Jackson Sherwood

Jackson Sherwood

AI Enablement + Agent & Application Builder · Housecall Pro Marketing
Got my start on the innovation team in late 2022, where GPT-3 first got me hooked, so I've been building with AI since its inception. Today I'm the bridge between Housecall Pro's marketing org and AI: shipping agents and apps, and getting the whole team building too.
6 Agents Running Live
Total Token Usage
0M
in + out + cache writes
AI Sessions
0
since jan 8, 2026
Messages Logged
0
human + ai turns
Lines of Code
0
written + edited, all projects
Active Agents
0
incl. master synthesis
Value Generated
$0
engineering equivalent
Build Log
Every commit I pushed and the AI sessions behind it
371 commits, 78 active days
less more
337github commits
34gitlab commits
406ai sessions
17repos, personal + company
6day streak, aug 2 to 7
total engineering value
$0
Equivalent cost to hire engineers and enablement leads to build and run all of this. Based on market rates for junior-to-mid SWE ($43–$55/hr) and AI program design.
Counter-Intel System (Daily + Weekly + Q&A + Emerging Threats)$18,500
PMM Brain v0, 5-agent GTM system$13,000
AI Enablement Program (3 qtrs, 301 builder track + Creative Office Hours)$10,000
Counter-Intel Master Synthesis Agent$9,000
Trades Thursday Hub v2 (66 events, self-serve CSV, QA suite), shipped live$8,000
Sherwin-Williams × HCP Prototype$7,500
HCP Maps, shipped behind Okta$6,500
Parker rollout: replaced Motion, ebook CPL −16%, weekly report$6,000
HCP Testimonials Hub, shipped behind Okta + Sept refresh$6,000
HCP Marketing Plugin Marketplace (2 plugins, 40+ users)$6,000
Misc & Ad-Hoc Builds (dashboards, consults, scrapes, skills)$6,000
PMM Brain pilot (two doors, T4 frontline pack, 3 PMMs)$5,000
HCP Labs Prototype + Research$4,000
Community LP + Community Hub (handed to eng)$4,000
Sites & Docs$3,800
Trade Academy Platform$3,600
HCP Landing + Workflow Pages$3,500
Desktop Reviews Prototype$3,200
Ultimate Higgsfield Workflow (Cowork)$3,000
May 2026 Release Moment Page$2,500
Meta Ads Deployer$2,500
Top 50 Names LP + Winners page (QA + review)$2,500
Returning-Pro Landing Page (churn A/B test)$2,000
40 Under 40 (v1 + app flow)$400
monthly automation + tool savings
$5,342/mo
6 autonomous agents, anchored by a master synthesis agent, eliminating manual competitive research, synthesis, paid-ads reporting, and on-demand intel every week. Plus Parker replacing Motion as the paid-ads analytics tool.
Motion replaced by Parker (tool cost)$1,300
Master Synthesis Agent (24 hrs/mo)$1,032
Daily Alerts (22 hrs/mo)$946
Q&A Bot (20 hrs/mo)$860
Weekly Digest (12 hrs/mo)$516
Emerging Threats Brief (8 hrs/mo)$344
Parker Weekly Paid-Ads Report (8 hrs/mo)$344
Annualized savings$64,104/yr
marketing org enablement value
$24,800/mo
What the enablement program returns across Marketing, on top of anything I build myself. Three quarters of AI Office Hours (now monthly, because the team builds on its own), a weekly “Did You Know?” drop, and 1:1 consulting: 79-person department, 62 active in Claude weekly, 50 daily active builders, average usage up 2.4× since Q2 start. Hours and rates held deliberately low.
