A Pragmatico AI Cultural Adoption Case Study
How Indiana Farmers Insurance Built an AI-Native Leadership Team in 16 weeks
Challenge
A 250-person mutual insurance company had deployed AI in its operational backbone, but generative AI for knowledge workers was largely untouched. Leaders were on the cusp of change, yet adoption hadn't happened. The barrier wasn't technical. It was cultural.
Outcome
In 16 weeks, IFM moved 44 senior leaders from a majority of non-users to 92% daily AI adoption. These leaders now save a combined 218 hours per week from AI-driven productivity, the equivalent of 5.4 FTEs of leadership capacity, representing $1.05M in time savings per year from AI.
HEADQUARTERS
Carmel, Indiana
INDUSTRY
Mutual Insurance
EMPLOYEES
~250
TIMELINE
16 Weeks
The Results
The transformation was both dramatic and measurable.
After 14 weeks:
92%
Leaders Using AI Daily
$1.05M
Annual time savings from AI
218 hrs
Saved Per Week (44 leaders)
3.4x
Usage Surge (Dec → Jan)
77%
Leaders Feeling Confident in AI, up from 19%
16 Weeks
From “On the Cusp”
to AI-Native
Adoption & Usage: Before and After
METRIC
BEFORE (Oct 2025)
AFTER (Feb 2026)
Daily AI Usage (multiple times/day)
<50% of leaders
92% of leaders
Confidence in AI Skills
19% felt confident
77% felt confident
Avg. Self-Rated Proficiency
3.5 / 10
6.4 / 10
Analysis/Research Confidence
17%
70%
Know Where to Get AI Help
14%
77%
Weekly Messages (Enterprise)
4,473 (December)
15,059 (January), a 3.4x increase
Hours Saved Per Week
Near zero
218 hrs across 44 leaders
Annual time savings from AI
$0
$1.05M
The largest jump: “Know where to go for AI help” went from 14% to 77% (+63 percentage points). This reflects the organizational infrastructure Pragmatico built and not just individual skill gains: the Teams channel, peer support network, and training resources.
How it Started
Wes Sprinkle, CEO of Indiana Farmers Insurance, had seen plenty of AI vendor pitches. Most were selling tools or one-off training. Pragmatico was selling cultural change management. That distinction resonated immediately.
Wes wasn't starting from zero. IFM had already deployed AI deep in its operational backbone for auto claims estimation, aerial roof scoring, and pricing algorithms. But generative AI for the 250 knowledge workers? Mostly untouched.
The Challenge:
Tools Deployed, Transformation Stalled
IFM's leadership team was ready for AI. Pre-program survey data established a clear baseline, consistent with what most mid-market organizations look like before structured AI adoption programs:
- Fewer than half of the leaders used AI daily going into the program
- Only 19% felt confident in their ability to use AI effectively for work tasks
- Average AI proficiency: 3.5 out of 10
- Top barriers: data privacy concerns, uncertain use cases, difficulty integrating AI into existing workflows
- No shared language, no policy guardrails, no leadership modeling
IFM’s situation mirrored what most mid-market organizations face. Leaders had some access to AI tools, but usage was ad hoc, confidence was low, and the organization had no common foundation for what "good" AI use looked like.
"I recognized early on that if we wanted AI to scale, we had to make using AI part of the culture. That’s where Pragmatico came in."
Wes Sprinkle
CEO, Indiana Farmers Insurance
Te next step was clear: move from AI deployment to AI adoption.
The Solution:
Cultural Transformation First, Technology Second
Pragmatico's approach recognized what most organizations miss: AI adoption is fundamentally a change-management challenge, not a technology one. The solution unfolded across three phases over 16 weeks.
PHASE 1.1
Align & Architect (Weeks 1–3)
Before any training began, IFM needed the cultural foundation to make adoption stick.
