KWKyle Whatnall
Click the court to rally against the agent
Senior Product Marketing Manager & AI Deployment Lead · CourtReserve

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.

See the systems Selected work Resume
Kyle Whatnall
K. WhatnallCR Connect 2026
Platform revenue$1M+from flagship 2026 launch
Clubs on the platform2,600+racquet and fitness clubs
Win rate+13%competitive & win/loss program
AI adoption22%→63%company-wide, in 90 days
What I do

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.
AI systems I've built

Built to run marketing with a small team.

Three systems in use every week, plus a demo of a fourth. Pick one on the left, press Run to watch a request move through it, and hover any step to see what that part does.

RallyPoint

Claude CodeSupabaseBolt.new

Hover or tap any step to see what it does.

Brief run · 00:00.0
  1. in
    Product input

    Public Booking. Clubs can take reservations from non-members.

  2. 01
    Brief generated

    Position it as a revenue-generating growth channel for clubs.

    AudienceClub owners and operators

    BetRevenue framing drives faster adoption than scheduling framing

  3. 02
    GTM plan structured

    LinkedInInstagramTikTokYouTubeEmailBlog

  4. 03
    Assets queued

    CanvaGammaElevenLabs

  5. 04
    Tracked in Monday.com

    Status set to Ready for review

Example run based on the Public Booking launch.

Brief-to-launch cycle
Before
1 week
With RallyPoint
½ day
07 days
Used byMarketing, product, and sales, every day
StackClaude Code and Supabase on the back end, with a Bolt.new dashboard on the front
Public versionHalden GTM Desk, the same loop rebuilt from scratch on invented data.Live demo ↗Code ↗
OutputCampaign brief · ready
Brief · v1

Public Booking

Clubs can take reservations from non-members.
Positioning
A revenue channel for clubs. Open court time becomes bookable by players who aren't members yet, and every booking is new money.
Audience
Club owners and operators who already run their scheduling on the platform.
Lead message
Your empty courts can earn. Let new players book them.
The bet
Revenue framing drives faster adoption than scheduling framing. Checked against activation after launch.
Channels
LinkedIn, Instagram, TikTok, YouTube, email and the blog.
Handoff
Visuals and the deck go to Canva and Gamma, voiceover to ElevenLabs, owners and dates to Monday.com.

Example output written for this site, based on the Public Booking launch.

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 users22%→63%
0100%
Skills in production6→28
030 skills
Connector configuration23%→80%
0100%
Provisioned seats logged in62%→94%
0100%
Day 0Day 90

CoverageEvery department contributed at least one skill to production during the program.

Baseline trainingCompany-wide courseBaseline Claude training course delivered company-wide
Office hoursEvery weekHands-on tutorials, troubleshooting, and tool support
Build sessionsBy departmentSales, customer success, onboarding, and marketing, shipping custom skills for each team
Measurement and iterationAdoption metrics tracked throughout the 90 days, roadmap adjusted based on what was working
Kyle presenting to a room, slide reads from customer signal to shipped campaign
From customer signal to shipped campaign
Selected work

Launches and systems I've led.

Launches and systems from CourtReserve and Selkirk Sport, plus the agency work I started in. Open any entry for the full story.

CourtReserve · B2B SaaSPublic Booking → 400+ Clubs Activated in 2 Weeks$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 weeksEach dot is 10 of the 2,600+ clubs
25,000+reservations booked on the platform
30%of total revenue for some clubs
$1M+in platform revenue
Kyle with a colleague at the CourtReserve booth on a trade show floor
CourtReserve boothAt a trade show with the CourtReserve team.
ProblemClubs had no way to monetize non-members, limiting new customer acquisition and overall revenue growth.
InsightOperators would adopt faster if the feature was positioned as a revenue-generating growth channel, since clubs already have scheduling tools.
RoleLed 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
CourtReserve · The onboarding betSetup Wizard → Betting That an Easier Setup Would Keep More Clubs40→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%
420accounts in the test, with a 10% holdout
BeforeAfter
SignalOnly 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 betIf setup got easier, more clubs would reach the version of CourtReserve that keeps them.
What shippedSetup 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

ResultSetup went from the place new clubs stalled to a tested path every new club starts on.

CourtReserve · Built systemRallyPoint → One Source for Every Brief, Cutting Launch Prep From a Week to Half a Day1 wk→½ daybrief to launch
ProblemAs 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.
InsightIf every brief and asset pulled from one approved source, launches would move faster and stay consistent.
RoleOwned 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
CourtReserve · AI enablementCompany-Wide AI Enablement → Designed and Led a Cross-Functional Adoption Program22→63%weekly active users

Designed and led a 90-day AI enablement program that reached every department at CourtReserve.

ProblemAI 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.
InsightAdoption 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.
RoleSelected 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
Selkirk Sport · Consumer + PalantirScaled Product Marketing → Built the Systems Behind a Nine-Figure BrandIncluding the Palantir Foundry deployment12 toolsreplaced by Palantir Foundry

Built and executed product marketing and go-to-market systems at Selkirk Sport, supporting growth across DTC, retail, and partnership channels.

ProblemSelkirk 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.
InsightScaling required moving from one-off campaigns to repeatable product marketing systems that could support launches across DTC, retail, and partnerships.
RoleLed product marketing and go-to-market efforts across key launches, working cross-functionally with product, marketing, and external partners.
Foundry12 tools → 1
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.

Kyle with the Selkirk team at a trade show booth holding paddles
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
BZA Public Relations · CONANStorytelling & Cultural Marketing → National Media for Brands and AthletesESPN · CBS · NBCnational coverage

Ran media, PR, and content work for brands and athletes around major sports and entertainment events.

ProblemBrands and talent were competing for attention in crowded media environments, where the usual messaging got ignored.
InsightStories landed when the message fit the moment, the channel, and how the audience was already behaving.
RoleSupported media strategy, content execution, and press coordination across high-visibility campaigns and productions, working with brands, athletes, and media partners.
Kyle on the field level at Super Bowl LVI
Behind the scenes at CONAN
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

I make complicated products easy to buy.

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

CourtReserveSenior Product Marketing Manager & AI Deployment Lead, leading a team of 4

Before

Selkirk SportJoined as employee #7 and stayed through growth past 200 people

Where it started

BZA Public RelationsFour years of sports PR, including on-site work at three Super Bowls

Kyle delivering a commencement address at a podium
Commencement address · Chapman University, 2025
Kyle hitting a forehand during a professional pickleball match
Former top 50, PPA Tour
Behind the scenes at CONAN
CONAN
Kyle at Super Bowl LVI
Super Bowl
Kyle with the Selkirk team
Selkirk Sport
Press and talks

Where I've spoken and been published.

TalkAI‑native
marketingMainsail · Austin
Talk · 2026AI-native marketingMainsail Marketing AI Summit, Austin
SpeechClass of
2025Chapman · Orange, CA
Speech · 2025Commencement addressChapman University, School of Communication
BroadcastKING 5NBC · Seattle
BroadcastPickleball phenomenonKING 5 Seattle (NBC), as Selkirk Sport's spokesperson
BylineNFCProject Boomstik
Byline · 2025The hidden tech inside Project Boomstik: NFC and the future of pickleball paddlesSelkirk Sport Read ↗
Contact

Let's talk go-to-market.

Always up for a conversation about product marketing, go-to-market, or building with AI.

linkedin.com/in/kylewhatnallOpen ↗ github.com/kylewhatnallOpen ↗ ResumePDF ↗

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