Everyday AI use · 50 daily builders, 1.5 hrs/wk at $45$14,600
Ad creative throughput · ~40 extra ads/mo at $150$6,000
Campaign pages in-house · 3–4 wks to 1 wk$3,000
20+ team-built skills & plugins, 40+ marketplace users$1,200
Annualized value$297,600/yr
Session History
What got shipped, fixed, and built · 35 highlighted, Jan to Oct 2026
01
jsher.online, Build & Deploy
Built personal portfolio from scratch, pushed to GitHub, got live on Vercel
Jan 8deploy
02
n8n Setup + Claude Integration
Wired Claude Code into company n8n, built first AI-powered workflow node
Feb 11build
03
Counter-Intel Chatbot, Full Migration
Migrated TypeScript Slack bot to n8n; Slack trigger + AI question parsing working
Feb 11build
04
HCP Maps, Glassmorphism UI + Deploy
Full UI polish with glassmorphism styling, security hardening, GitHub push
Feb 17deploy
05
Counter-Intel Alerts, Designed & Built
Designed + deployed daily competitor page monitor with Claude AI → Slack alerts
Feb 23build
06
jsher.online, Dark Redesign
Apple-inspired dark redesign, two feedback rounds, pushed live to Vercel
Feb 23design
07
Tyler's Feedback → Full System Upgrade
Shipped taxonomy, scoring, deduplication, digest restructure & caching in one session
Feb 26fix
08
MBR Prep + Weekly Digest Debug
Polished MBR slides & key results, found and fixed weekly digest agent failure
Feb 26docs
09
Counter-Intel Q&A Bot, Error Handling + Format
Adaptive response formats (reviews, pricing, comparisons), retry logic on Claude API, rate limit messaging, removed broken @ping on unknown competitors
Mar 4build
10
Q&A Bot, Deep Dive + Source Diversity Overhaul
11 node updates: platform-tagged citations (G2/Capterra/Reddit), source diversity rules, deep dive error handling, 50% token reduction, channel/thread passthrough bug fix
Mar 4fix
11
jsher.online, Pre-Ship Polish
Favicon with green ring, OG preview tags, Dad's Site project + value update, analytics refresh, pre-ship clean up before manager review
Mar 9design
12
jsher.online, Ship Day Edits
Project board reorder, HCP Maps → deploying (yellow), prototype links fixed, value recalculation, analytics refresh, ready for manager review
Mar 11deploy
13
Find Your Claude, AI Office Hours Quiz
Built 4-question personalized tool finder for HCP marketers, routes to Claude Chat, Cowork, or Code based on role and workflow. Shipped to /quiz.
Apr 12deploy
14
HCP Redesigned Landing + Workflow Pages
Built full React 19 + Vite 7 redesign of the HCP landing page with workflow pages, glassmorphism dark cinema aesthetic, production-ready, shipped to /hcp-landing.
Apr 20deploy
15
May 2026 Release Moment Page
Built and shipped the May 2026 product release moment landing page, live at housecallpro.com/lp/may-26-release/
May 19deploy
16
Jack's Ultimate Higgsfield Workflow
End-to-end AI creative pipeline for Cowork, text gen + critic → Motion analytics → Higgsfield ad creation. Packaged as a downloadable folder for the marketing team.
May 20build
17
Counter-Intel Master Synthesis Agent
Collapsed 5 separate competitive-intel bots into one master agent that orchestrates sub-agents and synthesizes a single prioritized weekly brief, with memory of what it already reported. Live in n8n.
Jun 3build
18
PMM Brain v0, 5-Agent GTM Planner
Built v0 of the PMM Brain: PRD ingest → draft writer + comp scraper + data intelligence (parallel) → GTM assembler, over a hybrid live-data + examples context. Demoed to leadership, one of the largest AI builds to date.
Jun 9build
19
HCP Maps + Testimonials, Shipped Behind Okta
Shipped the first two vibe-coded production apps at Housecall Pro behind Okta SSO, the internal Maps tool for sales reps and the Testimonials Hub for social proof on demos.
Jun 11deploy
20
jsher.online, Quarterly Board + Q2 Wrap
Reorganized the project board by quarter, promoted the Q2 flagship apps to shipped, refreshed all metrics and value, and laid out the Q3 roadmap.
Jun 15deploy
21
HCP Marketing Plugin Marketplace, v0.4.0
Shipped the org-wide marketing Claude plugin marketplace to main: marketing-core, community, and a brand-new seo-content plugin (7 skills) built in the same session.
Jun 18deploy
22
Mechanical Ads Engine, V0 Running
Built a multi-agent paid-creative engine end to end: generate, composite, and gate static ad assets. First two waves shipped (24 HVAC assets x3 sizes) with Supabase + Higgsfield wired in.
Jun 23build
23
AI Spotlight, Presented to 1,500
Built and delivered the marketing AI story to a 1,500-person company audience: how a 90-person marketing org went from using AI to building with it, with the shipped tools to back it up.
Aug 2talk
24
PMM Brain, Real PMM Inputs
Ran the Brain on live PMM work: rebuilt the Tier 4 output from Anna Earl's 22-comment review and promoted her rules into cross-cutting rules every run has to follow.
