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stack-ai·NYC Office - 307 7th Ave

VP of Sales

RemoteLead / ManagerAshbyDirect apply link

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.

What You’ll Do

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

What We’re Looking For

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

Who You Are

  • 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