Account Executive (Mid-Market) (San Jose)
Cascade AI, San Jose, California, United States, 95199
About Cascade
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.
We partner with forward-thinking employers to deliver instant, personalized, and secure AI-driven support to reduce administrative burden, improve service delivery, and modernize internal operations.
Backed by Gradient Ventures (Google’s AI fund) and trusted by large enterprise customers, Cascade is defining the next category of AI-native enterprise software.
The Role We’re hiring a Mid-Market Account Executive to drive new business across growth-stage and mid-market employers.
This is a quota-carrying, full-cycle sales role. Typical deal sizes range from $40K–$150K in ACV, with opportunities to expand accounts over time.
You will own the entire workflow, from pipeline generation and MQL conversion to discovery, proposal, negotiation, and close.
At Cascade, Sales owns revenue end-to-end. That includes: Generating outbound pipeline Converting inbound MQLs into qualified meetings Running structured discovery Advancing and closing opportunities
You are expected to maintain 3–5x pipeline coverage relative to quota and manage forecasting with rigor and discipline.
This is a hunter role with high autonomy and high accountability.
You’ll work closely with the CEO, Head of Sales, and Marketing to refine messaging, target the right accounts, and build a repeatable mid-market motion.
What You’ll DoGenerate Pipeline Prospect into target accounts through cold calls, email sequences, LinkedIn, referrals, and creative outreach. Build and maintain a healthy, self-sourced pipeline. Convert inbound MQLs into qualified discovery meetings and pipeline. Maintain 3–5x pipeline coverage at all times. Run Full-Cycle Sales Own every stage of the sales process, from first touch to signed contract. Run structured discovery and stakeholder mapping. Deliver tailored demos and executive presentations. Build ROI-driven business cases for HR, IT, and Finance buyers. Navigate procurement and negotiate contracts confidently. Operate as an AI-First Seller Leverage AI tools and Cascade’s internal agents to increase productivity and improve deal quality. Use automation and structured workflows to manage pipeline efficiently. Contribute ideas to improve how the sales team uses AI to win. Collaborate & Improve the Motion Partner with Marketing to optimize messaging and campaigns. Share field insights to sharpen positioning and competitive strategy. Help define what a repeatable mid-market playbook looks like at Cascade. About You 3–5+ years of B2B SaaS sales experience (AI, HR Tech, IT, or workflow platforms preferred). Proven ability to generate your own pipeline, not just work inbound. Comfortable converting MQLs into qualified meetings. Experience running full-cycle sales independently. Strong business acumen with the ability to build ROI-driven proposals. Disciplined pipeline management and accurate forecasting. Energized by startup environments and building from zero to one. Curious and proactive about using AI tools to improve performance. Success Looks Like Within your first year, you: Consistently hit or exceed quota through a mix of self-sourced and inbound-converted pipeline. Maintain strong pipeline coverage (3–5x) with disciplined forecasting. Close multiple mid-market deals. Build a predictable outbound motion for mid-market accounts. Improve sales productivity by effectively leveraging AI tools. Contribute meaningfully to Cascade’s evolving GTM playbook.
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.
We partner with forward-thinking employers to deliver instant, personalized, and secure AI-driven support to reduce administrative burden, improve service delivery, and modernize internal operations.
Backed by Gradient Ventures (Google’s AI fund) and trusted by large enterprise customers, Cascade is defining the next category of AI-native enterprise software.
The Role We’re hiring a Mid-Market Account Executive to drive new business across growth-stage and mid-market employers.
This is a quota-carrying, full-cycle sales role. Typical deal sizes range from $40K–$150K in ACV, with opportunities to expand accounts over time.
You will own the entire workflow, from pipeline generation and MQL conversion to discovery, proposal, negotiation, and close.
At Cascade, Sales owns revenue end-to-end. That includes: Generating outbound pipeline Converting inbound MQLs into qualified meetings Running structured discovery Advancing and closing opportunities
You are expected to maintain 3–5x pipeline coverage relative to quota and manage forecasting with rigor and discipline.
This is a hunter role with high autonomy and high accountability.
You’ll work closely with the CEO, Head of Sales, and Marketing to refine messaging, target the right accounts, and build a repeatable mid-market motion.
What You’ll DoGenerate Pipeline Prospect into target accounts through cold calls, email sequences, LinkedIn, referrals, and creative outreach. Build and maintain a healthy, self-sourced pipeline. Convert inbound MQLs into qualified discovery meetings and pipeline. Maintain 3–5x pipeline coverage at all times. Run Full-Cycle Sales Own every stage of the sales process, from first touch to signed contract. Run structured discovery and stakeholder mapping. Deliver tailored demos and executive presentations. Build ROI-driven business cases for HR, IT, and Finance buyers. Navigate procurement and negotiate contracts confidently. Operate as an AI-First Seller Leverage AI tools and Cascade’s internal agents to increase productivity and improve deal quality. Use automation and structured workflows to manage pipeline efficiently. Contribute ideas to improve how the sales team uses AI to win. Collaborate & Improve the Motion Partner with Marketing to optimize messaging and campaigns. Share field insights to sharpen positioning and competitive strategy. Help define what a repeatable mid-market playbook looks like at Cascade. About You 3–5+ years of B2B SaaS sales experience (AI, HR Tech, IT, or workflow platforms preferred). Proven ability to generate your own pipeline, not just work inbound. Comfortable converting MQLs into qualified meetings. Experience running full-cycle sales independently. Strong business acumen with the ability to build ROI-driven proposals. Disciplined pipeline management and accurate forecasting. Energized by startup environments and building from zero to one. Curious and proactive about using AI tools to improve performance. Success Looks Like Within your first year, you: Consistently hit or exceed quota through a mix of self-sourced and inbound-converted pipeline. Maintain strong pipeline coverage (3–5x) with disciplined forecasting. Close multiple mid-market deals. Build a predictable outbound motion for mid-market accounts. Improve sales productivity by effectively leveraging AI tools. Contribute meaningfully to Cascade’s evolving GTM playbook.