VP of Sales (AI)

Location: San Francisco headquarters; Wednesdays work from home.

Compensation: $300,000–$500,000 on-target earnings, plus equity and commission.

Company

Builds an AI-native CRM that turns email, calendar, and meeting interactions into organized account context, tasks, follow-ups, and insights.

What you will do

• Build the outbound sales motion from the ground up, including account selection, sequencing, and territory design.
• Move the business upmarket into larger commercial and mid-market deals in the $50,000–$100,000 range.
• Lead discovery, proof-of-value processes, implementation planning, and security and migration reviews with technical buyers.
• Hire and lead senior sales representatives while maintaining the existing high-velocity inbound motion.
• Shape ICP, segmentation, positioning, packaging, and headcount allocation with the founders, Product Marketing, and GTM leadership.
• Own quota, capacity planning, forecasting, deal reviews, qualification stages, and CRM discipline.

Requirements

• Experience building an outbound motion from zero, including account selection, sequences, and channel validation.
• Experience moving a company from smaller deals to larger commercial or mid-market sales.
• Recent experience selling to CTOs and CIOs and handling security reviews and migration planning.
• Experience hiring senior representatives who source their own pipeline and running velocity and upmarket motions simultaneously.
• Strong commercial fluency across segmentation, quota modeling, capacity planning, and headcount allocation.
• Experience selling a CRM, GTM tool, or another product purchased by sales leaders and RevOps.

Nice to have

• Founding AE or first sales hire experience.
• Experience navigating a pricing model transition, such as moving from seats to usage.
• Experience building a sales team on top of a self-serve or product-led motion.
• Experience being the first sales leader at a company that grew from single-digit to meaningful revenue in under two years.

Culture & Benefits

• Early-stage operating pace with direct reporting to the CEO.
• Meaningful early equity and competitive compensation.
• Medical, dental, and vision insurance.
• Three weeks of PTO, 11 paid company holidays, and a winter holiday break.
• Three months of paid family leave and a 401(k) plan.
• Regular team dinners, events, offsites, retreats, commuter and lunch stipends.