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In this episode of the Tech Trajectory Podcast, host Chris Davies sits down with John Sullivan (Sully) to explore what it takes to lead large-scale transformation, without losing sight of people, purpose, and impact.

Sully shares his journey from engineer to CEO, and how listening to customers and translating business needs into tech outcomes became a career-defining shift. From OKRs to flywheels, ride-alongs to data dashboards, this episode is packed with practical stories and clear-headed thinking on how to get alignment, and why buzzwords are no substitute for intent.

Whether you’re scaling a startup, transforming a product team, or simply trying to get business and tech to speak the same language, this one’s for you.

1. Tech strategy is business strategy

[02:00] Sully shares how his early experience riding along with sales teams helped him shift from building for tech’s sake to solving business problems with tech.

2. Why OKRs changed everything at Chargefox

[08:30] In a post-acquisition pivot, Sully introduced five company-wide OKRs to align teams and give structure to a newly evolving software business.

3. Driving transformation with data and purpose

[15:00] From dashboards to Python scripts, Sully doubled down on making data accessible and meaningful—building alignment from the numbers up.

4. Leading with intent (and ditching buzzwords)

[21:00] You won’t hear Sully say “data-led” or “people-first,” but you’ll see it in his actions. He shares why clarity of intent matters more than corporate speak.

5. Navigating the personal side of transformation

[23:30] Whether it’s changing operating models or growing teams, Sully breaks down why true transformation is always personal—and why setting the ‘stall’ is essential.

6. What doesn’t work (and what surprised him)

[28:00] Not every team needs Agile. Sully challenges blanket transformation methods and shares what really made a difference across business functions.

7. From chaos to clarity: lessons in leadership

[32:00] As a CEO, Sully reflects on loneliness, switching leadership styles, walking the walk, and how a “why” mindset can be both a superpower and a headache.

8. Defining success and building flywheels

[38:00] Sully explains how Chargefox moved from a vague directive (“become a software business”) to a platform strategy, accelerants, and a flywheel that made it all work.

Where to find John Sullivan:

• LinkedIn: John Sullivan

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In this episode of The Tech Trajectory Podcast, host Kavita Kerwar sits down with Karis Dorrigan to explore what leadership looks like when driven by clarity, values, and life’s changing seasons.

From negotiating for flexible work to growing through career transitions and motherhood, Karis shares her journey with candour. She speaks about how to lead with both empathy and commercial focus, why inclusive product teams matter, and the value of redefining success on your own terms.

You’ll hear advice on part-time leadership, the impact of mentorship, and what businesses can do to truly support diverse teams and individuals—not just on paper, but in practice.

1. Flexibility doesn’t mean less ambition

[03:00] Karis discusses working part-time in a senior leadership role—and how she reframed flexibility as a strength, not a sacrifice.

2. Making work work, for people and life

[06:15] Teams thrive when flexible work is seen as a competitive edge. Karis shares practical actions to make part-time and remote employees feel valued.

3. Redefining leadership through motherhood

[09:00] Parenthood shifted Karis’s leadership style, grounding it in empathy, prioritisation, and purpose.

4. Navigating big career transitions

[15:00] Karis reflects on leaving high-profile roles, listening to your instincts, and designing a career that aligns with your values.

5. Leading inclusive product teams

[21:00] Inclusion starts at the strategy stage. Karis shares how she builds empathy into team culture and product decisions.

6. Mentorship and giving back

[24:00] From being mentored to mentoring others, Karis champions honest conversations, advocacy, and opening doors.

7. Advice for future leaders

[27:00] Karis closes with reflections on confidence, clarity, and what she wishes she’d known earlier in her leadership journey.

Where to find Karis Dorrigan

• LinkedIn: Karis Dorrigan

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In this episode of The Tech Trajectory Podcast, host Kavita Kerwar sits down with Fiona Rose to explore what it takes to lead with clarity and conviction in a scaling business. Fiona reflects on her cross-sector leadership experience, shares how purpose anchors decision-making, and explains why experimentation, diversity, and accountability are cornerstones of her leadership style.

