Part strategist, part closer—map the AI roadmap, then sell the future state.

About Contextual

Contextual partners with clients to deliver cutting-edge AI solutions that transform tasks, processes and operations with a focus on scale and ROI. By leveraging the Contextual.io platform, we help organizations streamline and automate workflows, drive organization and operational efficiencies, and unlock new revenue opportunities.

About the Role

As an AI Transformation Partner at Contextual.io, you sit at the intersection of strategic consulting, technical architecture, and sales. You aren’t just selling a platform; you are selling a future state. Your mission is to work within our existing high-value accounts to identify friction points and translate them into a "Roadmap of the Possible."

This is a "consultative selling" role. You will be responsible for uncovering high-impact AI use cases, rapidly prototyping Proof of Concepts (POCs) using the Contextual.io platform, and closing expansion deals. You are the bridge between a client’s messy operational reality and a streamlined, AI-orchestrated future.

Key Responsibilities

1. Strategic Roadmap & "Art of the Possible"/Close the sale

• Visionary Consulting: Lead deep-dive discovery sessions with C-suite and VP-level stakeholders to map out AI maturity journeys.
• Opportunity Mapping: Identify repeatable patterns for AI orchestration within complex workflows, focusing on ROI and organizational scale.
• Account Expansion: Act as the primary engine for "land and expand" strategies, turning a single initial use case into a multi-year transformation roadmap.

• Deal Closure: Lead the end-to-end sales cycle for expansion opportunities, from initial demo to contract negotiation and closing.

2.  Client Success & Value Realization

• Value Engineering: Define and track the KPIs that prove the success of AI implementations, ensuring clients see measurable margin expansion or revenue growth.
• Strategic Advisory: Serve as a long-term advisor to clients, helping them navigate the rapidly evolving AI landscape.
• Feedback Loop: Partner with our Product team to funnel "front-line" insights into the development of the Contextual.io platform.

Required Qualifications

• 5+ years of experience in Technical Sales, Solutions Architecture 
• Consultative Solutioning: Ability to create roadmaps with ROI analysis, with a consultative solution approach
• The "Builder" Mindset: Comfortable working in "low-code/no-code" environments and a deep understanding of AI workflows. You don’t need to be a Senior Dev, but you must be able to configure a quick technical demo.
• Sales Hunter Instinct: Proven track record of closing six-figure expansion deals and navigating enterprise procurement.
• Exceptional Communication: Ability to command a room of executives and then whiteboard a technical workflow with an Ops manager.

Preferred Qualifications

• Hands-on experience with LLM orchestration, prompt engineering, or automation platforms (e.g., Zapier, UiPath, Make, LangChain)

What We Offer

• Competitive Compensation: High-upside commission structure tied to account expansion and revenue growth.
• Autonomy: The freedom to own your accounts and experiment with creative AI solutions.
• Growth: Be at the forefront of the AI revolution, using a platform (Contextual.io) that is actively reshaping industry standards.
• Benefits: Unlimited vacation, remote-first culture, and comprehensive health/wellness packages.