WinChoice is looking for a Director of AI Implementation to lead the charge in transforming how our business operates through artificial intelligence.

This is not a support role — it’s a strategic, executive-level position with real influence. You’ll define our AI vision, shape investment decisions, and drive adoption across the entire organization — from sales teams in the field to operations and back-office functions.

If you’re someone who can connect cutting-edge AI capabilities to real business outcomes, build systems from the ground up, and influence leaders without formal authority — this role is for you.

Own the AI Strategy

• Define and execute a company-wide AI vision and multi-year roadmap
• Present AI investment strategies and performance updates to executive leadership
• Ensure all AI initiatives are measurable, scalable, and aligned with business goals

Drive Real Business Impact

• Identify and implement AI tools that increase revenue, improve sales performance, and reduce manual work
• Lead AI integration across key systems like HubSpot CRM and customer communication platforms
• Build automation workflows and AI agents to improve productivity company-wide

Lead Implementation & Innovation

• Evaluate, test, and deploy AI platforms (e.g., Claude, OpenAI, automation tools)
• Run pilots, make build-vs-buy decisions, and manage full lifecycle deployment
• Stay ahead of emerging AI tools and trends

Establish Governance & Security

• Develop AI policies, ethical guidelines, and data privacy standards
• Partner with IT Security to mitigate risks and monitor AI usage
• Ensure compliance with evolving AI regulations

Enable the Organization

• Partner with department leaders to identify high-impact AI use cases
• Build and deliver AI training programs across all teams
• Champion adoption among sales reps, canvassers, and field teams

Build the Function

• Operate as a hands-on leader while building the foundation for a scalable AI team
• Manage vendor relationships, contracts, and performance
• Own the AI budget, KPIs, and ROI reporting

Required Experience

• Bachelor’s degree in IT, Computer Science, Business Systems, or related field
• 5–7+ years in technology, IT strategy, or similar roles
• Experience implementing AI or automation tools in a business environment
• Proven ability to influence senior leaders and drive cross-functional initiatives
• Strong project management experience (pilot ? full rollout)
• Experience building business cases and presenting to executive stakeholders
• Understanding of sales operations and how technology impacts revenue performance

Preferred

• MBA or advanced degree (nice to have, not required)
• Experience with HubSpot CRM, automation tools, or AI-driven sales platforms
• Background in home services, construction, or direct sales environments
• Familiarity with system integrations, APIs, and data workflows

• Strong knowledge of modern AI platforms (Claude, OpenAI, Copilot, Gemini, etc.)
• Prompt engineering and AI workflow design
• Ability to evaluate and implement automation tools (Zapier, Make, Power Automate, etc.)
• Executive-level communication and presentation skills
• Financial acumen and ROI-driven decision-making
• Change management and organizational influence
• Ability to thrive in ambiguity and build structure from scratch