1. Change is constant—communication is key

[02:20] Fiona reflects on the difference between public and private sector transformation, noting that speed is often faster in scale-ups—but communication must be deliberate and ongoing.

2. Purpose drives everything

[03:33] At Fitness Passport, the company’s purpose—helping people live healthier lives—shapes every decision across product, tech, and commercial priorities.

3. Customer insight is your compass

[04:56] Regular research and user testing guide Fitness Passport’s roadmap. “If you build without engagement, you won’t get the outcomes.”

4. The value of ceremony (and the surprise of sentimentality)

[06:59] Fiona shares an unexpected customer reaction to removing membership cards, and how the team reframed the loss by creating new moments of connection.

5. Experimentation reduces risk

[08:59] From A/B testing to beta features with edge-case bugs, Fiona champions progress over perfection and uses rich stakeholder input to validate strategy.

6. Leading high-performance teams

[10:28] Trust, accountability, and open communication underpin Fiona’s team culture. She shares how public initiative ownership builds clarity and cohesion.

7. North Stars and feedback loops

[12:02] A well-communicated North Star helps keep teams aligned during rapid change. Fiona values fast feedback, even if it’s not what leaders want to hear.

8. Accountability rituals and ring-fencing innovation

[13:24] Fitness Passport balances stability and innovation by ring-fencing the core business and giving space to more experimental initiatives.

9. In-person wins (and Slack fatigue is real)

[15:50] Fiona prefers face-to-face collaboration for culture and connection. “You can feel the side-eyes in the room—that’s feedback too.”

10. Partnerships are part of the team

[17:57] Fiona talks about DiUS' role in foundational delivery, and why shared values and cultural fit are critical when choosing tech partners.

11. Diversity builds better products

[20:50] A diverse team delivers stronger product-market fit and attracts even more diversity. Fiona shares how grassroots events and inclusive hiring practices are key to building great teams.

12. When in doubt: stay adaptable and bring in the experts

[24:46] Fiona’s mindset for uncertain paths? Stay calm, stay flexible, and call on trusted advisors to back decisions with evidence and experience.

Where to find Fiona Rose

• LinkedIn: Fiona Rose
• Website: fitnesspassport.com.au

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In this episode of The Tech Trajectory Podcast, host Chris Davies sits down with Amir Ansari to explore what it takes to build resilient design practices that scale. Through stories, frameworks, and some personal philosophy, Amir talks about aligning with executive stakeholders, balancing design literacy with capability uplift, and adapting leadership styles to suit context. 

1. Building design leadership like a Lego set

[02:04] Amir likens his leadership journey to receiving a surprise Lego set—thrown into leadership before he felt ready, but discovering joy in experimentation and adaptation.

2. What makes a strong design practice?

[05:28] Buy-in from executives is essential. Without it, designers risk being underutilised and misunderstood. Success depends on assessing appetite, leadership culture, and adapting the playbook accordingly.

3. Reframing design for business impact

[12:50] Many organisations still view design as a cost centre. Amir urges teams to “talk design without using the word design”—using business language like engagement, risk reduction, and evidence-based decision-making.

4. Uplifting capability vs. uplifting literacy

[20:18] Start with uplifting literacy across all teams before diving into design capability. This top-down approach ensures buy-in, sets expectations, and uncovers budget realities.

5. Internal advocacy and selling design

[30:00] Leaders must become internal salespeople—showcasing wins, tapping stakeholders, and building internal networks to create pull for design.

6. Democratising design

[40:41] Amir shares a model for enabling non-designers to take on basic HCD tasks—spreading capability across teams and creating internal evangelists.

