https://colin.gillingh.am/writing Notes on AI strategy, AI engineering and GTM automation, from building AI products at HubSpot and on my own. en Fri, 17 Apr 2026 12:00:00 GMT https://colin.gillingh.am/writing/gtm-technographic-qualifier https://colin.gillingh.am/writing/gtm-technographic-qualifier Fri, 17 Apr 2026 12:00:00 GMT How to enrich HubSpot company records with technographic data using BuiltWith or Clearbit, score tech stack fit with Claude. https://colin.gillingh.am/writing/the-three-kinds-of-ai-work-your-company-is-actually-doing https://colin.gillingh.am/writing/the-three-kinds-of-ai-work-your-company-is-actually-doing Thu, 16 Apr 2026 12:00:00 GMT Exploration, implementation, and operations are three different jobs. Most companies staff them as one — and that's why the AI team is always behind. https://colin.gillingh.am/writing/why-the-roi-framing-kills-good-ai-projects https://colin.gillingh.am/writing/why-the-roi-framing-kills-good-ai-projects Wed, 15 Apr 2026 12:00:00 GMT Demanding ROI at the pilot stage selects for safe, measurable, low-value work. Here's what to demand instead. https://colin.gillingh.am/writing/gtm-job-posting-analyzer https://colin.gillingh.am/writing/gtm-job-posting-analyzer Tue, 14 Apr 2026 12:00:00 GMT Build a job posting analyzer in n8n that monitors target accounts for hiring signals, uses Claude to extract buying intent. https://colin.gillingh.am/writing/what-responsible-ai-actually-requires-operationally https://colin.gillingh.am/writing/what-responsible-ai-actually-requires-operationally Tue, 14 Apr 2026 12:00:00 GMT Responsible AI isn't a principles document. It's a set of operational decisions about who reviews what, when, and what happens when something breaks. https://colin.gillingh.am/writing/the-ai-literacy-gap-is-a-leadership-problem https://colin.gillingh.am/writing/the-ai-literacy-gap-is-a-leadership-problem Mon, 13 Apr 2026 12:00:00 GMT AI literacy programs aimed at individual contributors miss the point. When leaders can't evaluate AI claims, everything downstream breaks. https://colin.gillingh.am/writing/how-to-scope-an-ai-project-before-you-quote-it https://colin.gillingh.am/writing/how-to-scope-an-ai-project-before-you-quote-it Sun, 12 Apr 2026 12:00:00 GMT AI projects blow their budgets because the scope was never real to begin with. The framing questions you need to ask before a number is ever written down. https://colin.gillingh.am/writing/gtm-competitor-analyzer https://colin.gillingh.am/writing/gtm-competitor-analyzer Fri, 10 Apr 2026 12:00:00 GMT How to build an automated competitor analysis workflow using n8n, Claude API, and HubSpot custom properties. https://colin.gillingh.am/writing/the-six-things-every-ai-strategy-document-should-answer https://colin.gillingh.am/writing/the-six-things-every-ai-strategy-document-should-answer Fri, 10 Apr 2026 12:00:00 GMT Most AI strategy docs answer questions nobody asked. Here are the six that force real decisions — and what good answers actually look like. https://colin.gillingh.am/writing/how-to-think-about-ai-risk-without-paralyzing-your-team https://colin.gillingh.am/writing/how-to-think-about-ai-risk-without-paralyzing-your-team Wed, 08 Apr 2026 12:00:00 GMT Risk-aversion is real and valid. But there's a version of risk management that enables action instead of blocking it. Here's the framing I use. https://colin.gillingh.am/writing/what-i-look-for-in-the-first-week-of-an-ai-engagement https://colin.gillingh.am/writing/what-i-look-for-in-the-first-week-of-an-ai-engagement Tue, 07 Apr 2026 12:00:00 GMT The first week of an AI engagement tells you almost everything. Here are the five signals I watch — and what they actually mean. https://colin.gillingh.am/writing/agents-vs-automation-how-to-know-which-one-you-actually-need