Nate Barrett

Ex-SVP Product | Helping product leaders scale teams and earn trust

Product School
Skillable

Available Sunday

Starting at 4:00 PM UTC

Questions?

You can start chatting with Nate before you get started.

Work with Nate

Protected by the Leland Experience Guarantee

About

I help product leaders and teams build with AI, not just talk about it. I've spent 20+ years in B2B SaaS product, most recently as SVP of Product at Skillable, where I led a 75-person org, drove 110% NRR, and brought generative AI into our product development lifecycle. Before that I led product at Pluralsight (through its $2B acquisition), Canopy (tripled ARR two years running, scaled from 2 to 9 teams), and Instructure. Today I build AI products myself. I created ProductOS, a 14-agent AI-native product development framework now used by 500+ people, and toolaudit.ai, an AI tools comparison platform built on Next.js and Supabase. Working with me is hands-on. We'll pick a real problem from your roadmap or workflow and build it together: agent workflows, AI-assisted PRDs and discovery, prototyping with Claude Code, or a plan for putting AI into your team's PDLC. You'll leave with something working, not a slide deck.

Nate also coaches for AI for Product Development and Product Management. View all.

Nate’s Leadership Coaching Qualifications

Experience level: Executive

I've spent 20+ years leading product in B2B SaaS, most recently as SVP of Product at Skillable, where I ran a 75-person organization, drove 110% net revenue retention, and led the team through bringing generative AI into how we build. Before that I was VP of Product at Canopy, where I grew the org from 2 to 9 product teams while ARR tripled two years in a row. I've also led product at Pluralsight through its $2B acquisition and at Instructure, where I grew the corporate business from about $6M to $15M ARR in 2 years. Along the way I've hired and developed 50+ PMs and managers, restructured orgs mid-growth, and learned (often the hard way) how to align executives, boards, and engineering partners around a strategy. I coach the leadership problems I've lived through: moving from IC to manager, managing managers, stepping into a VP seat, building a team's operating rhythm, and leading change when AI is resetting how product work gets done.

Nate can help with:

AI Automation

AI Fundamentals

AI Strategy

Change Management

Coaching and Mentoring

Innovation and Creativity

Problem Solving

Team AI Upskilling

Why do I coach?

The best part of every leadership role I've had was watching PMs grow into people who could own hard problems on their own. Scaling teams at Canopy and Skillable taught me that most of that growth happens through doing the work next to someone, not from frameworks. AI has reset the playing field. Experienced PMs are now relearning how products get built, and a lot of the advice out there comes from people who haven't shipped anything with it. I've spent the last two years building real AI products and systems, making mistakes, and turning what works into repeatable methods. Coaching lets me shorten that curve for others.

Work Experience

SVP of Product Management

Skillable

2024 - March 2026

Leading enterprise hands-on learning platform serving global cloud, cybersecurity, and DevOps teams. 6M+ learners across 1,200+ enterprises. - Defined long-term product vision and AI strategy, enabling 3× enterprise adoption, 110% net revenue retention, and expanded partner integrations. - Introduced generative AI into PDLC workflows, improving release velocity by 40% and quality metrics by 25%. - Built a high-performance product, UX, and data science organization of 75+, grounded in autonomy and accountability. • Led zero-to-one strategy for AI-powered content creation and student practice lab products.

Sr Director, Product Management - Hands-On Learning Platform

Pluralsight

2019 - 2023

Global B2B SaaS learning platform serving millions of developers and technology professionals. $500M+ ARR; serving 70% of the Fortune 500. - Directed product vision for hands-on labs and skill validation across cloud and cybersecurity verticals. - Led zero-to-one development of guided labs, challenge labs, and sandbox products. Forged partnerships with AWS, Azure, and GCP to launch practice labs, creating a new share-of-wallet category. - Introduced a Labs SKU in partnership with GTM teams, generating $4M+ incremental ARR in Q4 2022.

Founder & Principal Advisor

Product Labs Consulting

2017 - Present

Leveraging over twenty years of experience in product management, design, and leadership in startups, B2C business, and B2B enterprises. - Provided services including fractional CPO, strategy sessions, PDLC process improvements, speaking engagements, workshop facilitation, and mentoring - Advised early-stage and high growth SaaS companies on product and AI strategy, consistently delivering average 15%+ improvements in key product metrics (ACV, NRR, decreased TTV). - Launched AI Product OS (PDLC Framework in Claude) and AI ToolAudit (strategic AI review platform), in Q2 2026. Revenue streams through subscriptions, premium content placement, and affiliate partnerships. Metrics to follow in Q3 2026.

VP of Product Management

Canopy Tax

2017 - 2019

FinTech SaaS platform for accounting and tax practice management, supporting 10,000+ accounting firms. - Scaled the product organization from 2 teams to 9, recruiting 50+ professionals across PM, UX, analytics, product marketing, and tax SME disciplines. - Tripled ARR two consecutive years, supporting Series B ($20M + $12M extension). - Launched four new product lines generating $10M+ ARR within the first year; one named 2019 Product of the Year.