Trent Mankelow's CV, Extended Edition

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Hi, I'm Trent Mankelow. I grew up in Tauranga, decided at an early age that I wanted to be a programmer, studied Computer Science in Hamilton, and moved to Wellington after graduating.

I didn't last long as an employee of a large multinational, and instead ended up starting a usability consultancy with a friend. We started with observational research before moving into interaction and service design, spun out a separate SaaS business along the way, and were lucky enough to exit both. I spent time on the leadership teams at Vend (fast-growing SaaS), Trade Me (granddaddy of NZ's tech scene), and Summer of Tech (much-loved not-for-profit) before taking time out to spend more time with my kids. These days, I'm looking for the next thing to pour my energy into.

Chapter One · Tauranga to Wellington

1. Early career

1996–2002

I grew up on a farm in Tauranga and wanted to be a programmer from the age of 11. That took me to the University of Waikato for a computer science degree (where I first came across the field of human-computer interaction), and then straight to Wellington. I did my time as a C++ engineer at Unisys before escaping to co-found Last.co.nz, a startup doing last-minute deals that never quite got off the ground, despite 18 months of hard work. My first startup failure.

Chapter Two · The consultancy

2. Optimal Experience

2003–2014 · CEO, co-founder & director

In late 2002, my mate Sam and I reviewed the usability of a website called lawfuel.com. That review was the first project we completed under the banner of what would become Optimal Experience, a UX consultancy started with $5,000 my dad lent us.

We started out doing observational research—watching people interact with technology and finding the things that were confusing, annoying, and frustrating. Over the years, we increased the breadth of the research methods and became well known for interaction and service design.

Along the way, I felt like I had four distinct jobs: starting as a practitioner, then moving into sales, management, and then leadership, where I was ultimately responsible for the vision, values, and culture of the organisation.

We grew from two of us sharing a desk to 31 staff, three offices (Auckland, Wellington, Sydney), and 250+ of New Zealand's biggest organisations as clients.

I left in late 2012, almost 10 years to the day since our first usability review for lawfuel. I was restless and ready for something new.

PwC bought the business in 2014.

Chapter Three · The product company

3. Optimal Workshop

2007–present · co-founder

In late 2004, BNZ hired us to do a large scale card sorting project to help improve their online banking. At the time, our options were to do it in-person, ask participants to download some software, or use an online tool that didn't output the raw research data. So we built our own.

Two years later, we decided to spin out the card sorting tool from the consultancy and founded a SaaS business that helps user researchers like us understand how people find and make sense of information (through card sorting, tree testing, first-click testing and more).

Nineteen years on, participants from 150+ countries have completed studies on the platform, over 20 million research insights have been gathered, and the customer list includes Netflix, Apple, Lego, Uber, Tesco, HSBC and the NHS.

After bootstrapping the business (from 2006–2010 we channelled $648,693 of dividends across from the consulting business) we sold 60% to private equity in 2021 for $tens of millions ;-P.

Chapter Four · Getting fired

4. Vend

2013 · Chief Product Officer

In February 2013, I met with a guy with a mustache called Vaughan about a Chief Product Officer role at a company called Vend. Vend was an online point-of-sale SaaS business growing 10% month-on-month — and after stepping down as Optimal's CEO it sounded like a perfect gig for me. Plus it was based in Auckland and I was keen to get back there after an enjoyable couple of years setting up Optimal's Auckland office in 2005.

It was a hectic time. I joined as employee forty-something, we were sharing two bathrooms (one with a door that didn't lock), and the engineering team was suffering from frequent priority changes. I hit the ground running: grew the team by nine, led Vend's first acquisition, restructured the product organisation, introduced personas to underpin our product strategy, and earned a perfect 100% "Person I Report To" score in the Best Workplaces survey.

Then after nine months, I was abruptly fired. To this day, I can't even really tell you why (although I have a theory).

