Jen Heil

PEOPLE \ PLATFORM \ PROCESS
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Professional Summary

SENIOR EXECUTIVE & SOLUTIONS ARCHITECT — PRODUCT & OPERATIONS

High-leverage, technical builder-operator with over 20 years of experience architecturalizing, scaling, and managing digital platforms from initial concept to multi-million dollar acquisitions. Proven track record directing 80+ person engineering and operations orgs, deploying complex e-commerce SaaS infrastructures, and executing high-stakes post-merger integration playbooks. A rare executive who bridges the gap between deep technical implementation (HTML/JS, system design, API integrations) and corporate growth strategy.

Following a successful period optimizing private business ventures and real estate investments, returned to the technology sector to combine master-level operational mechanics with modern Generative AI engineering, custom LLM pipelines, and fractional leadership. Passionate about uniting cross-functional teams behind a unified vision, cutting operational waste by 20%+, and engineering high-utility software solutions to solve chaotic business problems.

Skills Showcase

Leadership Operations Product Management AI Systems Post-Merger Integration Planning Operational Systems Design Process Standardization & Optimization Crisis Management & Operational Recovery Cross-Functional Program Leadership SaaS & E-commerce Operations Product Operations & Strategy Technical Requirements Gathering (SDLC) Platform Migration Planning User Experience & Interface Design (UI/UX) AI Workflow Design & Automation AI Prompt Engineering & System Design OpenAI API Integration AI-Assisted Prototyping
$400M+ Successful M&A Integrations
$1B+ Sales Across Led Systems
3.5M Monthly Active Users Scaled
10,000+ Active Stores Migrated/Supported
Portfolio Composition
Startup Scale-Up
High
Enterprise Teams
High
SaaS Platforms
High
Ecommerce Architecture
Expert
Q&A Communities
Scale
Generative AI Pipelines
Active
Current Build Portfolio
Statement Fashion
Build
Resume Jedi
Launch
eProGen / Sandbox
Prototype
Portfolio Architecture
Live
Featured Outcomes
200+ Cross-functional personnel coordinated across 13 distinct teams
25%+ Average operational efficiency boost realized per client deployment
< 2% Customer churn maintained during multi-thousand store legacy migration
PCI Full Level 1 security compliance attained with VISA/MC accolades
Company Role Responsibilities Accomplishments Dates
Consulting Consultant / Solutions Architect / Creative Producer Marketing, ecommerce, software analysis, business analysis, change management, dog training, and creative production. 25%+ operations improvement; 50%+ sales lift; $1M+ revenue impact June 2014 – Present
↳ Marketing & advertising assets Creative / Production Create marketing, advertising, and video production assets across business and ecommerce use cases. Video, campaign, and visual asset production  
↳ Ecommerce design & development Ecommerce / Web Design and develop ecommerce experiences across multiple platforms. Multi-platform ecommerce execution  
↳ Graphic design systems Design / Production Create graphics for web, print, merchandise, photo restoration, and UI elements. 50+ merch designs; 10+ restorations; 100+ UI elements  
↳ Software analysis Solutions Architect Analyze software and workflow problems, then design operationally efficient solutions. Every case optimized operations by 25%+  
↳ Business analysis & change management Business Ops Assess business needs, define process changes, and support revenue-focused improvements. 50%+ sales lift; $1M+ revenue impact  
↳ Dog training & boarding Operations / Service Provide dog training, boarding, and service operations. Hands-on service business operations  
Answers Director of Project Management Coordinate acquisition integration, executive visibility, product roadmap execution, and cross-functional delivery. 475-line 100-day plan; 13 teams; 200+ team members April 2013 – January 2014
↳ Executive operating cadence Program Leadership Led weekly executive meetings and daily stand-ups across 13 teams. Executive visibility across high-priority work  
↳ Cross-functional coordination Project Management Coordinated tasks for 200+ team members across multiple locations and time zones. Managed dependencies across distributed teams  
↳ Acquisition integration Corporate Development / PM Created a Post-Acquisition Integration Playbook for Corporate Development. Reusable integration playbook  
↳ 100-day work plan Integration / Execution Drafted and managed a 475-line, cross-functional 100-day work plan for multiple acquisitions. $50M–$350M acquisition context  
↳ Board and employee updates Executive Reporting Provided updates to executives, board members, and employees while leading transition priorities. Board-ready reporting and transition visibility  
↳ Jira administration Systems / Program Ops Administered Jira dashboards, projects, workflows, and screens to improve collaboration and real-time reporting. Custom dashboards, dependency tracking, and risk visibility  
Juggle Chief Operating Officer Directed operations, product execution, company structure, workflow optimization, and planning across subsidiaries. 20%+ workflow efficiency improvement; 35% sales increase September 2009 – January 2013
↳ Strategic operations COO Directed operations in alignment with strategic initiatives and growth opportunities. Operating model aligned to growth priorities  
↳ Company structure Operations Design Established company structure with roles and responsibilities for all subsidiaries. Clearer ownership across business units  
