Stuart Watson
AI-Native RevOps & GTM Strategy
I help startups scale predictable revenue by combining sales leadership, RevOps architecture, and AI-native tools.
Since 2011, I've worked across startups, scaleups, and post-IPO companies as a seller, sales manager, multi-line leader, and GTM operator. If you need someone who can move from board-level planning to frontline coaching, let's talk.
What I Do
RevOps Architecture
Forecasting, pipeline health, territory, and quota design. Board-ready models and reporting that drive predictable growth.
Outbound Engine
SDR program design, ICP refinement, onboarding, enablement, and handoffs that build pipeline you can trust.
Sales Leadership & GTM Strategy
Process design, team structure, messaging frameworks, and headcount modeling for Seed through Series C.
The AI-Native Advantage
Using AI and code to ship the changes your team has been routing around for years: data cleanup, territory models, enrichment pipelines, and purpose-built tools that replace the SaaS you've outgrown.
Projects
Watson Family Tree ↗
Most family trees are a list of names. This one's an evidence-driven graph: hundreds of census returns, military files, ship manifests, and church registers live as first-class nodes next to the people they document. That unlocks a 3D globe showing four centuries of migration across the Atlantic, and an AI research assistant that reasons over real records and graph connections.
Forecast Tieout ↗
Open-source revenue planning for go-to-market operators. Forecast Tieout reconciles the revenue plan against pipeline reality: bookings trajectory, rep capacity, funnel conversion, and the target-setting math your board deck has to survive. Three synthetic cohorts show different failure modes, from early-PMF repeatability to scale-up ramp debt and mature-enterprise expansion risk.
Paragon Pickleball ↗
Helped create the website for Paragon Pickleball, led by Drew Diefenbach and based out of the East Bay. Tournaments, junior camps, and Parks & Rec partnerships across Orinda, Lafayette, and Concord.
Marin Monitor ↗
"Are you monitoring the situation anon?" Real-time fire risk, weather, air quality, hero dirt status, gas prices, home prices (one fewer Zillow tab), traffic cameras, tides, and whatever pathogen is having its moment in Marin's sewers.
Marin Families ↗
Optimize where to warehouse your children this summer. Find camps, daycare, preschools, and activities in Marin County: no group-chat panic or summer planning spreadsheet that makes A Beautiful Mind look like it was shot on set with Marie Kondo.
Pinned Repos
marin-civic-graph ↗
East-Peak/marin-civic-graph
Public-record graph work for Marin civic money, identity resolution, and accountability legibility.
forecast-tieout-oss ↗
East-Peak/forecast-tieout-oss
Revenue-planning engine that reconciles board targets against pipeline, capacity, and funnel reality.
watson-family-archive ↗
East-Peak/watson-family-archive
Read-only public snapshot of the Watson family graph and 3D migration-globe app.
marin-monitor ↗
East-Peak/marin-monitor
Local situation dashboard for Marin: fire risk, weather, air quality, tides, traffic, prices, and local signals.
agent-observatory ↗
East-Peak/agent-observatory
Local-first coding-agent cost and activity ledger for Claude Code, Codex, and OpenClaw.
Field Notes
Essays, interviews, and conversations on SDR operations, revenue strategy, and AI in GTM.
Podcasts
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Conversation with Matt Slotnick, Co-Founder and CEO of Poggio Labs →YouTube -
Jacob Warwick on Harnessing the Power of Negotiation →YouTube -
Jim Rose on the Power of Sales Enablement →YouTube -
Interview with former CTO and co-founder of Clever →YouTube -
Conversation with Lauren Volpi, SVP of Marketing at DataGrail →YouTube -
Pro Cyclist Sean Bennett's Journey to Tech Sales →YouTube - Navigating Growth: Strategies for Scaling Sales Organizations →Podcast Jan 2025
Essays & Posts
- Build or buy? Navigating the new era of GTM AI Agents →SignalFire
- How to use AI to augment SDRs, not replace them →SignalFire
- How to manage SDRs →SignalFire
- The SDR outreach guide for startups →SignalFire
- When to hire sales development representatives →SignalFire
- Advanced SDR Operations Guide →LinkedIn
- A Tale of Two Trades →LinkedIn
- Assessing SDR Candidates →LinkedIn
- Let's Go Back to the Office, Just Not Like That →LinkedIn
- Dr. Coldcall or: How I Learned to Stop Worrying and Love the Phone →LinkedIn
- Stop LARPing and Actually Run the Numbers →LinkedIn
- How should your SDR onboarding and enablement change as your team grows? →LinkedIn
- Operating Template for Your Early Stage SDR Team →LinkedIn
- An SDR Organization Plan Template for Mature Teams →LinkedIn
- Hiring Your Startup's First SDR →LinkedIn
Start a Conversation
I work as a consultant, fractional leader, and advisor. If revenue predictability, achieving outbound success at scale, or implementing agentic workflows for GTM are top of mind, let's talk.