Wes emailed the entire leadership team, positioning AI adoption as a CEO-backed priority rather than optional professional development. Technology options were evaluated for IFM’s needs, and ChatGPT Enterprise licenses were procured and configured. An “AI Together” Teams channel was created for daily support and coaching. A baseline AI survey was deployed. By the time 44 leaders gathered for Level 1 training, the stage was set.
The AI Vision & Addressing Employee Fears
When Wes saw a news article about Chubb, the world’s largest publicly traded P&C insurer, announcing plans to cut headcount by 20%, he forwarded it to the Pragmatico team with a brief note:
"I recognized early on that if we wanted AI to scale, we had to make using AI part of the culture. That’s where Pragmatico came in."
Wes Sprinkle
CEO, Indiana Farmers Insurance
That instinct became IFM’s formal AI Vision, connecting AI proficiency to IFM’s values and including annexplicit commitment: AI is about “elevating people, not replacing them."
For a mutual insurance company with a 95% employee retention rate, this created the psychological safety that enabled 44 senior leaders to experiment without fear.
PHASE 1.2
Activate Behaviors (Weeks 4–13)
6-Session Customized Training & Accountability Program
Pragmatico delivered a structured program across six sessions: three training levels and three
use-case sharing sessions. Each training level is built on the last:
- Level 1: COSTAR prompting framework, custom instructions setup, hands-on practice with real work tasks
- Level 2: ChatGPT Projects, Deep Research, advanced use cases with breakout sessions by department
- Level 3: Department-specific mastery, automation workflows, agentic AI introduction
After each level, a dedicated use case sharing session required participants to demonstrate homework and present how they apply AI learnings in their actual work. This cycle of skill building (applied practice through structured homework and peer accountability) is what turns new capabilities into daily habits.
The standout moment from Phase 1.2: Judy Tanzer, Vice President and Chief Marketing Officer, demonstrated how her team reduced a complex insurance regulatory document review from an estimated 40–50 hours to under 4 hours, producing a strong first draft that still required human review but eliminated the most time-intensive work. Massive AI productivity gains were no longer theoretical.
Leaderboard & Collaborative Culture
A leaderboard emerged from the analytics data and peer-voted "best Al use cases", and it ignited something. Leaders started checking their rankings. Peers motivated each other and shared learnings daily. The collaborative spirit that defines IFM's culture found a new outlet, accelerating adoption faster than any incentive program could have.
PHASE 1.3
Operationalize & Sustain (Weeks 13+)
- AI proficiency added as a formal 2026 leadership goal for all senior leaders and managers
- Phase I leaders designated as team-level AI champions for Phase II rollout
- Quarterly AI ROI measurement framework established with CFO involvement
- Phase II began: expanding the program to 200+ employees across claims, underwriting, IT, and all departments
Use cases
Breakthrough Use Cases
The numbers tell one story. The use cases tell another. Here is what 16 weeks of behavioral adoption looks like in practice:
Result
TIME SAVED
40–50 hrs →
4 Hrs
DEPARTMENT |
Cross Functional
Complex insurance regulatory document review 10x faster, producing a strong first draft for human review.
Result
TIME SAVED
60 min →
10 min
DEPARTMENT |
Claims
Adjuster claim statements summarized and analyzed for liability considerations, giving adjusters a 6x faster starting point for their review.
Result
TIME SAVED
Hours →
Minutes
DEPARTMENT |
IT / Security
Automated querying and review of 800,000+ server logs using AI-generated scripts.
Result
TIME SAVED
Days →
Hours
DEPARTMENT |
Claims
Bodily injury demand package summarizer: 250-page demand packages distilled into structured evaluation summaries, giving adjusters a faster starting point for human review and liability assessment.
Result
TIME SAVED
Weeks →
Days
DEPARTMENT |
Claims
AI-assisted new hire training system: all claims handling documents uploaded to generate coverage-specific training guidelines for CR2 onboarding, reviewed and refined by senior adjusters.
