Hello — I’m Andrew North. Before I built Northpoint, I learned much of what I know by reading programming books pulled from a library and experimenting with bulletin-board systems on dial-up. That background still shapes how I hire developers: hands-on, practical, and focused on outcomes rather than buzzwords.
Who should read this
This article is for city managers, IT procurement officers, recreation directors, or small-business owners who need to hire a developer to add AI-driven features to a WordPress site—chat assistants, automated content workflows, form processing, or integrations that connect WordPress with CRM, SMS, or back-office systems.
Start with the right job definition
Before interviewing candidates, decide which of these outcomes you need. Use clear acceptance criteria tied to real workflows.
- Conversational assistant for public FAQs (scope: domain, handoff, transcripts)
- AI-assisted content generation and scheduled publishing (scope: editorial roles, approval step)
- Form automation and triage (scope: data validation, webhook or API to service desk)
- Back-office integration (scope: secure API, auth, error handling, reconciliation)
Essential technical skills to look for
- WordPress plugin development: custom post types, hooks, REST API endpoints, and secure capability checks.
- Familiarity with major AI providers’ APIs (OpenAI, Anthropic, etc.) and experience handling rate limits and costs.
- Server-side languages and frameworks used with WordPress (PHP 7/8+, Composer, familiarity with Node or Python for auxiliary services).
- Experience with OAuth, API keys, JWT, and secure storage of secrets on hosted environments or via a secrets manager.
- Practical knowledge of webhooks, background jobs (WP-Cron vs. queue workers), and retry/error handling.
- Accessibility and privacy best practices, especially for municipal projects (PII handling, retention policies).
- Deployment and hosting experience: containerization, VPS or managed WordPress hosting setups, and rollback strategies.
Prioritized interview questions
Start with design and outcome, then probe implementation and risk management.
- Describe a recent WordPress project where you added a third-party API. What was the integration pattern and how did you handle auth and errors?
- How would you design an AI assistant that only answers from our published content and flags unknowns to staff? Ask for endpoints, caching, and fallback logic.
- How do you secure API keys and credentials on a hosted WordPress environment? What secrets-management approach do you prefer?
- Explain how you would limit costs with a token-based AI API (examples: prompt-engineering, caching responses, chunking content).
- What testing and monitoring would you put in place for an AI integration in production? (Unit tests, integration tests, logging, alerting.)
- When should a workflow be implemented inside WordPress vs. in an external microservice?
- Give a short plan for migrating an existing FAQ page into an AI-backed conversational assistant with an edit/approval workflow for responses.
30/60/90-day scope template (copy and adapt)
Below is a practical, copy-ready scope you can paste into an RFP or SOW. It’s prioritized so you get usable features early and reduce risk.
First 30 days — Discovery & MVP
- Discovery session with stakeholders: define user stories, data sources, auth needs, privacy rules.
- Technical audit of existing WordPress setup (plugins, PHP version, REST endpoints, hosting limits).
- Proof of concept: one AI feature—e.g., a site chatbot that answers from the site’s /help pages. Include basic logging.
- Security checklist completed: secrets storage, minimal permissions, HTTPS verification.
- Acceptance: working demo in staging; short walkthrough with staff.
Next 30 days (days 31–60) — Expand & Harden
- Expand AI coverage (add knowledge sources: FAQs, PDFs, policy pages) and build a content ingestion/process for indexing.
- Add workflow: staff review interface for suggested AI responses and an approval queue prior to publishing.
- Implement rate limiting, caching strategy for repeated queries, and cost monitoring hooks.
- Automated tests for critical integrations and basic performance benchmarks on staging.
- Acceptance: staff able to review/approve responses; load-tested for expected concurrency.
Days 61–90 — Operate & Integrate
- Integrate with back-office systems (CRM, service-desk) if needed; establish webhooks and reconciliation checks.
- Full logging, admin dashboards for usage/costs, and alerts for errors or unusual traffic.
- Accessibility checks and privacy documentation (how long AI logs are kept, redaction rules).
- Training for staff and handoff documentation: runbook for incidents, rollback plan.
- Acceptance: production release with monitoring and documented maintenance plan.
Evaluation criteria and red flags
Use a simple scoring rubric (0–5) for each area: technical fit, security, cost control, delivery plan, communication. Multiply score by importance for a ranked shortlist.
- Red flag: vague answers about securing API keys or handling PII.
- Red flag: no plan to limit AI costs or handle rate limiting.
- Red flag: insists on replacing your entire site instead of integrating safely with WordPress.
- Positive sign: proposes incremental delivery with a usable staging demo in 30 days.
Risk checklist for municipal and small-business projects
- Data ownership: ensure logs, transcripts, and user data remain under your control.
- Privacy: define retention and redaction policies for submitted data.
- Accessibility: AI outputs must be usable with screen readers and not introduce barriers.
- Cost caps: set monthly spending alerts and hard limits where possible.
- Fallbacks: provide clear UI pathways to reach a human when the AI cannot answer.
How Northpoint approaches these projects
One problem we encounter when building integrations is treating AI as a feature instead of a workflow component. In systems we build, AI assists staff—drafting content, triaging requests, or offering suggested answers—while staff remain in control. If you’d like to see an example assistant that’s been scoped for WordPress sites, check the Northpoint AI Assistant page for a quick overview of capabilities and integration patterns.
Next steps and a practical invitation
If you’re ready to hire, start by sharing your primary user stories and any compliance constraints. If you want help turning those into an RFP or need a shortlist of vetted developers, talk with Northpoint Web Solutions about your website, software or workflow problem. We can help determine whether an existing Northpoint product, a custom WordPress plugin, or a custom software solution is the best fit.
For further reading on when to build custom WordPress tools versus adopting SaaS, see our decision framework on custom vs. SaaS. For projects that grow into connected business systems, explore Northpoint Core and our custom WordPress software and plugin development page.
— Andrew North
