Ashley Kays

Portfolio · 20+ Years

I build products
from 0→1.

AI products. Enterprise data. Intelligent workflows.

Product leader with 20+ years turning ambiguous problems, emerging technology, and complex enterprise systems into products people can actually use.

0→1 AI Products
Founder-shipped, live in production
Enterprise Data & Technology
$8M BI initiative, 18,000+ users
Complex Operational Experiences
Conversational AI in banking, $100M+ engagement
View selected product leadership ·Book a call
0→1 · Track Record

0→1 product experience, at every scale.

ProductProblem0→1ScaleResult
Builder DNAPersonalized founder decision support✓8,000+ Waymaker usersLive AI product
Disney BIEnterprise information discovery✓18,000+ users$8M initiative
CodeTeachersModern STEAM education✓25,000+ learners300% growth
Ask KaiConversational banking✓EnterpriseMulti-brand AI
Waymaker AIAI product creation✓Multi-product platform4+ production AI products
Case Studies

Selected product leadership.

010→1 AI Product

Builder DNA

A personalized AI archetype assessment where the result is the acquisition loop.

Read the case study
02Enterprise Data Product

Disney BI

$8M business intelligence initiative supporting 18,000+ users inside a $40M+ Oracle Retek implementation.

Read the case study
0350+ Products · 300% Growth

CodeTeachers

Scaled one education concept into a 50+ product learning-pathway platform.

Read the case study
04Conversational AI · Banking

NCR Ask Kai

Conversational UX for consumer banking, before "ChatGPT for banking" was mainstream.

Read the case study
How I build products — my product philosophy
Additional workAI Products & Open SourceConsulting EngagementsMarketing Kits & Brand SystemsEnterprise & Consumer ExperienceEducation & ProgramsLifecycle MarketingGrowth — AEO & SEO
01 · AI Products & Open Source

Live products I designed, built, and ship updates to weekly. Operator-builder work that doubles as my marketing.

2022 — Present
View live product

Waymaker AI

Founder & Head of AI Product Marketing

Product · Design · Engineering · GTM

AI platform that takes non-technical founders from idea to a launched, hosted product — its core job is real AI adoption for people who can’t code. AI Chief of Staff (Cameron), Builder DNA assessment, an idea-to-live-URL build pipeline, agency white-label, community layer, audio library, cohort training, and a 60+ page marketing site — shipped live on Next.js + Vercel + Supabase + Anthropic Claude.

  • Shipped 4+ production AI products in 12 months including Cameron (AI Chief of Staff with tool use, multi-turn memory, voice)
  • Own the full product lifecycle solo — roadmap, design, engineering, GTM — for a multi-product AI platform
  • Built an idea-to-live-URL pipeline: generates an app and auto-deploys it to a stable per-user URL via the Vercel REST API
  • Designed + shipped the full community layer: real-time DMs, 7-reaction system, threaded discussions, marketplace
  • Ship maintainable, tested code on a production stack (Next.js App Router, Vercel Edge Middleware, Supabase Realtime + RLS, Stripe, Anthropic API, ElevenLabs) — e.g. cut the core home surface from 3,239 to 291 lines across 8 files while adding 21 tests
AI Product·GTM·Founder·Next.js·Claude·Supabase
2024 — Present
CoFounder
@waymakerai/aicofounder-core · MIT · NPM
View live product
2024 — Present
View live product

CoFounder

@waymakerai/aicofounder-core · MIT · NPM

Founder & Maintainer

Open-source AI agent guardrails SDK + CLI for safe AI-assisted development. Production-grade safety tooling — supports 9 LLM providers and integrates with the Vercel AI SDK, Supabase, LangChain, CrewAI, and Claude Code.

