Sales Account Executive

Contextual.io is a company that partners with clients to deliver cutting-edge AI solutions aimed at transforming tasks and operations. As a Sales Account Executive, you will manage the full sales cycle, from prospecting to closing, driving new customer acquisition and collaborating with partners to enhance sales efforts.

Responsibilities:

• Manage the complete sales cycle from prospecting and discovery to negotiation and close
• Build, maintain, and accurately forecast a high-quality pipeline aligned to revenue targets
• Drive outbound outreach to target accounts and industries; identify and engage decision makers across functional and executive levels
• Respond quickly and professionally to inbound leads, ensuring high-quality discovery, clear qualification, and rapid follow-up
• Work with Sales Engineering resources to determine solution feasibility and how best to demonstrate confidence in outcomes
• Deliver compelling presentations, demos, proofs-of-concept, and ROI/value narratives tailored to customer needs and use cases
• Collaborate with the Delivery Team to scope AI solutions that align with client goals and platform capabilities
• Get to signature
• Support partner-sourced opportunities by providing deal support, co-selling, and ensuring a seamless prospect experience
• Work alongside partners (e.g. investment firms, technology firms, consultants, boutique agencies) to progress referral-generated pipeline
• Provide feedback on partner engagement quality and deal outcomes to help evolve the partner program
• Work with Product and Delivery to translate customer problems into product feedback and roadmap insights
• Partner with Marketing to refine outbound campaigns, sales assets, and GTM messaging based on front-line buyer interactions
• Support Delivery and Customer Success with clear deal documentation and handoff to ensure seamless onboarding
• Maintain accurate and up-to-date CRM records, pipeline data, and deal documentation
• Follow established sales processes, playbooks, and qualification frameworks
• Track and report on key performance metrics including pipeline coverage, conversion rates, sales cycle length, and forecast accuracy
• Contribute to the refinement of outreach scripts, qualification guidelines, and sales collateral based on what's working in the field
• Develop deep expertise in Contextual's platform, value drivers, customer use cases, and competitive landscape
• Stay current on market trends, buyer personas, and emerging needs across target industries
• Share front-line insights and recommendations that inform GTM strategy, pricing, packaging, and positioning

Requirements:

• 3+ years of experience in B2B software or technology sales with demonstrated quota attainment
• Experience managing a full sales cycle, including prospecting, discovery, solution positioning, negotiation, and close
• Strong consultative selling skills with the ability to understand complex business problems and articulate solution value
• Excellent communicator - comfortable engaging stakeholders from end users to senior executives
• Ability to thrive in a fast-paced, early-stage environment: resourceful, adaptable, and energized by building
• Disciplined approach to pipeline management, forecasting, and CRM hygiene
• At this time, we are unable to hire outside of the US or sponsor employment visas (including H-1B, TN, or other work authorizations) for this position