VP of Sales

About the role

We're looking for a high-impact, hands-on VP of Sales to build StackAI's GTM motion from the ground up. This is a rare opportunity to join a fast-growing AI infrastructure company at a pivotal moment, owning everything from early playbook creation to hiring and scaling a high-performing sales organization. You'll partner directly with the founders, Product, Marketing, and Customer Success to turn an already-viral product into a predictable, scalable enterprise revenue machine. This role is ideal for someone who has built modern SaaS sales motions from $10 to $50M+ ARR, thrives in fast-moving environments, and loves being deeply involved in product and customer discovery.

Responsibilities

• Build the Sales Engine
• Own StackAI's revenue strategy, sales motion, forecasting, and execution
• Develop our GTM playbook across ICP definition, qualification, segmentation, and pricing
• Build and optimize repeatable sales processes for pipeline creation, deal management, and customer expansion
• Close Strategic Deals
• Personally run and close high-value pipeline in the first 6-12 months
• Partner with founders on enterprise sales cycles and strategic logo acquisition
• Serve as the executive sponsor for key customers and prospects
• Scale the Team
• Build and manage a world-class sales organization across AE, SDR, and Sales Engineering
• Establish hiring profiles, onboarding playbooks, compensation structures, and performance frameworks
• Create a culture of operational excellence, accountability, and continuous improvement
• Partner Across the Company
• Work closely with Product and Engineering to deliver customer feedback and influence our roadmap
• Collaborate with Marketing to align on messaging, content, pipeline generation, and GTM campaigns
• Align with Customer Success to ensure smooth onboarding, retention, and expansion
• Drive Predictable Growth
• Own sales forecasting, dashboards, KPIs, and pipeline hygiene
• Implement systems and tooling needed for scale
• Optimize pricing, packaging, and ROI storytelling to accelerate enterprise adoption

Requirements

• Must-Have Experience
• 6+ years in B2B SaaS sales, including 3+ years leading and scaling teams
• Experience owning ARR growth ideally from ~$10M → $50M+
• Demonstrated success closing enterprise deals ($50K-$500K+ ACV)
• Hands-on operator capable of both running deals and building repeatable systems
• Strong understanding of modern SaaS GTM motions (PLG + top-down enterprise)
• Proven track record hiring, coaching, and developing top sales talent
• Deep comfort selling technical products (bonus: workflow automation, developer tools, or AI/ML)
• Bonus Points
• Experience at a high-growth AI, automation, or infrastructure startup
• Familiarity with PLG → enterprise transition
• Experience in first-principles pricing/packaging and early enterprise contracting
• Strong network of AEs, SDRs, and sales engineers
• You're a builder, comfortable creating structure out of ambiguity
• You love rolling up your sleeves and setting the pace yourself
• You're obsessed with customers and equally obsessed with process
• You think strategically but execute rapidly
• You thrive in early-stage chaos and want to own the full revenue machine
• You are deeply metrics-driven and comfortable forecasting in imperfect conditions
• You communicate clearly, transparently, and cross-functionally
• Why Join StackAI
• Ownership of the entire GTM function in one of the fastest-growing AI workflow companies
• The chance to turn a viral product with huge bottom-up adoption into a scalable enterprise business
• Partner directly with founders (MIT PhDs) and a world-class engineering team
• Massive market tailwinds with AI workflow automation are exploding
• Competitive compensation, meaningful equity, and the ability to shape our culture and future

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