AI Enablement & Product Operations

Moving organizations from AI curiosity to confident adoption.

I'm Jennifer Feiock — a strategic leader with 20+ years of enterprise experience. I measure my own success by when the people I enable no longer need me in the loop to get the work done.

Let's connect See my work
20+
Years of enterprise product & operations leadership
1,800
Senior leaders onboarded in GenAI early-adopter programs
4
Cross-functional portfolios led at Paychex's #1 strategic priority

Featured Work

Projects that demonstrate the work

01
AI career market-fit analysis tool
GenAI-powered career analysis program for displaced colleagues — scoped, built, and operated as sole architect
Built with: Claude API · Claude Projects · React/JSX · Web search grounding

Designed a six-step analysis workflow producing a structured, citable PDF report for each candidate: market fit scoring, adjacent title mapping, live-searched skill demand ranking, cited learning paths, and line-level resume rewrites. A governing system prompt enforces tone, citation requirements, and output format across every analysis — functioning as the operational playbook for the program.

Governed analysis pipeline
Six discrete steps with a consistent scoring rubric — comparable across candidates over time, not re-calibrated per session.
React/JSX app with Claude API integration
Live web search for current job market data, .docx resume parsing, and self-contained PDF export. Built and iterated entirely solo.
Quality-gated rollout
Operator-run at launch to validate output quality. A candidate feedback rubric drives the go/no-go decision for self-service deployment.
Operating constraints
Candidates in active financial stress — outputs had to be immediately actionable. Operator-run at launch because quality had to be validated before candidates were handed a raw tool.
Enabling independence
Success means a candidate who reads the report, acts on it, and makes job search decisions without a follow-up conversation with me. Self-service deployment is the finish line, not a feature.
Concepts: System prompts as playbooks · Claude Projects governance · API + tool use integration · Web search grounding · Multi-step agent workflow · Deployment gating
02
Personal GenAI operating system
Daily AI use to plan and execute a 12-week professional transition — sprint planning, coaching, and quality assurance
Built with: Gemini · NotebookLM · Multi-turn prompting · NIST AI RMF

Structured an ambiguous 12-week career transition into six consecutive 2-week agile sprints, capped at 25–30 hours per week, governed by a 6-dimension personal rubric. Gemini served three distinct roles: structural planner, interactive learning coach, and deliverable auditor. NotebookLM organized large documentation volumes into queryable reference tools.

Strategic roadmap and boundary scorecard
A 12-week agile roadmap paired with a Family Decision Scorecard — quantitative thresholds filtered out unsustainable opportunities before investing time in them.
Interactive learning coach and talk-track development
Configured Gemini via multi-turn prompting to act as a mock stakeholder, critiquing reasoning and roleplaying as a skeptical enterprise executive.
Automated quality assurance workspace
Custom instructions directed Gemini to audit drafts against lean process efficiency, hard metrics enforcement, and NIST AI RMF alignment.
Operating constraints
No team, no manager, real financial stakes. Every framework had to function without external validation — built to work under ambiguity, not ideal conditions.
Enabling independence
Every artifact — the roadmap, the scorecard, the talk-track library — is transferable. Another professional in a similar transition could pick up these tools and run them without me.
Concepts: Multi-turn adversarial prompting · AI as interactive learning coach · Custom workspace instructions · Tool selection by task depth · Rubric-governed decision making · NIST AI RMF alignment
03
Enterprise GenAI platform pilot
Grassroots adoption enablement toolkit for diverse, cross-functional teams in a regulated enterprise environment
Built with: Gemini · OpenAI models · Meta-prompting

Rather than teaching prompting theory, designed a practical tool that integrated directly into existing daily workflows — solving both the blank-page problem and the inconsistent-quality problem simultaneously. The strategy had to scale horizontally across the organization while remaining deeply customizable for each individual contributor.

