AI sped up building. It didn't replace the judgment.

Engineer → Consultant → Full Stack Product Manager.

The Manhattan skyline at dusk, seen from across the water

My Strengths

What I'm good at

I wrote the code, I deployed it inside other people's organizations, and now as a product leader I'm accountable for what ships (and I can help you build it, too).

Shipped AI in production, and I build my own on the weekend.

GridStrong AI

Delivered an AI-powered compliance copilot for GridStrong, guiding power plant owners through plant profiles, compliance workflows, and cross-standard tasks. Early prototypes helped secure a $1.4M DOE grant.

HVAC.com

Defined and drove development of an LLM-powered assistant that answers homeowner questions conversationally and moves them toward replacement and repair. Read the case study

Hurd AI

Launched Whisper-powered on-device transcription, summarization, and a study chatbot for Hurd. 700% user growth off a ProductHunt launch.

Sendoso

Shipped AI-driven fraud detection alongside two-factor authentication, protecting gift card transactions from bot-driven attacks on the platform's most-used send type. Read the case study

Built for myself

QuietFeed, KevinOS, and a few open-sourced Claude plugins.

What I'm Building Now

Current work · 2026

What I'm Looking For

I do my best work where people can say what's actually happening

Primary

Product managementInternal toolsPlatforms Public sectorAI workflowsIntegrations

Also

Product operationsMarketing operationsConsulting

Not for me

Ad techCryptoWeb3

About Me

I make complex work feel simple.
Kevin Middleton

I build platforms, tools, and AI workflows that connect teams and systems.

In my experience, teams usually know what's wrong. They just need someone willing to name it and make it safe to act on. That's usually where I start.

I work across people, process, and product. I'm hands-on at every level: running meetings, cleaning up details, digging into data, or building a quick prototype.

Most of my best work happens between teams that don't usually talk to each other. Engineering and support. Product and marketing. I broker the agreements, bring the context, and make sure nobody's working in the dark.

My Values

How I actually work with people

Start With Understanding

Begin with the problem, the people, and the constraints. Good outcomes start with listening.

Give Grace, Get Grace

Lead with empathy. Assume good intent. People do their best work when they feel supported.

Make It Simple

Turn complex workflows into clear, reliable systems that people actually use.

Professional Experience

Startups, enterprise, and public sector
Newest first, or start at the beginning
GRIDSTRONG AIStartupDirector of Product Management (initially Product Advisor)

Began supporting GridStrong.ai in September 2024 as a part-time Product Advisor while at HVAC.com, creating early prototypes and helping secure a $1.4M U.S. Department of Energy grant. After seed funding closed in June 2025, joined full‑time as Director of Product Management, leading product strategy, engineering, and design across the compliance automation platform. Departed after company restructuring reduced the product team.

  • Funding & Early Traction: Built early AI prototypes that helped secure a $1.4M DOE grant, contributing to a $10M seed round.
  • Product Direction: Defined early product direction through SME discovery, workflow validation, and shaping the core patterns used across the GridStrong app.
  • Workflow Delivery: Delivered core compliance workflows including model quality testing, event analysis, document linking, and automated cross‑standard tasks.
  • Regulatory Translation: Translated complex regulatory requirements into clear product plans that guided engineering and design.
  • Process & Execution: Established cross‑company processes for roadmapping, sprint cadence, QA gating, and release workflows, improving reliability and team alignment.
0 to 1Product LeadershipProcess DesignCross-Functional CollaborationSaaSEnergy ComplianceRoadmapping
HVAC.COMAcquiredby Trane Technologies May 2024Senior Product Manager, HVAC.com and Branded Sites

Owned product strategy, UX, and growth for HVAC.com, a homeowner platform with ~2M annual visits that connects consumers to trusted HVAC dealers nationwide. Owned the full digital funnel, from first touch to dealer handoff, driving measurable conversion gains and shaping Trane's broader digital strategy.

  • Conversion Growth: Drove a ~50x conversion lift off a 0.1% baseline by launching high‑performing tools: calculators (7.3%), QuoteScore (6%), video content (3.4%), and optimized landing pages (2.3%).
  • Platform Expansion: Expanded the product surface area with HVAC repair services, new interactive calculators, and a redesigned blog that increased depth, engagement, and lead volume.
  • Funnel Efficiency: Improved lead quality and user flow using behavioral analytics, session‑to‑install data, and user paths to refine the homeowner journey.
  • Data‑Driven Execution: Drove measurable business results through continuous testing, analytics‑led iteration, and focused UX improvements.
ScaleProduct Lifecycle ManagementConversion Rate Optimization (CRO)A/B TestingCross-Functional LeadershipData-Driven Decision Making
Read the case study(opens in a new tab)
HURD AIStartupCo-Founder & Product Advisor

Shaped early product direction for an AI-powered learning platform that helped students, researchers, and professionals organize and study their notes. Led feature design, user research, and launch execution across the Mac app and web chatbot.

