Sail Into the Age of AI
Most business owners feel the shift: AI is everywhere... but your information is nowhere.
Bob Sails is a free, practical curriculum that helps you organize your business, clean up your information flows, and design systems that AI agents can actually plug into.
Course Modules
17 modules available

Charting Your Course: Mission & Vision for the Solo Sailor

Find real customer pains, craft a sharp value proposition, and validate fast.

Map your customer journey, design offers that meet intent, and align messaging across every stage.

Turn your value proposition into clear, consistent messages and high-converting copy across pages, emails, and ads.

Turn your message into a high‑clarity landing page, capture leads, and run a simple welcome funnel.

Pick the right channels, build a 30‑day content engine, personalize with your CRM, and measure what matters.

Measure what matters (PMF signals), run small experiments, and make confident persevere/pivot calls.

Design retention loops, measure loyalty (NPS + churn), and build advocacy through community and referral programs.

Design value-based pricing, check unit economics (LTV, CAC, margins), and model runway so you scale with confidence.

Install a simple, ethical sales system: qualification → discovery → demo → proposal → close, plus a lightweight partner/referral motion.

Catalog every core process, assign owners, and publish an Operating Manual index that links all specs.

Define lifecycle stages with entry/exit criteria, a clean data dictionary, enforceable data contracts, automations, dedupe rules, consent basis, and QA checks.

Define clear pipeline stages with observable exit criteria, set stage SLAs (speed-to-lead, follow-up rhythm), select a qualification model, and align stages to forecast categories.

A clear, 30-day onboarding that delivers first value fast: timeline, checklist, welcome pack, ‘Definition of Done’, risks, and metrics.

Publish a simple, auditable delivery process: start/stop, steps, acceptance criteria vs. Definition of Done, QA checklist, change/rework rules, and clean hand-offs.

Retention keeps the boat afloat; referrals and partnerships catch wind. In this module, you’ll design a practical referral system (who asks whom, when, and why), set up a partner playbook, and build tracking that doesn’t require a spreadsheet PhD. You’ll map your referral loop, write scripts you can actually send, set up automation in your CRM, and connect your outcomes to real revenue so you can scale what works.

Referrals and partnerships bring warm introductions—but you still have to convert. In this module, you’ll build a sales operating system: discovery that uncovers real pain, qualification that protects your time, a proposal format that reduces confusion, and a follow-up cadence that feels human (not desperate). You’ll translate it all into a pipeline in your CRM, automate reminders and next steps, and define the metrics that keep you improving week over week.
Built for Solo Sailors and Scrappy Crews
Solopreneurs & Freelancers
Who are the marketing team, ops team, and tech team—all at once
Service and Agency Owners
Who want clean pipelines, cleaner data, and automations that actually reflect reality
Ops-Minded Founders
Who know their next bottleneck isn't more leads—it's systems, documentation, and smart automation
If you've ever thought, "AI sounds great, but my business is too messy for that right now," this is exactly for you.
Ready to Get Started?
Bob Sails is completely free for solopreneurs and founders who are serious about building AI-ready businesses. Sign up now and start learning.