sales-led, product-led, and hybrid sales motions, including turning developer product-led demand into enterprise deals.
  • Sales rigor and judgment about when to standardize processes and when to remain flexible and experiment.
  • Candid, fast-moving, team-oriented approach with a focus on the team's results.

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 Account Executives, set performance expectations, and create onboarding that helps representatives ramp quickly on a technical product.
  • Define sales stages, qualification criteria, and pricing and discount approval processes.
  • Set pilot entry criteria, success metrics, and timelines to move pilots into production.
  • Own weekly forecasting and pipeline reporting, and partner with RevOps and finance on quota and compensation plans.
  • Bring deal insights to product and pricing, and work with growth to convert product adoption into pipeline.
  • Join founders and Forward Deployed teams on strategic opportunities.
  • 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).
  • 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.
  • A ride home when staying late.
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