About the role

Parasol Alliance is a technology solutions company exclusively serving the senior living industry. We provide leadership and comprehensive in-house technology support, helping our clients make smart strategic technology investments and effectively use technology to achieve their business objectives.

Our strategic focus forms the core of Parasol Partnerships. These partnerships lead to increased efficiency, productivity, and profitability for our clients. We make our clients more successful – and we have the data to prove it.

Leadership defines us. We are innovative leaders in everything we do.

VP of Innovation & AI

Parasol Alliance | Remote | Full-Time | ~30% Travel | Reports to CEO

ABOUT US

Parasol Alliance is an award-winning Managed Services Provider (MSP) exclusively serving the senior living industry. We've earned 24 Best & Brightest workplace awards and have been named a Top 501 MSP in the world by Channel Futures — five years running. We move fast, think big, and genuinely care about our people and the communities we serve.

THE OPPORTUNITY

This is a rare chance to shape the technology future of an entire industry. As VP of Innovation & AI, you'll own how Parasol Alliance thinks about, adopts, and scales artificial intelligence and emerging technology — both inside our organization and across our entire client portfolio.

This isn't a support role or an advisory title. You'll be the architect of our AI and innovation strategy, driving it from vision to execution and making sure every client we serve benefits from what we build. If you're energized by turning ambitious ideas into real outcomes — and by doing it at a company that's genuinely mission-driven — this role was made for you.

WHAT YOU'LL DO

AI Strategy & Internal Adoption

Own and drive Parasol Alliance's enterprise AI strategy — defining where we go, how fast, and what we build

Identify, prioritize, and implement AI use cases that improve how we deliver services, operate, and grow

Establish AI governance frameworks covering responsible use, privacy, security, and risk

Build internal AI fluency through training, enablement, and hands-on adoption programs for our team

Serve as Parasol Alliance's internal authority on the evolving AI landscape — keeping us ahead, not catching up

Technology Assessment & Senior Living Innovation

Lead technology assessments that go beyond infrastructure — uncovering strategic gaps, innovation opportunities, and AI readiness across client organizations

Monitor and evaluate emerging technologies across senior living, healthcare, and adjacent industries — from resident experience and clinical operations to analytics

Lead AI and innovation strategy across the full client portfolio — coordinating initiatives, identifying patterns, and scaling what works

Create client-facing AI readiness assessments, innovation roadmaps, and forward-looking technology strategies

Translate market trends and emerging technology into actionable, prioritized intelligence that sharpens our clients' competitive edge and informs multi-year investment decisions

Develop a consistent, scalable framework for how Parasol Alliance identifies, evaluates, and activates innovation across the client base

Create frameworks that help clients distinguish meaningful innovation from technology that isn't ready for real-world deployment

Organizational & Service Leadership

Collaborate with Client Success, Engineering, Security, and Sales teams to align innovation with service delivery

Develop scalable AI and innovation service offerings, methodologies, and intellectual property that differentiate Parasol Alliance

Support business development when AI, innovation, or strategic technology expertise is needed to win or expand relationships

Contribute to Parasol Alliance thought leadership through industry events, webinars, and content

WHAT YOU BRING

Significant experience in technology leadership, innovation strategy, AI adoption, or a related senior role

Demonstrated ability to develop and execute enterprise AI strategies — not just advise on them

Strong understanding of generative AI, automation, analytics, cybersecurity, and the emerging technology landscape

Experience with AI governance, responsible AI adoption, or enterprise-scale AI implementation

Proven ability to translate complex technology trends into clear, prioritized, business-ready recommendations

Knowledge of senior living or healthcare technology operations is a strong plus

Excellent executive communication, facilitation, and presentation skills

Comfortable leading cross-functional initiatives and influencing without direct authority

Bachelor's degree in IT, Business, Healthcare Administration, or a related field preferred; equivalent experience considered

Ability and willingness to travel approximately 30% for client engagements, strategic meetings, and industry events

WHY PARASOL ALLIANCE

• Generous paid time off

• Medical, dental & vision coverage

• Remote-first work environment

• 401(k) with company match

• Certification & development support

• Award-winning workplace culture

• Mission-driven work that matters

GEOGRAPHIC ELIGIBILITY NOTICE

We are currently unable to consider applicants residing in California, Colorado, Hawaii, Illinois, Maine, Maryland, Massachusetts, Minnesota, New Jersey, New York, Vermont, Virginia, Washington, or Washington D.C. We encourage candidates in all other states to apply.

Parasol Alliance is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate on the basis of race, color, religion, sex, national origin, age, disability, veteran status, or any other characteristic protected by law.

Originally posted on Himalayas

Interview prep

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Executive

Technology & IT Administration Business Development Data Analysis Operations Remote Collaboration Executive level

Likely questions

Tell us about work you have done that is close to the VP of Innovation & AI role.
How would you approach your first 30 days at Parasol Alliance?
Which of Administration, Business Development and Data Analysis have you used recently, and what did it help you achieve?
How have you led people, improved a process, or made a hard decision in a previous role?
How do you handle busy days, changing priorities, or pressure at work?

Prepare before the call

A recent example that proves your experience with Administration, Business Development and Data Analysis.
One short story with a problem, your action, and the result.
Two examples that show the strengths listed on your CV.
A clear reason why this role and company interest you.
Your availability, preferred work style, and salary expectations.

Ask them

What would success look like in the first 90 days?
What are the main problems this hire should help solve?
How does the team give feedback and measure good work?
What does a normal working week look like for this role?

Practice line

I am interested in the VP of Innovation & AI role because I can bring practical experience in Administration, Business Development and Data Analysis, learn the team quickly, and contribute to the outcomes Parasol Alliance needs from this hire.