Result
TIME SAVED
Minutes →
Seconds
DEPARTMENT |
Claims
Phone call documentation at scale: call transcripts converted to professional file notes in seconds, enabling adjusters handling hundreds of calls per month to maintain thorough, consistent documentation.
Result
TIME SAVED
Ground zero →
Operational
DEPARTMENT |
HR / Legal
Internal audit program development: audit charter, procedures, control-to-risk mapping, audit universe, and testing protocols drafted with AI and validated against COSO framework and internal audit standards.
Testimonials
The People Who Changed
Lisa Cameron
Lisa rated her AI proficiency at 1 out of 10 on the baseline survey. By November, she was the #1 user in the organization. Lisa didn’t just adopt AI personally. She distributed every training deck, posted every recording, managed every scheduling thread, created the analytics group on her own initiative, and volunteered to co-present at a regional conference. The program succeeded operationally because Lisa made it succeed.
I love the potential of AI, I just can’t learn it fast enough. It’s immediately helped efficiency and I can already see the impact. If you took ChatGPT Enterprise away from me today, my productivity would significantly suffer.
Lisa Cameron
CHRO, Indiana Farmers Insurance
Jerel Titus, COO
Jerel’s proficiency moved from 3 to 8 over the program. His favorite use case by the end: a custom GPT built as an executive coach based on the teachings of his most admired leaders. Jerel opened the Phase II all-employee training sessions by telling 200+ associates what his own journey looked like:
Before I used AI here and there for Google-like searches and light information, and now I use it every single day. I told the group I would be very disappointed if Wes said we're taking Al away now because with these new tools, I’m more effective than ever before. Everything from writing emails, synthesizing complex information, doing research, proactively organizing my workload and managing my calendar is easier with AI. It's really an incredible tool to accelerate the impact that you have.
Jerel Titus, COO
COO, Indiana Farmers Insurance
The Critical Insights:
Why This Worked
IFM's success illuminates why most organizations struggle with AI adoption despite significant investment. The difference came down to three principles, none of which are technical.
- The CEO went first and stayed visible
Wes used ChatGPT for his own work and told his leadership team about it openly. He introduced Pragmatico to his Executive Team. He regularly shared Al content with the group and made Al proficiency a formal 2026 goal for every leader. He was present at every major session. Then, when the system was working, he stepped back and let others lead. - Values came before velocity
Wes and Lisa proactively insisted that the AI Vision commit to no layoffs, setting the moral foundation. For a company with 95% retention, employees are the institution. The AI Vision connected to existing ICARE values and created psychological safety for 44 leaders to experiment without fear. - Proof earned trust, and trust earned expansion
When IFM’s CFO asked for ROI rigor, Pragmatico co-created a three-lens measurement framework (Capacity, Quality/Risk, Strategic). That pushed measurement toward outcomes, not activity counts. Every interaction deposited more trust than it withdrew. - Sophistication, not just adoption
Privacy/security concerns dropped 29 percentage points after the Enterprise deployment and governance communication. But accuracy concerns actually rose slightly. That’s a sign of sophistication, not regression. People who use AI daily develop a sharper awareness of its limitations. Healthy skepticism grew alongside confidence.
The symptoms were textbook. Leaders had some access to AI tools, but usage was ad hoc, confidence was low, and the organization had no common foundation for what "good" AI use looked like.
"Teams are no longer asking whether to use AI. They're asking how to use it better for their specific functions. That's successful adoption. Now we're focused on turning unconscious usage into conscious mastery."
Wes Sprinkle
CEO, Indiana Farmers Insurance
What's Next:
From Leadership to Organization-Wide Transformation
With Phase I complete, IFM has moved from "will people use this?" to "how do we use it better?"
Phase II is now underway, expanding the program to 200+ employees. Phase I leaders are serving as team-level AI champions, each responsible for modeling the behavior they learned in training.
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