  • Published on NPM as @waymakerai/aicofounder-core + @waymakerai/aicofounder-react
  • Enforces PII redaction, prompt-injection blocking, budget caps, and HIPAA/GDPR/SEC compliance frameworks
  • Shipped 5 React hooks, 4 CLI commands, full TypeScript types, comprehensive docs (API reference, architecture, governance, whitepaper)
Open Source·AI Safety·TypeScript·CLI
2026
Take the live assessment

Builder DNA

Waymaker AI

Product · Design · Engineering

Personalized AI archetype assessment with shareable cards and Vercel edge-middleware OG metadata. Conversion engine and viral acquisition loop in a single surface.

  • Edge-rendered OG meta system for client-rendered share routes (/dna/:slug)
  • Personalized 8-archetype output with social-share cards as the acquisition loop
  • Live conversion funnel: assessment → result → share → new-user signup
AI·Viral Loop·Edge Functions·Next.js
2026
Cockpit + Practice Engine
Waymaker AI
View live product
2026
View live product

Cockpit + Practice Engine

Waymaker AI

Product · Engineering

Two production surfaces shipped in 2026: Project Cockpit, an orchestration layer that infers what stage a project is in and wires launch, marketing, and the product brain together — and Principles Into Practice, a learning engine that turns abstract principles into trackable daily reps.

  • Project Cockpit: stage-inference orchestration connecting launch kits → brain nodes → marketing, with realtime build status
  • Principles Into Practice: rep/pathway learning engine — 12 pathways, ~60 reps, RLS-secured Postgres, 24 tests — live at go.waymaker.cx/practice
  • DNA-driven recommendations surface the right next rep for each user
AI Product·Orchestration·Supabase·Realtime
2026 — Present
Zero to One
Waymaker AI — Live Case Study Series
Read the case study
2026 — Present
Read the case study

Zero to One

Waymaker AI — Live Case Study Series

Product · Engineering · Content

A running, honestly-audited case study tracking real Waymaker side experiments from actual zero — not a highlight reel. First entry: found a live 9-hour production outage on one of them mid-writeup, root-caused it, and shipped the fix before publishing.

  • Diagnosed and shipped a production fix for a live outage (Expo Router static-export crash) while auditing it, verified against current main before merging
  • Audits four consumer experiments — thefamilygroupchat.xyz, southflai.com, mamabestie.com, codeteachers.com — plus the Waymaker flagship, for an honest infancy-to-growth record
  • Published as a living entry, updated as each experiment progresses
Building in Public·Case Study·Live Ops·Content
02 · Consulting Engagements

Senior consulting work — productized engagements with verifiable outcomes for B2B clients.

2026
Read the case study

AI Sales Engine — 14-Day Sprint

Healthcare Automation (RCM / Claims)

Lead Consultant

Revived a stalled healthcare-automation pipeline for a payer-workflow SaaS. Diagnosed the real leak — website interest never converting to booked meetings — then redesigned the CTA architecture, sharpened competitive positioning against their main AI competitor, rebuilt the funnel, launched signal-aware outbound, and shipped a client-facing campaign-approval portal.

  • 4 booked demos and 2 closed deals — in 11 days
  • Redesigned CTA architecture: Request-a-Demo primary path + Revenue-Leakage Review + an ROI calculator as the authority asset
  • Built a Supabase-backed campaign-approval portal so the client could review, comment on, and approve outbound content
  • Repositioned against the competitor’s retrofitted AI layer with a purpose-built-depth narrative and measurable-outcome proof
  • Productized into the AI Sales Engine consulting offer (founding rate $7,500, 14-day Sprint, booked-demos guarantee)
GTM·AI·Sales Ops·Conversion·B2B Healthcare
2026
View live product

Agency White-Label Platform

Waymaker AI — for marketing & growth agencies

Product · GTM · Onboarding

White-label AI platform agencies use to deliver AI services to their clients without hiring engineers. Embedded Stripe checkout, founding-rate coupon flow, multi-tenant Postgres with RLS, magic-link onboarding.

