The RoleWe'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 DoBuild 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 ForMust-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
