Regional Sales Director (East Region) - Senior Living & Skilled Nursing SaaS

About Sage

Millions of people depend on senior care getting better, and Sage is a collaborative team of ambitious, multi-disciplinary entrepreneurs on a mission to reinvent senior care with a modern operating system for caregivers. The first baby boomers turn 80 this year, and the population most likely to need daily care will grow faster than the buildings, staff, or systems available to serve it. Sage connects hardware senior care runs on, including nurse call, fall management, and wander management, with software caregivers actually use. This consistent use produces reliable data, giving operators a true picture of how their communities are running.

About This Role

Sage has raised $124M, including a $65M Series C led by Goldman Sachs Alternatives, and is rapidly scaling its new business sales organization. We're looking for a Regional Sales Director to lead our East region, managing a growing team of enterprise Business Development Executives selling complex, multi-site solutions into senior living and post-acute operators.

This is a hands-on sales leadership role focused on coaching and talent development, enterprise deal execution, and operational excellence. You'll help sellers navigate complex, multi-stakeholder sales cycles, drive MEDDPICC adoption, and build the structure and accountability needed to deliver predictable revenue growth. You'll have direct access to the CSO and founders and play a key role in shaping how Sage scales its sales organization, from recruiting and developing top talent to strengthening our sales methodology, forecasting discipline, and regional GTM strategy.

The role is preferably based in New York City, but we are open to candidates located elsewhere along the East Coast. The position requires approximately 40–50% travel across the region.

Responsibilities

• Own new business performance across the East region, driving Signed ARR, Live ARR, win rates, and consistent quota attainment
• Lead, coach, and develop a growing team of enterprise Business Development Executives through structured 1:1s, deal reviews, call coaching, and individualized development plans
• Drive execution across complex enterprise sales cycles, partnering with sellers on deal strategy, executive engagement, negotiations, and closing
• Champion MEDDPICC and establish a structured sales operating rhythm across pipeline reviews, territory planning, forecasting, and performance accountability
• Build relationships with senior executives and key decision-makers across communities, management groups, and ownership organizations
• Recruit, assess, hire, and ramp top sales talent through structured hiring and onboarding processes, while managing performance with clear expectations
• Partner cross-functionally with Implementation, Client Success, Revenue Operations, Finance, and Product to improve sales execution, customer handoffs, and scalable GTM processes

Minimum Qualifications

• 8+ years of enterprise B2B SaaS sales experience, including 3+ years leading quota-carrying enterprise sales teams
• Proven experience leading complex, multi-stakeholder, long-cycle enterprise sales motions involving $500K+ ACVs or multi-site agreements
• Demonstrated ability to coach and develop sellers, improve team performance, and consistently deliver against revenue targets
• Strong command of MEDDPICC or MEDDIC, with experience building or operating within a structured sales operating system, including pipeline management, forecasting, territory planning, and performance accountability
• Proven ability to recruit, assess, and hire top sales talent, with experience scaling teams or regions in high-growth, venture-backed companies
• Vertical SaaS experience selling into operationally complex, regulated environments

Preferred Qualifications

• Experience developing sales playbooks, enablement programs, or training initiatives that improve team performance
• Hands-on experience with HubSpot, Gong, and modern AI-assisted sales tools
• Based in the East region with flexibility to travel 40–50% for customer and team engagements