  • AI-Powered Features: Launched Whisper-powered on-device transcription, fast summarization, structured note organization, and a web-based chatbot for interactive study sessions.
  • User Growth: Drove 700% user growth through a ProductHunt launch supported by targeted messaging and lightweight paid campaigns.
  • User Research: Worked directly with journalists, researchers, and students to validate pain points, workflows, and privacy expectations.
0 to 1Natural Language Processing (NLP)AI-Powered AutomationGo-To-MarketData Analysis
LEVERAcquiredby Employ July 2022Senior Product Manager, HRIS Sync Lead

Owned end-to-end development of HRIS Sync, a core enterprise integration that strengthened Lever's upmarket positioning through automation, workflow reliability, and enterprise-grade data sync.

  • HRIS Sync Launch: Launched HRIS Sync with 37% Q1 engagement, enabling org chart-aware approvals, automated user provisioning, and manager-relationship sync for enterprise customers.
  • Bulk Importer: Delivered a self‑serve Bulk Candidate Importer that reduced upload times from days to minutes, cutting support and implementation workloads and enabling customers to manage large volumes on their own.
  • Enterprise Discovery: Uncovered key enterprise pain points through deep discovery with IT teams, recruiters, and admins, shaping the roadmap for Sync, provisioning, and hiring workflows.
  • Cross‑Functional Alignment: Strengthened alignment by partnering with professional services, implementation, customer success, and support to integrate real‑time feedback into product updates.
ScaleHRIS IntegrationAPI DevelopmentQuantitative & Qualitative ResearchWorkflow Automation
Read the case study(opens in a new tab)
SENDOSOStartupSenior Product Manager, Core Platform & eGift Global Expansion

Joined between Sendoso's Series B and $100M Series C to scale the eGift platform while the market window was open. eGifts were the most popular send option on the platform, representing over half of all sends in 2021. I owned eGift partnerships, catalog growth, and the operational infrastructure behind it.

  • Catalog Expansion: Doubled active eGift coverage from 800 to 1,600 options across 47 countries. Negotiated directly with vendors (Tango, XOXODAY, Gyft, NGC, TOPPS) for better terms and faster onboarding.
  • Square Partnership: Landed Square as a strategic partner, enabling personalized small business gifting in 4 major markets (U.S., Canada, Australia, and U.K.).
  • Platform Consolidation: Unified three parallel eGift redemption flows into a single experience, reducing user confusion and technical debt.
  • Fraud Prevention: Implemented two‑factor authentication and AI‑driven fraud detection, protecting gift card transactions from bot‑driven attacks.
  • Operational Efficiency: Streamlined eGift deactivation, refunds, and swaps, freeing engineering from operational tasks and speeding support resolutions.
ScaleFraud PreventionStrategic PartnershipsMarket Expansion StrategiesSaaS PlatformRevenue Optimization
Read the case study(opens in a new tab)
ROCKET LAWYERStartupSenior Product Manager, Core Product & Platform

Owned product strategy and execution for Rocket Lawyer's Platform and Legal Document teams, expanding market reach, improving mobile engagement, and diversifying revenue streams while advancing Rocket Lawyer's mission to make legal services more accessible.

  • Co‑Branded Partner Sites: Created and launched co‑branded partner sites reaching 11.5M users, which expanded Rocket Lawyer's presence in Europe and enabled configurable authentication, pricing, feature gating, and theming for enterprise partners.
  • Mobile Conversion Growth: Increased mobile gross conversions by 5% through targeted A/B testing and UX improvements for the Legal Document product line, which drives 90% of U.S. revenue.
  • eSign Experience Upgrade: Improved eSign start rates by 13% by integrating Legal Documents with RocketSign, replacing a legacy flow with a more reliable, user‑friendly experience.
  • Analytics‑Driven Optimization: Achieved record‑high checkout conversion rates (2.34%) by building internal analytics tools that linked site performance to user behavior, directly informing optimizations to site speed and checkout.
ScaleMobile Conversion OptimizationAnalytics Tools DevelopmentA/B TestingNew Revenue ChannelsCross-Platform Integration
Read the case study(opens in a new tab)
ORACLEEnterpriseSenior Product Manager, Engage, Integrations, & Social Network Expansion

Promoted to lead Oracle Social Cloud's Engage product through a full platform modernization, doubling supported social networks and shipping a year-long series of upgrades across UI, performance, and workflow design. I led two agile teams and collaborated with three UX/UI designers across Austin (Platform), Atlanta (Frontend), and India (Engineering) to deliver a more global, scalable platform.

