Learning Ship: Ship to Learn, Not Perfect

Melissa Cheals leads Smartly, a payroll and people management platform serving 24,000 small and medium businesses in New Zealand. In this conversation, she shares how AI is reshaping product development, leadership, and how organizations operate.

A key moment comes when her team estimates new features will take 12 months and $1M to build. Instead of accepting it, Melissa pushes back, using AI to better understand her team’s perspective and communicate the need for change more effectively. This becomes a broader shift in how she approaches leadership, using AI to think more clearly and navigate conversations with less friction.

The discussion expands into strategy. Companies now face a fundamental choice: become AI-native or continue building on existing systems. As AI adoption increases, it also exposes silos and bottlenecks. Melissa shares why cross-functional collaboration—and leaders actively engaging with AI themselves—is critical to navigating this shift.

Key Takeaways: 

• Becoming AI-native is a defining decision
  It’s not just a technology shift. Leaders need to decide whether to rebuild around AI or continue layering it onto existing systems, and that choice shapes how the company operates.
• AI shifts us from scarcity to abundance
  Many organizations still think in terms of limited time and resources, but AI changes what’s possible and forces leaders to rethink how big they can think and what they can achieve.
• AI is a leadership amplifier
  Beyond productivity, AI helps leaders think more clearly, reframe conversations, and communicate change in a way that is both effective and respectful.
• Leaders can’t delegate AI
  Without hands-on experience, it becomes difficult to challenge assumptions, guide teams, or make informed decisions about what’s possible.

Smartly: smartly.co.nz
LinkedIn Melissa: linkedin.com/melissa-cheals
LinkedIn Smartly: linkedin.com/company/smartlynz/

00:00 Intro: Challenging AI Assumptions
00:28 Meet Melissa Cheals
01:17 The Spark For Change
02:36 Vision And Early Signals
03:48 Hiring For Transformation
06:12 Unlocking Data With AI
08:27 Breaking Silos Across Teams
10:39 Why Leaders Must Learn AI
13:42 Leading With AI And Clarity
17:05 The AI-Native Decision
21:45 Thinking Bigger With AI
25:23 Less Meetings More Writing
26:33 The Self-Disruption Imperative
29:11 Breaking Silos With Value Streams
31:28 Managing Fear And Change
32:50 Learning And Shipping Faster
34:58 Debrief

📜 Read the transcript for this episode: ai-native-or-not-the-defining-choice-for-companies-right-now-with-melissa-cheals-ceo-of-smartly/transcript

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Show edited by Emma Cecilie Jensen.