Michael Kalmakis

AI Product Executive | SVP / VP / Head of Product | Building ML & AI Products Since 2013

Boston, MA  ·  linkedin.com/in/kalmakis

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Executive summary

Product executive with 15+ years leading AI/ML platforms and enterprise SaaS. Executive team member at True Fit, leading a 10+ person Product, UX, and Analytics organization to $30M+ EBITDA growth; owned the company-wide roadmap at Evertune, scaling a seed-stage AI startup's ARR 10x in one year. Building ML and AI products since 2013, from Spotify's personalization and playlisting engines to LLM-era analytics, with hands-on depth in Python, RAG pipelines, and LLM evals.

AI/LLM Product Strategy Generative AI & Agentic Systems RAG & LLM Evals ML Personalization P&L Ownership Enterprise SaaS (B2B, B2B2C) Go-to-Market Strategy Zero-to-One & Scale

Professional experience

Evertune AI

AI brand analytics: how LLMs perceive and recommend brands
Senior Vice President of Product Management
Remote / New York, NY  ·  6/2025 - 6/2026
  • Scaled seed-stage Answer Engine Optimization startup's ARR 10x in 12 months as the sole product hire
  • Owned the company-wide roadmap, shipping 130 epics via bi-weekly force-ranked prioritization across sales, customer service, marketing, engineering, and data science; led sprint planning and resource capacity allocation
  • Directed day-to-day UX design; mentored teammates across engineering, data science, sales, and customer service
  • Drove enterprise revenue, converting platform trials to contracts for Novartis, BMW, Apple, and Disney
  • Set technical product direction for the frontier-model upgrade engine, integrating every major LLM and AI assistant (GPT, Claude, Gemini, Llama, DeepSeek, Copilot, Perplexity) within days of release, with evals across global markets
  • Architected citation analytics pipeline: RAG-based relevance scores with content classification of AI chatbot answer sources
  • Built and deployed Tuney, an internal AI analyst on the Claude API: an agentic tool-use loop with 70+ tools across session analytics, platform data, and the codebase, with tiered Haiku/Sonnet/Opus model routing; also built Python prototypes with Claude Code (agentic data analyst, LLM fact checker, AI site audit tool) that data science and engineering productionized

Kalmakis Product Advisory

Product consulting for AI-native SaaS
Founder & Executive Product Consultant
Remote  ·  11/2024 - Present
  • Advised Yonder Media Mobile, an AI-powered MVNO, on product strategy, full platform redesign, and go-to-market
  • Partnered with C-suite on roadmap; instituted PM practices to facilitate alignment

True Fit Corporation

Market-leading AI fashion intelligence personalization platform
Senior Vice President of Product Management
Promoted Director to VP (2020) to SVP (2023)
Remote / Boston, MA  ·  8/2019 - 9/2024
  • Drove $30M+ in EBITDA growth and 7x customer increase by expanding into the Shopify SMB market; executive team member leading the 10+ person Product, UX/UI, and Analytics organization
  • Led product strategy for the B2B2C AI size-and-fit personalization platform used by Macy's, Gap, and J.Crew, serving 435M+ registered shoppers; grew users 355% via a mobile-first conversational UX redesign
  • Validated the roadmap through Voice of Customer programs and innovation sessions with key customers
  • Directed rebuild of the deep learning recommendation engine on Vertex AI, improving accuracy 30%
  • Conceived and launched Fit Hub, an LLM-powered narrative sizing experience featured in TechCrunch; applied generative AI to backend data labeling and shopper-facing insights
  • Consolidated 12 legacy product versions into 3 configurable ones, unlocking faster experimentation and deployment
  • Slashed B2B implementation from 12 weeks to 10 minutes via data ingestion redesign and UX standardization
  • Redefined pricing, packaging, and GTM strategy with Sales, Finance, and Legal, backed by financial modeling
  • Authored product sections of quarterly board materials; presented strategy and results in board meetings
  • Established A/B testing at scale; won 2023 Retail Tech of the Year and NRF VIP awards (2021, 2022)

Brandwatch (via Crimson Hexagon merger)

$100M+ ARR AI social media intelligence platform
Senior Director of Product Management
Promoted from Director (2018)
Boston, MA  ·  4/2016 - 5/2019
  • Led 3 PMs across ML pipelines, NLP analytics, vision analysis, and data collection infrastructure analyzing 1B+ daily social posts
  • Improved client retention 15% with ML-powered social consumer research tools for Twitter, Verizon, Google, and GM
  • Boosted engineering feature delivery 3x by restructuring product-engineering teams; cut data acquisition costs 20%
  • Coded proof-of-concept for S&P Global that used real-time NLP sentiment from Twitter chatter to build a social stock index

Spotify

Joined via acquisition of The Echo Nest, MIT Media Lab music-AI spin-off
Senior Product Manager, ML Personalization & Playlisting
Somerville, MA  ·  10/2013 - 2/2016
  • Drove creation of Daily Mix, one of Spotify's first hyper-personalized playlist products
  • Overhauled Spotify Radio's UX and station logic, growing Radio MAU 81%
  • Product lead for The Echo Nest music intelligence platform APIs, which leveraged audio signal ML, NLP, and web mining at scale
  • Built Truffle Pig, a music playlist editorial discovery tool covered by TechCrunch, Wired, and The New Yorker

TravelClick

Hotel SaaS acquired by Thoma Bravo ($930M), then Amadeus ($1.52B)
Product Manager, API Platform
New York, NY  ·  11/2011 - 10/2013
  • Led platform APIs that facilitated $1.73B in annual bookings; grew revenue 40% via 30+ new partner integrations

Early career

  • MTV Networks, Platform Technology PM: Built rights management systems for 350+ web properties (2008 - 2009)
  • EMI Music, Digital Project Manager: Delivered 3,000+ digital products monthly to Apple and 350+ retailers (2005 - 2008)
  • Avis Budget Group, Senior Decision Technology Analyst: Built forecasting and pricing models used by the group CEO (2004 - 2005)
  • Apogent Discoveries, Operations Consultant: Led ERP implementation across two manufacturing plants (2002 - 2003)

Technical skills

Python SQL BigQuery Agentic AI Coding (Claude Code, Cursor, Codex) LLM APIs (Anthropic, OpenAI, Gemini, Llama) RAG & LLM Evals Prompt Engineering Vertex AI A/B Testing & Product Analytics

Education

Hiring a product executive?

Open to CPO, SVP Product, and VP Product (AI) roles at companies that are serious about AI. Let's talk.

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