# Kyle Whatnall

Senior Product Marketing Manager & AI Deployment Lead at CourtReserve. This is a plain Markdown copy of kylewhatnall.com for people and AI agents. Section ids in braces match the anchors on the site (for example kylewhatnall.com/#rp).

Contact: kjwhatnall@gmail.com · linkedin.com/in/kylewhatnall · github.com/kylewhatnall · Resume: kylewhatnall.com/resume

## Intro {#top}

Senior go‑to‑market leader who builds the AI systems marketing runs on.
At CourtReserve, I lead product marketing and a team of 4 for a B2B SaaS platform used by 2,600+ clubs, and I run AI adoption across every department.
I ship flagship product launches, own positioning and the pipeline it drives, and build the AI agents my team runs on, in Claude Code, Supabase and Slack. You can run them below.

## What I do {#what}

I do product marketing, and I build the systems it runs on.
I write the positioning and sales materials for launches on a platform 2,600+ clubs operate on, and I own the pipeline those launches produce. The last flagship launch activated 400+ clubs in its first two weeks and has since done $1M+ in platform revenue.
Most of the job is making a complicated product make sense to an operator who has ten minutes between lessons.
I also lead company-wide AI enablement at CourtReserve, a 90-day program covering baseline training, weekly office hours, and department-specific build sessions. It lifted weekly active users from 22% to 63% and took custom skills in production from 6 to 28 across the company.
Product marketing at CourtReserve.
I market to five buyer types, from single-site owners to university athletic departments. I also own the security review larger deals have to clear, and the marketing for Catalyst, our multi-city tour with Invited and its 150+ clubs. I also named and positioned Pulse Connect, an MCP connector that lets a club ask its own AI assistant about its CourtReserve data, and I lead its go-to-market.
Building a nine-figure brand.
I joined Selkirk Sport as employee #7 and built the product marketing systems as the company grew past 200 people. I also led the Palantir Foundry deployment that replaced 12 tools across operations.

## RallyPoint {#rp}

RallyPoint is a system Kyle built, in short: Product input to launch plan.
RallyPoint flow: product inputs go into an AI campaign brief generator, which produces a structured go-to-market plan, then design, audio and planning outputs through Canva, Gamma, ElevenLabs and Monday.com, tracked in a central dashboard.
Product inputs: The feature we are launching, who it is for, and what it changes for a club.
Brief generator: Claude Code turns those inputs into a campaign brief with positioning, audience, channels, and the angle to lead with.
GTM plan: The brief becomes a plan with messaging, an asset list, and the order each channel runs in.
Design and decks: Canva and Gamma pick up the plan and produce the visuals and the deck.
Audio: ElevenLabs produces voiceover for video and product walkthroughs.
Planning and tracking: Monday.com gets the tasks, owners and dates, so the launch has a schedule the team can see.
Dashboard and bets: One place to see every campaign, its brief, its status, and the bet behind it: a written hypothesis and prediction, checked against what moved after launch.
Used by: Marketing, product, and sales, every day.
Stack: Claude Code and Supabase on the back end, with a Bolt.new dashboard on the front.
Public version: Halden GTM Desk, the same loop rebuilt from scratch on invented data. Live demo: https://halden-gtm-desk.onrender.com · Code: https://github.com/kylewhatnall/halden-gtm-desk
RallyPoint is built with Claude Code, Supabase, Bolt.new.

## Backboard {#bb}

Backboard is a system Kyle built, in short: Slack request to on-brand draft.
Backboard flow: an emoji reaction on a Slack request fires a Zapier webhook. A Claude Code routine reads the thread and drafts in brand voice using skills versioned in a private GitHub repo. If the request needs a person, it flags a person. Otherwise it posts the draft back in the Slack thread.
Slack: Anyone on the team reacts to a message with an emoji, and the reaction is the whole request. Nobody has to file a ticket.
Zapier: The reaction fires a webhook, which hands the thread to the agent.
Claude Code: Reads the whole thread for context, then writes the draft in our voice.
Brand skills: Voice, tone and format rules live in a private GitHub repo and are versioned like code, so the agent and the team work from the same source.
Needs a person: The agent checks whether the request is routine or needs judgment.
Flag a person: Anything sensitive or unclear goes to a person, and the agent declines to draft it.
Post the draft: Routine requests come back as a draft in the same Slack thread, ready for a quick review.
Human in the loop: It drafts the routine requests and hands anything that needs judgment to a person.
Where it's going: I'm setting up the same agent for other departments at CourtReserve.
Backboard is built with Slack, Zapier, Claude Code, GitHub.

