Ashley Gross

Enterprise AI Strategist, Wiley Author & Fortune 500 AI Trainer

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Starting at 2:00 PM UTC

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About

I help leaders and teams turn AI from something they keep meaning to figure out into workflows they actually use every week. I'm the founder and CEO of The Alliance, an enterprise AI advisory and implementation firm, and the author of The AI Workweek (Wiley). I have trained more than 2,500 professionals at companies like Microsoft, Visa, Abbott, ResMed, HP and Unilever, and I have guest lectured at MIT. I coach in three areas. First, AI strategy and roadmaps that tie back to real revenue and time savings. Second, hands on workflow builds with tools like ChatGPT, Claude, Copilot, n8n and Zapier, with no code required. Third, career moves into AI, including how to position your AI experience for leadership, consulting and enterprise AI roles. Working with me is practical and direct. We start with your actual week, find where the hours are going, and end each session with something built or decided. I keep it simple, I tell you the truth, and you walk away with workflows you can use the same day.

Ashley also coaches for Build with AI and Break Into AI Careers. View all.

Ashley’s free events

Live interactive sessions you can join for free.

Put Your Job Search on Autopilot in Claude (Live, No Code)

Nov 17 at 6:30 PM UTC

7 people going

Ashley’s AI Services Qualifications

Experience level: Associate

100+ AI Services clients

I help leaders and teams turn AI from scattered experiments into measurable business results. I'm the founder and CEO of The Alliance, an enterprise AI advisory and implementation firm, where I've led AI strategy, agentic workflow builds and adoption programs for Microsoft, Visa, Abbott, Unilever, Snowflake and L'Oreal. One system I architected, AI procurement validation across 22 ERP instances, cut compliance cycles from 6 days to under 8 minutes and delivers $2M+ in recurring annual cost avoidance. I've also taught this at scale: 3,200+ corporate leaders as Executive Faculty for Section's AI for Business Mini-MBA (4.9/5 CSAT), 1,400+ founders and operators in my applied AI accelerator on Maven, 2,500+ professionals at Fortune 500 companies, plus a guest lecture at MIT. I'm the Wiley-published author of The AI Workweek, a Forbes-recognized AI consultant, a credentialed Claude Partner, and a Certified Chief AI Officer. I can help you build an AI roadmap and business case your CFO will sign, pick the right tools for your team, design AI governance that gets through InfoSec, automate real workflows with agents, n8n or Zapier, and upskill your team so adoption actually sticks.

Ashley can help with:

AI Agents

AI Automation

AI-Driven Marketing

AI-Driven Sales

AI Policy & Governance Design

AI Readiness Assessment

AI Roadmap Development

AI Strategy

AI Tools & Integration

Fractional AI Strategist

Team AI Upskilling

Why do I coach?

When my son was born I had zero maternity leave and an 80 hour work week. AI is how I got my evenings back. I took that week down to 15 hours with the same output, then helped stand up an early AI steering committee across the Insight Partners portfolio. I have been bringing AI into enterprise teams since 2020, and my favorite moment is always the same one, when someone realizes they can do this themselves. Coaching lets me give one person the same playbooks I build for Fortune 500 companies, without the enterprise price tag or the jargon. I started working in hospitality at 14, so taking care of people is how I'm wired, and coaching is the most direct way I know to do that.

Work Experience

Executive Faculty

Section AI

2024 - 2026

Taught live enterprise AI curriculum in the AI for Business Mini-MBA to 3,200+ corporate leaders and MBA executives, earning a 4.9/5.0 CSAT.

Lead Instructor and Curriculum Architect

Maven

2023 - Present

Launched Building a Business with AI, a cohort-based applied AI accelerator, mentoring 1,400+ founders and operators through prototyping, agent deployment, and automation.

Founder & CEO

AI Workforce Alliance Inc

March 2022 - Present

Hiring Manager

Founded and lead The Alliance, a boutique enterprise AI advisory and implementation firm serving Microsoft, Visa, Abbott, Unilever, Snowflake and L'Oreal. Architected an AI procurement validation system across 22 ERP instances ($2M+ recurring annual cost avoidance, 94% fewer audit exceptions), deployed multi-agent workflows, and trained 2,500+ professionals, including leadership AI workshops at IMI, CleanSlate, Geospace, Jasper, HP, YPO and Zoom.

GTM Leader & AI Transformation Advisor

commercetools

2019 - March 2022

Directed 4 cross-functional enterprise teams at this Insight Partners portfolio company, building AI adoption frameworks, KPI scorecards and value-selling playbooks that influenced $25M+ in revenue. Cut my own 80-hour workweek to 15 hours at the same output with AI workflows, then stood up the company AI committee and joined an early AI steering committee across the Insight Partners portfolio.

Education

Illinois Institute of Technology

Bachelor's Degree, Information Technology

Garrett College

Associate of Arts (AA)