"Jordan, I hate to pun this, but we got about eight minutes. We gotta land this plane."
This happens when Jordan gets caught up in a ‘data moment’.
We were 52 minutes into the Livestream and Jordan was reveling in the minutiae of the PVP results and we hadn’t nailed the money shot. That moment from Friday's livestream perfectly captured what happened when Jordan and I first laid eyes on WingWork's opportunity. What started as our typical brand exploration quickly turned into something that had me bouncing in my chair: public data, gobs and gobs and gobs of it.
This is why I picked WingWork to kick off Season 3 of the Livestream.
Welcome to Season 3: Back to Our Roots
After experimenting with different formats in Season 2 (some hits, some definite misses), we're returning to what works: deep-dive OG Cannonballs combined with practical builds. This season, we're dedicating three episodes to each brand, giving us the space to show you not just the methodology, but how to systematically build the tools that make it scalable.
The Season 3 Format:
Episode 1: OG Cannonball (understanding the brand and identifying opportunities)
Episode 2: Agent Build for Research (automating data collection and analysis)
Episode 3: Agent Build for Messaging (scaling PVP creation and deployment)
Meet WingWork: The Future of Aircraft Maintenance
WingWork is a next-generation, cloud-based Aircraft Maintenance and Compliance Platform. It's purpose-built to replace manual workflows, Excel trackers, and outdated Maintenance Tracking software. But what caught our attention wasn't just their clean value proposition—it was the industry they're serving.
The Aircraft Maintenance Industry by the Numbers:
$119 billion global market with steady 5.2% annual growth
Over 5,000 aircraft maintenance companies globally
Fleet aging crisis: average aircraft age has risen to a record 14.8 years
Industry needs 716,000 new maintenance technicians by 2042
WingWork's Target Market:
Part 91 operators: Corporate jets, flight schools (less regulatory oversight)
Part 135 operators: Charter and on-demand commercial operations (strict maintenance requirements)
Part 145 repair stations: Dedicated maintenance facilities serving the above
What makes this particularly interesting for Cannonball GTM is the regulatory environment. WingWork is purpose-built for Part 91 and 135 mechanics, operating in a world where maintenance tracking is required by CFR 14 Part 43 regulations and where failing compliance can literally ground your business.
Why Aircraft Maintenance Is PVP Gold
During our livestream analysis, Jordan's excitement was palpable as we discovered layer after layer of publicly available data sources. Here's what got us so fired up:
The FAA Enforcement Database
The FAA enforcement database tracks civil penalties, certificate suspensions and revocations, warning notices, letters of correction, and emergency orders. Translation: we can identify exactly which operators are struggling with compliance before they even know they need help.
Real-Time Aircraft Data
Aircraft registration data is updated each federal working day at midnight, providing daily insights into fleet composition, ownership changes, and airworthiness status.
Maintenance-Driven Revenue Impact
The industry operates on clear existential data points. For charter operations, aircraft downtime directly correlates to revenue loss. WingWork promises to reduce maintenance package completion time by 75% and cut compliance timelines from days to seconds, metrics that translate directly to financial outcomes.
The Perfect Storm of Pain Points
What makes aircraft maintenance such fertile ground for pain-based segmentation isn't just the regulation—it's the convergence of multiple industry crises:
Manual Workflows in a Safety-Critical Industry
Companies are still drowning in manual workflows, Excel trackers, and outdated Maintenance Tracking software. In an industry where maintenance records are the lifeblood of the aircraft and proof the aircraft has been maintained in accordance with manufacturer's documentation, manual processes create both compliance risks and operational inefficiencies.
Supply Chain-Driven Aging
Aircraft deliveries have fallen sharply from the peak of 1,813 aircraft in 2018 to an estimated 1,254 aircraft in 2024, a 30% shortfall. This means operators are maintaining older equipment longer, increasing both maintenance complexity and compliance requirements.
Fear of FAA Audits
As Jordan noted during our analysis: "Fear of FAA audit findings due to incomplete records" represents an existential threat to operators. The FAA enforcement database reveals patterns of violations that most operators don't track systematically, creating opportunities for predictive compliance alerts.