https://colin.gillingh.am/writing/agents-vs-automation-how-to-know-which-one-you-actually-need Mon, 06 Apr 2026 12:00:00 GMT AI strategist's guide to agents vs. automation: when to use each, how to sequence them in real workflows, and the cost of choosing wrong. https://colin.gillingh.am/writing/how-to-write-an-ai-job-description-that-attracts-real-talent https://colin.gillingh.am/writing/how-to-write-an-ai-job-description-that-attracts-real-talent Sun, 05 Apr 2026 12:00:00 GMT Most AI job descriptions fail before the first candidate reads them. Here's how to write one that signals you've actually done the thinking. https://colin.gillingh.am/writing/gtm-email-sequence-writer https://colin.gillingh.am/writing/gtm-email-sequence-writer Fri, 03 Apr 2026 12:00:00 GMT Step-by-step guide to building an AI email sequence writer using HubSpot, n8n, and Claude. https://colin.gillingh.am/writing/what-a-good-ai-proof-of-concept-looks-like https://colin.gillingh.am/writing/what-a-good-ai-proof-of-concept-looks-like Thu, 02 Apr 2026 12:00:00 GMT Most AI POCs prove nothing useful. Here's how to design one that actually tells you whether AI will work in your context. https://colin.gillingh.am/writing/how-to-train-your-team-to-use-ai-without-making-it-mandatory https://colin.gillingh.am/writing/how-to-train-your-team-to-use-ai-without-making-it-mandatory Wed, 01 Apr 2026 12:00:00 GMT Mandating AI training creates compliance theater, not real enterprise AI adoption. Here's how to build pull so your team seeks out AI on their own. https://colin.gillingh.am/writing/gtm-objection-handler https://colin.gillingh.am/writing/gtm-objection-handler Tue, 31 Mar 2026 12:00:00 GMT Step-by-step guide to building a Claude-powered objection handler connected to HubSpot. https://colin.gillingh.am/writing/the-job-titles-that-will-disappear-and-the-ones-that-wont https://colin.gillingh.am/writing/the-job-titles-that-will-disappear-and-the-ones-that-wont Tue, 31 Mar 2026 12:00:00 GMT AI isn't replacing jobs wholesale — it's moving the line between assembly work and judgment work. The problem is that line keeps moving. https://colin.gillingh.am/writing/what-good-ai-governance-looks-like-for-a-50-person-company https://colin.gillingh.am/writing/what-good-ai-governance-looks-like-for-a-50-person-company Mon, 30 Mar 2026 12:00:00 GMT Governance sounds like enterprise bloat. It's not. Here's the minimal AI strategy every 50-person company needs before something goes wrong. https://colin.gillingh.am/writing/how-to-run-an-ai-sprint-in-a-non-technical-company https://colin.gillingh.am/writing/how-to-run-an-ai-sprint-in-a-non-technical-company Sun, 29 Mar 2026 12:00:00 GMT You don't need engineers to run an AI sprint. Here's a five-day format that works for ops, marketing, and product teams with no ML background. https://colin.gillingh.am/writing/the-difference-between-an-ai-feature-and-an-ai-product https://colin.gillingh.am/writing/the-difference-between-an-ai-feature-and-an-ai-product Sat, 28 Mar 2026 12:00:00 GMT Most 'AI products' are just products with a GPT call in the middle. Here's how to tell the difference — and why it changes everything about how you build. https://colin.gillingh.am/writing/gtm-data-cleaner-normalizer https://colin.gillingh.am/writing/gtm-data-cleaner-normalizer Fri, 27 Mar 2026 12:00:00 GMT Step-by-step guide to building an automated CRM data cleaner and normalizer using n8n and HubSpot. https://colin.gillingh.am/writing/stripe-projects-agents-can-now-provision-their-own-stack https://colin.gillingh.am/writing/stripe-projects-agents-can-now-provision-their-own-stack Fri, 27 Mar 2026 12:00:00 GMT Stripe Projects lets AI agents provision their own cloud stack — Supabase, Vercel, Clerk, Neon, Posthog — without human sign-ups. https://colin.gillingh.am/writing/why-smaller-companies-have-an-ai-advantage-right-now