Director of AI Implementation

Description:

Build the Future of AI at WinChoice 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

Requirements:

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 Key Skills 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