IT & Strategy Manager

The Pinnacle Companies; Northern (KY); Hybrid; USD 80,000 - 110,000; Full time

Benefits offered by this job

Paid Time Off 3 weeks

Volunteer hours

Health Insurance

Stock Ownership Program

Annual Team Trip

Tech allowance

Job summary

The Pinnacle Companies in Frisco seeks an IT & Strategy Manager to shape technology and infrastructure across its luxury portfolio. You will partner with business leaders to roll out software, evaluate platforms, and drive value from existing investments while building new tools, including AI-enabled solutions.

This hands-on leadership role requires you to bridge infrastructure and business needs, manage vendor relationships, and keep the organization ahead of AI trends, with a clear focus on

Qualifications

• 3+ years in IT leadership or technology strategy with business impact.
• Hands-on experience with AI frameworks and cloud platforms.
• Proven ability to develop and execute a technology roadmap.
• Strong strategic thinking and decision-making skills.
• Excellent communication with non-technical stakeholders.
• Curious, adaptable mindset and willingness to experiment with AI tools.

Responsibilities

• Define and drive the technology and infrastructure roadmap.
• Evaluate platforms and tools across Pinnacle companies.
• Lead AI-assisted development and internal AI agents.
• Oversee IT operations, security, and onboarding/offboarding.

Skills

IT leadership

AI frameworks

Cloud platforms

Vendor management

Strategic thinking

Communication

Tools

TensorFlow

PyTorch

Claude

ChatGPT

AWS

Azure

GCP

Job description

At The Pinnacle Companies, our success isn’t just built on the homes we design, the properties we manage, or the services we provide it’s built on our people. We are a team driven by passion, collaboration, and a shared commitment to creating exceptional experiences. As a leader in the luxury vacation home industry, we specialize in architecture, construction, interior design, property management, and vacation rentals, but what sets us apart is our culture.

At Pinnacle, we believe in pushing boundaries, embracing challenges, and growing together. We balance professionalism with authenticity and confidence with humility. Success here isn’t just about business growth it’s about the relationships we build, the experiences we create, and the meaningful impact we make every day.

Not everyone is meant to work here and that’s okay. Pinnacle is a place for people who take pride in their work, who bring their whole selves to the table, and who believe excellence and optimism aren’t simple acts, but daily habits. We’re looking for people who lean into challenges, own their outcomes, believe in the possible, and show up for their community.

If you’re looking for a job, you’ll find thousands. If you’re looking for a place to grow, contribute, and push your own limits, you might belong here.

The question is simple: Are you someone who thrives where expectations are high, accountability is real, courage is celebrated, and relationships run deep? If so, we’d love to meet you.

The Role:

As our IT & Strategy Manager at The Pinnacle Companies, you’ll be the strategic force behind the technology backbone that powers our entire organization. You’ll define and drive our technology and infrastructure roadmap, evaluate the platforms and tools each of our companies relies on, and help us decide what to keep, what to consolidate, and where we can get more value out of the dollars we’re already spending. You’ll partner with business leaders across all of our companies to roll out new software and to build tools of our own, including through vibe coding and other AI-assisted development, and you’ll provide light, ongoing support for the five internal AI agents we run on OpenClaw across our businesses. A smaller piece of the role covers the day-to-day fundamentals: managing on-ramps and off-ramps for new and departing employees and serving as a resource for general IT support when our team needs a hand. This position works directly with our Tech & Strategy team to elevate every department with smart, forward-looking technology decisions. This is an in-person role based in our Frisco office, giving you the ability to be hands-on with our infrastructure while still shaping the bigger picture. We’re looking for someone who builds relationships as naturally as they read a spreadsheet — relational enough to bring business leaders along, data-driven enough to back every recommendation, and genuinely excited about what AI can do for this business. Your ability to bridge the gap between infrastructure, IT support, and business needs will be essential to our success.

Key Responsibilities:

• Technology & Infrastructure Strategy: Define and drive the organization’s technology and infrastructure roadmap, evaluating the platforms, tools, and systems that form the backbone of our tech stack across every Pinnacle company. Decide what to keep, what toconsolidate, and where to redirectspendto get more value out of our technology dollars. Partner with the Director of Strategy and leadership to align technology investments with business priorities across our local and remote teams.
• Innovation & Development: Research, evaluate, and pilot emerging AI frameworks, platforms, and cloud technologies (e.g., Anthropic, OpenAI, Azure, AWS, GCP). Partner with business leaders to implement new software and to build tools in-house, including through vibe coding and other AI-assisted development. Provide ongoing, intermittent support for our five internal AI agents running on OpenClaw across the business. Lead IT projects such as system upgrades, migrations, integrations, and security enhancements from concept through execution.
• Leadership & Communication: Communicate technology strategy and outcomes to managers and stakeholders across the organization. Manage relationships with software and technology vendors to ensure the tools we rely on perform. Keep the company ahead of emerging IT and AI trends and best practices.
• IT Oversight & Support: Oversee IT infrastructure, systems, and compliance with policies and standards. Manage on-ramps and off-ramps for new and departingemployees, andserve as an escalation point for complex technical issues, ensuring hardware, software, and network problems are resolved quickly by the right resource. This is a smaller slice of the role, but a steady one.

Qualifications:

• 3+ years of experience in IT leadership, technology strategy, or a related field, witha track recordof aligning technology initiatives to business goals.
• Hands-on experience with AI frameworks and platforms (e.g., TensorFlow,PyTorch, Claude, ChatGPT, Midjourney) and cloud computing platforms (e.g., AWS, Azure, GCP), with the ability to evaluate and champion emerging tools.
• Proven ability to develop and execute a technology roadmap, manage vendor relationships, and lead cross-functional projects.
• Strong strategic thinking, analytical, and decision-making skills, balanced with the ability to jump into hands-on troubleshooting when needed.
• Excellent communication skills, with experience presenting technology strategy and outcomes to non-technical stakeholders.
• A curious, adaptable mindset with a genuine interest in how AI and emerging technology can transform business operations — including hands-on experimentation with vibe coding and AI tools to help build solutions for the business.
• A natural relationship-builder who is just as comfortable with data as with people — someone who brings warmth, energy, and enthusiasm to working with business leaders across the organization, while staying methodical, detail-oriented, and precise when evaluating platforms, costs, and outcomes.

What We Offer:

Competitive pay ranging from $80,000 - $110,000 inclusive of volume-based performanceincentives, based on experience & skill level.

• 3 weeks of Paid TimeOff annually
• 16 Paid Volunteer hours per year, because giving back to this community matters to us
• Health Insurance with a 100% employer-paid option available, with Dental and Vision options
• Employee Stock Ownership Program. This is not a checkbox benefit. It means you have a real stake in the success of what we are building together
• Annual Team Trip to Mexico – Strengthen team bonds while creating unforgettable experiences
• $500 annual tool and technology allowance, $50 monthly cell phone reimbursement, and mileage allowance when applicable

About The Pinnacle Companies:

Our family of companies, including Pinnacle Mountain Homes, Collective Design, Collective Architecture, Pinnacle Lodging, andVisitBreck, work closely togetherto deliver exceptional luxury mountain living experiences. We have been recognized by Outside Magazine, Builder Magazine, Mountain Living, and others for both the caliber of our work and the strength of our culture.

Pinnacle is a place for people who take pride in their work, bring their whole selves to the table, and believe that excellence and optimism are daily habits, not occasional achievements. We lean into challenges, own our outcomes, and show up foreachother and for this community.

Ifyou'relooking for a place to grow, contribute, and do the best work of your career, we would love to meet you.