Kevin Middleton

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: Secured foundational funding by building early prototypes and sourcing a $1.4M DOE grant, directly contributing to $10M seed funding.
• 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.

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: Increased conversions by launching high‑performing tools—calculators (7.3%), QuoteScore (6%), video content (3.4%), and optimized landing pages (2.3%)—each materially lifting the 0.1% baseline.
• 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.
• Cross‑Functional Leadership: Aligned engineering, SEO, marketing, design, and sales ops around a clear roadmap, accelerating delivery across the organization.
• Data‑Driven Execution: Drove measurable business results through continuous testing, analytics‑led iteration, and focused UX improvements.

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.
• Roadmap & Onboarding: Owned early roadmap and onboarding to improve usability, engagement, and new‑user activation across Mac and web.
• Strategic Path: Explored funding options and team expansion; paused operations after validating demand and without the runway to scale.

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 SCIM-based 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.
• Upmarket Expansion: Advanced Lever's upmarket strategy by shipping enterprise‑ready features that improved hiring workflow efficiency, reduced errors, and increased customer satisfaction.

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.

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 conversion rates by building custom analytics tools that linked site performance to user behavior, directly informing speed and checkout improvements.
• Cross‑Functional Alignment: Partnered across design, engineering, marketing, leadership, and enterprise teams to drive prioritization and strategic direction.
• Market & Revenue Impact: Supported long‑term growth through initiatives that expanded market reach, strengthened funnel efficiency, and diversified revenue channels.

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.

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.

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.