Tyler Singletary
AI/ML Product Leader & Developer Ecosystems
20+ years building developer platforms, shipping AI products, and turning startups into scalable businesses. From API ecosystems to GenAI playbooks, I make complex technology land with developers and enterprises alike.
About
I'm a product leader with 20+ years across developer relations, AI/ML startups, and product management. I've built and scaled API platforms, led product turnarounds, and helped dozens of early-stage startups go from POC to production.
At AWS I support AI/ML startups with developer-first positioning, fine-tuning strategies, and GenAI playbooks. Before that, I led Tagboard as CPO through a turnaround that grew ARR from $600K to $7.2M, and scaled the Klout Data Platform to $10M in revenue with partnerships across Twitter, Salesforce, and Microsoft Bing.
I also build things — from custom ML models for expressive music generation to generative storytelling apps for historic locations. Stanford ML Specialization (DeepLearning.AI).
Projects
Historic
Location-aware generative storytelling — walk up to any landmark and get an AI-narrated history podcast on the spot. Built a Python backend with fine-tuned Gemma 3 edge models, a Swift iOS app with AR overlays, and a React web frontend. Custom TTS pipeline produces broadcast-quality narration.
Express MIDI Orchestrator
Trained a custom ML model and tokenizer to generate expressive MIDI data — dynamics, articulations, and phrasing that sound human. Includes an A/B testing framework so composers can compare orchestration variants side-by-side.
Orchestrately
A proactive LLM agent that listens to Slack threads in real time, detects when teams are talking past each other, and surfaces the missing context before misalignment turns into wasted sprints.
Stockstead.com
A mortgage calculator built for high net worth individuals. Models SBLOCs, tax-loss harvesting, and portfolio-backed lending — scenarios that no standard calculator handles.
Cubase MCP
An MCP server that connects AI assistants to Cubase, enabling prompt-driven music production workflows — from arranging to mixing — through the Model Context Protocol.
Obligator Bujo
An Obsidian plugin that turns daily notes into a virtual bullet journal. Automatically carries over unchecked tasks and surfaces scheduled items so nothing falls through the cracks.
Experience
AI/ML Startups Product Specialist
Amazon Web Services (AWS) · 2024 — Present
- Supporting 25+ seed-to-Series B startups on developer GTM, positioning, and productization
- Increased adoption of AWS Bedrock and SageMaker, influencing $1.2M+ in net new cloud consumption
- Authored GenAI/SLM playbooks for LoRA fine-tuning and evaluation frameworks
Chief Product Officer
Tagboard · 2016 — 2024
- Led turnaround as dual CPO/COO, growing ARR from $600K to $7.2M and reducing churn from 65% to 8%
- Scaled product team from 1 to 4 and engineering from 4 to 16 within 12 months
- Led API platform strategy and ecosystem integrations across Twitter, Facebook, Instagram, Snap, and Reddit
VP & GM, Klout & Consumer Data
Lithium Technologies · 2014 — 2016
- Integrated Klout's influence and consumer data assets into Lithium's platform, managing a 10-person team
- Scaled the Klout Data Platform to $10M in revenue with partnerships at Twitter, Salesforce, and Epsilon
Director of Platform Product
Klout (exited to Lithium) · 2011 — 2014
- Increased developer conversion 280% y/y by productizing API data insights
- Built API platform to 7-figure ARR and 60% of company revenue with usage-based tiers and partner programs