Middle Sales Account Executive

Own the full cycle—from first conversation to signed contract—selling AI solutions that drive real business outcomes.

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 a Sales Account Executive at Contextual, you will drive new customer acquisition through inbound lead conversion, targeted outbound selling, and referral partner collaboration. You'll own the full sales cycle—from prospecting and discovery through negotiation and close—for AI-powered solutions built on the Contextual.io platform. This is a high-impact individual contributor role ideal for someone who is energized by consultative selling, enjoys learning new businesses, comfortable navigating complex solution conversations, and motivated to grow alongside a fast-moving company.

Key Responsibilities

Own and Execute the Full Sales Cycle

• 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.

Partner Collaboration & Co-Selling

• 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.

Cross-Functional Collaboration

• 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.

Sales Discipline and Reporting

• 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.

Customer & Market Insight

• 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.

Required Qualifications

• 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.

What We Offer

• Competitive salary and benefits package.
• Unlimited vacation, where time off is encouraged.
• Flexible working hours and remote work options.
• Opportunities for professional growth and development.
• Collaborative and inclusive work environment.
• The chance to work on innovative projects with a talented team.