Aug 18build
25
AI Office Hours 301, Builder Track Wrapped
Three weekly sessions taking marketers from repo to shipped landing page with zero lines of code written by hand. Recordings and guides in Drive.
Aug 24talk
26
Community Landing Page, Built from Figma
Built the Community landing page from the Figma file with band-measure and overflow QA harnesses, then handed it to the Community team with the Hub.
Sep 2build
27
Trades Thursday Hub v2, Self-Serve Events
18 to 66 events (17 hubs + 49 local meetups, 63 cities), live seat counts, CSV defects fixed at build time, and a browser regression suite. Updated live Sep 11.
Sep 8deploy
28
Top 50 Winners Page, QA + Code Review
QA and code review on top of Bassel's build for the Top 50 Unforgettable Names winners reveal. Live at housecallpro.com/lp/top-50-unforgettable-names/.
Sep 10deploy
29
PMM Brain, Two Doors + T4 Frontline Pack
Split the Brain into two doors over one shared core, added a frontline pack that matches the PMM team's generator app, and a test door for Sam. 3 PMMs using it in pilot.
Sep 23build
30
Creative Office Hours, 4 Self-Serve Skills
Co-ran the first Creative Office Hours and launched the creative-production plugin: Resizer, Email Copy Refresh, Legacy Email Refresh, and Slide Deck Builder.
Sep 25deploy
31
Parker Replaces Motion, First Ad Win
Four-week read on the Parker-briefed ebook ads: CPL $50.47 vs $60.39 (16% cheaper) and CPM 30% cheaper. Now rolling out to every ebook campaign, and Parker replaced Motion, saving $1,300/mo.
Sep 28ads
32
Testimonials Hub, September Refresh
156 testimonials across 30 verticals, two new pain-point filters, a simpler hero selector, and headshots for 16 more Pros. Live behind Okta.
Sep 29deploy
33
Marketing Core 0.12 & 0.13
Shipped Claim Validator, Copy Editor, and a creative brief skill that names paid ads automatically. Five marketplace releases since August, several built by teammates.
Sep 30deploy
34
Comp-Intel Posts, Smart Brevity Rewrite
Rewrote all four #competitive routines to a 180-word cap (120 for Daily Pulse) after leadership said the posts ran long.
Oct 5fix
35
Returning-Pro Landing Page
Built the churn-ad landing page for an A/B test. Churned Pros converted at 1.8% on the generic demo page vs 4.9% for cold traffic. Handed off, not live yet.
Oct 5build
Project Board
Everything built with AI
shipped 30
🛠️ Trades Thursday Hub live · v2 🏆 Top 50 Names + Winners Page live
🧩 HCP Marketing Plugin Marketplace live · 40+ users
🧠 PMM Brain Pilot pilot · 3 PMMs
📈 Parker, Replaced Motion $1.3K/mo saved
🛰️ Emerging Threats Brief live
🎓 AI Office Hours 301 + Creative OH delivered · Q3
🤝 Community LP + Community Hub handed off
🔁 Returning-Pro Landing Page handed off · A/B
Q4 2026 · building / deploying 5
🗂️ HCP GTM Context Layer Q4 · building
🎬 AI Creative Intelligence Pipeline flagship
🧠 PMM Brain, Full PMM Rollout next
📋 Templatized Competitive Teardowns in works
🎓 AI Office Hours: Monthly ongoing
Live Agents
Autonomous workflows in production
6 active
Counter-Intel Master Synthesis
active
schedule weekly sub-agents 5
5 sub-agents→ synthesize→ memory→ slack
Jackson's Weekly Digest
active
schedule every monday nodes 18
firecrawl→ scrape→ claude→ slack
Counter-Intel Daily Alerts
active
schedule daily nodes 22
scrape→ diff→ claude→ slack
Counter-Intel Q&A Bot
active
trigger on slack message nodes 28
slack→ firecrawl→ claude→ reply
Emerging Threats Brief
active
schedule 1st + 15th runs on cowork
scan→ score threats→ claude→ slack
Parker Weekly Paid-Ads Report
active
schedule every monday owners 3
parker→ compare→ split by owner→ slack
output vs. seniority level
junior
$80–100K
mid
$115–140K
senior
$155–185K
staff
$200K+
→
Jackson's Output: Mid SWE
production apps · agent fleets · org enablement
analytics from claude code session logs · updated oct 7, 2026 · linkedin