VP, Enterprise Sales (Post-Acute Care)

Cascala Health; Boston (MA); Remote; USD 145,000 - 275,000; Full time

Job summary

Cascala Health is seeking a motivated VP of Enterprise Sales to establish and lead their sales strategy targeting post-acute care providers. This role requires a proactive, consultative sales leader with a proven record in healthcare technology sales and a passion for improving care transitions through innovative solutions.

Benefits

Competitive base salary

Commission-heavy incentive structure

Equity stake

Unlimited PTO

401k with company match

Qualifications

• 8+ years of B2B enterprise sales experience in healthcare technology.
• Proven track record with provider organizations.
• Experience in post-acute care is a plus.

Responsibilities

• Develop and execute an enterprise sales strategy.
• Manage end-to-end sales cycles for complex deals.
• Build and manage a robust sales pipeline.

Skills

Negotiation

Consultative Selling

Pipeline Management

Strategic Thinking

Interpersonal Skills

Education

Bachelor’s degree

Tools

Salesforce

Job description

Join to apply for the VP, Enterprise Sales (Post-Acute Care) role at Cascala Health

Join to apply for the VP, Enterprise Sales (Post-Acute Care) role at Cascala Health

Company Overview

Cascala Health is an early-stage, mission-driven healthcare technology company dedicated to revolutionizing care transitions. Our comprehensive platform facilitates meaningful engagement across care teams, activating personalized interventions to prevent hospital readmissions and promote long-term health for patients in risk-based care models.

Company Overview

Cascala Health is an early-stage, mission-driven healthcare technology company dedicated to revolutionizing care transitions. Our comprehensive platform facilitates meaningful engagement across care teams, activating personalized interventions to prevent hospital readmissions and promote long-term health for patients in risk-based care models.

About The Role

As our first VP of Enterprise Sales, you will design and execute Cascala’s enterprise sales strategy from the ground up. This is a hands-on sales leadership role (100% focused on direct sales, not partnerships) in which you will target post-acute care providers – including skilled nursing facilities (SNFs), home health agencies, and related organizations – to drive adoption of Cascala’s platform. You will own the entire sales lifecycle from pipeline generation through closing deals, crafting a consultative sales approach that addresses the complex needs of healthcare enterprises. We seek a consultative, entrepreneurial sales leader who can operate autonomously while collaborating closely with the CEO, investors, board members, and other cross-functional leaders. The ideal candidate is highly accountable and thrives in a fast-paced startup environment, capable of building out a sales function while simultaneously selling hands-on. You will be expected to implement a rigorous sales process (from initial contact to negotiation and contracting) and lay the foundation for a future sales team. Compensation for this role includes a competitive base salary, a commission-heavy incentive structure, and an equity stake in the company. In sum, this position offers an opportunity to shape our go-to-market strategy and make a direct impact on Cascala’s growth and mission.

Key Responsibilities

• Sales Strategy & Execution: Develop and execute an enterprise sales strategy to rapidly grow Cascala’s customer base in the post-acute care sector. Define target segments, sales playbooks, and KPIs aligned with company goals.
• Pipeline Building: Proactively build and manage a robust sales pipeline. Identify leads among SNFs, home health providers, and other post-acute organizations, and drive outreach, demos, and relationship-building to convert prospects into customers.
• Enterprise Deal Management: Lead end-to-end sales cycles for complex enterprise deals – from initial discovery and solution pitching to navigating procurement and closing contracts. Engage in consultative selling, understanding each customer’s workflow and needs to tailor solutions.
• Sales Process & Rigorous Approach: Establish a disciplined sales process and utilize CRM tools to track opportunities, forecast revenue, and ensure a rigorous, repeatable sales cadence. Drive accountability for meeting sales targets and continuously refine the approach based on lessons learned.
• Collaboration & Feedback Loop: Work closely with Cascala’s CEO, product team, and clinical experts to align on value proposition and pricing. Provide market feedback to inform product development and ensure our offering meets the needs of post-acute providers and risk-bearing entities.
• Market Presence: Serve as an evangelist for Cascala at industry conferences, webinars, and customer meetings in the post-acute and value-based care space. Build relationships with key stakeholders and establish Cascala as a trusted partner in improving care transitions.
• Scaling the Sales Function: While initially an individual contributor, lay the groundwork for scaling the sales organization. Develop onboarding materials, playbooks, and performance metrics so that you can recruit and mentor future sales team members as the company grows.
  
  

Qualifications

• Education: Bachelor’s degree required. Advanced degree or relevant certifications in business or healthcare management are a plus but not required.
• Proven Enterprise Sales Experience: 8+ years of B2B enterprise sales experience in healthcare technology or related fields. A track record of selling software or services to provider organizations is required; experience with post-acute care providers is a strong plus.
• Domain Knowledge: Deep understanding of the post-acute care landscape (e.g. SNFs, home health agencies) and familiarity with value-based care models. Experience selling into ACOs or health plans is highly desirable Google Drive, as it indicates ability to navigate complex healthcare ecosystems.
• Consultative Sales Skills: Demonstrated ability to lead a consultative sales process – identifying client pain points, aligning solutions to strategic goals, and building long-term relationships with clinical and executive stakeholders.
• Deal Leadership: Excellent negotiation and deal management skills, with experience closing complex, multi-stakeholder contracts (e.g. involving clinical leadership, IT, finance, and procurement). Ability to manage long sales cycles and still consistently drive toward close.
• Entrepreneurial Drive: Self-starter who thrives in an early-stage environment. Must be comfortable creating structure in ambiguity – developing sales processes, KPIs, and collateral from scratch. Prior startup experience is required, preferably as a first or early sales hire.
• Collaborative Leadership: Strong interpersonal and communication skills. Able to work closely with the CEO and cross-functional teams (product, marketing, clinical) to advance opportunities. Collaborative and accountable working style, with a willingness to roll up your sleeves.
• Results & Accountability: High degree of personal accountability and a metrics-driven mindset. Passion for meeting and exceeding targets. Proven ability to work independently toward goals while keeping leadership informed of progress and obstacles.
• Mission Alignment: Genuine enthusiasm for Cascala’s mission and the ability to articulate the value of our platform in improving patient outcomes. A mission-driven mindset and integrity in selling a product that impacts patient care are essential.
  
  

Bonus Skills

• Experience using Salesforce for CRM and pipeline management.
• ACO, health plan, and/or health system sales experience.
  
  

Why You'll Want To Work Here

• At Cascala Health, we believe the handoff is the heartbeat of healthcare. Our AI-powered platform ensures care teams have the right knowledge at the right time—guiding every transition with clarity, confidence, and compassion. As part of our mission-driven team, you’ll help reimagine how care is delivered, joining a culture rooted in clinical excellence, purpose-driven innovation, and real human impact. We offer competitive pay, comprehensive health and disability benefits—including access to One Medical, Teledoc, Kindbody, Talkspace, and more—plus a 401k with company match, unlimited PTO, 11 company holidays, and equity opportunities for select roles. Join us and make every care transition count.
  
  

Location: Boston, MA (Remote); Travel up to 15% may be required

Seniority level

• Seniority level

  Executive

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales and Business Development

• Industries

  Hospitals and Health Care

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