https://colin.gillingh.am/writing/why-smaller-companies-have-an-ai-advantage-right-now Fri, 27 Mar 2026 12:00:00 GMT Enterprise AI adoption is slow because of legacy systems, politics, and process. Small companies can move faster — if they're intentional about it. https://colin.gillingh.am/writing/the-questions-to-ask-before-any-ai-vendor-demo https://colin.gillingh.am/writing/the-questions-to-ask-before-any-ai-vendor-demo Thu, 26 Mar 2026 12:00:00 GMT Every AI vendor demo looks great. That's the point. Here are the questions that tell you whether the product matches the pitch. https://colin.gillingh.am/writing/what-ai-native-actually-means-for-a-product-team https://colin.gillingh.am/writing/what-ai-native-actually-means-for-a-product-team Wed, 25 Mar 2026 12:00:00 GMT What does AI-native product mean? An AI product strategist breaks down the difference between AI features and AI-native design. https://colin.gillingh.am/writing/gtm-linkedin-profile-analyzer https://colin.gillingh.am/writing/gtm-linkedin-profile-analyzer Tue, 24 Mar 2026 12:00:00 GMT Build an AI LinkedIn profile analyzer using n8n and HubSpot. Automate prospect research and prioritization from LinkedIn data at scale. https://colin.gillingh.am/writing/how-to-get-your-exec-team-aligned-on-ai https://colin.gillingh.am/writing/how-to-get-your-exec-team-aligned-on-ai Tue, 24 Mar 2026 12:00:00 GMT AI strategist's guide to getting executive alignment on AI. Closes the four gaps — definitional, priority, accountability, and mental model. https://colin.gillingh.am/writing/the-hidden-cost-of-not-having-an-ai-strategy https://colin.gillingh.am/writing/the-hidden-cost-of-not-having-an-ai-strategy Mon, 23 Mar 2026 12:00:00 GMT The absence of an AI strategy isn't neutral. It's a series of compounding decisions being made without anyone in the room. https://colin.gillingh.am/writing/when-to-build-vs-buy-ai https://colin.gillingh.am/writing/when-to-build-vs-buy-ai Sun, 22 Mar 2026 12:00:00 GMT AI build vs. buy decisions require a different framework than SaaS. Here's the decision tree I use across AI consulting engagements to get it right. https://colin.gillingh.am/writing/why-ai-projects-need-a-product-manager https://colin.gillingh.am/writing/why-ai-projects-need-a-product-manager Sat, 21 Mar 2026 12:00:00 GMT AI projects fail when they're run like software migrations. Here's why product management — not project management — is the right model for AI work. https://colin.gillingh.am/writing/gtm-icp-scorer https://colin.gillingh.am/writing/gtm-icp-scorer Fri, 20 Mar 2026 12:00:00 GMT Step-by-step guide to building an AI ICP scorer using n8n and HubSpot. Automate ideal customer profile scoring with fuzzy matching and structured reasoning. https://colin.gillingh.am/writing/the-stack-a-modern-ai-strategy-actually-runs-on https://colin.gillingh.am/writing/the-stack-a-modern-ai-strategy-actually-runs-on Fri, 20 Mar 2026 12:00:00 GMT What does a modern AI implementation stack actually look like? An AI strategist's honest breakdown of the model, orchestration, memory, eval. https://colin.gillingh.am/writing/ai-roi-why-most-companies-measure-it-wrong https://colin.gillingh.am/writing/ai-roi-why-most-companies-measure-it-wrong Thu, 19 Mar 2026 12:00:00 GMT Most companies measure AI ROI with a cost-savings lens. That lens was built for a different kind of automation. Here's what you're missing. https://colin.gillingh.am/writing/how-to-pick-your-first-ai-use-case https://colin.gillingh.am/writing/how-to-pick-your-first-ai-use-case Wed, 18 Mar 2026 12:00:00 GMT Picking your first AI use case? The wrong question kills more AI strategies than bad tech. Here's the filter I use when advising companies on AI implementation. https://colin.gillingh.am/writing/gtm-personalization-writer https://colin.gillingh.am/writing/gtm-personalization-writer