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+
3.5MMonthly Active Users Scaled
10,000+Active Stores Migrated/Supported
Industry Expertise
AI & Automation
2+ Years
E-commerce
High
SaaS
High
Web Development
High
Online Communities
Expert
Graphic Design & Animation
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, and freelance creative. 25%+ operations improvement; 50%+ sales lift; $1M+ revenue impact June 2014 – Present
  Animation & Design Create marketing, advertising, and video production assets across business and ecommerce use cases. Video, campaign, and visual asset production  
  Ecommerce design & development Design and develop ecommerce experiences across multiple platforms. Multi-platform ecommerce execution  
  Design / Production Create graphics for web, print, merchandise, photo restoration, and UI elements. 50+ merch designs; 10+ restorations; 100+ UI elements  
  Software Solutions Analyze software and workflow problems, then design operationally efficient solutions. Every case optimized operations by 25%+  
  Business Ops Assess business needs, define process changes, and support revenue-focused improvements. 50%+ sales lift; $1M+ revenue impact  
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
  Program Leadership Led weekly executive meetings and daily stand-ups across 13 teams. Executive visibility across high-priority work  
  Project Management Coordinated tasks for 200+ team members across multiple locations and time zones. Managed dependencies across distributed teams  
  Corporate Development / PM Created a Post-Acquisition Integration Playbook for Corporate Development. Reusable integration playbook  
  Integration / Execution Drafted and managed a 475-line, cross-functional 100-day work plan for multiple acquisitions. $50M–$350M acquisition context  
  Executive Reporting Provided updates to executives, board members, and employees while leading transition priorities. Board-ready reporting and transition visibility  
  Agile Project Management 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 Directed operations in alignment with strategic initiatives and growth opportunities. Operating model aligned to growth priorities  
  Company structure Established company structure with roles and responsibilities for all subsidiaries. Clearer ownership across business units  
  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 Developed and implemented a quarterly planning process with weekly checkpoints. Aligned team members and tasks with strategic initiatives  
  Product / Operations Directed product and operations for ecommerce platforms, improving user experience and product offerings. Expanded product offerings and customer experience  
  Strategy Spearheaded strategic initiatives to enhance customer experience for ecommerce solutions. 35% increase in sales  
  Leadership meetings 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
  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  
  Product / Operations Defined platform business logic for user participation, content workflows, and moderation features. Operational foundation for scalable community platform  
  Growth / SEO Established SEO best practices and grew organic traffic. 3.5M monthly unique visitors  
  Moderation policy Wrote and published moderation policies to improve content quality and user value. Quality and trust framework for user-generated content  
  Revenue Strategy Developed formulas for data driven content, sponsorship, network and affiliate opportunities. Advertising monetization support  
  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 / 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 Defined company vision, mission, strategy, business plan, product roadmap, and communication visuals. Business strategy and launch plan  
  Product and service design Designed product and service offerings and prioritized launch schedule. Market-aligned product and service roadmap  
  Financial Budget and Forecasts Managed finances, including sales forecast, operating budget, and pricing strategy. Forecasting, budget, and pricing structure  
  Ecommerce Built an online store selling drop-ship products, affiliate products, and stocked inventory. SaaS-based ecommerce store launched  
  Product Management Directed design, development, and testing of online education software. Education platform launched from concept to launch  
  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  
  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 Facilitated the transition of the MonsterCommerce technical division into Network Solutions despite cultural and procedural challenges. Technical division integration  
  Feature scoping and prioritization Worked with multiple departments to scope and prioritize feature development for flagship ecommerce software. Roadmap and release prioritization  
  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 Oversaw migration work for thousands of online stores during ecommerce platform transition. 8,500+ online stores migrated  
  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. Top Five SaaS ecommerce platform in the world October, 2002 - December, 2006
(acquired by Network Solutions)
  Technical division leadership  Led the technical division of an ecommerce company through rapid customer and team growth. 1,000 → 10,000 customers; 5 → 200 employees  
  Department leadership 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 Led creation, testing, and support of software products for ecommerce SaaS customers. Scaled ecommerce software product operations  
  Security / Compliance Attained CISP certification and PCI compliance. Accolades from Visa and MasterCard  
  Migration / Customer Ops Migrated customers from legacy software to the newer platform version. 3,000 customers migrated with <2% cancel rate  
  Operations / Governance Established standards and best practices across the entire company. Company-wide operating standards  
  MC Family of 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 Revamped design and marketing copy for Design, SEO, Payments, and Domain service websites. 35% increase in sales across service divisions  
  Product innovation 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
  Web Developer Implemented designs from creative teams for Fortune 500 companies. Interactive web solutions for major corporate clients  
  Flash animation Built Flash animation for interactive advertisements and splash pages. Interactive advertising and digital experience work  
  Sales pitch support Managed technical delivery for sales presentations to companies including Kodak and Genentech Pharmaceuticals. Large-scale sales presentation support  
  Knowledge Management Built and managed a knowledge base for Fleishman-Hillard’s global network. Global internal knowledge system  
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.