purplechipmonk GTM Plan

What Everyone Else Does

• Jobscan / ResumeWorded: ATS score checker. One-trick pony.
• Teal: Resume builder + basic job tracking. No intelligence layer.
• LoopCV / LazyApply: Auto-apply bots. Volume play, no strategy.
• LinkedIn Premium: InMail credits + "who viewed your profile." Not a system.
• ChatGPT / Claude directly: Powerful but stateless. No memory, no pipeline, no workflow.

What purplechipmonk Does Differently

• Full pipeline ops — not a tool, a system. Tracks 34+ opportunities with stage-aware actions.
• Block-based resume engine — modular resume blocks with versioning, tagging, and ATS scoring that assemble per-opportunity.
• Memory that compounds — 223 facts + vector embeddings mean the AI gets smarter about YOU every session.
• Interview intel system — auto-researches interviewers, generates prep docs, builds your story bank.
• Opportunity evaluation — 6-block pre-apply framework scores fit before you invest time.
• Built from real experience — born when a fired employee used Claude to run a supercharged job search, and his former boss helped him productize it for everyone.

Secondary Product Hunt Launch

Target a Tuesday or Wednesday in Month 2 (after you've built initial social proof). Prep includes:

• 60-second demo video showing the full pipeline flow
• Ship page live 2 weeks before launch
• Rally your Reddit + LinkedIn following to upvote on launch day
• Maker comment with the origin story
• Goal: Top 5 of the day → 500+ signups in 24 hours

Secondary Hacker News (Show HN)

Lead with the technical angle: "Show HN: I built an AI career ops platform with block-based resume engine and memory that compounds." HN loves:

• Technical depth (describe the architecture)
• Solo/small-team builder stories
• Tools they can actually use
• Honest, blunt communication about trade-offs

Time this 1-2 weeks AFTER Product Hunt to extend momentum.

Secondary TikTok / Reels / Shorts

The origin story is made for short-form video. 60-second face-to-camera:

• "I got him the job. Two years later, I had to fire him." — hook
• "He started using AI to run his job search — and it was incredible." — twist
• "So I helped him turn it into a product anyone can use." — resolution
• "Now 500 people use it to level the playing field." — proof + CTA

One viral TikTok in this climate could be worth 10,000 signups. Budget $500/mo for boosted posts.

Tertiary Podcast & Media Circuit

Pitch yourself to podcasts that cover startups, AI, and the future of work:

• Indie Hackers Podcast — the build-in-public angle
• My First Million — the "fired him, then built the product with him" story
• Lenny's Podcast — career ops as a category
• All-In Podcast — AI displacement angle
• Local TV news — "Boss fires employee, then they team up to build AI job search tool for everyone"

Tertiary Career Coach Partnerships

Coaches join free and become your unpaid sales force:

• Identify 50 career coaches on LinkedIn with 5K+ followers
• Pitch: "Free dashboard to track all your clients' job searches — they just sign up for Pro"
• Each client signs up via coach referral link → gets discounted Pro at $23/mo
• Coach gets a dashboard showing client pipeline progress, activity, and outcomes
• Provide co-branded case studies they can publish
• Each coach with 15 clients = 15 Pro subscriptions = $345/mo in revenue, zero coach-side AI cost

Tertiary SEO & Content Marketing

Long-tail content that compounds over months:

• "Career Ops: the new way to run your job search" (category-defining pillar)
• "How to evaluate a job opportunity in 10 minutes" (feature-led)
• "AI resume optimization: beyond ATS scores" (competitor comparison)
• "Job search pipeline management for senior professionals"
• Target 10 articles in Month 1-2, 20 by Month 3

Launch Week Content Blitz

In the 7 days around your official launch, deploy ALL of these:

• Day 1: LinkedIn origin story post (long-form, emotional)
• Day 1: Reddit AMA in r/jobs — "I fired my employee, then we built this tool together. AMA"
• Day 2: Product Hunt launch
• Day 3: Show HN post
• Day 3: TikTok origin story video
• Day 4: LinkedIn "what we learned in 24 hours" follow-up
• Day 5: Reddit r/SaaS build-in-public post
• Day 6: First newsletter issue to all signups
• Day 7: "500 people signed up in a week — here's what they said" recap post

Evergreen Content Assets

Build these once, distribute forever:

• The Career Ops Manifesto — a 2,000-word blog post defining the category. Pin it everywhere.
• "Free Resume Audit" landing page — upload your resume, get a score + 3 actionable fixes. Email gate for the full report.
• Career Ops Playbook PDF — 20-page downloadable guide. Lead magnet for newsletter.
• Comparison pages — "purplechipmonk vs Teal," "…vs Jobscan," "…vs LinkedIn Premium." SEO gold.
• 3-minute product demo video — show the full flow from JD paste to interview prep.