  • Live in production with embedded Stripe checkout and a founding-rate coupon flow
  • $999 setup + $299/mo founding rate locked for first 10 agencies
  • Productized API surface, 48-tool agent layer, white-label branding, tenant-aware dashboard
B2B·White-Label·Stripe·Multi-Tenant
03 · Marketing Kits & Brand Systems

Complete brand + marketing kits — strategy, voice, visual identity, content calendars, funnels, and 90-day roadmaps. Built for client brands and my own ventures. The kind of $5K kits agencies sell, packaged as live, usable systems.

2026
Read the case study

PopPop Events

Abbey Oliva Lopez · Luxury Balloon + Event Brand

Brand Strategy · Marketing · Content System

Complete brand + marketing kit for a luxury balloon decorating, event planning, and favors brand. Family-first voice, fun-luxury aesthetic, 5 content pillars, 30-day calendar, 10 ready-to-post captions, welcome email sequence, lead-magnet countdown checklist, and 90-day growth roadmap.

  • 12-section kit Abbey can implement today — positioning, voice, visual identity, audience personas, content calendar, captions, landing page structure, email sequence, lead magnet, hashtags, growth roadmap
  • Brand collateral I designed for her: logo marks, banner, triptych spread, quote graphics, about-page mockup — all integrated into the kit as the visual foundation
  • Built on top of Abbey's real reach: 12K+ followers, 1,567 posts, 250+ events celebrated, 100% recommend rate. The kit doubles down on what's working.
Brand Strategy·Content System·Influencer·Event Brand
2022 — Present
Read the case study

Waymaker AI

My own AI platform — multi-product brand

Brand · GTM · Content · Pricing

Master brand kit covering 4 sub-launches: AI Sales Engine (consulting offer), Builder DNA (viral acquisition loop), Agency White-Label, and Two Mondays cohort. One brand voice, four monetization paths, multi-tenant funnel architecture.

  • AI Sales Engine: full landing page + 3 cold email templates + Loom script + booked-demos guarantee
  • Agency White-Label: live LP + founding-rate Stripe coupon + 5-post LinkedIn campaign + 6 DM templates by archetype
  • Builder DNA: assessment + 8 archetype share cards + edge-middleware OG metadata = conversion + viral loop in one surface
AI Brand·Multi-Product·GTM·Pricing
2016 — Present
Read the case study

CodeTeachers

STEAM + AI Builder Education · Founder-led

Brand · Curriculum · Community · Growth

Brand kit for a 10-year STEAM education platform — K–12 and adult learners. Family-friendly tech voice, community-led growth, curriculum-as-marketing model. The original education brand that became the model for Two Mondays and future CodeTeachers ecosystem (Learn/Earn/Build/Guide).

  • 300% platform growth · 40% downtime reduction · 25% lift in course completion
  • 10+ years of brand equity in a family-tech education niche
  • 4-brand ecosystem roadmap (Learn / Earn / Build / Guide) on shared Waymaker infrastructure
Education Brand·AI Builder·Wellington Camp 2026·K-12 + Teens
2026
Read the case study

BumpBestie

Gamified pregnancy journey app · "Candy Crush meets What to Expect"

Brand · Product · Marketing System

Complete brand + product + marketing kit for the gamified pregnancy companion app. Match-3 puzzles unlock real weekly pregnancy content. 52-week journey map. Daily dashboard. Pregnancy journal with photos. Live React Native app with Skia-powered game canvas.

  • 15-section kit: brand snapshot, positioning, voice, visual identity, logo concepts, mascot suite, brand mood, product surfaces, audience, content, lead magnets, acquisition, email sequences, applications, 90-day roadmap
  • Full brand identity: 5-color palette (Coral Hug · Peach Glow · Warm Cream · Sage Green · Soft Lavender), Poppins Rounded + Inter typography, 5-mascot icon suite
  • Built on the live BumpBestie React Native app (Expo + Skia + Supabase) — the kit documents the brand and product as one unified system
Mom-Tech·Gamified·Mobile App·Pregnancy + Beyond
2026
Read the case study

Link Summarizer

My SaaS product · Embedly alternative

Brand · GTM · Pricing · Developer Marketing

Brand kit for an AI-powered link summarization and metadata API — Embedly alternative. Developer-first positioning, transparent pricing, embeddable widget, API + dashboard product surface.

