Sr Account Executive

Senior Account Executive

San Francisco, CA • Hybrid • Full-Time

About Cascade AI 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.

Why We Are Hiring

Cascade AI is expanding its sales team to capture significant market demand. We have a proven partnership-led growth model, a strong inbound pipeline, and enterprise clients already seeing measurable results. We need a Senior Account Executive who can close, self-source, and own the full revenue cycle — not wait for deals to be handed to them.

The Role

This is a quota-carrying role focused on mid-market and enterprise opportunities with organizations of 1,000+ employees. Many deals will be partner-influenced through HR consultancies, brokers, and ecosystem partners, but you will own the sales process end-to-end, from initial outreach through procurement and close. At Cascade, Sales owns the full workflow. While Marketing and partners contribute demand, you are responsible for ensuring it turns into revenue.

What You Will Own

Drive New Logo Revenue

• Prospect, develop, and close mid-market and 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 across HR, IT, Finance, and Procurement

stakeholders

• Drive executive-level conversations around ROI, AI transformation, and operational

efficiency

Convert and Control Partner-Sourced Pipeline

• Run point on opportunities introduced by brokers, consultants, and ecosystem

partners

• Lead joint discovery, demos, and executive presentations in co-sell environments

• Maintain full ownership of deal strategy, progression, and close while aligning with

partners

• Build trust and mindshare with partner contacts to generate consistent referral flow

Operate as an AI-First Seller

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. This

means more than using ChatGPT to draft emails.

• Leverage AI tools and Cascade’s internal agents to increase pipeline quality and

personal output

• Build and refine AI-assisted sales workflows — prospecting, data enrichment, meeting

prep, follow-up

• Continuously improve throughput through automation and structured execution

• Share workflows and tools with the broader team to lift collective performance

Build and Expand Strategic Accounts

• Create and execute detailed account plans for key enterprise targets

• 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

About You

• 3–5+ years of experience in mid-market or enterprise SaaS sales

• Proven track record of consistent quota attainment — start to finish, not just pipeline

contribution

• Experience self-sourcing a meaningful portion of your own pipeline

• Comfortable owning inbound conversion from MQL to meeting to qualified opportunity

• Experience selling into complex, multi-stakeholder environments

• Strong executive presence and outcome-based selling skills

• Curious and proactive about using AI tools to improve performance

• Some experience in a startup or early-stage environment where ambiguity is the

norm

We are open to candidates from two backgrounds: those who have sold AI solutions to CIOs, and those who have sold HR or benefits solutions to CHROs and VPs of Total Rewards. You will need to learn the other side — what matters is the right mindset, not a perfect resume match. Experience selling through or building PE or HR consultancy channels is a meaningful advantage. Candidates who have built those channels are especially welcome.

Non-Negotiables

• Demonstrable track record of closing deals on quota — at least two full cycles, start to finish

• Hunter mentality — if your expectation is a full pipeline handed to you, this is not the

right role

Success in Year One

• Meet and exceed quota attainment through consistent sales execution

• Build a healthy, self-generated pipeline alongside partner-sourced opportunities

• Consistently convert MQLs into qualified executive meetings

• Establish repeatable, AI-driven sales workflows that improve your own and the team’s

performance

• Expand at least one enterprise account post-initial close

Compensation & Location

• Location: San Francisco, CA — Hybrid, 3 days per week in office (address TBD)

• Base Salary: $110,000–$125,000

• OTE: $220,000–$250,000 (50/50 split)

• Equity: Stock options — details to be confirmed

• Travel: Estimated 25–30% for client meetings and industry events

Our Culture

Our founders honed their craft under Satya Nadella’s learn-it-all culture at Microsoft, where listening first drove the best outcomes. We carry that into everything we build. We operate with analytical rigor, customer obsession, and a bias toward action. We value people who take ownership, navigate ambiguity without losing focus, and contribute to a culture of transparency and collective success. Our core competencies: Drive for Results, Customer Focus, Collaboration, Analytical Thinking, Innovation & Leadership, and Dealing with Ambiguity.

Our Commitment to Diversity

Cascade AI is an equal opportunity employer. We believe diversity drives innovation and are committed to building a team that reflects a variety of backgrounds, perspectives, and skills. We do not discriminate on the basis of race, religion, color, national origin, gender identity or expression, sexual orientation, age, disability, or veteran status.

Ready to Apply?

If you are a driven sales professional ready to shape the future of enterprise AI, we want to hear from you. Apply today and help us transform how the world’s leading companies support their people.

Compensation:
$220,000-$250,000 per year