↳ Workflow optimization Process Improvement Assessed operations and optimized processes within each business unit. Cut time and effort by at least 20% in each major workflow  
↳ Quarterly planning Planning / Execution Developed and implemented a quarterly planning process with weekly checkpoints. Aligned team members and tasks with strategic initiatives  
↳ Product and ecommerce operations Product / Operations Directed product and operations for ecommerce platforms, improving user experience and product offerings. Expanded product offerings and customer experience  
↳ Customer experience initiatives Strategy Spearheaded strategic initiatives to enhance customer experience for ecommerce solutions. 35% increase in sales  
↳ Leadership meetings Leadership Ops Led company and leadership team meetings and facilitated offsite sessions. Improved leadership alignment  
GirlsAskGuys Co-Founder & General Manager Designed, launched, scaled, and operated a Q&A platform with product, content, moderation, SEO, advertising, and growth systems. 3.5M monthly unique visitors March 2007 – December 2011
↳ Website product system Product / UX / Systems Designed front-end and back-end systems for questions and answers, articles, user roles, accounts, points, and moderation. Built core Q&A platform logic and user systems  
↳ Business logic Product / Operations Defined platform business logic for user participation, content workflows, and moderation features. Operational foundation for scalable community platform  
↳ SEO growth Growth / SEO Established SEO best practices and grew organic traffic. 3.5M monthly unique visitors  
↳ Moderation policy Content / Trust Wrote and published moderation policies to improve content quality and user value. Quality and trust framework for user-generated content  
↳ Advertising partnerships Revenue / Partnerships Developed partnerships with advertising agencies and created and managed ad campaigns. Advertising monetization support  
↳ Media calendar and training Marketing Ops Created media calendar, trained team members, and established task management and reporting for SEO, social, and marketing tactics. Repeatable marketing execution system  
↳ Ecommerce integration Ecommerce / Growth Leveraged SEO and user engagement strategies to support ecommerce integration and conversion. Traffic and conversion growth support  
Dog Academy Founder & Owner Built a dog training, ecommerce, and online education business spanning strategy, product, services, software, content, finance, and marketing. Online store and education platform launched January 2008 – January 2020
↳ Company strategy Founder Defined company vision, mission, strategy, business plan, product roadmap, and communication visuals. Business strategy and launch plan  
↳ Product and service design Product / Services Designed product and service offerings and prioritized launch schedule. Market-aligned product and service roadmap  
↳ Finance and pricing Business Ops Managed finances, including sales forecast, operating budget, and pricing strategy. Forecasting, budget, and pricing structure  
↳ Ecommerce store Ecommerce Built an online store selling drop-ship products, affiliate products, and stocked inventory. SaaS-based ecommerce store launched  
↳ Online education platform Product / Software Directed design, development, and testing of online education software. Education platform launched from concept to launch  
↳ Course and content system Content / Product Outlined courses, classes, and an online library, then directed content creation by internal team members, partners, and crowdsourced contributors. Course and learning library structure  
↳ Advertising and creative assets Marketing / Creative Managed online advertising campaigns and created graphics and video assets. Advertising, graphics, and video execution  
Network Solutions Vice President, E-commerce Led ecommerce transition, platform roadmap scoping, feature prioritization, and large-scale technical migration planning. 52-server plan; 10,000-store migration scope December 2006 – March 2007
↳ MC technical division transition VP E-commerce Facilitated the transition of the MonsterCommerce technical division into Network Solutions despite cultural and procedural challenges. Technical division integration  
↳ Feature scoping and prioritization Product / Ecommerce Worked with multiple departments to scope and prioritize feature development for flagship ecommerce software. Roadmap and release prioritization  
↳ Server and store migration Technical Ops Created a detailed plan to migrate 52 servers and 10,000 online stores from Rackspace to Savvis. Resource allocation, budget, and communications plan  
↳ Online store migration execution Ecommerce / Infrastructure Oversaw migration work for thousands of online stores during ecommerce platform transition. 8,500+ online stores migrated  
↳ Ecommerce platform rewrite Product / Technology Led ecommerce platform rewrite work to improve scalability and customer shopping experience. Improved platform scalability and shopping experience  
MonsterCommerce Chief Technical Officer Led technical division, software products, systems operations, security, QA, technical support, compliance, migrations, and ecommerce service growth. 1,000 → 10,000 customers; 5 → 200 employees October 2002 – December 2006
↳ Technical division leadership CTO Led the technical division of an ecommerce company through rapid customer and team growth. 1,000 → 10,000 customers; 5 → 200 employees in 4 years  
