Regional Sales Leader
Who you are 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 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 What the job involves 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 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
Benefits
You and your health: Your health comes first. Sage covers 100% of your individual medical premium, plus dental and vision. Every employee also gets a free OneMedical membership for modern primary care, plus access to mental health support through Talkspace, fertility care through KindBody, and virtual medicine through Teladoc. Your family and time: When life happens, we're with you. Sage grants eight weeks of parental leave to non-birthing parents and 12 weeks to birthing parents. We also offer a hybrid work schedule and unlimited PTO, which we encourage you to use. In addition, Sage has seven company holidays and closes for two weeks at the end of December. Your financial future: You're building something here, so you should own a piece of it. All full-time employees receive equity as part of their compensation package, along with a 401(k) through Empower, flexible spending accounts for medical and dependent care, and commuter benefits through Optum Financial.