## Inbound Bets {#ib}

Inbound Bets is a system Kyle built, in short: One site change to a scored result.
Inbound bets flow: each bet makes one change to the website or a marketing channel, with a win target set before it starts. Claude Code ships the change and runs scheduled check-ins over a fixed window. If the bet hits its target it stays live as a permanent change; if not it is rolled back. A weekly update records every bet, and that record steers where time and budget go next.
The bet: Each bet makes one change to the site or a marketing channel, with a win target written down before it starts. One change at a time, so the result means something.
Claude Code: Claude makes the change itself, on the website or in the channel, so a bet goes from idea to live without waiting on a sprint.
Check-ins: Scheduled check-ins track the bet across a fixed window, so nobody has to remember to look.
Hit the target: At the end of the window the bet is scored against the target it set at the start.
Stays live: Small bets that win stay live as permanent changes.
Rolled back: Bets that miss are rolled back. Riskier bets, and any that need a discussion, go back to the team before anything stays.
Weekly update: A weekly update covers running and finished bets. The record of what gets more clubs to book a demo decides where time and budget go next.
Why it's built this way: One change per bet and a target set in advance, so every result is clean enough to act on.
What stays: Bets that clear their targets become permanent parts of the site. The rest come back out.
Inbound Bets is built with Claude Code, Scheduled tasks, Website.

## Value Messaging demo {#vm}

Value Messaging demo is a system Kyle built, in short: What a rep opens before a call.
Value messaging flow: win and loss debriefs, call intelligence, field submissions and product or pricing changes feed a messaging system of ICP, value pillars, trap cards and a persona matrix. It powers pre-call prep, a leakage calculator and objection handling, and what reps learn loops back into each review.
Win and loss debriefs: Every closed deal over the threshold gets a short debrief, won or lost. Losses get scheduled first because they teach more.
Call intelligence: Recorded calls get scanned for competitor mentions and for objections that do not have a card yet.
Field submissions: Reps submit lines that worked. Most are not adopted, and the ones that are get credited in the changelog.
Product and pricing: A release that changes what we can claim triggers a messaging review before it ships.
Messaging system: ICP and segments, three value pillars with seven layers each, competitor trap cards, and the persona matrix that says which message leads for which buyer.
Pre-call prep: Pick who you are meeting and what they run today, and the guide builds the call flow in about thirty seconds.
Leakage calculator: Puts a dollar figure on the cost of staying put, in the buyer's own numbers. Try it below.
Objection handling: What sits under each objection, the question to ask first, and the answer that sounds reasonable and loses the deal.
This is a demo: The original system is confidential, so this version is rebuilt around Halden, an invented field service software company. Halden, its market, its customers and every number here are made up.
Why it's built this way: In the demo, most lost deals go to a buyer who decides to wait another year, so the guide starts every first call with what waiting costs, in the buyer's own numbers.
Full walkthrough: The complete field guide is available on request. Get in touch ↓.
Value Messaging demo is built with Sales enablement, Field guide, Demo.

## AI enablement {#enablement}

Company-wide AI enablement.
22% to 63% weekly active users in 90 days.
Designed and led a 90-day AI enablement program that reached every department at CourtReserve.
Weekly active users 22%→ 63%.
0 100%.
Skills in production 6→ 28.
0 30 skills.
Connector configuration 23%→ 80%.
0 100%.
Provisioned seats logged in 62%→ 94%.
0 100%.
Coverage Every department contributed at least one skill to production during the program.
Baseline training.
Company-wide course Baseline Claude training course delivered company-wide.
Office hours.
Every week Hands-on tutorials, troubleshooting, and tool support.
Build sessions.
By department Sales, customer success, onboarding, and marketing, shipping custom skills for each team.
Measurement and iteration Adoption metrics tracked throughout the 90 days, roadmap adjusted based on what was working.
From customer signal to shipped campaign.

## Case: Public Booking {#case-booking}

Public Booking: 400+ Clubs Activated in 2 Weeks, with $1M+ platform revenue.
Launched a new acquisition and monetization channel for a B2B SaaS platform (CourtReserve) used by 2,600+ clubs.
400+ clubs activated in the first two weeks.
25,000+ reservations booked on the platform.
30% of total revenue for some clubs.
$1M+ in platform revenue.
CourtReserve booth.
At a trade show with the CourtReserve team.
Problem.
Clubs had no way to monetize non-members, limiting new customer acquisition and overall revenue growth.
Insight.
Operators would adopt faster if the feature was positioned as a revenue-generating growth channel, since clubs already have scheduling tools.
Role.
Led go-to-market for the launch, including positioning, messaging, and launch execution, in close partnership with product and engineering.
Execution.
Repositioned the feature from a scheduling tool to a revenue-generating growth channel.
Translated product functionality into clear, outcome-driven value propositions for operators.
Built and managed the launch plan and rollout strategy across product, marketing, and operations.
Supported enablement and onboarding to drive feature adoption and activation.
Impact.
Some clubs generated up to 30% of their total revenue through the feature.
Established a new monetization channel for both operators and the platform.

