Senior Account Executive

Cascade AI is an AI-first, agentic platform for back-office operations automation, with initial use cases in HR and IT.

Our specialized AI agents automate high-impact internal workflows, from employee-facing support like benefits decision support, leave planning, onboarding, and policy guidance, to operational automation across HR and IT teams, including analytics, service workflows, and compliance processes.

By combining vertical intelligence with enterprise-grade security and infrastructure, Cascade helps large organizations modernize internal operations, reduce administrative burden, and elevate the 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 enterprises. We are defining the category of agentic AI for enterprise operations and scaling rapidly into large, complex organizations.

We are hiring an Enterprise Account Executive to close large, complex enterprise deals.

This is a quota-carrying role focused on 6–7 figure ARR opportunities with Fortune 100–1000 employers. Many deals will be partner-influenced (brokers, consultants, ecosystem partners), but you will own the sales process end-to-end, from initial outreach and meeting conversion through procurement and close.

At Cascade, Sales owns the full workflow. That includes:

• Generating pipeline
• Converting MQLs into qualified meetings
• Running discovery and progressing opportunities
• Closing and expanding accounts

While Marketing and partners contribute demand, you are responsible for ensuring it turns into revenue.

Cascade is an AI-first company. We expect every team member, especially in Sales, to leverage AI tools and internal agents to drive productivity, insight, and execution quality.

You’ll work closely with the CEO, Head of Sales, Marketing, Product, and Customer Success to win and expand enterprise accounts.

• Prospect, develop, and close enterprise opportunities.
• Generate qualified pipeline through outbound, account-based strategies, executive networking, and partner relationships.
• Convert inbound MQLs into executive meetings and qualified pipeline.
• Lead complex, multi-threaded sales cycles (6–12+ months).
• Engage senior stakeholders across HR, IT, Finance, and Procurement.
• Drive executive-level conversations around ROI, AI transformation, and operational efficiency.

• Run point on opportunities introduced by brokers, consultants, and ecosystem partners.
• Lead joint discovery, demos, and executive presentations in co-sell environments.
• Maintain ownership of deal strategy, progression, and close while aligning with partners.

• Leverage AI tools and Cascade’s internal agents to increase productivity and pipeline quality.
• Collaborate with the team to build and refine AI-assisted sales workflows.
• Continuously improve personal output through automation, insight generation, and structured execution.

• Create and execute detailed account plans.
• Identify land-and-expand opportunities across functions and geographies.
• Navigate enterprise procurement, security reviews, and legal processes.

• Provide structured feedback to Product and Marketing based on live deal cycles.
• Help refine messaging, pricing strategy, and enterprise packaging.
• Contribute to building a repeatable, AI-enhanced enterprise sales playbook.

• 5–8+ years of enterprise SaaS sales experience.
• Proven track record of closing 6–7 figure ARR deals.
• Experience self-sourcing a meaningful portion of your pipeline.
• Comfortable owning inbound conversion (MQL → meeting → qualified opportunity).
• Experience selling into complex, multi-stakeholder environments.
• Strong executive presence and value-based selling skills.
• Disciplined pipeline management and accurate forecasting.
• Curious and proactive about using AI tools to improve performance.

Bonus if you’ve sold into CHRO, CIO, Head of Benefits, HR Ops, or IT leadership.

• Build a healthy, self-generated enterprise pipeline.
• Consistently convert MQLs into qualified executive meetings.
• Close multiple enterprise deals (direct and partner-influenced).
• Establish repeatable, AI-driven sales workflows.
• Expand at least one major enterprise account post-initial sale.