VP of Sales
$250k - $350k USD
About Chalk
Chalk is building the data platform that powers the future of machine learning applications. We tear down complexity, latency, and scale barriers that have traditionally constrained ML capabilities. Our platform combines Rust-speed performance with elegant tools that developers love to use. Leading companies depend on Chalk for everything from stopping fraudulent credit card swipes, verifying identities, and maximizing clean energy capture. We've recently raised a $50 million Series A, led by Felicis.
The Role
We’re hiring a VP of Sales to take a strong early GTM motion and scale it into a world-class revenue engine. Chalk already has traction with leading enterprise customers and a proven motion led by the founding team. Your mandate is to build on that foundation—bringing structure, repeatability, and leadership to help us scale revenue, grow the team, and win key markets.
You'll report directly to the CEO and work closely with product, engineering, and marketing to drive strategic deals and build a sales org that thrives in complex, technical environments.
What You’ll Do
- Scale a Working Sales Motion Take an early-stage GTM engine and professionalize it—refining process, defining KPIs, tightening forecasting, and codifying what’s working.
- Own the Sales Strategy Define how we scale ARR, set the roadmap for growth, segment focus, team structure, and build pipeline.
- Close Strategic Deals Continue running high-value enterprise sales cycles yourself—especially in the near term. Lead by example with rigor, technical depth, and a sharp understanding of customer needs.
- Build & Lead the Team Hire, develop, and retain a top-tier sales team. Define roles, comp plans, onboarding, and performance management as we grow.
- Collaborate Cross-Functionally Partner with product, engineering, and marketing to sharpen our ICP, tighten feedback loops, and align roadmap with market signals.
- Bring Operational Excellence Implement the right tools, reporting, and systems for a modern, data-driven sales org. Forecast with accuracy and coach with clarity.
About You
- Proven Experience at This Stage You’ve led sales at a Series A/B startup through rapid growth—owning revenue and growing a team as the company scaled from $XXm to $YYYm+ in ARR.
- Enterprise Sales Expertise You have a strong track record closing complex, multi-stakeholder enterprise deals—often with technical buyers and long sales cycles.
- Technically Fluent You’re comfortable selling to engineering, data, and ML teams. You ask sharp questions, understand the architecture, and engage productively with deeply technical stakeholders.
- Team-Oriented Operator You thrive in collaborative environments, especially alongside product and engineering. You’re not territorial—you’re here to win as a team.
- Hands-On and High-Ownership You’re willing to get in the weeds, close deals directly, and hold a high bar. You bring urgency, structure, and clarity.
- Candid and Outcome-Driven You communicate directly, act with intensity, and care deeply about performance. You’re competitive, focused, and coachable—and you expect the same from your team.
Nice to Have
- Experience with ML/AI infrastructure, developer tools, or data platforms
- Familiarity with selling to technical audiences (e.g., ML engineers, infra teams, heads of data)
What We Offer
Benefits
- ⚕️Comprehensive medical, dental, and vision insurance
- 🏦 Flexible Spending Account (FSA), Health Savings Account (HSA)
- 🦮 Expert Healthcare Guidance
- 💵 Retirement savings
- 🎄15 company holidays each year
- 🏖️15 days of personal time off each year
- 🚌 Flex Commuter Benefits
- 🌮 Daily lunch and dinner on Chalk
- 🥤Office is fully-stocked with drinks and snacks to fuel your work day.
- 🍽️ Staying late? Dinner is on us
- 🚖 Staying even later? Grab an Uber / Lyft home on Chalk
Compensation
Salary Range
$250,000 – $350,000 // OTE $500,000 - $700,000 - Offers equity + benefits
Chalk offers early team members a generous salary + equity package based on experience and competitive benefits.
Actual compensation awarded to successful candidates will be based on several factors, including but not limited to: market, location, scope of the position and individual qualifications objectively assessed during the interview process.
Our comprehensive total package plays a major role in how we recognize individuals for the impact they will have on Chalk’s growth and us achieving our goals.
Why Chalk?
You’ll be joining a technical, fast-moving team at the inflection point: strong product-market fit, happy customers, and a clear path to scale. If you’ve done this before—and you’re excited to do it again, with even more ownership—let’s talk.
Inclusivity
Chalk is an equal opportunity employer. We value diversity and inclusion and provide reasonable accommodations to anyone in need of individualized support.