Tue, 17 Mar 2026 12:00:00 GMT Step-by-step guide to building an AI email personalization writer using n8n and Claude, connected to HubSpot. Automate personalized B2B outreach at scale. https://colin.gillingh.am/writing/what-i-tell-every-company-in-the-first-meeting https://colin.gillingh.am/writing/what-i-tell-every-company-in-the-first-meeting Tue, 17 Mar 2026 12:00:00 GMT An AI consultant's five most repeated truths: why prioritization beats picking use cases, why your data isn't ready, and why AI projects die by committee. https://colin.gillingh.am/writing/the-difference-between-an-ai-strategy-and-an-ai-plan https://colin.gillingh.am/writing/the-difference-between-an-ai-strategy-and-an-ai-plan Mon, 16 Mar 2026 12:00:00 GMT Most companies think they have an AI strategy. What they have is a project list with 'AI' written at the top. Here's why that distinction costs you. https://colin.gillingh.am/writing/the-rise-of-agentx https://colin.gillingh.am/writing/the-rise-of-agentx Mon, 16 Mar 2026 12:00:00 GMT AI agents are intelligent users that engage with platforms like humans but scale like software. https://colin.gillingh.am/writing/why-your-ai-pilot-failed https://colin.gillingh.am/writing/why-your-ai-pilot-failed Sun, 15 Mar 2026 12:00:00 GMT AI pilots fail for predictable reasons: wrong metric, wrong team, wrong timeline. Here's the pattern — and how to design one that actually produces something. https://colin.gillingh.am/writing/gtm-company-research-agent https://colin.gillingh.am/writing/gtm-company-research-agent Sat, 14 Mar 2026 12:00:00 GMT Step-by-step guide to building an AI company research agent using Claude Agent SDK and HubSpot. https://colin.gillingh.am/writing/the-ai-audit-what-to-do-before-you-build-anything https://colin.gillingh.am/writing/the-ai-audit-what-to-do-before-you-build-anything Sat, 14 Mar 2026 12:00:00 GMT Before writing a line of code or buying a single tool, there are five questions every company needs to answer. Most skip all of them. https://colin.gillingh.am/writing/sdr-to-gtm-engineer https://colin.gillingh.am/writing/sdr-to-gtm-engineer Fri, 13 Mar 2026 12:00:00 GMT 90% of the SDR function is being absorbed by AI. That's not a prediction — Vercel already did it. Here's what the people who understand this move do next. https://colin.gillingh.am/writing/how-to-evaluate-an-ai-consultant https://colin.gillingh.am/writing/how-to-evaluate-an-ai-consultant Fri, 13 Mar 2026 12:00:00 GMT Before you hire an AI consultant, ask these questions. Most companies hire based on credentials that don't matter and miss the red flags that do. https://colin.gillingh.am/writing/your-first-90-days-with-an-ai-strategy https://colin.gillingh.am/writing/your-first-90-days-with-an-ai-strategy Fri, 13 Mar 2026 12:00:00 GMT AI strategy without a 90-day execution arc is just a roadmap. Here's the sequence that actually moves from strategy to shipped AI implementation. https://colin.gillingh.am/writing/agents-outnumber-humans https://colin.gillingh.am/writing/agents-outnumber-humans Wed, 11 Mar 2026 12:00:00 GMT The internet already has more automated traffic than human. Here's what that means for every SaaS business built around the per-seat model. https://colin.gillingh.am/writing/autoresearch-business-flywheel https://colin.gillingh.am/writing/autoresearch-business-flywheel Mon, 09 Mar 2026 12:00:00 GMT Andrej Karpathy's 'autoresearch' pattern is a secret weapon for business: AI that improves itself every night. Here are 8 business use cases for this loop. https://colin.gillingh.am/writing/humanoid-robots-for-software https://colin.gillingh.am/writing/humanoid-robots-for-software Sun, 08 Mar 2026 12:00:00 GMT Computer use agents inherit every interface humanity ever built. They don't need your permission, your API, or your integration roadmap.