  • Global Network Expansion: Expanded social network coverage by integrating LinkedIn, Instagram, Sina Weibo, and Tumblr, doubling supported networks and addressing top customer demand.
  • Product Overhaul: Launched a full Engage product overhaul with 36 new features in 12 months, guided by beta testing, customer feedback, and UX improvements.
  • Internationalization: Internationalized the platform across 30+ languages, improving usability and accelerating adoption in EMEA and APAC regions.
  • Go‑to‑Market Leadership: Led coordinated rollouts with Customer Success, Marketing, and Sales to ensure alignment, smooth adoption, and strong market penetration.
ScaleGlobal Product RolloutsInternationalizationSocial Media IntegrationsGo-To-Market StrategyBeta Testing
Read the case study(opens in a new tab)
CACI INTERNATIONALPublic SectorConsultant, Product Specialist, & UAT Lead

Momentum Financial Management System Analyst supporting large-scale federal financial transformation across six Department of Justice component agencies (DOJ, DEA, ATF, BOP, USMS, FBI). Managed UAT strategy, deployment coordination, and triage for a system handling budgets up to $200M. Held a Top Secret security clearance.

  • Enterprise Deployment: Led UAT and deployment coordination across six federal agencies, ensuring system reliability for critical financial operations.
  • Triage Leadership: Managed a 10-person triage team during system go-lives, resolving production issues in real time across global stakeholder groups.
  • Stakeholder Management: Earned the respect of stakeholders worldwide through deep system knowledge, patience, and consistent follow-through.
  • Process Design: Built training programs and internal processes that ensured teams had the information they needed to succeed during and after deployment.
Federal ConsultingFinancial SystemsUAT StrategyStakeholder ManagementTop Secret Clearance
CGI FEDERALPublic SectorSoftware Engineer & QA Automation

Started as a C++ software engineer on Momentum, the federal government's core financial management system. Transitioned into QA automation, building automated test suites and providing functional support for the testing team.

  • Software Development: Contributed to C++ development on Momentum, the government's enterprise financial management platform.
  • QA Automation: Built and maintained automated test suites, accelerating test coverage and improving release confidence.
  • Technical Foundation: Developed the deep technical fluency that later became a differentiator in product management roles.
C++QA AutomationSoftware EngineeringFederal Systems

Case Studies

What shipped, and what it moved

Skills & Expertise

What I actually do

Strategic

  • Product Strategy
  • Roadmap & Vision
  • Competitive Analysis
  • eCommerce & Marketplace
  • B2B Customer Success
  • Growth PM
  • Funnel Optimization

Leadership

  • Cross-Functional Leadership
  • Stakeholder Management
  • Team Building
  • Mentorship
  • Agile (Scrum, Kanban)

Analytical & Research

  • Data-Driven
  • User-Centric Design
  • A/B Testing
  • User Research
  • Continuous Improvement

Certifications & Education

Education

B.S. Business Information TechnologyVirginia Tech · Blacksburg, VA
Academic focuseBusiness Technology · C++, HTML, JavaScript, PHP, SQL (yes, PHP)
CourseworkSupply Chain · E-Commerce · DB Management · Software Engineering · UI Design

Certifications

Certified ScrumMaster (CSM)Scrum Alliance · active through July 22, 2028
Certified Scrum Product Owner (CSPO)Scrum Alliance · active through July 22, 2028
Product-led CertificationPendo · 2023
Product-Led Growth FundamentalsProductLed · 2023
AI for Product ManagementPendo · 2023
Introduction to Generative AIGoogle · 2023
Product Analytics CertificationPendo · 2023

Recommendations

People I worked for, and with

Different roles, different companies, same conclusion. The work got easier and better when we were on it together.

On hiring him

Start with the right people. Kevin is the right people.

Wesley BarnesFormer Manager · Director of Product Management · Oracle
On ambiguity

Kevin brings structure without killing creativity, clarity without slowing momentum, and a rare ability to help teams move faster together. He makes even ambiguous work feel navigable, and the people around him consistently do their best work.

Matt TriplettFormer Manager · Product Leader · HVAC.com + GridStrong
On cross-functional work

Kevin fought for the best possible experience, and brokered agreements across PM, UX, and Engineering. His work ethic, attention to detail, and obsession with delivering great experiences for customers earned my respect.

Emily Leahy-ThielerDesign Leader · Oracle
On quality

Kevin is a top-notch PM who fights for quality products and for his team.

Christina JamesStaff Quality Assurance Analyst · Rocket Lawyer
All recommendations on LinkedIn(opens in a new tab)

Bring me something messy.

Away from the desk

The rest of it

I live in New York with three cats who supervise every deploy. I cook most nights. I am reliably great at useless pop-culture facts and should probably find a new trivia team to join.