## Case: Setup Wizard {#case-wizard}

Setup Wizard: Betting That an Easier Setup Would Keep More Clubs, with 40→75% setup completion.
I run launches and campaigns as bets: the signal behind them, what we shipped, and a check on what moved. Setup Wizard is the clearest one.
40→75% of new clubs finishing setup.
−48% time-to-first-value.
28.9% day-14 activation in a holdout test, up from 21.5%.
420 accounts in the test, with a 10% holdout.
Signal.
Only about 40% of new clubs finished setup, while clubs that finished retained at 88 to 92% after 30 days. The drop-off was happening in setup.
The bet.
If setup got easier, more clubs would reach the version of CourtReserve that keeps them.
What shipped.
Setup Wizard, an AI onboarding agent, as the default path for every new club, backed by a 14-day in-product lifecycle in Appcues and Pendo.
Execution.
Took Setup Wizard to market as the standard onboarding path for every new club.
Built a 14-day lifecycle triggered by what each club did in the product.
Tested the onboarding flow across 420 accounts against a 10% holdout before rolling it out.
Folded the winning flow into the lifecycle every new club now gets.
What moved.
Setup completion rose from 40% to 75%.
Time-to-first-value fell 48%.
Day-14 activation rose from 21.5% to 28.9% in the holdout test.
Every new club now onboards through Setup Wizard.
Result Setup went from the place new clubs stalled to a tested path every new club starts on.

## Case: RallyPoint {#case-rallypoint}

RallyPoint: One Source for Every Brief, Cutting Launch Prep From a Week to Half a Day, with 1 wk→½ day brief to launch.
Problem.
As the only product marketer, every launch meant rebuilding the same brief, calendar and assets by hand across separate tools, and the copy drifted. A battlecard would say one thing and the one-pager another.
Insight.
If every brief and asset pulled from one approved source, launches would move faster and stay consistent.
Role.
Owned the design and development of RallyPoint, defining the system architecture, workflows, and AI outputs with the marketing and product teams.
Watch RallyPoint run a brief.
Execution.
Built an AI-driven campaign brief generator that converts product inputs into structured go-to-market plans.
Designed workflows to automate campaign strategy, messaging, and content outputs.
Connected Canva, Gamma, ElevenLabs, and Monday.com into one system.
Developed a Bolt.new dashboard for planning, collaboration, and execution tracking, on a Claude Code and Supabase back end.
Logged every campaign as a bet, with a written hypothesis and prediction in the brief and a check on what moved after launch.
Impact.
Cut the brief-to-launch cycle from a week to half a day.
Used daily by marketing, product, and sales.
Gave every campaign one shared brief, calendar, and status.

## Case: Company-Wide AI Enablement {#case-enablement}

Company-Wide AI Enablement: Designed and Led a Cross-Functional Adoption Program, with 22→63% weekly active users.
Designed and led a 90-day AI enablement program that reached every department at CourtReserve.
Problem.
AI tools were being provisioned across the company, but adoption was uneven and most employees weren't using them in their daily work. Departments outside of marketing had limited context on how AI could help in their roles.
Insight.
Adoption needed a structured program that combined education, hands-on building, and ongoing measurement. The fastest path to real usage was shipping custom tools alongside the people who'd use them.
Role.
Selected to design and lead the company's AI enablement program, covering training, hands-on building, and adoption measurement.
Execution.
Built a baseline Claude training course delivered company-wide.
Hosted weekly office hours for hands-on tutorials, troubleshooting, and tool support.
Ran department-specific build sessions with sales, customer success, onboarding, and marketing, shipping custom skills tailored to each team.
Tracked adoption metrics throughout the 90 days and adjusted the roadmap based on what was working.
Impact.
Weekly active users rose from 22% to 63% in 90 days.
Skills in production grew from 6 to 28, with every department contributing.
Connector configuration climbed from 23% to 80%.
Provisioned seats logged in went from 62% to 94%.
What I learned.
Pairing training with hands-on build sessions worked better than either one alone.
The clearest adoption signal was teams building their own tools without help.

