VP, Senior Living Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Take ownership of new bookings for the Senior Living business unit.

• Establish the go-to-market engine and reverse the trend of declining bookings.

• Collaborate with the SVP & GM to segment the market and define coverage strategies.

• Recruit, onboard, and develop a national team of Enterprise and Regional sales professionals.

• Protect and expand the existing Enterprise customer base while increasing Regional volume.

• Build and oversee teams of Enterprise and Regional Account Executives.

• Conduct weekly forecasts and pipeline inspections, coverage modeling, and ensure accurate commits.

• Engage personally in key strategic opportunities to mitigate risks and expedite sales cycles.

• Design territories, quotas, CRM structures, forecasting cadences, and reporting systems.

• Develop, standardize, measure, and refine sales processes, qualification criteria, playbooks, and deal strategies.

• Facilitate conversations regarding legacy-to-new product transitions alongside new-logo pipelines.

• Establish and maintain a five-star prospect experience, including response-time SLAs, discovery sessions, customized demos, business cases, and handoffs.

• Lead weekly one-on-ones and deal strategy discussions; set expectations, provide feedback, and manage performance.

• Collaborate cross-functionally with Marketing, SDRs, Solution Design, Professional Services, Revenue Operations, Data Science, Customer Success, Partnerships, and Senior Care.

• Build relationships with REITs and private equity ownership groups.

• Represent the Senior Living sector at trade shows, industry summits, and speaking engagements.

• Monitor market trends, competitor activities, and win/loss patterns.

• Leverage AI for account research, personalization, call and deal intelligence, and forecasting.

⛳️ Requirements

• 10+ years of experience in healthcare IT or SaaS sales to provider organizations, including senior living, post-acute care, health systems, or large ambulatory groups.

• Proven track record of consistently exceeding quotas, including experience competing against better-funded or better-resourced rivals.

• 4+ years of experience leading sales teams, with a demonstrated history of meeting or surpassing bookings targets and developing sales talent.

• Proven success in building operations from the ground up in startup, carve-out, or transformation settings.

• Capacity to quickly recruit, onboard, and ramp quota-carrying Enterprise and regional sales personnel.

• Proactive mindset and comfort with ambiguity.

• Demonstrated ability to collaborate across functions with Marketing, Sales Development, Solution Design, Professional Services, Customer Success, Revenue Operations, and Data Science.

• Strong discipline in forecasting and CRM management using Salesforce or similar tools.

• Ability to translate pipeline data into executive-level narratives.

• Willingness and capability to travel 60% or more.

• Direct experience in the senior living market and established relationships with operators and industry stakeholders are preferred.

• Experience in launching a new business unit, segment, or go-to-market strategy is preferred.

• Familiarity with building relationships with institutional owners, such as REITs and private equity, is preferred.

• Experience implementing a formal sales methodology, such as MEDDICC, Challenger, or Miller Heiman Strategic Selling, is preferred.

• Experience using AI tools to enhance research, personalization, deal assessment, and forecasting accuracy is preferred.

🏝️ Benefits

• Competitive base salary plus commission and benefits.

• Benefits begin on Day 1.

• Retirement Plan Matching (RRSP & 401K).

• Flexible Paid Time Off.

• Lifestyle/Wellness Spending Account.

• Parental and Caregiver Leaves.

• Support for Fertility and Adoption.

• Continuous Development Support Program.

• Employee Assistance Program.

• Learning Programs and Resources.

• Employee Recognition initiatives.

• In-office events including onboarding, team gatherings, and semi-annual and annual team meetings.