Ashley Gross

Land Your AI Role With an Enterprise AI Leader and Wiley Author

Available tomorrow

Starting at 2:00 PM UTC

Questions?

You can start chatting with Ashley before you get started.

Work with Ashley

Protected by the Leland Experience Guarantee

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 AI Services and Build with AI. 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 Break Into AI Careers Qualifications

Experience level: Associate

I sit on the hiring side of AI work every day. As founder and CEO of The Alliance, I've built and hired an AI team across strategy, engineering and client delivery, and I work with enterprise leaders at companies like Microsoft, Visa, Abbott, ResMed and Snowflake who are deciding which AI skills they need on their teams. I know what makes a candidate's AI experience credible to them and what makes it sound like buzzwords. I made my own move into AI from enterprise go to market, leading AI adoption at commercetools before starting my firm, so I know how to reframe a non-technical background into an AI story. I've trained 2,500+ professionals, taught enterprise AI as Executive Faculty in Section's AI for Business Mini-MBA, and wrote The AI Workweek (Wiley). Together we'll sharpen your positioning, build a portfolio project you can actually demo in interviews, and prep you for the AI questions hiring managers are asking now.

Ashley can help with:

AI Agents

AI Fundamentals

Interview Prep

Job Search Strategies

LinkedIn Review

Resume

Skill Building

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)