  • Developer-marketing voice: technical, transparent, no fluff
  • Live at waymaker.cx/link-summarizer with embeddable preview widget
  • Pricing model: free tier + usage-based scale, designed for indie hackers + agency tooling teams
SaaS·Creator-Built·AI Product·Browser Extension
2026
Read the case study

Vinyl Doctor Systems

Florida's commercial upholstery brand · est. 1979

Brand · Site · Content · B2B Sales Intelligence

45+ year-old commercial upholstery brand. Built marketing site (Next.js 16), 11 SEO blog articles, full B2B sales-intelligence stack (RB2B + Leadfeeder + Snitcher visitor identification), Google Places lead-finder tool, admin pipeline dashboard, and modern GTM playbook on top of a legacy reputation.

  • Established 1979 · 2,000+ restaurants serviced · 24–48hr standard turnaround · regional FL/GA/VA coverage
  • Live site (vinyldr.waymaker.cx) + 11 SEO articles + visitor ID across 3 providers + lead-finder tool + admin dashboard
  • Complete kit: brand, audience, services tiers, content engine, lead magnets, B2B funnel, local SEO, sales intel, email sequences, sales scripts, metrics, 90-day roadmap
B2B Services·Local SEO·Sales Intelligence·Legacy Brand
2024 — Present
CoFounder OSS
Open-source AI guardrails SDK
View live product
2024 — Present
View live product

CoFounder OSS

Open-source AI guardrails SDK

Brand · Developer Marketing · OSS Strategy

Developer-marketing kit for an open-source AI agent safety SDK. NPM publication, GitHub repo positioning, API documentation, architecture whitepaper, governance docs, and multi-provider competitor positioning (Anthropic, OpenAI, Google, xAI, Mistral, Cohere, Together, Groq, Ollama).

  • Published @waymakerai/aicofounder-core + @waymakerai/aicofounder-react on NPM (MIT)
  • Full docs system: API reference, architecture, governance, whitepaper, roadmap
  • Positioned as safety-first ("not a ship-a-startup-in-30-min button") — credible to engineering teams
OSS Brand·Developer Marketing·AI Safety
04 · Enterprise & Consumer Experience

Earlier work as Creative Director (UX/UI) at NCR and Walt Disney World, and through Nerds Agency.

Walt Disney era

Disney Vacation Ownership

Walt Disney World · Disney Vacation Club

Creative Director, UX/UI

End-to-end experience design for Disney Vacation Ownership — landing pages, "A Lifetime of Memories" storytelling surfaces, "Discover a World of Disney Magic" booking journey, and the multi-collection content architecture under one experience.

  • Designed the experience-planning surface for one of Disney's highest-LTV product lines
  • Storytelling-led approach bridging Disney emotional brand to functional booking UX
  • Multi-collection content architecture (DVC, Cruise, Adventures by Disney) under one experience
UX·UI·Brand Experience·Consumer
Walt Disney era

Disney Adventure Collection

Walt Disney World

Creative Director, UX/UI

Content-led product surface for Disney's adventure and travel collections. Mythic copy paired with curated imagery, integrated into the broader booking funnel.

  • Integrated multiple travel product lines (Disney Cruise, Adventures by Disney, Aulani) into one surface
  • Storytelling-first IA designed for cross-sell and audience expansion
  • Worldwide rollout across Disney travel and adventure product lines, reaching millions of guests
Content·UX·Brand Experience
2014 — 2016

NCR NextGen ATM

NCR — Global ATM Software · "Talk to Teller"

Creative Director, UI/UX

End-to-end ATM software UX for NCR's next-generation banking platform. Touchscreen-first interaction, tablet-style flexible UI, iconography + animations library built in HTML/CSS, and the global look and feel deployed across NCR's ATM fleet.

