Transform How You Care for Your Employees

Small Signals. Smart Impact.

PennyWise helps you care for your employees in the moments that count—quietly, precisely, and without surveys.

Connect employees to existing benefits first, then provide precisely-timed support that makes managers the heroes, not AI.

Live Demo See How It Works

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Meet PennyWise

Use AI to make your workplace more human

Employee Chat

"I'm working late every night and feeling burned out..."

"Did you know we have flexible PTO for exactly this situation? You can take mental health days when you need to recharge."

Behind the scenes: Manager gets email: "Your team member has been working extra hours. Here's a suggested gesture: mental health day + spa gift card."

From Signal to Support

How PennyWise transforms employee signals into manager-delivered support while maximizing your existing benefits

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Employee Shares Concern

Anonymous chat about burnout, stress, or workplace challenges. AI immediately connects them to existing benefits first.

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AI Analyzes & Recommends

System analyzes emotional signals, identifies unmet needs, and generates precise gesture recommendations for HR approval.

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Manager Gets Email

Direct supervisor receives contextual email with gesture suggestion and delivery template - they become the hero, not the AI.

From: PennyWise Employee Support <pennywise@yourcompany.com>

To: Sarah Johnson <sarah.johnson@yourcompany.com>

Subject: Team Member Support Opportunity - Confidential

Hi Sarah,

One of your team members could use some extra support right now. They've been working extra hours and mentioned feeling burned out.

💡 Suggested Gesture:
"I've noticed how hard you've been working. Take Friday as a mental health day, and here's a $50 spa gift card to help you recharge."

Why this works: Personal recognition from you shows leadership cares about people, not just productivity.

Cost: $50 + 1 PTO day

Thanks for being an awesome leader!
The PennyWise Team

How PennyWise Works

Listen

PW provides gentle check-ins at employer-determined moments. PW enables conversations that can be anonymous or identified by employee choice. PW captures both explicit concerns and subtle friction signals.

Support

PW links employees to support options they might not know about. PW identifies barriers preventing use of available resources. PW suggests thoughtful gestures to fully address needs.

Grow

PW helps learn what's working to better care for future team members. PW helps develop deeper understanding of employee experiences. PW helps build a more supportive workplace.

Precisely-Timed Support

PennyWise matches the right resources and gestures to the right moment

SUGGESTED GESTURE

After employee shows strain from hard week

$50 spa gift card
and
2 hours of PTO

SUGGESTED GESTURE

When caregiving strain emerges

Calm app subscription + flexible work arrangement + EAP outreach

SUGGESTED GESTURE

Summer schedule changes detected

Movie gift card + tailored resource list (library programs, summer camps)

SUGGESTED GESTURE

Hidden effort signs detected

"We saw the lift" — coffee delivery + leadership recognition email

SUGGESTED GESTURE

Employee worried about special needs support

529A account guidance + special needs attorney appointment + family support services

Revolutionary HR Intelligence

Technology that makes your workplace more human through intelligent support and genuine connection

Early Intervention System

Address quiet frustrations before they escalate into burnout, turnover, or performance issues.

Proactive Support: Small gestures prevent big problems

Manager-as-Hero Design

Employees receive support from their direct manager, not an AI system. PennyWise provides the intelligence; managers provide the human touch.

Human Connection: Personal recognition builds stronger relationships than automated systems

Intelligent Barrier Detection

Identifies why benefits aren't being used—complexity, stigma, awareness gaps—and provides targeted solutions.

Resource Optimization: Turn underused benefits into valuable employee support

Benefits-First Philosophy

Before recommending any new spending, PennyWise connects employees to existing benefits they didn't know about or couldn't access.

Smart Impact: Maximize your existing benefits investment before spending on new gestures

Real-Time Analytics

Live dashboard showing conversation patterns, benefit discovery rates, gesture effectiveness, and organizational health metrics.

Data-Driven Insights: Make informed HR decisions with actionable intelligence

Privacy-First Architecture

Anonymous conversations with selective disclosure. Employees control their privacy while organizations get strategic insights.

Trust Building: Higher engagement when employees feel safe to share

Experience AI That Makes Your Workplace More Human

See how PennyWise transforms employee support from reactive surveys to proactive, intelligent care.

Try Employee Chat View HR Dashboard Explore Settings

Live Demo: All features working with real AI analysis and intelligent support recommendations