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Chalk is a production AI platform trusted by enterprises including Whatnot, Grindr, Mission Lane, Turo, and Apartment List. The platform combines a Context Engine (delivering live context by querying data across warehouses, databases, streams, and APIs), a runtime for agents and models with governed LLM access, and learning capabilities. The company recently raised a $50M Series A led by Felicis.
As Director of Sales, you will lead new business growth and build the sales organization at scale. You'll report to the VP Revenue and lead the Account Executive team while collaborating daily with founders, SDRs, Forward Deployed teams, post-sales, product, and marketing.
Key responsibilities include:
- Owning new business pipeline and bookings; building coverage and hiring plans for the next wave of Account Executives
- Leading and developing the AE team through coaching, performance management, and building fast-ramp onboarding for a technical product
- Designing the sales process including stage definitions, qualification criteria, and pricing/discount approvals
- Converting pilots to production commitments by setting entry criteria, success metrics, and timelines
- Running weekly forecasts, pipeline reporting, and partnering on quota and compensation plans
- Shaping go-to-market strategy by feeding deal learnings back to product and pricing teams
- Closing strategic deals alongside founders and Forward Deployed teams
- Cross-functional partnership with SDRs on meeting quality, post-sales on expansion, and marketing on pipeline targets
The role requires in-person presence Monday through Friday at SF and NY offices; remote and hybrid positions are not currently offered.
REQUIREMENTS:
- 7+ years in B2B sales with 2+ years leading a team; consistent quota achievement as an individual contributor and proven ability to hire and develop reps past quota
- Data-driven, first-principles operator who has scaled early sales teams to repeatable motions; systems-oriented with strong analytical discipline
- Track record selling technical products (developer tools, data platforms, APIs, cloud, AI infrastructure) to engineering, data, and ML teams; ability to engage deeply with engineers
- Experience closing consumption-based or committed-spend deals with forecasting expertise
- Fluency in sales-led, product-led, and hybrid motions; understanding of how product-led demand converts to enterprise deals
- Sales rigor and judgment; experience in organizations known for sales discipline; ability to identify which processes to harden versus where to experiment
- Direct communication style, high standards for feedback, fast execution, and team-focused mindset
BONUS: Experience with cloud marketplace selling, co-selling with cloud/data partners, or designing territory, compensation, and forecast plans.