7. Structuring design teams at scale

[52:15] From centralised to decentralised to hybrid models, Amir breaks down the pros and cons. The hybrid approach—with clear reporting lines and shared tooling—is his go-to for maintaining cohesion and autonomy.

8. Mentorship, values, and staying human

[01:06:33] Amir advocates for mentorship, honest conversations, and leading from a place of empathy. Supporting individual strengths helps create lasting team culture.

Where to find Amir Ansari

• LinkedIn: Amir Ansari
• Website: amiransari.com.au

Amir also offers mentoring and coaching for emerging design leaders.

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In this episode of The Tech Trajectory Podcast, host Kavita Kerwar sits down with Roby Sharon-Zipser, Co-Founder and CEO of hipages Group, to explore how leadership evolves as a business scales—from garage startup to ASX-listed tech company. Roby unpacks what it takes to move from being a hands-on founder to an enabler of innovation, how to build a culture of strategic execution, and why staying curious about technology—especially large language models—is key to future growth.

1. Evolving from founder to enabler

[04:42] How Roby’s leadership style shifted from micromanagement to team empowerment as hipages scaled.
 [06:32] What it means to step back and elevate your team with trust, clarity, and accountability.
 [07:24] The importance of letting go of low-value tasks and building out an executive team.

2. Building purpose into strategy

[10:04] How hipages keeps its dual customer base—tradies and homeowners—at the centre of decision-making.
 [11:38] Roby breaks down how AI and cross-functional teams are improving customer experience across the board.
 [14:22] End-to-end customer journeys: why true innovation requires integration beyond the top of the funnel.

3. Leveraging large language models (LLMs)

[11:48] Roby’s first reaction to LLMs: from confusion to realising their transformative potential.
 [15:37] The risks and rewards of LLMs—why hallucinations, security, and accuracy matter.
 [17:52] How hipages is using AI to streamline internal processes and customer interactions.

4. Scoring innovation and strategic execution

[19:47] Scaling the tech team and building a product-led culture from the ground up.
 [22:11] Internal scoring frameworks: how Roby weighs commercial value, customer impact, and long-term ROI.
 [24:57] Why not every idea has a direct revenue line—but some drive lasting retention and experience gains.

5. Advice to his younger self

[26:09] Network early, network often—the compounding power of shared founder experience.
 [28:56] Favourite books, podcasts, and frameworks that shaped Roby’s thinking, including The Hard Thing About Hard Things and Seven Powers.
[31:36] Why listening, learning, and structured strategy execution are key to scale.

6. Founder reflections and what’s next

[32:53] What Roby loves most about his job—from company-wide presentations to robust debates.
 [34:59] His least favourite part? The admin-heavy side of performance reviews.
 [38:48] The hardest part of scaling: capital management, making tough calls, and staying focused on long-term survival.
 [41:36] What’s next for hipages.

Where to find Roby Sharon-Zipser

•  Website: hipages.com.au
•  LinkedIn: Roby Sharon-Zipser

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In this episode of The Tech Trajectory Podcast, host Chris Davies sits down with Alex Young to explore the transformative role of mentorship in leadership and career development. As a mentor, industry fellow, and innovation leader, Alex shares insights on fostering meaningful mentor-mentee relationships, the importance of self-awareness, and how mentoring can shape not only individual careers but also entire organisations.

1. The power of mentorship in leadership

[02:06] The best mentoring advice Alex ever received and why indirect guidance is often the most impactful.
[03:16] Mentorship isn’t always formal—sometimes, the most valuable lessons come from small, casual conversations.
[05:28] Why Alex dedicates time to mentoring and how it has shaped his perspective as a leader.

2. Lessons from being both a mentor and a mentee

[08:20] How Alex’s first mentor influenced his approach to leadership and ethical decision-making.
[10:50] Why mentorship matters most at the start of a career—helping people who "don’t know what they don’t know."
[14:43] The importance of vulnerability in leadership and how sharing failures fosters a culture of learning.

