Senior Account Executive

About Cascade AI

Cascade AI is an AI-first, agentic platform changing the operating stack for HR and IT teams.

Our specialized AI agents automate high-impact back-office workflows across two core modules: HR and IT. For HR teams, By combining vertical intelligence with security, integrations, and workflow automation, Cascade helps large organizations modernize how internal operations run, reduce administrative burden, and deliver a better employee experience.

We’ve raised $5.4M led by Gradient Ventures, Google’s AI fund, built strategic partnerships with Microsoft and Google, and are live with Fortune 100 customers. We are defining a new category of agentic AI for enterprise service delivery and scaling quickly.

The Role

We are hiring an Account Executive to own full-cycle sales across Cascade’s four core channels: events, partnerships, inbound, and outbound.

This is a quota-carrying Sales role focused on complex, high-value opportunities with large organizations. You will own the sales process end-to-end, from generating demand and converting meetings through discovery, business case development, procurement, close, and expansion.

This is an early-stage sales role. There is no SDR. You are expected to generate your own pipeline across outbound, events, partner relationships, and inbound follow-up. Marketing and partners will contribute demand, but you are accountable for turning that demand into qualified pipeline and revenue.

You’ll work closely with the CEO, other AEs, Marketing, Product, and Customer Success to win customers across HR and IT, sell both Cascade modules, and shape the repeatable sales motion for a category-defining company.

What You’ll Do

Own Revenue Across All Sales Channels

• Build and close pipeline across outbound, inbound, events, and partnerships.

• Generate qualified opportunities through direct prospecting, account research, executive networking, partner relationships, and event follow-up.

• Convert inbound interest into discovery calls, executive meetings, and qualified opportunities.

• Own full-cycle sales from first touch through procurement, security review, legal, close, and expansion.

• Lead complex, multi-stakeholder sales cycles with HR, IT, Finance, Procurement, and executive buyers.

• Drive conversations around AI transformation, operational efficiency, employee experience, and business impact.

Build Your Own Pipeline

• Create and execute outbound strategies for priority accounts.

• Turn events into qualified meetings and active opportunities.

• Follow up quickly and thoughtfully on inbound demand.

• Develop partner-influenced opportunities while maintaining ownership of the sales process.

• Maintain disciplined pipeline hygiene, forecasting, and next-step execution.

Sell Across HR and ITSM

• Position Cascade’s HR and IT modules clearly and credibly.

• Understand customer pain across HR service delivery, IT service management, employee support, workflow automation, analytics, and internal operations.

• Identify land-and-expand opportunities across departments, functions, and geographies.

• Help customers understand how agentic AI changes the way HR and IT work gets done.

Operate With a Product Mindset

• Develop deep fluency in Cascade’s product, workflows, integrations, and customer use cases.

• 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.

• Help refine messaging, packaging, pricing, competitive positioning, and the sales playbook.

• Think beyond closing the deal: understand what will make the customer successful after purchase.

Operate as an AI-First Seller

• Use AI tools and Cascade’s internal agents to improve productivity, research, outreach, meeting preparation, follow-up, and pipeline quality.

• Build and refine AI-assisted sales workflows.

• Continuously improve your own output through automation, structured execution, and better insight generation.

About You

• 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; you have built meaningful pipeline without relying on 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.

• Able 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 if you’ve sold to CHROs, CIOs, Heads of Benefits, HR Ops, Employee Experience, IT, ITSM, or Service Delivery leaders.

Success in Year One

• Build a healthy self-generated pipeline across outbound, events, partnerships, and inbound.

• Consistently convert demand into qualified meetings and active opportunities.

• Close multiple high-value customer deals across HR and ITSM use cases.

• Establish repeatable, AI-driven workflows for prospecting, discovery, follow-up, and deal execution.

• Expand at least one major customer beyond the initial use case or module.

• Provide Product and Marketing with high-quality market feedback from real sales cycles.

Cascade is an equal opportunity employer. We celebrate diversity and are committed to building an inclusive team.