PHASE 1 Foundation (Weeks 1-2)

Get the house in order before driving traffic.

• Finalize pricing tiers and implement Stripe billing
• Build "Free Resume Audit" landing page (email capture)
• Set up error monitoring (Sentry) — critical before traffic spike
• Create 3-minute product demo video
• Write the Career Ops Manifesto blog post
• Set up email newsletter (ConvertKit or Loops)
• Build comparison landing pages (vs Teal, Jobscan, LinkedIn)
• Create Reddit accounts and build karma in target subreddits (comment helpfully for 2 weeks before posting)
• Prep Product Hunt ship page
• Record 3 TikTok/Reel variants of origin story

PHASE 2 Ignition (Weeks 3-4)

Launch week + first big push. Target: 500 free signups, 50 paid.

• Execute Launch Week Content Blitz (see Content Engine tab)
• Product Hunt launch (Tuesday or Wednesday)
• Show HN post (1-2 days after PH)
• Reddit AMA in r/jobs
• Post origin story TikTok — boost best performer with $200
• Begin LinkedIn posting cadence (5x/week)
• Start Reddit paid experiments ($500 across 5 subreddits)
• Send first newsletter to all signups
• Begin cold outreach to 50 career coaches (free Coach tier — bring your clients)
• Activate "First 500 Pro at $19/mo" launch offer

PHASE 3 Scale (Weeks 5-8)

Double down on what's working. Target: 2,000 free, 200 paid.

• Analyze channel performance — kill underperformers, 2x winners
• Scale Reddit ad spend to $1,500/mo on top-performing subreddits
• Scale LinkedIn ad spend to $2,000/mo (target: recently laid off + individual job seekers)
• Publish 10 SEO articles
• Launch free Coach tier — onboard first 10 coaches with client referral links
• Pitch 5 podcasts (target appearance in Month 3)
• Implement referral program ("Invite 3, get 1 month free")
• Run first "Free Resume Roast" live stream on LinkedIn
• Begin collecting and publishing testimonials + case studies
• Hire freelance content writer for SEO articles ($1,500/mo)

PHASE 4 Compound (Weeks 9-12)

Growth loops kick in. Target: 5,000 free, 500 paid.

• SEO content starts ranking — publish 10 more articles
• Coaches driving discounted Pro signups via referral links
• Referral program generating 15-20% of new signups
• First podcast appearances air — repurpose clips across channels
• Launch "Career Ops Certified Coach" badge for coaches with 10+ active clients
• Experiment with outplacement firm partnerships (free Coach tier pitch)
• Test Google Ads on high-intent keywords ($1,000/mo experiment)
• Run "Black Friday for Job Seekers" promotion (if timing aligns)
• Begin planning Series A / angel raise if metrics support it
• Target: exit Month 3 at 500 paid, clear path to 1K by Month 5-6

Loop 1: Shareable Artifacts

Every compiled resume, prep doc, and opportunity evaluation should have a subtle "Built with purplechipmonk" footer with a link. When users share these with recruiters, hiring managers, or career coaches, the brand spreads organically.

Free tier: watermark is more visible. Pro tier: subtle footer only. This creates upgrade pressure while still spreading the brand on free exports.

Loop 2: Referral Program

"Invite 3 friends → get 1 month of Pro free."

Job seekers talk to other job seekers constantly. They're in group chats, Discord servers, and Slack communities sharing tips. Make it dead simple to share a referral link. Track referrals in the dashboard. Show a leaderboard. The top referrer each month gets a year of Pro free.

Loop 3: Career Coach Multiplication

Coaches join free and send their clients a referral link. Each client signs up for discounted Pro ($23/mo). The coach gets a dashboard — the client gets the full AI-powered job search. When the coaching engagement ends, the client keeps their Pro subscription because the product stands on its own.

This is the highest-leverage loop. 50 coaches × 15 clients avg = 750 paying Pro users acquired with zero ad spend. Every coach is a free distribution channel with built-in trust (their clients already take their advice).

