WordPress / LearnDash Developer — Ongoing Role, Online Boater Safety Education

About us AnchorPoint Boater Safety builds state-approved online boater safety courses. We're a small, profitable, owner-operated business — not a startup burning through a runway and not an agency with layers of process. Our course is live in multiple states, driving real revenue from real students, and we're actively expanding into new state markets. Because we're small, the work is direct: you'll talk to the owners, not a project manager relaying tickets. The role We have one developer and enough roadmap for two. We're looking for a second developer to take real ownership of parts of the platform — not to sit in a queue waiting for tasks. We're hiring an individual freelancer, not an agency or a dev shop. We want to work directly with the person writing the code — same person on every project, building up real knowledge of our platform over time. Please don't apply if the work would be handed off to a rotating team, subcontracted out, or routed through an account manager. The most important thing about this role: we're hiring for judgment, not just execution. We've been burned by the pattern where every problem gets a plugin, a snippet, or a CSS override, and eighteen months later the site is a pile of patches nobody can reason about. We want someone who asks why the problem exists, considers how a fix fits the rest of the system, and occasionally tells us "the thing you asked for is a symptom — here's the actual issue." That means you'll sometimes push back on us. We consider that a feature. What you'll work on Ongoing feature development and improvements to our LearnDash course platform Building out new state course offerings as we expand — new content structures, state-specific requirements, compliance and reporting logic Stripe checkout, payment flows, and purchase/enrollment reliability Infrastructure and deployment work on AWS Performance, site health, and technical SEO fundamentals Integration work across our stack (analytics, conversion tracking, third-party tools) Cleaning up and consolidating things that have accumulated over time Our stack WordPress + LearnDash (LMS core) Stripe (payments) AWS (hosting/infrastructure) GitHub (version control — we work in a repo, not by FTPing files to production) GA4 / Google Tag Manager (analytics and conversion tracking) What we're looking for Required: Strong production experience with WordPress at the code level — custom plugins, hooks, filters, child themes. Not a page-builder generalist. Real LearnDash experience: course structures, quizzes, enrollment logic, user progress, certificates PHP, MySQL, JavaScript Stripe integration experience — webhooks, subscriptions or one-time purchases, edge cases around failed and duplicate payments Comfortable in Git-based workflows: branches, pull requests, code review, staging before production AWS familiarity (EC2/RDS/S3/CloudFront or comparable) Communication and organization — we weight these as heavily as technical skill: You communicate proactively. We hear about a blocker, a scope change, or a delay when you discover it, not when we ask for a status update. You write clearly for non-engineers. Two of us are not developers, and we need to understand tradeoffs well enough to make business decisions about them. You're responsive within a reasonable window and you close loops — questions get answered, threads get resolved. You're organized in how you track work: tickets or a shared task list, clear commit messages, notes on what changed and why. We should never have to reconstruct what happened from memory. You give realistic estimates and flag early when one slips. What actually gets you hired: You think in systems. When you touch one part of the platform, you understand what else it affects. You ask about the business goal before you build the feature. You document what you did and why, so the next person (including future you) isn't archaeology-ing through the codebase. You're honest about tradeoffs, including "this quick fix is fine for now, and here's what it'll cost us later." You want a long-term relationship with one product you know deeply — not a churn of one-off gigs. Nice to have: Experience with regulated or compliance-driven education (state approvals, reporting requirements, audit trails) Conversion tracking / GTM / GA4 Experience scaling a content or course platform across multiple markets or jurisdictions How to apply Please include: A short note on a WordPress or LearnDash system you inherited or built — what was structurally wrong with it, what you changed, and why you chose that approach over a faster fix. Relevant work samples or repos (or a description if the work is under NDA) Your availability and rate Skip the generic cover letter. We read every application and we're much more interested in how you think than in a list of technologies. Applications from agencies or teams will not be considered. We're looking for the right long-term fit, so we'd rather take a few extra weeks to find them. If that's you, we'd like to hear from you.