Health Systems Sales Director - Hybrid/Boston, MA

Brook•Boston, MA

10h•$140,000 - $170,000•Hybrid

About The Position

About Brook Health Brook Health delivers care beyond the walls of the doctor’s office. We provide people living with chronic conditions a highly personalized experience enhanced by AI and powered by mobile apps, connected devices, and a team of health coaches and clinicians. Brook helps people achieve their long-term health goals by supporting smart, daily decisions and partnering with their primary care physicians. Our product suite includes continuous remote monitoring, population health management tools, and a CDC-approved diabetes prevention program. Brook has an intentional, user-centric culture with high expectations for delivering better health outcomes for patients, providers, and health systems. Job Overview The Health Systems Sales Director plays a pivotal role in bringing the future of healthcare to health systems, hospitals, integrated delivery networks, and large medical groups. Brook is redefining continuous care—combining real-time patient data, AI-powered insights, and human clinical expertise to help providers deliver better outcomes with greater efficiency. In this role, the Director opens doors, builds belief, and drives enterprise adoption of Brook’s model. They lead complex, multi-stakeholder sales cycles, translate provider needs into actionable solutions, and serve as a trusted voice connecting the market to Brook’s product, clinical, and operational teams. This position is designed for a high-caliber enterprise seller who thrives in dynamic environments, operates with executive presence, and brings the strategic judgment needed to help health systems embrace what’s next. The work directly fuels Brook’s growth and shapes the partnerships that will define our impact for years to come.

Requirements

Minimum 7 years of enterprise sales experience in digital health, healthcare technology, or clinical services selling to hospitals/health systems.
Demonstrated success securing multi-year enterprise agreements with senior health system leaders.
Experience partnering with clinical, operational, and product teams to shape integrated, high-impact solutions.
BA/BS required; advanced degree or clinical background preferred.
Deep understanding of health system operations, reimbursement dynamics, and digital health innovation.
Strong executive presence with the ability to influence C-suite and multi-disciplinary stakeholders.
Exceptional communication, storytelling, and virtual presentation skills.
Proven capability in navigating complex enterprise sales cycles with resilience and precision.
High degree of ownership, strategic thinking, and urgency in driving outcomes.
Proficiency with CRM systems (HubSpot preferred) and sales enablement tools.

Responsibilities

Drive Strategic Growth & Market Penetration Builds and executes bold, targeted sales strategies that expand Brook’s footprint across leading health systems and medical groups.
Develops and sustains a healthy pipeline through disciplined prospecting, relationship management, and market insight.
Identifies high-value opportunities by translating provider pain points and market trends into strategic commercial pathways.
Lead Complex Enterprise Deals Orchestrates multi-stakeholder sales cycles with C-suite, clinical, operational, and financial leaders.
Designs compelling, scalable solutions in close collaboration with Product, Care Team, Marketing, and Operations.
Navigates sophisticated negotiations that balance partner needs with Brook’s long-term goals and operational realities.
Influence, Connect, and Build Executive Relationships Cultivates trusted relationships with senior decision-makers across hospitals, IDNs, and large medical groups.
Represents Brook at national conferences, innovation forums, and industry events to elevate brand visibility and generate demand.
Acts as a connective force between external partners and internal teams, ensuring seamless handoff from sales through activation.
Drive Accountability & Commercial Excellence Maintains rigorous forecasting, pipeline hygiene, and deal documentation within Brook’s CRM.
Consistently achieves or exceeds quarterly and annual revenue targets through disciplined execution and follow-through.
Surfaces market intelligence that informs Brook’s go-to-market strategy, product roadmap, and clinical model evolution.

Benefits

Healthcare Coverage Employee & Child(ren): Brook pays 100% of premiums for full-time employees and their child or children for Medical, Dental, and Vision coverage. This means there are no paycheck deductions for you or your child(ren).
Spouse/Domestic Partner: Brook contributes 50% of premiums for coverage of a spouse or domestic partner.
HSA Contribution: Employees who enroll in our HSA-eligible medical plan receive a Brook-funded contribution to help cover medical expenses such as deductibles, prescriptions, and office visits.
Medical Concierge: Brook provides a concierge service to help employees and their families manage healthcare needs like claims, referrals, and care coordination.
Mental Health & Wellbeing Mental Health Support: Brook supplements the mental health coverage included in our medical plan with additional resources.
Employees have access to free therapy sessions through Spring Health, providing confidential, professional support when it’s needed most.
Flexible PTO: Our PTO program is truly flexible — no accruals and no preset limits. You and your manager decide what’s reasonable, so you can take the time you need to recharge. In addition, we provide dedicated sick time to support your health and well-being, and a generous holiday schedule that ensures time to rest and celebrate with family and friends.
Financial Wellness & Security Income Protection: Brook provides Short-Term and Long-Term Disability insurance to all full-time employees, helping replace income during an illness or injury. Short-Term Disability works alongside any state or insurance benefits and Brook coverage to provide added financial support while you’re away from work.
Life Insurance: Brook provides company-paid life insurance equal to one times salary, up to a set maximum.
401(k) Retirement Savings: All employees (full-time and part-time) are automatically enrolled in our 401(k) plan. Brook provides a company match to help employees grow their retirement savings.
Emergency Savings Account (ESA): Brook helps employees build financial resilience by supporting contributions to an emergency savings account. Brook matches a portion of employee contributions, helping the fund grow faster. The account is completely flexible — you decide what qualifies as an emergency and how to use the funds.
Recognition & Community Employee Referral Bonus: Great people know great people. When you refer a candidate who is hired, you’ll receive a referral bonus.