  • Designed the visual + interaction system for NCR's flagship ATM software
  • Built the iconography & animations library: card scan, currency, deposit, transfer, hide/show balance — production tablet-style HTML/CSS components
  • Part of NCR's largest financial design initiative — a $100M+ enterprise engagement
UX·UI·Financial Services·Enterprise
2014 — 2016

NCR Financial Wellness

NCR — Consumer Banking Mobile App

Creative Director, UI/UX

Integrated set of mobile tools to help bank customers save money — "First Digital" brand. Goal-setting UI ("Be Fully Prepared", "Smart Small", "Save Today for a Rainy Day"), Rainy Day Fund tracking, account overview, Earn Cash Back, and savings recommendations.

  • Designed a coherent system of consumer savings + goal-setting tools across mobile screens
  • Friendly illustration system that softened a financial product without diluting trust
  • Built on the NCR Design System for cross-product consistency
UX·UI·Mobile·Consumer Banking
2014 — 2016

NCR Financial Chatbot · Ask Kai

NCR — Conversational AI in Banking

Creative Director, UI/UX

Conversational AI ("Ask Kai") integrated into NCR's consumer banking apps — for North Bank and First Digital brands. Web + mobile interaction patterns, transaction shortcuts ("Show Transactions", "Cards", "Pay someone", "Help me"), and an integrated banking surface where the chatbot lives alongside accounts.

  • Designed conversational UX patterns for consumer banking before "ChatGPT for banking" was mainstream
  • Multi-brand chatbot system (North Bank + First Digital) using the NCR Design System
  • Integrated chat as a first-class banking tool — bill payment, transaction lookup, fraud help in one surface
Conversational AI·UX·Banking·Multi-Brand
2014 — 2016

NCR NextGen Merchandising

NCR — Cloud Inventory Management

Creative Director, UI/UX

Cloud-based inventory management system for retail merchandising. Mobile-first authentication, task management, "Release Price to POS", "Manual Scan", price changes, and end-to-end retail operations from user journeys through Android/iOS templates.

  • Designed the end-to-end retail inventory experience — login → task → execute
  • From user journeys and wireframes through Android/iOS production templates
  • Cloud-native architecture for multi-store retail operations
UX·Retail·Mobile·Enterprise
2014 — 2016

NCR Design System + Mobile MVP

NCR — iOS & Android Foundation

Creative Director, UI/UX

Comprehensive UI design system + iOS/Android MVP applications built on top of it. Hundreds of icons, typography, components, personas, user journeys — standardized across NCR product lines.

  • Created a Product Center of Excellence for Wells Fargo and National Bank of Canada
  • Standardized UX patterns, design systems, and delivery practices across teams
  • Mobile MVPs built on the system as proof of scalable application
Design System·iOS·Android·Enterprise
2014 — 2016

NCR Digital Insight

NCR — FinTech Developer Hub & Design System Docs

Creative Director, UI/UX

Marketing + developer hub for NCR's FinTech app development platform. Brand expression, IA, copy direction, visual identity for an enterprise developer-facing surface — including API documentation, CSS components, and the public Digital Banking Design System.

  • "Your Hub for Developing FinTech Apps" — positioning for the developer pillar
  • Multi-variant website mockups + public design-system documentation (API ref, CSS components)
  • Translated enterprise engineering capability into a marketing-facing developer story
Developer Marketing·Brand·FinTech·Documentation
2014 — 2016

NCR Self-Checkout

Publix · Target · CVS

Creative Director, UX/UI

Self-checkout UX deployed at Publix, Target, CVS, and other major retailers. From the "Start Scanning" entry surface through item selection, payment, and assistance flows.

