SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
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 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:
- Building and closing pipeline across outbound, inbound, events, and partnerships through direct prospecting, account research, executive networking, and event follow-up
- Owning full-cycle sales from first touch through procurement, security review, legal, close, and expansion
- Leading complex, multi-stakeholder sales cycles involving HR, IT, Finance, Procurement, and executive buyers
- Creating and executing outbound strategies for priority accounts
- Positioning and selling both Cascade's HR and IT modules, identifying land-and-expand opportunities
- Developing deep product fluency and translating customer pain into compelling demos and business cases
- Providing structured feedback to Product, Marketing, and Customer Success to refine messaging, packaging, and sales playbook
- Using AI tools and Cascade's internal agents to improve productivity, research, outreach, and pipeline quality
This is an early-stage sales role with no SDR support—you are expected to generate your own pipeline while working closely with the CEO, other AEs, Marketing, Product, and Customer Success.
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.
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
