Regional Sales Leader (East Coast)

Sage; New York (NY); Hybrid; USD 200,000 - 225,000; Full time

Benefits offered by this job

Stock options

Health and dental coverage

Vision insurance

Unlimited PTO

Company holidays

Job summary

Sage is seeking a Regional Sales Director to lead our East region, driving enterprise ARR and coaching a growing team of BDEs selling multi-site, complex SaaS solutions to senior living and post-acute operators. The role emphasizes MEDDPICC, structured forecasting, and scalable GTM processes.

Based in New York City preferred, with 40–50% travel; remote work allowed up to two days per week. Competitive base, stock options, and performance-based commission accompany generous benefits.

Qualifications

• 8+ years of enterprise B2B SaaS sales experience, including 3+ years leading quota-carrying enterprise sales teams.
• Proven experience guiding complex, multi-stakeholder, long-cycle enterprise deals.
• Strong MEDDPICC or MEDDIC discipline with structured pipeline management, forecasting, and territory planning.

Responsibilities

• Own new business performance across the East region with ARR targets and quota attainment.
• Coach and develop a growing team of enterprise Business Development Executives.
• Drive complex sales cycles, negotiate with executives, and close multi-site deals.
• Implement MEDDPICC-based governance and a clear sales operating rhythm.
• Partner with cross-functional teams to improve handoffs and scalable GTM processes.
• Recruit, assess, hire, and ramp sales talent with structured onboarding.

Skills

Enterprise B2B SaaS sales

Leadership

Coaching

Forecasting

MEDDPICC

Sales strategy

Recruiting

Cross-functional collaboration

Tools

HubSpot

Gong

Job description

About Us

The first baby boomers turn 80 this year. Over the next decade, the population most likely to need daily care will grow faster than the buildings, the staff, or the systems available to serve it.

About Us

The first baby boomers turn 80 this year. Over the next decade, the population most likely to need daily care will grow faster than the buildings, the staff, or the systems available to serve it.

Sage is the care intelligence platform for senior living and skilled nursing. We connect the hardware senior care runs on, including nurse call, fall management, and wander management, with software caregivers actually use. That consistent use is what produces reliable data, and reliable data is what gives operators a true picture of how their communities are running.

Sage is a collaborative team of ambitious, multi-disciplinary entrepreneurs on a mission to reinvent senior care with a modern operating system for caregivers. Millions of people depend on this care getting better, and we move with the urgency that deserves.

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.

This 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

Benefits and Pay

Our headquarters are located in New York City's Union Square, and we value cross-team collaboration and in-person connection. We encourage participation from all team members—great ideas can come from anywhere. While we take our mission seriously, we don't take ourselves too seriously. We host offsites, outings, and team meals to stay connected as people. We offer office lunch, a fully stocked snack bar, and an in-office culture with flexibility for up to two remote days per week.

We provide competitive base compensation along with stock options and performance-based commission. The expected annual base salary range for this role is $200,000–$225,000 USD, with total on-target earnings (OTE) of $400,000–$425,000 USD. Compensation within the range will depend on experience and interview performance.

We offer fully paid health and dental coverage, plus vision insurance, premium primary and urgent care memberships, online health providers, unlimited PTO ("take what you need"), seven paid holidays, and a company-wide winter break.

EEO Statement

Sage is an equal opportunity employer committed to diversity and inclusion. We prohibit discrimination and harassment based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic under federal, state, or local laws.

This policy applies to all employment practices, including hiring, promotion, termination, compensation, benefits, training, and apprenticeships. Sage bases hiring decisions solely on qualifications, merit, and business needs.