Kevin Middleton

Began supporting GridStrong.ai in September 2024 as a Product Advisor, creating early prototypes and helping secure a $1.4M U.S. Department of Energy grant. After seed funding, joined full‑time as Director of Product Management, leading product strategy, engineering, and design across the compliance automation platform.

• 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.

Led 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% engagement in Q1, delivering org chart–aware approvals, accurate user statuses, and SCIM‑based data sync for enterprise‑grade reliability.
• 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.

Led product strategy for the Core Platform and eGift expansion. Owned partnerships and internal tools for the eGift ecosystem, driving catalog growth, platform security, operational efficiency, and revenue-aligned feature development.

• Catalog Expansion: Doubled active eGift coverage from 800 to 1,600 options across 47 countries. Landed the Square partnership for local gifting in the U.S., Canada, Australia, and U.K.
• Platform Security: Increased platform trust by implementing two‑factor authentication and AI‑driven fraud detection, reducing bot‑driven attacks.
• Revenue Enablement: Enabled new revenue opportunities through feature tiering and plan‑limit enforcement, increasing upgrade incentives and platform adoption.
• Operational Efficiency: Streamlined eGift deactivation, refunds, and swaps, reducing engineering reliance and speeding customer support resolutions.
• Product Alignment: Partnered with the Head of Product to align the platform strategy with Sendoso's marketplace goals, ensuring scalable growth across global markets.
• Business Impact: eGifts represented over half of all sends through the platform in 2021.

Led 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. Directed two engineering teams and a UX group across the U.S. and APAC 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 32 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.