# Craig Winter

**Canonical URL:** https://www.craigwinter.com/

Six live commercial apps built and run by one AI-first founder. Every app has a free tier. Hard problems, simple products.

## Summary

Craig Winter is an AI-first solopreneur who builds and operates commercial software for markets that big SaaS overcomplicates or ignores. This site is a portfolio of six live products, not vanity prototypes. Each app has its own domain, customers, paid plans, and a free way to start.

Stack across the portfolio: Vercel and Neon Postgres.

## Apps

### 1. Schedule a Coach — https://scheduleacoach.com

**Audience:** Independent coaches, trainers, tutors, and consultants  
**Free tier:** Yes

White-label booking site on your own domain, with payments and live video built in. Clients see your brand, never a marketplace.

- Zero session fees: flat monthly price; coaches keep every dollar clients pay
- Your brand, your domain: no marketplace competing for clients
- AI that coaches the coach: session analysis for follow-ups and growth

### 2. CalTogether — https://caltogether.com

**Audience:** Nonprofits, schools, HOAs, and faith groups  
**Free tier:** Yes

Publish a community calendar once and share it everywhere: polished public pages, website embeds, and ICS subscribe feeds.

- Beautiful public month and list views with photos on events
- Owners, editors, and viewers without shared passwords
- Text reminders for events

### 3. StreetHighlighter — https://streethighlighter.com

**Audience:** Firewise communities and neighborhood emergency volunteers  
**Free tier:** Yes

Turn U.S. street addresses into highlighted street segments and evacuation routes on an interactive map, organized by POD.

- Fills the gap between spreadsheets and full GIS
- Geocode addresses into points and street segments
- Built by a Firewise chair in the Santa Cruz Mountains

### 4. ContextUpdater — https://contextupdater.com

**Audience:** Teams running AI agents in production  
**Free tier:** Yes

One API call returns a ranked, deduplicated briefing so agents stay current on regulatory, economic, and competitive signals.

- Agent-ready output, not analyst dashboards
- Macro, regulatory, competitor, and supply-chain signals in one integration
- Fresh twice a day from scheduled sweeps of news and filings

### 5. ScriptTuner — https://scripttuner.com

**Audience:** Screenwriters revising a draft  
**Free tier:** Yes

Talk through a screenplay with Riley, an AI script consultant that pitches changes inside a properly formatted script. The writer accepts or rejects every edit.

- Voice-driven writers'-room style collaboration
- Writer stays in charge with full edit history
- Import, autosave, export FDX

### 6. MailJolly — https://mailjolly.com

**Audience:** Small businesses, nonprofits, and community groups  
**Free tier:** Yes

Organize contacts and send campaigns without enterprise email complexity, with deliverability protection built in.

- Paced sending and send windows to protect sender reputation
- Automatic list hygiene for bounces and spam complaints
- AI deliverability checks and first-party open/click tracking

## Approach

AI changed the math: a focused product for a few thousand customers no longer needs a large team. Working AI-first, one person who understands the problem can design, ship, and maintain commercial software.

1. **AI-first, end to end** — Design, code, testing, and copy with AI agents; AI also powers product features (coaching insights, deliverability, agent briefings, script consulting).
2. **One lean platform** — Shared serverless stack (Vercel + Neon) keeps idle cost near zero so free tiers stay sustainable.
3. **Built to last** — Each app is a long-term business with its own domain and paid plans; free tier is a real start, not a disappearing demo.

## Founder

Craig Winter. Background: assembly language for rocket control systems; 11 years as a product manager on marketing cloud platforms (Cheetah Digital, Revinate, MovableInk). Community roles: board director, Felton Fire Protection District; chair, Forest Lakes Firewise. WGA-registered screenwriter. Also advises a small number of teams as fractional CPO/CTO through GenAI Fuel.

Contact: https://www.craigwinter.com/#contact