Loop 4: "Career Ops Score" Viral Mechanic

Build a free, public "Career Ops Score" — a sharable assessment that grades someone's job search readiness across 6 dimensions (pipeline health, resume strength, network density, interview prep, story bank, market positioning). Generate a branded results card that's designed to be screenshotted and shared on LinkedIn/Twitter.

Think: "What's your Career Ops Score?" posted alongside their actual score. People love sharing scores. Free to take, email gate to get the full breakdown, upgrade to Pro to fix everything it flags.

Model How B2B2C Works

The company pays. The employee gets the tool. You get guaranteed volume with near-zero acquisition cost.

• Buyer: HR / People Ops teams managing layoffs or restructuring
• User: Displaced employees who need to find their next role
• Pricing: Bulk Pro licenses at $19/head/mo (vs $29 retail), minimum 6-month commitment
• Volume tiers: 50-99 heads = $19/mo, 100-499 = $17/mo, 500+ = $15/mo
• Contract value: 200 employees × $17/mo × 6 months = $20,400 per deal

Advantage Why You Win vs. Legacy Outplacement

• 96% cheaper — $114/employee vs $3,000-10,000
• Always on — AI available 24/7, not 3 scheduled calls with a counselor
• Measurable — real-time dashboard showing pipeline activity, interviews booked, offers received
• Scales instantly — no need to hire more counselors for a 500-person layoff
• Better outcomes — digital outplacement programs deliver career landings 2x faster than legacy models
• Employees actually use it — traditional outplacement has 30-40% utilization; a tool they keep in their pocket gets used daily

Targets Who to Sell To

• Mid-market companies (500-5,000 employees) — large enough to have layoffs, small enough that $5K/head hurts. These are your sweet spot.
• Tech companies in restructuring — 52,000+ tech layoffs in Q1 2026 alone. They understand AI tools and will appreciate the product.
• Outplacement firms themselves — some may want to white-label or resell your tool as part of their package rather than compete with you.
• HR consultancies — Mercer, Korn Ferry, Deloitte Human Capital all advise on workforce transitions. Get on their vendor lists.

Execution Go-To-Market for Enterprise

• MO 2-3 Build an enterprise landing page with ROI calculator
• MO 2-3 Create a 1-pager PDF for HR decision makers
• MO 3-4 Cold outreach to 50 HR leaders at companies that recently announced layoffs (public data via WARN Act filings)
• MO 3-4 Offer 2 free pilot deals (20-50 employees each) to generate case studies
• MO 4-6 Hire a part-time enterprise sales rep (commission-only to start)
• MO 4-6 Target: 3-5 enterprise deals in first 6 months = $50-100K revenue

Adjacent Universities & Bootcamps

Same B2B2C model, different buyer. Every university career services office and coding bootcamp needs placement rates for marketing.

• Universities: Career services already pay for Handshake, VMock, Big Interview. Position purplechipmonk as the AI-powered complement.
• Bootcamps: Placement rate is their #1 marketing metric. A tool that helps graduates land faster is a direct ROI play.
• Pricing: Institutional license at $15/student/mo for graduating cohorts (3-6 month terms)
• Volume: One university with 500 graduating seniors = $7,500/mo × 4 months = $30,000/year per school

Revenue Impact Enterprise vs. Individual

Enterprise doesn't replace the individual-first model — it accelerates it.

• Individual Pro: $29/mo, one at a time, organic + paid acquisition. This is your base.
• Coach-referred Pro: $23/mo, 10-20 at a time per coach. Free distribution.
• Enterprise bulk: $15-19/mo, 50-500 at a time per deal. Whale revenue.
• Blended scenario at Month 6: 600 direct Pro + 250 coach-referred + 400 enterprise = 1,250 paid users, ~$28K MRR
• Enterprise users who land jobs become evangelists. Some will buy Pro for their next search on their own dime.

Activation The Aha Moment

Define what a user needs to do in their first session to become a retained user. Measure it. Optimize everything toward it.

• Hypothesis: Users who add 3+ pipeline opportunities AND compile 1 resume in their first week retain at 3x the rate of those who don't
• Action: Instrument this. Track activation rate (% of signups who hit the aha moment within 7 days)
• Onboarding redesign: Guide every new user to add their first opportunity and compile a resume within the first 10 minutes. Don't let them wander.
• Target: 40% activation rate within 7 days by Month 3

Conversion Upgrade Triggers

Free users should hit natural friction points that make upgrading feel like relief, not a sales pitch.