↳ Department leadership Technical Executive Directly responsible for 80+ team members across Software Development, Systems Operations, Security, QA, and Technical Support. 80+ direct technical organization scope  
↳ Ecommerce SaaS product delivery Product / Technology Led creation, testing, and support of software products for ecommerce SaaS customers. Scaled ecommerce software product operations  
↳ CISP and PCI compliance Security / Compliance Attained CISP certification and PCI compliance. Accolades from Visa and MasterCard  
↳ Legacy software migration Migration / Customer Ops Migrated customers from legacy software to the newer platform version. 3,000 customers migrated with <2% cancel rate  
↳ Company standards Operations / Governance Established standards and best practices across the entire company. Company-wide operating standards  
↳ MC Family of Services Revenue / Services Created profitable service packages for second-generation service offerings and established structure, goals, and metric reports. Profitable service package structure  
↳ Design and marketing revamp Marketing / Ecommerce Revamped design and marketing copy for Design, SEO, Payments, and Domain service websites. 35% increase in sales across service divisions  
↳ Product innovation Product / Technology Implemented ecommerce platform product innovations and technical improvements. Grew company from 1,000 to 8,500+ customers and achieved PCI compliance  
Fleishman-Hillard Web Developer Built interactive web, Flash, presentation, and knowledge-base solutions for global corporate communications and Fortune 500 client work. Fortune 500 client work; Kodak and Genentech sales presentations November 2000 – October 2002
↳ Fortune 500 web development Web Developer Implemented designs from creative teams for Fortune 500 companies. Interactive web solutions for major corporate clients  
↳ Flash animation Interactive Developer Built Flash animation for interactive advertisements and splash pages. Interactive advertising and digital experience work  
↳ Sales presentation leadership Technical Project Manager Managed technical delivery for sales presentations to companies including Kodak and Genentech Pharmaceuticals. Large-scale sales presentation support  
↳ Global knowledge base Knowledge Management Built and managed a knowledge base for Fleishman-Hillard’s global network. Global internal knowledge system  
Current Product Portfolio Founder / AI Product Builder Build modern AI tools and a portfolio that proves current product, UX, systems, and AI workflow capability. Live prototypes and launch work Current
↳ Statement Fashion Founder Connect values, language, action, and merch-backed engagement. Launch-stage system  
↳ Find Your Voice / Write My Rep / Find Your Officials Product Features Turn concern, confusion, and friction into usable civic outputs. AI workflow prototypes  
↳ Resume Jedi / eProGen / Portfolio Website Product Lab Turn hard writing, positioning, and workflow problems into usable interfaces. Active development  
Full Stack Skills
  • Operational Systems Design
  • Post-Merger Integration Planning
  • Process Standardization & Scale
  • Workflow Mapping & Optimization
  • SaaS & E-commerce Operations
  • Business Analysis & Growth Strategy
  • Change Management Implementation
  • Data-Driven Decision-Making
  • Cross-Functional Program Leadership
  • Crisis Management & Operational Recovery
  • Executive Communication & Board Reporting
  • Stakeholder Engagement & Alignment
  • Strategic Operating Cadence Design
  • Quarterly Planning (OKR / KPI Frameworks)
  • Team Enablement & Scaling
  • Product Operations & Roadmapping
  • Technical Requirements (SDLC Ecosystems)
  • Risk, Issue & Dependency Mitigation
  • Agile Delivery Systems (Scrum/Kanban)
  • Jira Administration & Dashboard Design
  • Platform Migration Planning
  • User Stories, Epics & Backlog Management
  • Launch Readiness & Product Release Planning
  • Information Architecture & System Documentation
  • AI Workflow Design & Automation
  • AI Prompt Engineering & System Design
  • OpenAI API Integrations
  • AI-Assisted Prototyping & Testing
  • Fine-Tuning, Embeddings & Model Training
  • Human-in-the-Loop Workflow Architecture
  • Google Apps Script Automation Pipelines
Featured Proof Artifacts
8 Selected Deliverables
Workflow Logic
Automation & Logic Find Your Voice Workflow Architecture Conversational routing and logic states mapped out for automated AI-assisted civic solutions.
Data Embeddings
Data Engineering Consumer-Brand Values Embeddings Matrix Vector embedding and scoring models matching complex corporate values against key consumer indices.
Cloud Infrastructure
Cloud Architecture Firebase Infrastructure State Saving Dynamic multi-tenant storage pipelines monitoring data integration sync metrics over secure endpoints.
Strategic SWOT
Strategic Planning Cross-Functional Alignment Matrix Systematic risk mitigation plans mapping environmental architecture indicators against operational targets.
QA Checklist
Quality Assurance Comprehensive Deployment Checklist Rigorous QA validation matrices evaluating edge cases, environmental dependencies, and system readiness.
Analytics Console
Frontend Orchestration Interactive Analytics Console Clean state machines parsing operational workflows and system states into crisp UI elements.
Release Plan
Operational Optimization Release Sequencing Template Workbook Strategic resource utilization charts planning milestones and functional dependency metrics.
AI Integration
AI Integration Intent Verification Debugger Tool Custom administrative interfaces logging text generation arrays, parsing thresholds, and token logs.