AI strategy and advisory
Enterprise AI strategy that turns into running workflows
Ashley Gross helps leadership teams move from AI curiosity to measurable ROI. Clear priorities, safe governance and agents your people actually use.
Implementing enterprise AI since 2020. 2,500+ professionals trained at Fortune 500 companies.
Where most AI plans stall
If any of these sound familiar, advisory is the fastest way to get unstuck.
Tools bought, adoption stalled
Copilot, ChatGPT or Gemini licenses are live, but usage never took hold beyond a few power users.
Too many pilots, no priority
Every team has an AI idea. Nobody can say which one deserves budget first or how to measure it.
Governance is unclear
Without clear rules on data and permissions, teams either stall or work around IT.
What enterprise AI advisory delivers
Strategy you can act on the next morning, built around your real workflows.
Scalable AI governance
Clear rules for who can use what, with which data, so adoption can grow without creating exposure.
High-ROI tool selection
An evidence-based shortlist of the AI tools worth paying for, matched to your workflows and your stack.
Internal AI agent frameworks
Agent frameworks your teams can deploy and maintain, built around the work they already do.
An adoption plan that sticks
Champions, training and simple habits that turn licenses into daily use.
ROI you can report
Baseline metrics before the build and a scorecard leadership can read in two minutes.
A roadmap your team owns
A 90-day plan with owners and dates, not a slide deck that sits in a drive.
How an engagement runs
Four phases. Each one ends with something your team can use.
Assess
Stakeholder interviews, a workflow and tool audit, and a check of your data and permissions.
Prioritize
Every use case scored on value, effort and risk. You leave with the first three to fund.
Build
Agents and automations built with your team, inside the guardrails you agreed on.
Scale
Training, champions and KPIs so the wins spread past the first team.
Advisory engagement options
Pick the depth that fits where you are. Every option is scoped and priced to your organization.
Strategic AI roadmap
For leadership teams that need a clear, defensible plan before they spend.
- Current-state AI and tool audit
- Scored use case portfolio
- Governance one-pager
- 90-day rollout plan with owners
Fractional AI advisory
A senior AI advisor in your corner without a full-time hire.
- Monthly executive working session
- Office hours for your team
- Vendor and tool reviews
- Quarterly roadmap refresh
Structured advisory engagement
Roadmap, build and enablement in one engagement, measured end to end.
- Everything in the roadmap
- Two to three agents or workflows built live
- Team training and champions
- ROI scorecard at 90 days
What leaders leave with
Select any outcome to see the exact deliverables your team receives.
Security, privacy and data handling
Enterprise AI only scales when security, legal and IT trust it. These standards apply to every engagement.
SOC 2 aligned vendor standards
Every platform we recommend or build on is reviewed for a current SOC 2 Type II report, encryption in transit and at rest, single sign-on and audit logging. If a vendor cannot show it, it does not make the shortlist.
Data privacy by design
We work inside your environment with least-privilege access, under NDA, and follow your data classification rules. Client data is never used in demos, training materials or other engagements. Requirements such as GDPR, CCPA or HIPAA are mapped before any build starts.
Zero-retention API policies
Agents and automations use enterprise API tiers configured so prompts and outputs are not used to train models, with zero data retention enabled wherever the provider offers it. Retention settings are documented for your security team.
Your security team gets a written summary of every tool, data flow and retention setting before anything goes live.
Engagement timelines and scope
Every engagement starts with a defined scope, a timeline and clear owners, so you always know what is included and when it lands.
Strategic AI roadmap
4 to 6 weeks- Week 1Discovery and stakeholder interviews, baseline metrics captured
- Weeks 2 to 3Tool audit, AI Capability Matrix and scored use case portfolio
- Weeks 4 to 5Governance guardrails and Custom Agent Roadmap
- Week 6Executive Briefing Deck and 90-day rollout plan
In scope: Strategy, audit, governance and architecture
Not included: Building agents and team training (available in a structured engagement)
Fractional AI advisory
Monthly, ongoing- Month 1Onboarding, priorities and a 90-day focus list
- Every monthExecutive working session and team office hours
- As neededVendor, tool and security reviews
- Every quarterRoadmap refresh and progress readout
In scope: Senior guidance, reviews and decision support
Not included: Hands-on builds unless added to the scope
Structured advisory engagement
One quarter (about 12 weeks)- Weeks 1 to 6Everything in the strategic AI roadmap
- Weeks 5 to 10Two to three agents or workflows built live with your team
- Weeks 8 to 12Role-based training, prompt library and AI champions
- Day 90Executive ROI scorecard and next-quarter plan
In scope: Strategy, builds, enablement and measured ROI
Not included: Ongoing support after day 90 (continue with fractional advisory)
Advisory at a glance
- Format
- Roadmap, fractional or structured engagement
- Delivery
- In person or virtual
- Audience
- Executive, operations and IT leaders
- Advisor
- Implementing enterprise AI since 2020
Leaders Ashley has advised and trained
Questions leaders ask
Do you work with Microsoft 365 Copilot?
Yes. Ashley has a deep Microsoft 365, Power Platform and Copilot Studio background, and also works across ChatGPT, Claude, Gemini and Perplexity. Recommendations are tool-agnostic.
Do you sell software?
No. The goal is the right tools for your workflows and your stack, including the ones you already pay for.
Can advisory include hands-on workshops?
Yes. Most structured engagements include live build sessions so your team leaves with working agents, not just a plan.
Is this in person or virtual?
Both. Kickoffs and workshops are often on site, and ongoing advisory runs virtually.
How fast can we start?
Most engagements start within two to four weeks of the first conversation.
Find the right first move for your organization
Fifteen minutes is enough to know whether a roadmap, fractional advisory or a structured engagement fits.