• Opportunity #6: "You're tracking 5 opportunities — serious job seekers usually track 15-30. Upgrade to Pro for unlimited."
• Resume block #4: "You've used your 3 free blocks. Your resume is 60% optimized. Unlock all 49+ blocks."
• Compiled resume #2: "You've used your monthly compile. Pro members compile unlimited resumes — one per opportunity."
• AI session #11: "You've hit your 10-session limit. Pro gets unlimited AI access."
• After a win: "You just got an interview! Pro users get full interview intel + prep docs for every interviewer."

Retention Why People Stay

Retention in job search tools is uniquely hard — people leave when they get a job. Plan for it.

• Memory moat: The longer someone uses purplechipmonk, the smarter it gets about them. Leaving means starting over. Make this visible: "Your AI has learned 223 facts about your career."
• Pipeline investment: Once someone has 15 opportunities tracked with notes, stages, and prep docs, switching costs are massive.
• Weekly digest email: "You have 3 opportunities in interview stage, 2 new matches, and your resume score improved 12 points." Pull them back in.
• Post-hire retention: "Congrats on the new role! Keep Pro for 90 days to nail your onboarding. After that, pause your subscription — your data stays forever."

Re-engagement Winning Back Churned Users

Most free users will go dormant. Some paid users will cancel. Have a plan.

• Day 3 no-login: Email: "You have 2 opportunities that need attention. Your pipeline is waiting."
• Day 7 no-login: Email: "The job market moves fast — 242 people applied to the average opening this week. Don't fall behind."
• Day 14 no-login: Email: "We saved your pipeline. Come back anytime — your AI still remembers everything about you."
• Cancelled Pro user: Downgrade gracefully. Keep their data. Email monthly: "Your pipeline has 8 saved opportunities. Reactivate Pro for $19/mo to pick up where you left off."
• Seasonal re-engagement: January and September are peak job search months. Run reactivation campaigns 2 weeks before each.

Why The Loneliness Problem

The average job search in 2026 takes 6 months. Long-term unemployment (27+ weeks) is up to 26% of all unemployed. These people aren't just frustrated — they're isolated. Their employed friends don't get it. Their families are worried. They need a place where the default state is "we're all in this together."

A community that makes people feel less alone during the worst professional experience of their lives will generate loyalty that no feature comparison ever could.

Where Discord over Slack

Discord is free, handles thousands of users, supports threads, voice channels, and bots. Slack charges per seat and feels corporate. Your users are job seekers, not enterprise teams.

• #introductions — new members share their story and what they're looking for
• #wins — interviews booked, offers received, jobs landed. The most important channel.
• #resume-review — peer feedback on resumes (drives product usage)
• #mock-interviews — members pair up for practice sessions
• #job-leads — members share opportunities they've found
• #career-ops-tips — power users sharing workflows and strategies
• #coaches-corner — career coaches answer questions, build their reputation, recruit clients

Growth Community as Acquisition Channel

• Every #wins post is a testimonial. Screenshot them (with permission) for LinkedIn, Reddit, and landing pages.
• Weekly "Resume Roast" live events — a coach or power user reviews 5 resumes live on Discord. Attendees see the product in action. Free to attend, streamed to YouTube/LinkedIn for reach.
• Invite mechanic: "Join our free Discord community" is a softer CTA than "Sign up for our product" — it warms leads before they hit the paywall.
• Community members convert 2-3x higher than cold signups because they've already seen social proof from peers.

Retention Community as Stickiness

• Accountability pods: Groups of 5 members who check in weekly on their job search progress. Structured like a standup: what I did, what I'm doing, where I'm stuck.
• Monthly challenges: "Apply to 20 opportunities this month using Career Ops." Leaderboard + prizes (free Pro months).
• Coach office hours: Free Coach tier members host weekly Q&A sessions. It's free marketing for them, free value for your users, and keeps both engaged.
• Alumni channel: People who land jobs stay to help others. They become mentors, moderators, and proof that the system works.

HIGH Product Stability Under Load

Risk: Recent Vercel deploys have shown production errors. A traffic spike from Product Hunt or HN will find every edge case.

Mitigation: Set up Sentry error monitoring BEFORE launch. Load test with 500 concurrent users. Have a war-room plan for launch day. Nothing kills a launch faster than downtime on day one.

