Deployment Strategist

Location: New York, NY (NYC preferred)
Work Model: Remote (optional NYC office access); field-based travel expected (~40%)
Industry: Healthcare SaaS / AI
Compensation: $160,000–$300,000 OTE (50/50 split). Equity/benefits details available during process.

About the Company

Our partner is a Series A–stage healthcare SaaS company building an AI-native platform that helps home care agencies deliver care more efficiently. The team operates with a high-velocity, innovation-driven culture and a personable brand that stands out in a legacy-heavy industry. With strong momentum and a lean, high-ownership environment, they are scaling their enterprise motion across the U.S.

The Opportunity

This Deployment Strategist (Enterprise) role is a full-cycle, field-forward position responsible for taking enterprise opportunities from initial outreach through close. You’ll inherit an active pipeline and also build net-new pipeline, helping scale a repeatable enterprise motion. Enterprise deals are defined as $500K+ and typically involve complex, multi-stakeholder buying processes.

You’ll partner closely with the Head of Sales and a small GTM team (currently three people) in a high-agency environment where execution, responsiveness, and strong deal ownership matter. As enterprise expands nationally, this role offers meaningful runway to grow scope and help lead enterprise efforts over time.

Responsibilities

• Own the full enterprise cycle: prospecting, discovery, multi-threading, negotiation, and close
• Take over and advance an existing enterprise pipeline while sourcing and developing new opportunities
• Lead complex buying processes with multiple decision-makers and stakeholders
• Execute field-based selling, including customer meetings, on-site visits, and industry events (~40% travel)
• Collaborate with internal teams to refine enterprise playbooks, messaging, and deployment approach
• Maintain accurate CRM hygiene, pipeline forecasting, and consistent deal progression reporting
• Represent the company at conferences and in-market events, building trusted relationships with senior stakeholders
• Bring structured customer feedback into the organization to strengthen GTM execution and enablement

Requirements

• 3+ years of closing experience in a quota-carrying role (SaaS required)
• Proven success closing complex, multi-stakeholder deals (enterprise-level; $500K+ strongly preferred or equivalent complexity)
• Strong outbound/prospecting skills and comfort running a true full-cycle motion
• Clear ability to articulate closed-won deal stories, qualification rigor, and how you drive deals to completion
• Comfort operating in a fast-moving, high-ownership environment with evolving processes
• Willingness to travel frequently (~40%) for in-person selling, deployments, and conferences
• Experience selling into healthcare or home care is a plus, but not required