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Cascade AI is an AI-first, agentic platform automating high-impact back-office workflows for HR and IT teams at large enterprises. The company has raised $5.4M led by Gradient Ventures (Google's AI fund), built partnerships with Microsoft and Google, and is live with Fortune 100 customers.
As Senior Account Executive, you will own full-cycle sales across Cascade's four core channels: events, partnerships, inbound, and outbound. This is a quota-carrying role focused on complex, high-value opportunities with large organizations. You will manage the entire sales process from demand generation and discovery through business case development, procurement, close, and expansion.
Key responsibilities include:
• Build and close pipeline across outbound, inbound, events, and partnerships through direct prospecting, account research, executive networking, and event follow-up.
• Own full-cycle sales from first touch through procurement, security review, legal, close, and expansion, managing complex multi-stakeholder sales cycles with HR, IT, Finance, Procurement, and executive buyers.
• Generate your own pipeline with discipline and rigor; there is no SDR support. You are accountable for turning marketing and partner-contributed demand into qualified pipeline and revenue.
• Position and sell both Cascade's HR and IT modules, identifying land-and-expand opportunities across departments, functions, and geographies.
• Develop deep product fluency and translate customer pain into sharp discovery, compelling demos, and clear business cases.
• Bring structured feedback from live deals back to Product, Marketing, and Customer Success to refine messaging, packaging, pricing, competitive positioning, and the sales playbook.
• Use AI tools and Cascade's internal agents to improve productivity, research, outreach, meeting preparation, follow-up, and pipeline quality.
• Work closely with the CEO, other AEs, Marketing, Product, and Customer Success to shape the repeatable sales motion for a category-defining company.
Year-one success metrics include building a healthy self-generated pipeline, consistently converting demand into qualified meetings, closing multiple high-value customer deals, establishing repeatable AI-driven workflows, expanding at least one major customer, and providing high-quality market feedback to Product and Marketing.
REQUIREMENTS:
• 5–8+ years of SaaS sales experience, including selling to large, complex organizations.
• Required: experience selling in an early-stage startup environment.
• Proven track record closing high-value, multi-stakeholder deals.
• Strong self-sourcing discipline; demonstrated ability to build meaningful pipeline without SDR support.
• Comfortable owning all channels: outbound, inbound, events, and partnerships.
• Experience selling technical, workflow, AI, HR, ITSM, or operational software.
• Strong executive presence and value-based selling skills.
• Ability to run rigorous discovery, build business cases, manage complex sales cycles, and navigate procurement.
• Product-minded, curious, and able to connect customer needs to product capabilities and roadmap signal.
• Proactive about using AI tools to improve sales performance.
• Bonus: experience selling to CHROs, CIOs, Heads of Benefits, HR Ops, Employee Experience, IT, ITSM, or Service Delivery leaders.