The Data Goldmine We Discovered
Here's what separated this exploration from our typical brand analysis, the sheer volume of actionable, public data sources:
Regulatory Data Sources:
FAA enforcement actions and compliance history
Aircraft registration and airworthiness records
Maintenance incident reports and safety filings
Parts manufacturer service bulletins and airworthiness directives
Operational Intelligence:
Equipment utilization patterns from flight tracking data
Maintenance scheduling conflicts from public flight logs
Fleet composition and aging analysis
Market-based aircraft valuation trends
Evolving Our Methodology: From Prompts to Agents
This WingWork series also marks an important evolution in how we're approaching the Cannonball GTM methodology. As I explained during the livestream, we're transitioning from individual prompts to use-case-focused agents.
The V4 Prompt Library Evolution: Instead of separate prompts for each step of the F.I.N.D. methodology, we're building agents around specific use cases:
"I need to understand my market segments" (EDP identification, pain-based segmentation, scoring)
"I need to create targeted messaging" (PVP development, message testing, deployment guidance)
"I need to scale my research" (data source automation, pattern recognition, alert systems)
During the livestream, Jordan demonstrated his "all-in-one uber mega double awesome wings of death and glory prompt" that took us from zero knowledge of WingWork to multiple gold-standard PVP candidates in under an hour. For our paid subscribers, we'll be creating a Cannonball version of this comprehensive approach, combining Jordan's Blueprint methodology with our proven F.I.N.D. framework.
What's Coming in Episodes 2 & 3
Next Week (Episode 2): Agent Build for Research We'll build an automated research agent that can:
Monitor FAA enforcement databases for compliance patterns
Track aircraft registration changes and fleet composition shifts
Identify maintenance scheduling conflicts from public flight data
Generate real-time alerts for operators showing signs of compliance stress
Episode 3: Agent Build for Messaging Using the research foundation from Episode 2, we'll create a messaging agent that can:
Generate specific PVPs using WingWork's public data sources
Customize compliance risk assessments for individual operators
Create asset value protection alerts based on maintenance quality indicators
Scale personalized outreach using predictive compliance scoring
The Three Core Values in Action
This WingWork exploration perfectly demonstrates our three core principles:
You Are the Guide, Not the River: The excitement in Jordan's voice wasn't about the AI model, it was about understanding the industry context well enough to recognize golden opportunities when the data revealed them.
Process Over Prompts: While we're evolving toward more sophisticated prompts, the systematic exploration of WingWork's industry, pain points, and data sources remains the foundation that makes everything else possible.
Tooling Is for Tools: The most sophisticated AI in the world can't help you if you don't understand what questions to ask. Our deep dive into Part 91/135/145 regulations wasn't just research, it was building the domain knowledge that makes our PVPs valuable rather than obvious.
Ready to dive deeper? Our paid subscribers get access to:
Our PVP training series, The Guide to Creating PVPs and the Guide to Data Mining for PVPs
Jordan's all-in-one mega prompt (Cannonball version coming Friday, July 25th along with V4 of the Cannonball Prompt Library )
Live office hours every Friday to workshop your own brand applications
Complete episode and office hours transcripts
The aircraft maintenance industry is just the beginning. When you can systematically identify pain-based segments and create genuinely valuable messaging using public data, every vertical becomes an opportunity.
PS - Doug here (Jordan didn’t have hand in today’s post) we recently had a brand throw a hissy fit (those of you paying attention know who this is) when we announced we’d be Cannonballing them. They had a fair point, which was the liberal use of the word ‘with’ in the title when we promote a Livestream. That’s my bad. If you find your brand loaded in the Cannon, please give us a shout. But, before you do, don’t be a noodge, watch an episode. If I’d been handed this much insight on a silver platter in my CMO days, well, there would have been an expensive bottle of bourbon on your doorstep faster than you could say Cannonball.
Next week: We build the research agent that makes this methodology scalable. See you Friday at 9am AM Pacific for Episode 2 of our WingWork series.
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