Leadership Roadmap

🚨 Out now!! Last week I sat down in the studio with 3 people deep in the thick of AI right now

Federico Lucignano – CTO at Honey Insurance, previously at AWS where he led the launch of Amazon Polly, one of their flagship AI services.

Paulwyn Devasundaram – 2 weeks into her role as Head of Engineering at Relevance AI, building the tools companies are now using to deploy AI agents across their businesses.

Devesh Maheshwari – CTO at Lendi Group, leading one of the most ambitious transformations in Australian fintech to become AI native this year.

We covered a lot of ground, here’s a few things that stuck with me…

Regulated industries have real consequences. One mistake can cost you your license, so you don’t get to ship first and fix later. (14:50)

Seat-based SaaS pricing is under serious pressure. Usage and outcome models are coming, but token costs haven’t been fully figured out yet. (01:03:50)

The death of the software engineer gets thrown around a lot right now, but what’s actually dying is inflated hiring. (43:40)

For years, tech companies hired for headcount as a vanity metric, or hired people to just sit in the corner and code because that’s what was needed at the time. Now what companies actually need are product minded engineers who can think critically. (48:00)

I left the studio feeling very optimistic about the future.

Full convo below if you want to jump around:
00:00 – Intro + who’s on
02:30 – Anthropic leak: real or marketing?
06:15 – What “AI native” actually looks like
10:15 – Building AI products vs transforming companies
14:50 – Why regulated industries move differently
21:20 – Where AI is already working (support, ops)
28:00 – Why agents are getting better
35:00 – What Relevance AI actually does
43:40 – “Death of the engineer” debate
48:00 – Product engineers vs traditional devs
55:00 – The real hiring problem over the last decade
01:03:50 – SaaS pricing pressure + token economics
01:10:00 – AI-native vs AI-first companies
01:15:00 – Where this is all heading

🎧 Episode available on Apple and Spotify - Link in comments 🎙️

Leadership Roadmap
LinkedIn Page: @Leadership Roadmap
Youtube Channel: @Leadership Roadmap YT

What better way to kick off 2026 than getting back in the studio,
Series 2 of the Leadership Roadmap starts with Mike Leonard, VP of Engineering & Data at Pet Circle.
Mike shares practical insights on managing technical debt, the reality of "build vs. buy" decisions, and how to scale technical teams using AI as a force multiplier.
We got into:
02:14 The Journey of Replatforming a 13 Year Old Monolith → modern stack
14:57 Vendor selection + integrating an agency team for the long haul
32:31 Why e-comm is not “just a shop”
25:38 AI inside the business + what’s coming customer-side
42:08 Build vs buy - software decisions
Mike’s perspective is super practical, especially around agility, risk appetite, and what really changes when you scale.
Out next week on Apple & Spotify.

LinkedIn Page: @Leadership Roadmap
Youtube Channel: @Leadership Roadmap YT

Leader. Ultra-runner. Mental health volunteer. Dad.

Glenn Hangan’s the kind of leader who doesn’t just talk about resilience... he lives it.

He’s run 100 miles in one go.
And he’s currently training for his 10th ultra.

We talked about the crossover between endurance and leadership.

👉 What pushing past limits really teaches you about leading
👉 Why most leaders think they’re done long before they actually are
👉 How choosing discomfort sharpens your mindset
👉 Why your support crew matters
👉 How mental health fits into all of it

This wasn’t a motivational chat.

It was a raw, real conversation about what it takes to endure...in leadership, and in life.

If you’re a leader who thrives on challenge, or you’ve ever wondered what keeps people showing up when it hurts... this one’s for you.

And yes… we turned up in matching outfits. Should’ve called ahead.
LinkedIn Page: @Leadership Roadmap
Youtube Channel: @Leadership Roadmap YT

Kish Modi - ex-CPO at Me&u and now Co-founder of new AI start-up Hey Buddy.
His journey from scaling me&u during explosive growth from 4 to 150+ employees, to overcoming a life-changing battle with cancer is truly inspiring.
This isn't your typical startup story. Kish's journey includes:
• His unconventional path from quitting law to product leadership
• Building HelloFresh Australia into a market leader
• Scaling me&u from 4 employees to 150+
• Raising capital for his own pet startup
• Fighting and beating Leukemia
• Coming back stronger to launch his next venture
What you'll learn:
• Why culture gets forgotten during hyper growth (and how to fix it)
• The real truth about raising capital as a first-time founder
• How one investor refused to back his pet business because of its name
• Leadership lessons learned from battling cancer
• Why perspective changes everything about stress and priorities
Kish's vulnerability about his health journey and the wisdom he's gained hits different.
This conversation goes deep on resilience, leadership, and what really matters when building something meaningful.
LinkedIn Page: @Leadership Roadmap
Youtube Channel: @Leadership Roadmap YT

Had the privilege of recording with the brilliant Rajini Carpenter, CTO at Beforepay Group, for The Leadership Roadmap Podcast!

Rajini's path from studying computer science in India (thanks to her dad's guidance!) to leading engineering teams across IRESS, Deputy, and now Beforepay is packed with insights every tech leader needs to hear.

What hit me most:
Her raw honesty about returning from maternity leave within 3 months (twice!) because of fear of falling behind in tech's fast pace
How she influences without authority by prioritising customer focus over technical jargon
Her commitment to hiring problem solvers who work with product and business, not just coders
Her call for male allies in leadership to lean in and pull women up in the industry
Listeners will get practical advice on:
Transitioning from IC to leadership
Building confidence
Balancing career with family
Staying relevant as AI reshapes engineering
Creating inclusive environments
This conversation is a masterclass in resilience, growth, and paying it forward.

Episode drops next week! 🚀
LinkedIn Page: @Leadership Roadmap
Youtube Channel: @Leadership Roadmap YT