Remote VP of Technology Strategy & Executive Advisory

Dual Path LLC; United States; Remote; USD 150,000 - 200,000; Full time

Benefits offered by this job

Remote work flexibility

Benefits package

Job summary

Dual Path Connected Solutions is seeking a VP of Technology Strategy to lead strategic client engagements, shape long-term technology planning, and support growth across the organization. This remote, US-based role emphasizes trusted advisory work with senior living operators and executive teams.

You’ll bridge technical depth with business communication, translating goals into scalable technology strategies and contributing to Dual Path’s evolving vCIO capabilities across Sales, Managed

Qualifications

• 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 translate operational and business goals into scalable technology strategies.
• Experience building technology roadmaps, assessments, or strategic recommendations.

Responsibilities

• 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.
• Participate in client technology assessments and strategic reviews.
• Collaborate with Engineering and Operations teams to align strategy with execution.
• Support continued development of vCIO and advisory offerings.
• Partner with Sales leadership on strategic opportunities and late-stage pursuits.
• Communicate technology strategy clearly in client discussions and during onboarding.

Skills

Executive comms

Relationship building

Strategic planning

vCIO advisory

Roadmap creation

Client leadership

Job description

Dual Path Connected Solutions is seeking a VP of Technology Strategy to lead strategic client engagements, shape long-term technology planning, and support growth across the organization. This remote, US-based role emphasizes trusted advisory work with senior living operators and executive teams.

You’ll bridge technical depth with business communication, translating goals into scalable technology strategies and contributing to Dual Path’s evolving vCIO capabilities across Sales, Managed