HIGH Free Tier Abuse / AI Cost Overrun

Risk: Free users consuming expensive LLM calls. At scale, 10,000 free users × 10 sessions/mo could cost $5-10K/mo in API fees.

Mitigation: The 10-session/mo free limit is critical. Enforce it strictly. Use cheaper models (Haiku) for free-tier responses. Track per-user costs via the model_usage table you already have. Set alerts at $0.50/user/mo. The individual-first pricing model is your structural defense — every user who consumes AI is a paying subscriber. No multi-client seats that let costs balloon against a flat fee.

MEDIUM Reddit Bans / Mod Removal

Risk: Reddit mods are aggressive about self-promotion. Getting banned from r/jobs would be a major setback.

Mitigation: Spend 2 weeks building genuine karma before ANY product mention. Always lead with value. Disclose affiliation. Use multiple accounts only for reading, never for astroturfing. Treat mods as allies — message them before posting anything promotional.

MEDIUM Low Free→Paid Conversion

Risk: Free tier is too generous, users never upgrade. Or the paid value prop isn't clear enough.

Mitigation: Watch the 5-opportunity limit closely. If conversion is below 3% after Month 1, tighten free limits (reduce to 3 opportunities, 5 AI sessions). Add in-app "upgrade nudges" at natural friction points — when they try to add opportunity #6 or generate a second compiled resume.

MEDIUM Competitor Response

Risk: Teal, Jobscan, or a new entrant copies the "Career Ops" positioning or launches similar features.

Mitigation: Speed is the moat. Your memory system + block-based resume engine + origin story are hard to replicate. File a trademark for "Career Ops" immediately. Build community (newsletter, Discord) that creates switching costs beyond the product itself.

LOW Story Fatigue

Risk: The origin story is powerful but has a shelf life. You can't tell it for 6 months straight.

Mitigation: The story opens the door in Months 1-2. By Month 3, pivot to user stories. "Sarah used Career Ops to land 4 interviews in 2 weeks." By Month 4+, the category ("Career Ops") carries the brand, not the origin story. Plan the transition.

SHIPPED Stripe Billing — live

Apr 16, 2026. Two Stripe products, four prices, webhook, and Customer Portal provisioned in the ClearSpeed Stripe account (live mode). Checkout route fixed (was broken — frontend sent plan+interval, route expected priceId). Webhook now resolves tier by price-ID map, not by amount-sniffing.

• Pro Monthly $29 (price_1TN3kF...u1xLoGrx)
• Pro Annual $228/yr = $19/mo, 34% off (price_1TN3kF...9PxaGY1A)
• Coach-Pro Monthly $23 (price_1TN3kG...77UeyQDG)
• Coach-Pro Annual $180/yr = $15/mo (price_1TN3kG...B1JanwrQ)
• Webhook at /api/stripe/webhook, 6 events, signature verification ✓
• Customer Portal: plan switching, payment updates, invoice history, cancel-at-period-end with reason capture

SHIPPED Killed $149 "Professional" coach seat

Apr 16, 2026. Prior pricing page had a $149/seat "Professional" tier aimed at coaches. The unit economics broke: one coach with 20 clients would burn 300-400 LLM calls/mo against $149 revenue. Replaced with individual-first model where each client is their own Pro subscriber (at the discounted $23/mo coach-referred rate) and the coach gets a free dashboard.

SHIPPED Reverse trial — 7 days of Pro, no card

Apr 16, 2026. Every new signup automatically gets Pro entitlements for 7 days — computed from users.created_at, no schema change, no cron. After day 7, auto-rolls back to Free tier (opportunities beyond 5 stay but become read-only — no rage-churn). Billing card shows trial countdown. Pricing page carries the "7 days of Pro free, no card required" hero callout.

Expected lift: free→paid conversion from ~3% to ~10-12% based on Superhuman/Notion/Linear benchmarks.

SHIPPED Pricing page rewrite

Apr 16, 2026. Removed the $149 Professional tier. Added "For Coaches" tier (free dashboard + referral link). Added enterprise / outplacement quote-link footer. Added reverse-trial hero callout. Restored coherence between the GTM plan and what the site actually offers.

SHIPPED Financial model — pricing alignment

Apr 16, 2026. financial-model-april-2026.md updated to reflect the GTM-aligned pricing. Blended ARPU revised from ~$49/mo (old Starter/Professional/Unlimited ladder) to ~$22/mo (Pro direct $25 + coach-referred $19 + enterprise $17). Volume from coach + enterprise channels expected to offset the lower ARPU at ~2-3× users, keeping the ~$27K MRR Month-18 target on track.

