ProvideSure Saves 135+ Monthly Coaching Hours and Accelerates Medicare Sales Readiness with Outdoo
ProvideSure is a Medicare health insurance provider helping seniors navigate complex insurance plans seamlessly.
Located
Indianapolis, Indiana
Industry
Insurance
525+
135+
73x
See How Outdoo Turns Practice Into Performance with AI Roleplays?
Book a DemoOperating a high-volume, phone-based GTM model, the company serves an older, highly regulated customer base where conversations are long, emotionally charged, and compliance-critical.
ProvideSure’s sales team scales rapidly during Annual Enrollment Period, requiring continuous onboarding and consistent readiness across new and experienced agents.
The Challenge
ProvideSure faced persistent enablement challenges driven by staggered onboarding, seasonal hiring surges, and the complexity of Medicare conversations.
New agents joined continuously, often mid-training cycle, making it difficult to maintain consistent cohorts or update existing courses. Traditional mock calls relied heavily on peer roleplays, which failed to reflect how real seniors communicate.
Managers spent excessive time running manual mock calls during the busiest sales period of the year, creating a coaching bottleneck. Leadership had limited visibility into agent readiness, performance trends, and skill gaps across different customer personas.
As a result, readiness assessments were reactive, and coaching efforts were often generic rather than targeted.
The Solution
ProvideSure made Outdoo its primary practice and coaching system, enabling agents to train continuously while leadership gained real-time insight into readiness and performance.
The platform was selected for its ability to combine realistic AI roleplays with configurable scoring and scalable coaching insights aligned to live call behavior.
Flexible, Campaign-Based AI Roleplays for Continuous Onboarding
To solve staggered onboarding and course duplication issues, ProvideSure restructured training into dynamic, campaign-based AI roleplays. New agents could be added instantly without rebuilding entire programs, and bots could be updated without relaunching curriculums. This allowed onboarding to operate continuously instead of in fixed cohorts.
Agents practiced real Medicare call flows tied directly to live campaigns, ensuring alignment between training and production environments.
“We no longer had to duplicate entire courses every time someone joined mid-cycle. Outdoo gave us flexibility without sacrificing structure.”
Realistic Senior Personas for Complex, Service-Led Conversations
To better prepare agents for real-world Medicare conversations, ProvideSure built multi-persona AI bots that reflected actual senior caller behavior.
These personas mimicked story-driven, skeptical, distracted, confused, and emotionally escalated callers. Unlike peer mock calls, the AI roleplays recreated long, nonlinear conversations where seniors jump topics, use metaphors, and require patience and clarity.
Agents could repeatedly practice handling unpredictable dialogue before speaking with real customers.
“Our seniors don’t talk in straight lines. They tell stories, shift topics, and sometimes test your patience. The AI personas finally reflected what our agents experience in the field. ”
Data-Driven AI Coaching and Real-Time Readiness Visibility
Outdoo replaced manual mock call dependency with scalable AI coaching and structured scorecards. Managers gained visibility into who completed each course, how agents performed across specific personas, and whether performance trends were improving or declining.
Strict scoring criteria differentiated top performers from those at risk, allowing leaders to intervene early. With AI handling repetitive drills and initial feedback, managers redirected time toward strategic coaching and performance acceleration.
“Instead of spending hours running mock calls, we could look at the data and immediately see who was ready and who needed help. That completely changed how we coach. ”
The Impact
By replacing manual mock calls with AI-driven roleplays and coaching, ProvideSure significantly increased practice volume, reduced manager workload, and gained predictive insight into real-world sales performance.
Coaching Time Reduced Without Sacrificing Quality
ProvideSure saved more than 135 hours of coaching time per month as agents completed over 550 roleplays independently. This equated to more than 17 full working days of additional practice without requiring manager involvement.
Clear Visibility into Skill Gaps and Readiness
Outdoo surfaced persona-level performance insights, showing exactly which senior profiles each agent handled well and where they struggled. Coaching shifted from generic feedback to targeted, high-impact interventions.
Predictive Performance and Scalable Enablement
Performance trends from AI roleplays closely mirrored real call outcomes, allowing leadership to proactively identify underperformance before it affected live customers. ProvideSure established a scalable, repeatable enablement system capable of supporting seasonal growth without increasing coaching headcount.
“Looking back at Outdoo’s data, it was extremely predictive of ongoing agent performance. The reps who struggled in AI roleplays almost one-for-one struggled on real calls. That gives us confidence to rely on this system moving forward. ”
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