  • Used daily by millions of retail shoppers across Publix, Target, CVS, and partner stores
  • Designed the full transaction journey: scan → select → pay → assistance handoff
  • Multilingual and accessibility-considered for one of the highest-traffic NCR interfaces
UX·Retail·Accessibility·Consumer
2014 — 2016

National Bank of Canada

Bank of the Future — Banking Experience

Creative Director, UX/UI

Bank-of-the-future ATM and tablet experience for National Bank of Canada. Modernized the transaction surface — Retrait (Withdrawal), Dépôt (Deposit), bilingual UI, processing states, customer-facing waiting screens.

  • Designed bilingual (French/English) transaction surfaces for Canadian banking customers
  • Part of NCR's Product Center of Excellence engagement with NBC + Wells Fargo
  • Modernized the look-and-feel from legacy ATM patterns to a contemporary product surface
UX·Financial Services·Bilingual
Nerds Agency era

Villageluxe

Luxury Item Rentals

Creative Director, UX/UI

Mobile-first luxury rental app — high-end fashion and accessories. Editorial-led product surfaces, item discovery, collections architecture, and a brand voice tuned to luxury consumer expectations.

  • Mobile-first experience for a luxury consumer audience
  • Editorial product photography + premium typography aesthetic
  • Item collection architecture supporting both browsing and curated discovery
UX·UI·Luxury·Mobile-First
05 · Education & Programs

Curriculum, cohort, and platform work — building the developer and product audience over a decade.

2016 — Present
View live product

CodeTeachers

STEAM & AI Builder Education

Chief Marketing Officer (Founder)

STEAM education platform delivering coding, UX/UI, product design, engineering, and maker-science programs for K–12 and adult learners. Live for 10+ years across multiple regions.

  • 300% platform growth · 40% downtime reduction · 25% lift in course-completion
  • Built community, curriculum, onboarding, content, and event programming end-to-end
  • Trains the next wave of developers and AI practitioners — the audience modern AI products market to
Education·Community·Curriculum·Founder
2026
View live product

Two Mondays AI Automation

Waymaker AI — Paid Cohort

Founder · Curriculum · Instruction

Paid cohort program teaching business owners to ship AI-powered operations, content, and lead-gen workflows on the modern AI dev stack (Next.js, Vercel, Supabase, Claude/OpenAI).

  • Assessment-to-curriculum personalization based on each operator's business
  • Live instruction + hands-on labs over two intensive weekends
  • Lifetime access to curriculum + private cohort community
Cohort·AI·Education·Operators
2020 — 2022
Flatiron · Thinkful · Chegg
Product Design + Data Engineering Programs
2020 — 2022

Flatiron · Thinkful · Chegg

Product Design + Data Engineering Programs

Product Education Leader · Founding Faculty

Founding faculty for accredited Product Management, UX, and Data Engineering programs at Thinkful (Chegg). Built end-to-end: curriculum, pedagogy, live instruction, mentorship, state-level authorization.

  • 100% NPS score maintained across program cohorts
  • Designed scalable instructional systems and industry-bridge programming
  • Prepared career-changers for product, design, and engineering roles industry-wide
Curriculum·Product·UX
06 · Lifecycle Marketing

Full customer-journey programs — email sequences, funnel diagnosis, and the UX/registration work that sits between a click and an activated user.

2026
AstraLynk
Founding Actor Lifecycle Program
Read the case study
2026
Read the case study

AstraLynk

Founding Actor Lifecycle Program

Lead Consultant — Lifecycle Strategy · Email · UX · Market Research

End-to-end lifecycle marketing engagement for AstraLynk, a self-tape and audition-prep platform for actors. Mapped the full Founding Actor journey — invite → registration → activation → survey — and built the program, UX research, and market strategy needed to move real people through it.