3. The difference between mentorship and coaching

[19:56] Coaching vs. mentoring: What’s the difference? Coaching is goal-driven, while mentoring is an open-ended journey.
[23:08] What separates a great mentor from a good one—why real mentors care beyond structured sessions.
[27:16] The best mentees are open-minded, proactive, and committed to applying what they learn.

4. Future-proofing leadership in the age of AI

[33:36] How AI is shifting the value of technical skills, and why leadership is about human connection, creativity, and vision.
[36:33] Remote mentorship—how digital transformation has changed how we connect and learn.
[37:49] Where to start if you want to become a mentor, from university programs to startup accelerators.

5. The one piece of advice Alex would give his younger self

[30:11] Say “yes” more often—how taking chances can shape your career in unexpected ways.
[41:17] If mentorship could be summed up in one word, it would be "enriching"—for both mentor and mentee.

Where to find Alex Young

• LinkedIn: Alex Young

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In this episode of the Tech Trajectory, host Chris Davis sits down with Pete Cohen to explore the often-overlooked role of creativity in leadership. With a unique perspective bridging multiple disciplines, Pete shares insights on fostering innovation, balancing structure with creative freedom, and making room for unconventional ideas in high-pressure environments.

1. Creativity as a leadership skill

[03:36] Leadership is often associated with strategy and decision-making, but creativity plays a crucial role in navigating uncertainty and fostering innovation.
[04:05] Creativity in business and tech: “bringing something new into the world,” particularly in early-stage ideation.
[05:19] Great leaders balance vision and inspiration with collaboration, encouraging others to contribute creatively.

2. Real-world examples of creative leadership

[07:06] Pete recalls a telco project where shifting to platform-as-a-service (Heroku) allowed the team to move significantly faster—an unconventional decision that led to a project breakthrough.
[08:49] Creativity can often accelerate progress rather than slow it down, challenging the misconception that innovative thinking is inefficient.

3. The role of innovation in high-pressure environments

[11:52] Leaders must define what innovation means within their business—whether it’s transformative, sustaining, or efficiency-driven.
[14:08] Storytelling is key to maintaining stakeholder buy-in and momentum when testing new ideas.
[16:11] Encouraging teams to take creative risks requires creating a psychologically safe environment where failures are seen as learning opportunities rather than setbacks.

4. Lessons from music and psychology

[23:38] Pete draws parallels between leadership and music, emphasizing the importance of intuition, flow, and improvisation.
[24:13] Referencing Daniel Kahneman’s Thinking, Fast and Slow, he highlights the need to balance rapid, intuitive creativity with structured, methodical execution.
[27:19] Creativity can be cultivated by giving oneself space—whether through running, engaging in hobbies, or simply slowing down to allow ideas to surface naturally.

5. Building a culture of creativity in tech teams

[29:09] Unconventional methods, such as using physical artifacts like zines to document ideas, can unlock new perspectives in workshops and discussions.
[30:00] Leaders should facilitate open-ended problem-solving sessions rather than relying on pre-defined solutions.
[31:36] While music can inspire creativity, Pete prefers organic team interactions over background noise when fostering innovation.

Where to find Pete Cohen

• LinkedIn: Pete Cohen
• Music: Smith and Cohen (formerly Sodastream) – New album releasing this year!

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The world of tech is evolving at lightning speed, and behind every innovation is a human story worth telling.

The Tech Trajectory Podcast brings you raw, honest conversations with the founders, leaders and pioneers who aren’t just navigating change, they’re driving it. From bold ideas to hard-won lessons, we go beyond the buzzwords to uncover what it really takes to lead, build and stay ahead in today’s fast-moving world.

Hosted by Chris Davies and Kavita Kerwar, each episode dives into the grit, vision and breakthrough thinking shaping the future of tech.

If you’re a tech leader, innovator or just someone who loves to hear what’s next before it happens, hit follow and join us for the ride.

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