Custom instructions preset generator
A prompt-for-a-prompt meta-template: employees input their role, department, goals, and communication preferences. The AI outputs a tailored system prompt saved as a reusable preset — giving every user an owned, personalized AI assistant without requiring any prompting expertise.
Operating constraints
Regulated enterprise environment, diverse non-technical users across multiple business units. Enablement had to work at scale without creating dependency on a central trainer or ongoing facilitation.
Enabling independence
Once a user has their preset, they own it. The tool was designed so that the first conversation with the AI is the last conversation they need to have with me about how to set it up.
Concepts: Meta-prompting · Reusable system prompt presets · Persona-based customization · Horizontal enterprise scaling · Workflow-integrated deployment · Zero-theory onboarding design

Capabilities

What I bring to the table

Strategy & governance

Ethical AI frameworks
Acceptable use policy authoring
AI risk self-evaluation
Center of Excellence design
Executive alignment

Enablement & upskilling

AI literacy programs
Prompt engineering
Conversation design
Coaching & mentoring
Zero-theory onboarding

Platforms & tools

Claude
Gemini
NotebookLM
LibreChat
Jira, Jira Automations
Confluence
Miro

Ops & methodology

Lean Six Sigma (Black Belt)
Agile / Scrum (CSPO)
Business analysis
Process optimization
SDLC

Career

Experience

Sep 2025 – May 2026
Paychex Inc
Senior Product Operations Manager — AI, Analytics & Platform
  • Strategic enablement: Led Product Operations for Paychex's #1 strategic priority, aligning resources across 4 portfolios for customer-facing delivery.
  • Multi-portfolio scope: Directed operational enablement across a 3-pillar portfolio spanning AI, Reporting & Analytics, and Platform.
  • AI leadership: Bridged technical execution and operational strategy, fostering alignment with AI leadership on user-facing AI solutions.
Apr 2023 – Sep 2025
Paychex Inc
AI Product Manager
  • Platform & strategy: Led enterprise chatbot migration to Google Dialogflow CX; defined the multi-year GenAI roadmap focused on customer outcomes.
  • Governance: Secured AI Ethics Committee approval 1 month ahead of schedule for the company's first client-facing GenAI features; pioneered a Conversational AI intake playbook.
  • Policy: Authored the corporate AI Acceptable Use Policy, giving enterprise stakeholders a self-evaluation framework for assessing AI risk.
  • Upskilling: Coordinated GenAI early-adopter activities for 1,800 senior leaders, building custom prompt libraries ahead of a 10,000-user rollout.
Jul 2020 – Apr 2023
Paychex Inc
Process Improvement Manager
  • Spearheaded process improvements and automation across an 80-person product team.
  • Revamped new leader onboarding, cutting administrative time from weeks to hours and boosting early competency by ~50%.
Jun 2017 – Jul 2020
Mindex
Service Delivery Manager (Contractor)
  • Managed contract BAs and Product Leaders; positioned team as preferred professional services provider to Paychex.
  • Developed a Business Analyst Skills Maturity Matrix to elevate professional development and service delivery quality.
2008 – 2017
Earlier roles
Product Manager / Product Owner
  • Soleo Communications — UX redesign of call-based advertising platform (2016–2017).
  • Paychex Inc — Product Owner (2015–2016).
  • IDI Billing Solutions — Product Manager (2008–2015).

Credentials

Certifications & recognition

AI Agent Course
DeepLearning.AI · 2025
AI & ML Project Management +Ethics
PMI · 2023
Lean Six Sigma Black Belt
Advanced Innovation Group · 2022
TechRochester Woman of the Year
Finalist · 2020

Recommendations

From the people who saw the work firsthand

"She picks up new concepts, models, and tooling quickly enough that engineers stop treating her like 'the PM' and start treating her like a peer who happens to own the roadmap. She has a real grasp of the technical tradeoffs behind AI products — not just the buzzwords — which means she asks the right questions early and saves teams from chasing dead ends."

Chris McCann
Head of Platform Engineering · Paychex
Collaborated cross-functionally while Jen owned the AI product roadmap.

"She comes deeply prepared, documents clearly what is known and what still needs to be understood, and brings a level of diligence that raises the bar for everyone around her."

Visweshwar Ganesh
Enterprise AI Platform Leader · Paychex
Worked together through Paychex's early AI adoption, including governance and AI platform buildout.

"Jen was one of the earliest AI thinkers at Paychex — and not in the hype-chasing sense. Her experiments didn't always make headlines, but her research laid the groundwork for systems being used today. I'm now a Product Owner in the AI space, and that trajectory has Jen's fingerprints on it."

Brenton Dalgliesh
AI Product Owner · Paychex
Peers on the enterprise GenAI pilot.

Contact

Let's talk about your next AI initiative.

Whether you're standing up an AI Center of Excellence, designing a governance framework, or scaling adoption across a large workforce — I'd love to hear what you're working on.

jennifeiock@gmail.com 585.766.0766 linkedin.com/in/jenniferfeiock North Chili, NY

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