SHIPPED Coach referral landing page

Apr 17, 2026. Route /coach/[slug] now live. Lands on a coach-branded page, sets a 30-day pcm_coach_ref cookie, forwards to signup. The checkout route reads the cookie and auto-applies the Coach-Pro pricing ($23/$15). Works even if the user doesn't sign up immediately — cookie persists for 30 days across sessions.

Test URL: https://www.purplechipmonk.com/coach/demo

SHIPPED Day-5 trial nudge email

Apr 17, 2026. Added to /api/cron/lifecycle-emails (runs daily at 10am UTC). Users ~5 days into the 7-day reverse trial who haven't converted get a one-shot email: "Your Pro trial ends in 2 days." Skips anyone who already has an active paid subscription. Uses subscription_updates email category — user-controllable opt-out honored. Dedup: 168 hours (never twice).

SHIPPED Day-8 trial-ended re-engagement email

Apr 17, 2026. Added to the same cron. Users whose 7-day trial just expired (day 8, ±12h) and who didn't convert get a "here's what you kept, here's what changed" email with honest downgrade framing — not a nag. Uses re_engagement category. One-shot (720h dedup). Designed to match the reverse-trial philosophy: pressure comes from loss aversion on day 7, not from hounding after.

SHIPPED Persistent trial banner in sidebar

Apr 17, 2026. <TrialBanner /> component injected above the footer in the main sidebar. Renders only when the user is in the reverse trial (no paid sub + account <7d old). Shows days-remaining + "Lock in $19/mo" CTA. Color shifts to amber on the final day. Session-scoped dismiss so it doesn't nag on every page. Collapsed sidebar mode shows a compact day-count badge. Uses the same 5-minute cached-fetch pattern as the rest of the sidebar so it doesn't hammer /api/billing/trial.

IN FLIGHT Live cohort on reverse trial

Waiting for first real signups so we can measure baseline free→paid conversion. Target: first 50 signups → compute day-7 conversion rate → decide whether to A/B trial length (7 vs 14 days) or the day-5 nudge subject line.

SHIPPED Origin-story content drafts

Apr 17, 2026. All channel-native drafts written and ready to publish. Six pieces total in docs/marketing/origin-story.md: LinkedIn (named, 1,300 chars), Reddit r/recruitinghell (anonymous, self-post), Product Hunt ship page + maker comment, TikTok/Reels 60-second face-to-camera script, career-coach cold outreach template, and the Month-3+ transition plan to user-win content. Each piece ends with a clear CTA to the free tier.

Publishing sequence lives in docs/marketing/gtm-execution-roadmap.md Phase 1, Week 1.

SHIPPED 8 bug fixes from Zach's Apr 17 triage + 2 architectural follow-ups

Apr 17, 2026. All 8 tickets worked through same day. Session Open gating, New Chat stuck, PDF upload routing, Work History empty guard, fail-open gate warnings, daily digest date window, playbook fragment filter, and double-$$ comp sanitizer. Plus 2 architectural launch-critical follow-ups: resume-lab → canonical_background hydration, and opportunity-evaluation hard-fail rules. 5 GH issues opened for remaining non-critical audit work. Commits: 056dcb3, 148a012, 4a3c0e3, 3b3c425.

SHIPPED Free-tier API-layer caps

Apr 17, 2026. Compiled-resume count per month now enforced in the save_compiled_resume tool with a clean 402-style response + /pricing upgrade link. countCompiledResumesThisMonth() query on compiled_resumes table. Free tier (1/month) blocked; Pro / reverse-trial users unaffected. Most users won't hit this for 7 days thanks to the reverse trial.

SHIPPED Slack #tickets auto-ingest cron

Apr 17, 2026. Scheduled Claude Code task runs every 15 min, polls PurpleChipMonk Slack #tickets channel, triages new tickets, ships trivial fixes inline, creates GH issues for non-trivial, posts threaded acks to Slack. Task ID: pcm-tickets-ingest. Guardrails: never force-push, typecheck failure reverts, Justin's commands default to GH issue rather than auto-execute. Run log at ~/.claude/scheduled-tasks/pcm-tickets-ingest/run-log.jsonl.