## Case: Scaled Product Marketing {#case-selkirk}

Scaled Product Marketing: Built the Systems Behind a Nine-Figure Brand (Including the Palantir Foundry deployment), with 12 tools replaced by Palantir Foundry.
Built and executed product marketing and go-to-market systems at Selkirk Sport, supporting growth across DTC, retail, and partnership channels.
Problem.
Selkirk was growing fast, adding product lines, retail distribution, and athlete partnerships while building its brand in pickleball. Launches needed more structure, clearer positioning, and tighter alignment between product, brand, and distribution.
Insight.
Scaling required moving from one-off campaigns to repeatable product marketing systems that could support launches across DTC, retail, and partnerships.
Role.
Led product marketing and go-to-market efforts across key launches, working cross-functionally with product, marketing, and external partners.
Foundry.
Palantir partnership.
Brought Foundry, Palantir's enterprise data platform, into a sports equipment company and led the company-wide rollout, replacing 12 third-party tools and modernizing reporting, operations and decision workflows. Palantir featured the partnership in their Builders series and a full-page New York Times ad, and hosted me at their Palo Alto HQ as one of five leaders.
Execution.
Supported product launches with positioning, messaging, and campaign strategy across DTC and retail.
Partnered with product and R&D to translate new products into clear go-to-market strategies.
Managed campaigns that drove product visibility, demand, and sell-through.
Led the Palantir Foundry deployment across operations.
Impact.
Helped scale Selkirk into a nine-figure brand.
Expanded distribution into Costco and DICK'S Sporting Goods.
Six-figure monthly cost savings from the Foundry deployment.

## Case: Storytelling & Cultural Marketing {#case-bza}

Storytelling & Cultural Marketing: National Media for Brands and Athletes, with ESPN · CBS · NBC national coverage.
Ran media, PR, and content work for brands and athletes around major sports and entertainment events.
Problem.
Brands and talent were competing for attention in crowded media environments, where the usual messaging got ignored.
Insight.
Stories landed when the message fit the moment, the channel, and how the audience was already behaving.
Role.
Supported media strategy, content execution, and press coordination across high-visibility campaigns and productions, working with brands, athletes, and media partners.
Execution.
Supported national PR campaigns tied to major events including the Super Bowl, NFL Draft, and PGA TOUR.
Coordinated media strategy and press execution across broadcast, digital, and on-site environments.
Before BZA, interned on the talent team at CONAN, where tight timing and reading the audience were the whole job.
Ran communications for technology clients including The Famous Group, building AR and VR experiences for stadium audiences, and Caesars Sportsbook through its expansion into newly legalized markets.
Impact.
Secured national media coverage across major networks including ESPN, CBS, and NBC.
Contributed to campaigns reaching millions of viewers across broadcast and digital channels.

## About {#about}

I'm the Senior Product Marketing Manager & AI Deployment Lead at CourtReserve. I own go-to-market for a B2B SaaS platform used by more than 2,600 clubs, and I lead AI adoption across every department.
Most of my time goes to positioning, the launches that carry it, and the pipeline those launches produce.
Before CourtReserve, I was part of the team that helped scale Selkirk Sport into a nine-figure brand, expanding from PR into product marketing, campaign systems, and growth execution across DTC and retail.
Alongside the go-to-market work, I build the AI systems marketing runs on, including RallyPoint and Backboard, and I've presented on AI-native marketing at Mainsail's Marketing AI Summit.
I'm most useful on technical products that are hard to position, especially where the team can build with AI.
I started in sports PR, with four years at BZA Public Relations working campaigns around the Super Bowl, the NFL Draft and the PGA TOUR.
Outside of work, I played professional pickleball, ranking in the top 50 on the PPA Tour, and captained the New Zealand Hustle in Major League Pickleball Australia. I also perform improv with National Comedy Theatre in San Diego.
Now.
CourtReserve Senior Product Marketing Manager & AI Deployment Lead, leading a team of 4.
Before.
Selkirk Sport Joined as employee #7 and stayed through growth past 200 people.
Where it started.
BZA Public Relations Four years of sports PR, including on-site work at three Super Bowls.

## Press and talks {#press}

Talk · 2026, AI-native marketing, Mainsail Marketing AI Summit, Austin. Speech · 2025, Commencement address, Chapman University, School of Communication. Broadcast, Pickleball phenomenon, KING 5 Seattle (NBC), as Selkirk Sport's spokesperson. Byline · 2025, The hidden tech inside Project Boomstik: NFC and the future of pickleball paddles, Selkirk Sport.

## Contact {#contact}

You can reach Kyle by email at kjwhatnall@gmail.com or on LinkedIn at linkedin.com/in/kylewhatnall. His code is on GitHub at github.com/kylewhatnall. His resume is at kylewhatnall.com/resume.