Heypenny

What Heypenny does

HeyPenny (legally Wellbeing-Check-in Limited, NZBN 9429051022150) is a New Zealand-based SaaS company that provides an AI-powered leadership coaching platform centered on 1:1 check-in conversations. The platform captures conversation content via manual notes or the HeyPenny Scribe audio transcription feature, then processes it through an AI Agent that classifies observations against a psychosocial factor framework aligned with ISO 45003 guidelines. Outputs are anonymized insights linked to factors such as workload, recognition, role clarity, autonomy, and psychological safety, surfaced through a Data Dashboard, with a Resource Library providing follow-up materials. The platform is packaged into four solution tracks: Leadership Development, Employee Performance, Business Performance, and Health & Safety. Target users are business leaders, HR/People & Culture professionals, and Health & Safety professionals, with explicit positioning for SMBs without dedicated HR resources.

The business model is a per-seat SaaS subscription at $100 per user per year, billed annually. Distribution combines direct website sales (Discovery Call CTA), a two-tier partner channel (Delivery Partners with recurring revenue share and Referral Partners earning first-year contract percentages), and a web-based, self-service SaaS platform accessible via Microsoft/Google SSO or Magic Link authentication. The platform is hosted on AWS, uses end-to-end encryption, and is compliant with the NZ Privacy Act 2020. The company was founded in 2023 by Kevin Gudmundsson, operates as a Founder-led private entity with 1-10 employees, has no disclosed external funding, and has not raised any institutional investment rounds.

HeyPenny has accumulated 14+ named logos spanning startups (Litmaps, CreativeHQ, Storbie, Blacklock, JAS), NFPs (HASANZ, Wellbeing Tick, ShopCare, NZISM), enterprise (Transgrid, ValueWork, MADE), government (Capital & Coast DHB), and academia (Victoria University of Wellington). A flagship longitudinal study with Victoria University of Wellington, supported by researchers from Griffith University, is validating conversational data as a scientific measure of employee wellbeing and performance. The company lists 90% of trial employees wanting to continue with the approach and cites a 15-40% potential reduction in presenteeism costs as core outcome claims.

Name

Heypenny

Legal name

Wellbeing-Check-in Limited

Website

https://heypenny.co.nz

Company type

Private

Founded year

2023

Operating status

Operating

Headcount range

1–10 employees

Short description

HeyPenny is a New Zealand-based SaaS platform that uses AI to analyze leader-led 1:1 check-in conversations against an ISO 45003-aligned psychosocial framework, delivering anonymized workforce wellbeing insights to business leaders, HR teams, and Health & Safety professionals at $100 per user per year.

Ownership category

akta.pro rank

Product category

Employee Wellbeing Analytics Software

NAICS

Human Resources Consulting Services (541612)

SIC

Services-Prepackaged Software (7372)

akta.pro primary industry

Performance Management & OKRs (BPACAPAF)

Keywords

• Leadership development platform
• Employee wellbeing software
• Workforce analytics SaaS
• AI conversation insights
• Psychosocial risk management

GTM type

B2B

Offering type

Software

Cost components

Technology or R&D, Personnel, Marketing or Sales, Infrastructure, Operations

Revenue model

1. Annual Subscription: SaaS subscription model billed annually at $100 per user per year. Platform access is provided for the subscription period with automatic rollover at the end of each billing period.

Pricing tiers

Go-to-market motion2 records

Distribution channels4 records

Marketing channels7 records

Core offering

HeyPenny is a cloud-based SaaS wellbeing management platform that captures and analyzes leader-led 1:1 check-in conversations to generate anonymous workforce and performance insights. Leaders record check-ins via transcription (HeyPenny Scribe) or manual notes, and the platform's AI Agent analyzes inputs against a psychosocial factor framework aligned with ISO 45003 to produce concise, anonymized insights, follow-up drafts, and organizational trend data via a Data Dashboard.

Product overview

HeyPenny is a cloud-based wellbeing management platform built around a core AI-powered analytics engine. The platform centres on leader-led 1:1 check-in conversations, where leaders use HeyPenny Scribe (audio transcription) or manual note entry to capture conversation content. The HeyPenny AI Agent then analyses these inputs against a Factor Framework aligned with ISO 45003 to generate anonymous insights linked to psychosocial factors. The Data Dashboard surfaces organisational patterns and trends, while the Resource Library provides follow-up materials. The platform is offered as a unified system with four solution tracks (Leadership Development, Employee Performance, Business Performance, Health & Safety) that share the same core platform, AI Agent, and analytics infrastructure. Pricing is $100 per user, per year.

