AI Strategy & Enablement Lead

AI Strategy & Enablement Lead at Greencastle Consulting

Wanted: Trailblazer for uncharted AI frontier.
Shifting landscape. Ambiguous waters. Rapid change. Purpose over perks.
Your mission: chart the course, cut through the hype, and harness AI to make our people faster, sharper, and more impactful — to us and our clients.
Comfort not guaranteed. Impact certain. Recognition in success inevitable.

The AI Strategy & Enablement Lead will spearhead Greencastle’s AI strategy by identifying, piloting, and scaling sustainable AI solutions that improve internal efficiency and create new client-facing capabilities. At Greencastle, we are mission-driven and outcome-obsessed — a team of veterans proving what’s possible when grit, precision, and strategy meet the toughest challenges. This role requires a strategic thinker who can bridge technical understanding and business needs, harnessing AI not just to deliver faster, higher-value results, but to raise the standard for what veterans can achieve in the business world. By driving the adoption of AI tools in a way that aligns with company goals, the AI Strategy & Enablement Lead will help us transform chaos into clarity, and leave a lasting legacy of impact with every engagement.

What You'll Experience as the AI Strategy & Enablement Lead at Greencastle:

At Greencastle, we believe the future belongs to those willing to venture into the unknown with purpose. Artificial Intelligence isn’t just the next shiny tool — it’s the next frontier in how we think, work, and deliver value. This role exists to lead us into that frontier with a clear mission: to harness AI in ways that make our consultants faster, sharper, and more impactful, and to help our clients unlock the potential of tools they already have but aren’t yet realizing.
Greencastle is not seeking people drawn to comfort. This position is for someone who thrives in uncharted territory, who sees ambiguity not as a barrier but as an open sea to navigate. As the AI Strategy & Enablement Lead, you will be our guide — charting a course that is constantly 1–2 years ahead, steering us past hype toward sustainable, high-impact solutions, and building the playbooks and training that make AI part of Greencastle’s DNA.
The work will be challenging. The landscape is shifting. Success will come not from the tools themselves, but from the shared belief in why we’re doing this: to ensure Greencastle remains highly effective, future-ready, and a trusted partner to our clients in their own AI journeys. If you’re driven by purpose, not perks, and you want to prove what’s possible when humans and AI work seamlessly together — this is your expedition.

What You’ll Work On: 

• Develop and maintain Greencastle’s AI strategy and roadmap with a 1–2 year forward-looking perspective.


• Develop and maintain Greencastle’s AI Governance policies to ensure compliance and ethical use to align across all Client MSAs.


• Research and evaluate AI tools (off-the-shelf or internally built) for internal efficiency and client-facing opportunities.


• Translate complex AI concepts into clear recommendations for leadership and consultants.


• Identify and prioritize high-impact internal AI use cases for pilot testing


• Build AI playbooks and best practices for consultant enablement.


• Utilizing change management, Partner with Talent Management to facilitate training programs to improve AI literacy across consultants and drive adoption rates to meet program goals.


• Gather internal feedback from consultants and back-office teams to guide AI priorities.


• Lay the foundation for client-facing AI enablement offerings in 2026 and beyond


• Other duties as assigned
  

Who Will You Work With: 

• Diverse client stakeholders, from hands-on team members to top-level executives. 

• A team of over 100 military veteran consultants dedicated to client success and professional growth. 

• Greencastle's leadership and staff, supporting your excellence in client projects and career development. 

Qualifications: 

• Required: Military veteran, experienced in military planning processes: Military Decision-Making Process – MDMP, Navy Planning Process – NPP, Marine Corps Planning Process –MCPP, Joint Operations Planning Process for Air – JOPPA, or equivalent. 

• Required: Bachelor’s degree. 

• Required: A desire to play by adult rules, GSD™, a genuine commitment to client success, and a commitment to making our veteran communities better places in which to live and work. 

• Preferred: 5+ years in consulting, product strategy, or technology program management.


• Preferred: Python, SQL, APIs, vector databases, LLMs (OpenAI, Claude, open-source models), LangChain/RAG pipelines or similar.


• Required: Strong understanding of AI tools and emerging trends.


• Required: Understands consulting workflows and business process automation, and the ability to translate technical detail into actionable strategy.


• Required: Experience leading initiatives in ambiguous environments.


• Required: Familiar with data privacy (both internal and Client external), internal deployment, secure APIs


• Required: Exceptional communication and presentation skills.
  

Salary and Benefits: 

Greencastle offers a comprehensive benefits package to help you thrive personally and professionally:  

• Performance based bonus paid monthly (1/12 per month).  

• Eligible for semi-annual raises after the acclimation period.  

• 401k (traditional or ROTH) with guaranteed Safe Harbor profit share and discretionary profit share contributions.  

• Health, dental, vision, life, accidental death and dismemberment and long-term disability insurance with HSA options.  

• Flexible PTO/leave options.  

• Professional development opportunities.  

• Monthly performance feedback.  

• Dedicated time to give back to the veteran community.  

Salary Range:
Salary to be determined based on experience and alignment with role scope. Compensation progression is based on a merit-based system with transparent, objective rewards.

Work Environment: 

Greencastle Consulting is headquartered in Malvern, PA, serving clients nationwide. This role's work environment primarily involves working on-site in our office, with some hybrid flexibility when appropriate. We emphasize intentional in-person interactions to strengthen relationships with the Greencastle team. 

Personal and Professional Well-being is a priority—our team supports one another through tough times and prioritizes personal and family needs. 

We foster a culture of innovation, valuing fresh perspectives and diverse ideas from Day 1. Our commitment to continuous improvement is reflected in initiatives like Shadow Boards, collaborative feedback mechanisms, and the CEO Captain’s Call, ensuring every team member has a voice in shaping the company’s future. Our team enjoys monthly happy hours and annual events like VetFest, camping trips, and family events—because we genuinely enjoy spending time together. 

Why Greencastle Consulting? 

As the world's largest 100% Veteran-owned and operated company, we continue serving the nation by delivering solutions for some of the country’s largest companies. Our adult rules culture, commitment to client success, and dedication to having fun set us apart. 

If you're ready to show the world that veterans are the most capable, dynamic, and effective leaders in the workforce today, apply to join our team! 

Greencastle Consulting is an Equal Opportunity Employer.