  • Designed and built a 12-email lifecycle sequence (invite → activation → founding-member survey) across 4 creative directions, in light and dark themes
  • Pulled and diagnosed real Mailchimp funnel data to find exactly where the registration flow was losing signups, not just where email engagement was
  • Built and tested three competing registration/onboarding flows (Full, Standard, Simple) as interactive prototypes for a head-to-head comparison
  • Delivered a market sizing + competitive whitespace brief and a UX review of the live product's Dashboard and Practice screens
  • Scoped the post-pilot roadmap: swapping the time-based drip for behavior-triggered sends (profile complete, materials uploaded, rehearsal used)
Lifecycle Marketing·Email Program·Funnel Diagnosis·UX Research·Consumer
2026
Waymaker AI
Waymaker AI — Onboarding & Activation
View live product
2026
View live product

Waymaker AI

Waymaker AI — Onboarding & Activation

Lifecycle Strategy · Email · Backend

A Day 0/2/4/7 onboarding welcome series for new Waymaker signups, replacing a single outdated welcome email with four touchpoints that orient new users and drive them to the same milestones the product already gamifies — Builder DNA, a first project, and their first week of use.

  • Fixed a live branding bug: the only existing welcome email said "Welcome to VisionStack" — replaced with real Waymaker AI copy and brand tokens
  • Wrote and shipped 4 new email functions (Day 0/2/4/7) tied to real product milestones — Builder DNA, first project/mission, and the Cameron/Cowork surfaces
  • Created the sequence and its 4 steps as a real record in the production drip-campaign system, in draft status pending enrollment-trigger review
  • Reused the existing generic email-sequences engine rather than building new send infrastructure
Lifecycle Marketing·Onboarding·Email Series·Backend
2026
CodeTeachers
Wellington Summer Camps — Registration Welcome
Read the email copy (GitHub PR)
2026
Read the email copy (GitHub PR)

CodeTeachers

Wellington Summer Camps — Registration Welcome

Lifecycle Strategy · Copywriting

A ready-to-send welcome email for the "welcome email from Ashley within 24 hours" already promised to parents on the registration confirmation page — venue, prep checklist, what to bring, and drop-off/pickup, personalized per camp (AI Creator Camp, AI Builder Bootcamp).

  • Closed a gap between a real promise on the live site and what actually existed — no automation, no written reference, before this
  • Grounded every detail in what registration actually collects and what each camp actually includes, not invented content
  • Recommended staying a manual, personal send for the founding cohort, with a concrete automation path (Resend on the existing Stripe webhook) scoped for later
Lifecycle Marketing·Copywriting·Email
2026
southflai.com
South Florida AI — Newsletter Welcome Series
Read the email copy (GitHub PR)
2026
Read the email copy (GitHub PR)

southflai.com

South Florida AI — Newsletter Welcome Series

Lifecycle Strategy · Copywriting

A Beehiiv welcome email plus a 2-step automation for new South Florida AI & Tech Weekly subscribers — confirms the subscription, drives them to a real upcoming local event, then orients them to the rest of the ecosystem (Learn, CodeTeachers, Waymaker).

  • Built on the infrastructure already chosen (Beehiiv) instead of adding a new service
  • Used real, verified event data for the event-nudge email rather than a generic CTA
  • Also closed a second, parallel gap: reference copy for the RSVP-confirmation email promised on the Partner With AI event page
Lifecycle Marketing·Newsletter·Events·Copywriting
07 · Growth — AEO & SEO

Answer-engine and search visibility work — the AEO/SEO infrastructure already shipped for Waymaker and Waymaker Agency, plus the channel build-out ahead.

2026 — Present
AEO — Answer Engine Optimization
Waymaker AI + Waymaker Agency
Read the case study
2026 — Present
Read the case study

AEO — Answer Engine Optimization

Waymaker AI + Waymaker Agency

Growth · Technical SEO/AEO

The traffic that used to come from ranking in ten blue links increasingly comes from being the source an AI cites when it answers a question directly — in ChatGPT, Perplexity, and Google AI Overviews. AEO is the discipline of making a site legible and citable to those systems, not just to a search-ranking algorithm.

