How Sentry Insurance Cut $1M in Training & Support Costs With Whatfix
In the fast-shifting world of insurance, experience is becoming the new competitive advantage. Whether it’s helping an agent navigate a new claims system or supporting customers through a complex policy update, the experience behind those micro-moments defines loyalty.
Yet, many insurance enterprises struggle with one persistent challenge — digital adoption. As legacy systems merge with new-age digital tools, employees often face steep learning curves. For Wisconsin-based Sentry Insurance, this friction was turning into soaring costs, delayed onboarding, and inconsistent customer experiences. Something had to change.
The Challenge: Complex Systems, Rising Costs, and Unmet Expectations
Sentry Insurance, one of the largest mutual insurance firms in the U.S., manages a broad portfolio — from commercial property and auto coverage to life insurance and annuities. With more than 4,400 associates and $3.5 billion in annual revenue, its scale presents both strength and complexity.
Internally, Sentry teams were managing policy administration, claims, underwriting, and HR workflows across multiple enterprise systems — Workday, Guidewire PolicyCenter, Alloy, and customer portals. But static training modules, instructor-led sessions, and scattered resources slowed productivity. Employees, especially new hires, struggled to navigate platforms efficiently.
Each support query or re-training session consumed productive hours. The learning and performance teams felt the drag — time and cost spent on repetitive help requests instead of advancing workforce readiness.
Colleen Behnke, Learning and Performance Specialist at Sentry, captures this reality well: “We needed a way to help people learn in the flow of work — not outside it. Manuals and classroom sessions couldn’t keep pace with how fast our systems and processes evolved.”
The challenge wasn’t just operational. Every delay in internal system adoption rippled outward — to customer response times, claims accuracy, and overall service experience.
The Turning Point: Embracing a Digital Adoption Mindset
After evaluating multiple solutions, Sentry chose the Whatfix Digital Adoption Platform (DAP). Unlike conventional learning management platforms, Whatfix embeds contextual learning directly into an organization’s digital ecosystem — guiding users through tasks, nudging them toward next actions, and providing on-demand help without leaving the workflow.
For Sentry, Whatfix promised something compelling — a scalable bridge between rapid digital adoption and human experience. As Behnke explains, “The difference with Whatfix is people genuinely enjoy using it. It’s intuitive, requires no technical background, and integrates seamlessly across our entire portfolio.”
From Confusion to Flow: How Sentry Reimagined Workday Experience
One standout implementation began with Workday, Sentry’s HR and payroll backbone. Rolling out Whatfix over Workday transformed how 2,000 sales, underwriting, and operations associates interacted with the system.
Through in-app walkthroughs, pop-ups, beacons, and smart tips, Whatfix guided users step-by-step — whether submitting timesheets, managing payroll tasks, or exploring new HR features.
The results were immediate and measurable:
- 94% user engagement rate within months of launch
- 91% self-help search success rate
- Marked reduction in support queries and manual interventions
HR teams, previously stretched between administrative tasks and talent management, now reclaim significant time for skills development and employee engagement. The workplace learning culture also evolved — from reactive support to proactive, self-driven discovery.
The Broader Rollout: Scaling Across Systems and Stakeholders
Encouraged by early success, Sentry extended Whatfix to key insurance and customer-facing applications — including Guidewire PolicyCenter, the Alloy claims system, and portals such as Sentry Insight and Insight for Agents.
This inclusion wasn’t limited to employees. Whatfix now supports over 700 external agents and service representatives, along with more than 75,000 customers who access data through digital portals.
Sentry’s “Sentry University,” its internal learning Center of Excellence (CoE), partnered with business units to maintain governance, ensure content relevance, and measure adoption analytics.
Innovations that drove rapid adoption included:
- Tying learning objectives directly to behavior change metrics
- Securing executive sponsorship for visible leadership backing
- Crowdsourcing end-user input on self-help design elements
- Gamifying awareness campaigns to promote feature utilization
- Gathering and acting on user feedback after each content release
Sentry treated digital adoption as a cultural transformation, not a one-time project.
Quantifiable Impact: Turning Efficiency Into Enterprise Value
Within 12 months of implementing Whatfix, Sentry achieved over $950,000 in savings — nearly $1 million reclaimed from what were formerly sunk costs in repetitive training, content creation, and support manpower.
Operational benefits cascaded across functions:
- 40% faster content creation: Modules that took 50 hours now took 20.
- Reduced instructor-led training: Employees mastered systems through in-app guidance without workshop dependency.
- Productivity uplift: Onboarding time shortened, and application adoption rates soared.
- Error reduction: Whatfix’s smart nudges helped employees correct policy or claims data in real time, cutting down avoidable rework.
These efficiency gains freed Sentry’s workforce to focus on value generation — faster claims resolution, improved underwriting accuracy, and more responsive customer service.
Lessons for Insurance CX Leaders
The Sentry-Whatfix story highlights critical lessons for CX and EX leaders across industries, especially in sectors juggling compliance-heavy, legacy-rich digital environments.
- Digital Adoption is Foundational to Experience Success
CX initiatives often fail because employees can’t navigate new tools efficiently. A DAP bridges that gap by embedding contextual guidance right where work happens. - User Experience Isn’t Just for Customers
When employees experience frictionless workflows, that ease translates directly to the customer side. Every reduction in internal complexity compounds into smoother, faster service delivery. - Learning Should Happen in the Flow of Work
Traditional training models separate learning from doing. Whatfix’s in-app learning allows insurance associates to solve problems in real time while staying productive. - Analytics Create a Continuous-Improvement Loop
Sentry plans to use Whatfix analytics to track unsuccessful search queries, spot content gaps, and proactively create new guidance material — ensuring learning evolves with system updates.
Expert Perspective: Bridging Digital and Human Journeys
Industry research agrees with Sentry’s approach. Gartner predicts that by 2027, 75% of organizations will use digital adoption platforms to accelerate enterprise software ROI. Meanwhile, a McKinsey survey shows employees waste nearly 20% of their workweek navigating software complexity — a figure digital adoption tools aim to cut dramatically.
As Behnke summarizes, “The real value isn’t just cost savings. It’s confidence. When associates feel empowered by technology, they serve customers better. That’s the true measure of our digital transformation.”
Future Outlook: Scaling Experience-Driven Transformation
Sentry’s next phase will expand Whatfix analytics deeper — identifying patterns in content use, optimizing feature awareness, and using feedback loops to guide onboarding for future apps.
“We’re exploring what else these insights can do,” says Behnke. “Our goal is to ensure that no associate or agent ever feels lost in a system. Every digital touchpoint should feel like an experience designed for them.”
By embedding digital adoption into its DNA, Sentry is creating a model for the modern insurance enterprise — one that balances operational agility with a genuinely human experience.
Key Takeaways for CX and EX Professionals
- Anchor every digital transformation in user empathy and contextual design.
- Use analytics from DAP platforms to continuously refine training relevance.
- Foster co-ownership between learning teams, IT, and business units.
- Replace static training with in-the-flow support to shorten time-to-proficiency.
- Celebrate small adoption wins publicly; they accelerate culture change.
Closing Thought
Technology transformations often stumble not because the tools fail — but because the people behind them aren’t guided through the change. Sentry’s success with Whatfix shows how pairing technology with empathy can rewrite that narrative.
As CX and EX leaders look ahead, this case offers a vivid reminder: sustainable experience excellence begins not at the point of customer contact, but at the heart of the employee journey.
