VP of Sales
$50k - $500k USD
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