  • Shipped: a host-aware /llms.txt endpoint following the emerging llms.txt convention (llmstxt.org) — gives AI crawlers a canonical, structured index of services, pricing, and positioning, and keeps agency.waymaker.cx and waymaker.cx from being conflated as the same product
  • Shipped: sitemap auto-includes every published blog post with no manual step, so new citable content is discoverable immediately
  • Opportunity ahead: FAQ/Q&A structured data (schema.org) on service and blog pages, more directly citable long-form answers, and tracking AI-referral traffic as its own channel alongside organic search
AEO·AI Search·Technical SEO·llms.txt
2026 — Present
SEO — Content, Local & Authority Channels
Waymaker AI + Waymaker Agency
Read the case study
2026 — Present
Read the case study

SEO — Content, Local & Authority Channels

Waymaker AI + Waymaker Agency

Growth · Content · Local SEO

The content engine is real and running — the blog isn't the bottleneck. The next layer is entity consistency and authority: getting Waymaker recognized as the same trusted business everywhere it shows up, and earning links from other people's pages instead of only publishing on our own.

  • Shipped: an active blog content engine (40+ published posts) feeding the sitemap and AEO layer above
  • Opportunity — local & directory presence: Google Business Profile, Apple Business Connect, and a DUNS number to anchor a consistent business identity across data aggregators and knowledge panels
  • Opportunity — off-site authority: a backlink program, relevant directory listings, and guest posts on the sites actors, founders, and operators already read
  • Opportunity — distribution: cross-linking between the product, agency, and blog properties, plus a social posting cadence that points back at the content already being written
SEO·Local SEO·Backlinks·Content
06 · About

Product leadership, AI, and growth — one throughline. Not three separate jobs.

20+ years defining products, designing the experience, leading delivery, and driving adoption — pairing Fortune-500 tenure with founder-shipped AI products. I design and ship what I market.

The range comes from owning outcomes end to end — at Nerds Agency, that meant defining a client’s real problem, assembling and directing the team, delivering across design, engineering, and content, managing the relationship, and being accountable for the result. It is the same underlying job as leading product at Disney and NCR, and the one I now run solo at Waymaker — just at a different scale each time.

Brand-name credentials: Walt Disney World, NCR ($100M+ engagement), Wyndham, Wells Fargo, Sephora, NBC, National Bank of Canada. Founder-led ventures: Waymaker AI, CoFounder OSS, CodeTeachers, Nerds Agency.

Most recent receipt — 14-day rebuild for a healthcare-automation client: 4 booked demos, 2 closed deals, 11 days, from a previously stalled 3-month pipeline.

My unfair advantage
Product Strategy + UX + AI + Technology + GTM

I don’t stop at product requirements. I understand the customer experience, the technology required to build it, how to communicate the value, and how to get it adopted.

AI Product Strategy & Adoption
Anthropic, OpenAI, multi-LLM orchestration
Go-to-Market & Product Marketing
Launch motions, demand gen, category creation
Storytelling & Editorial
Brand narrative, positioning, content
Product Design & UX
IDEO HCD, Flatiron Product Design founding faculty
Sales Enablement & Training
CodeTeachers, Flatiron, Two Mondays cohort
SEO, AEO & GEO Strategy
Content, search visibility, AI search optimization
My Builder DNA
The Polymath

“Learns faster than anyone and connects ideas across domains.” My own result from Builder DNA — the archetype assessment I designed and shipped. I market the products I take myself.

Take the assessment
07 · Contact

Want to talk about a project like one of these?

Taking a small number of senior consulting engagements per quarter — strategic GTM, AI product, and senior UX work for B2B companies and AI-native startups. Free 15-min discovery call.

Book a discovery call ashleykaystech@gmail.com
See the flagship consulting offer → AI Sales Engine · 14-day Sprint