VP of Technology Strategy

About the role

This is a highly strategic, client-facing technology leadership role focused on trusted advisory relationships, technology planning, and executive engagement.

You’ll work closely with senior living operators, executive teams, and internal leadership to help clients align technology investments with operational goals and future growth.

This role is ideal for someone who combines strong technical credibility with executive presence — someone who can simplify complex technology conversations, build trust with stakeholders, and help clients make smart long-term decisions.

You’ll partner closely with leadership across Sales, Managed Services, Engineering, and Operations while helping evolve Dual Path’s vCIO and strategic advisory capabilities.

What You’ll Do

• Strategic Client Leadership
• Lead quarterly business reviews and strategic technology planning sessions with clients
• Help clients build practical 12-, 24-, and 60-month technology roadmaps
• Serve as a trusted technology advisor to executive teams and IT leaders
• Translate operational and business goals into scalable technology strategies
• Provide executive-level guidance around infrastructure, security, modernization, and connected experiences
• Technology Advisory & Assessments
• Participate in client technology assessments and strategic reviews
• Help shape recommendations, standards, and long-term improvement plans
• Collaborate with Engineering and Operations teams to align strategy with execution
• Support the continued development of Dual Path’s vCIO and advisory offerings
• Strategic Sales Support
• Partner with Sales leadership on strategic opportunities and late-stage pursuits
• Participate in executive presentations, discovery conversations, and solution discussions
• Help communicate technology strategy in a way that is clear, practical, and business-focused
• Support client confidence throughout the sales and onboarding process

What We’re Looking For

• Required Experience
• 10+ years of senior IT leadership or strategic technology consulting experience
• Strong executive communication and relationship-building skills
• Experience leading strategic technology conversations with non-technical stakeholders
• Ability to balance technical depth with business-focused communication
• Experience building technology roadmaps, assessments, or strategic recommendations
• Strongly Preferred
• Senior living industry experience
• MSP or multi-client technology services experience
• Experience serving in a vCIO, VP of IT, Solutions Executive, or strategic advisory role
• Familiarity with infrastructure, networking, cybersecurity, and cloud modernization initiatives

Why Join Dual Path?

• Opportunity to shape technology strategy across a growing national client base
• Highly collaborative leadership environment
• Meaningful impact in the senior living industry
• Growth-oriented culture

Compensation & Benefits

• Expected Base Range: $150,000 - $200,000.
• Performance-based variable compensation. Total compensation will depend on experience, industry background, and overall alignment with the role.
• Long-term incentive structure aligned with company leadership
• Remote work flexibility
• Benefits – Medical, dental, vision, 401(k), AD&D insurance, PTO, floating holidays, and paid holidays.

Location

Remote — United States