Differentiator

Problem solved

Functional benefit

Brands

• HeyPenny Scribe: AI-powered transcription feature for logging check-in conversations directly into the platform
• AI Agent
• Penny's Good Sorts
• Pennies of Wisdom
• Dear Penny

Products and services

• HeyPenny Platform A web-based wellbeing management platform that helps organisations understand how work impacts their people in real time. Leaders use the platform within existing 1:1 check-ins to capture insights and access AI-powered analytics, with solutions spanning Leadership Development, Employee Performance, Business Performance, and Health & Safety.
• HeyPenny AI Agent An AI-powered analytics engine that analyses conversation notes and transcripts to generate concise, anonymous insights linked to psychosocial factors, classified against the ISO 45003-aligned Factor Framework. Designed for leaders and HR teams to save time in 1:1 check-ins and receive unbiased, structured insights.
• HeyPenny Scribe An audio transcription capability within the HeyPenny platform allowing leaders to directly transcribe spoken 1:1 check-in conversations into the platform. Supports pause/resume functionality with automatic processing and converts speech to text for AI analysis.

Quantifiable outcome

• 90% of employees during trials wanted to continue with the approach
• +2 more outcomes

Named customers8 records

Segments4 records

Ideal customer profiles4 records

Technology focussed Yes

API detail

Has API

Yes

API docs

API detail

Core technology

AI maturity

App detail

Integration2 records

AI capability4 records

Feature6 records

Partnerships

Six partnerships are on record, tiered flagship, core and minor.

• Victoria University of WellingtonflagshipStrategic or Co-development Partner · 1 January 2026Major longitudinal study partnership testing the hypothesis that leader-led check-in conversations can predict and improve employee wellbeing, engagement, and performance. Led by Dr. Dan Langerud with support from world-leading organizational psychologists. Study grounded in Job Demands-Resources (JD-R) model. First study of its kind in Aotearoa and one of first globally to validate conversational data as scientific measure.
• Dr. Paula BroughcoreStrategic or Co-development PartnerGriffith University researcher supporting the Victoria University longitudinal study as part of the research team of world-leading organizational psychologists and wellbeing experts.
• Dr. Hillary BennettcoreStrategic or Co-development PartnerLeading Safety researcher supporting the longitudinal study research team, bringing expertise in workplace health, safety and wellbeing from Aotearoa.
• Dr. Rebecca DownescoreStrategic or Co-development PartnerResearcher supporting the Victoria University longitudinal study as part of the team of world-leading organizational psychologists and wellbeing experts.
• Delivery PartnerscoreChannel Partner/ Reseller/ DistributorPartners who sell and implement the HeyPenny platform including onboarding and ongoing client support. Manage entire client relationship from first conversation through embedding process and platform usage. Generate recurring revenue from percentage of annual subscriptions managed. Enhanced service offering beyond traditional consulting.
• Referral PartnersminorChannel Partner/ Reseller/ DistributorPartners who recommend HeyPenny to their network and facilitate introductions. Ideal for those wishing to advocate for the mission without direct delivery involvement. Earn percentage of first-year contract value for successful referrals. Receive 12 months free platform access for up to 4 users.

Scale indicators2 records

Recent moves6 records

Expansion highlights6 records

Direct peers

• 15Five: Continuous performance management platform built around weekly check-ins between managers and employees. Closely aligned with HeyPenny's 1:1 check-in model and performance management focus.
• Lattice: Performance management and employee engagement SaaS with OKRs, 1:1s, and feedback tools. Directly comparable in the HCM/performance management category, with broader OKR tooling.
• Officevibe: Employee feedback and engagement platform focused on pulse surveys and manager coaching. Overlaps with HeyPenny's wellbeing-and-leadership positioning, though survey-led.
• Limeade: Employee wellbeing and engagement platform with a focus on workplace wellbeing outcomes. Comparable in the wellbeing-measurement and ISO-style framework positioning.
• BetterUp: Leadership development and coaching platform combining AI with human coaching. Comparable in the leadership-coaching category and the AI-augmented development thesis, but at higher enterprise price points.
• Culture Amp: Employee engagement and performance platform offering surveys, feedback, and performance reviews. Most directly comparable as a SaaS tool measuring employee sentiment, though survey-based rather than conversation-based.

Emerging players

• Leapsome: People enablement platform combining performance reviews, OKRs, engagement surveys, and learning. Comparable in HCM scope with growing AI features; competes for the same HR buyer.

Broad incumbents

• Workday Peakon: Employee listening/engagement platform owned by Workday, an enterprise HCM incumbent. Comparable in the employee-insights category but bundled into a much larger HCM suite.
• Glint (LinkedIn): Employee engagement/survey platform acquired by LinkedIn. Overlaps in workforce-insights but is owned by a much larger ecosystem and is survey-based.

Regional players

• Qlaire (or similar NZ workplace wellbeing player): Regional workplace wellbeing platforms operating primarily in Australia/New Zealand that compete for similar mid-market H&S and HR buyers in HeyPenny's home geography.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks5 records

Key highlights7 records

Customer concentration

Compliance1 record

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Heypenny