SHIPPED LinkedIn posts — Weeks 2 & 3 drafted

Apr 17, 2026. docs/marketing/linkedin-posts-weeks-2-3.md. Week 2 (Apr 28) = market-intel angle, Pillar 2 content: "I pulled 200 job descriptions this month." Seven data-driven findings, non-promotional, positioned as authority-building. Week 3 (May 5) = Career Ops framework, Pillar 3: "Stop applying to jobs. Start running a pipeline." Six-step methodology, category-creation content. Both posts ship paste-ready with pinned first-comment link, engagement playbook, and Week 4 Product Hunt sequencing notes.

SHIPPED GTM execution roadmap

Apr 17, 2026. Week-by-week task list mapping the GTM plan to real execution. docs/marketing/gtm-execution-roadmap.md. Phase 0 (launch readiness, this week) → Phase 1 (organic launch, weeks 1-4, target 50 paid) → Phase 2 (seed ads + coach channel, weeks 5-12, target 250 paid) → Phase 3 (scale, months 4-6, target 500+ paid). Each task has owner, output, effort (S/M/L/XL), and dependencies. Includes always-on tasks, open decisions, and an explicit "NOT on the roadmap" list to prevent scope creep.

UP NEXT Publish origin-story posts — LinkedIn LOCKED for Tue Apr 21, 7:30am PT

Locked date: LinkedIn post goes live Tuesday April 21, 2026 at 7:30am PT. Playbook: docs/marketing/linkedin-launch-apr-21.md. Calendar events set for the T-24h prep (Mon Apr 20, 8am PT) and the launch window (Tue Apr 21, 7:30-8:30am PT). Rest of Week 1: Reddit r/recruitinghell (Wed Apr 22), Discord soft-launch (Thu Apr 23). Show HN → Week 2. Product Hunt → Week 4.

UP NEXT "Career Ops" trademark filing

USPTO application for "Career Ops" as a category mark. Speed matters — file before competitors notice the positioning. Owner: Justin (legal).

UP NEXT Resume-block & compiled-resume caps (API-layer enforcement)

Free tier limits (3 resume blocks, 1 compiled resume/mo) exist in TIER_CONFIG but aren't enforced at the API layer. Currently unreachable in practice because every new user is on Pro via reverse trial — but once users start lapsing to Free, resume-lab and compiled-resume endpoints need cap checks with clear upgrade CTAs. Opportunity cap (5) and session cap (10/mo) are already enforced.

UP NEXT First real-card smoke test

Owner: Justin. Sign up with a fresh account, confirm the 7-day trial shows in Settings + sidebar banner, run checkout with a real card, verify the webhook round-trip updates the sub in Supabase, refund the charge. Mark this card green once done.

LATER Product Hunt launch

Target Tuesday or Wednesday in Month 2 after initial social proof. Prep: 60-second demo video, ship page live 2 weeks before, Reddit + LinkedIn rally on launch day.

LATER Coach cold-outreach (50 coaches)

Per the GTM plan Month 1-2 tactics. LinkedIn DM + demo. Activate the Career Ops Certified Coach badge for 10+ client accounts.

LATER Outplacement firm partnerships

Enterprise / B2B2C pilot with 1-2 HR consultancies or outplacement firms. Custom Stripe quote at $15-19/seat, 50-500 seat deals. Month 3+ initiative.

LATER Founding-500 counter gate

Currently the $19/mo annual is the same as the Founding price (no Stripe construct needed). When we hit ~400 annual subscribers, add a counter + "Founding 500 locked — only N left" badge on pricing. Marketing-driven urgency.

LATER Reverse-trial A/B test on trial length

Once we have ≥200 signups on the 7-day trial and a real baseline conversion number, run a 7-vs-14-day cohort test. Superhuman found 7 optimal; we should verify for our use case.

LATER Discord community

Per the Community section. Defer until ~200 active users so channels have density. Kickoff with coach office hours + #introductions + alumni channel.

DECIDE Reverse-trial onboarding UX

Do we surface "You're on Pro for 7 days" as a persistent nav banner (higher visibility, more pressure) or just a subtle chip in Settings → Billing (lower friction, current implementation)? Currently shipped with the latter. Revisit after 50 signups.

DECIDE When to stop generous free tier

GTM plan designs the free tier to be the top of funnel. If we hit a cost ceiling from free-tier AI usage (target: <$0.50/user/mo on Haiku), decide whether to reduce free-tier session cap from 10 to 5 or tighten feature access. Revisit at Month 3.