The good news is that I invested some money when I joined which returned 8x when Vend sold to Lightspeed in 2021. Yay, me.

Chapter Five · The big leagues

5. Trade Me

2014–2019 · Chief Product Officer, then Chief Customer Officer

Shortly after telling the CEO he shouldn't hire a Chief Product Officer, I got hired as Trade Me's inaugural Chief Product Officer. As it was awkwardly worded in the 2015 annual report, "Trent is responsible for making sure we build the right things, and make them great."

I was in the big leagues now: an officer of a $2.5B NZX/ASX-listed online marketplace and classifieds business with 464 staff and 800,000 visits a day.

As CPO, I managed a diverse 48-person team covering UX, design, mobile, business agility, product development, and BI, as well as having a dotted-line relationship with another 22 product managers who worked in the revenue-generating business units.

I set about building the product management practice, redesigned the homepage (23M page views a month), sponsored a $20M programme to redo the Trade Me mobile and website frontends, and chaired the internal monthly "board meetings" for the revenue-generating business units.

After a couple of years, as a result of a restructure at the exec level, I then took on the role as Chief Customer Officer. My remit changed to include customer support (11,000 contacts a week), Trust & Safety (who processed a suspicious-activity alert every 80 seconds on average), and Marketing & Comms (30-200 media mentions/week). All up, 127 people and an $11.4M budget, a step up from leading the Product function.

After four-and-a-half years I was ready to move on: the exec had stopped feeling like a team, and I felt like my best work had been in the first 18 months when I was the new guy. (Side note: probably the most impactful six words I ever said at Trade Me was early on when I commented in our all-hands that there were "too many dicks on the dancefloor," due to the all-male speaking line-up. My friend Ruth talked about it on the BraveUX podcast.)

“You are capable of doing big things, and you are inspiring to be around. When you joined Trade Me, I remember the enormous feeling of optimism and excitement you brought about the future... having vision, tackling hard problems, and building a team is a gift.”

Chapter Six · The give-back

6. Summer of Tech

2019–2023 · CEO, then Chair

After such a commercial gig, I wanted more of a give-back role, and Summer of Tech was the perfect fit: a not-for-profit that helps tech students launch their careers through internships. They needed someone to help cover the CEO's maternity leave, and my teams had been hiring their interns for over a decade.

It's hard to overstate how lean Summer of Tech was. During my time there, we had just 2.6 FTE employees (supported by two part-time interns, 21 ad hoc workers and 214 volunteers). Yet in 2019 alone, 4,800 people attended our in-person events, including skills workshops, career fairs, and practice interviews.

When COVID hit in 2020, I had to figure out how to run an events-based organisation without any in-person events. Somehow we held placements within 4% of the prior year.

It was supposed to be a one-year stint, but I ended up staying for two "seasons". By the time I left, placements had increased 45% to 352 interns, our sponsors had nearly doubled, and our financial situation was a lot more stable. I then chaired the board for another two years.

Chapter Seven · Now

7. Now

2021–Present · Director, investor, advisor

I deliberately left full-time work in 2021 to dial down my career and dial up the kids. Road patrol, camp dad, cross-country marshal, touch rugby coach, and running the school fair's silent auction (about $50k raised over three years, thanks for asking).

I haven't exactly been twiddling my thumbs, though.

I've run strategy workshops for service businesses across Melbourne, Auckland and Wellington, helping founders clarify their personal and business aspirations, align around a shared North Star, and define a path to get there.

In 2025, I helped develop a five-year strategy for the Samoa Business Hub on behalf of MFAT.

I also spent three years on the Creative HQ board. It felt like a nice full-circle moment, having been one of its first tenants back in 2002. I'm currently an independent director at Dot Loves Data, a data insights business owned by ANZ.

“QUOTE TBC”

Then there's the investing (a dozen early-stage startups across New Zealand, the US and UK), the writing (including Dear Sam, my Substack about retiring early), and the occasional speaking gig, most recently MCing the 2025 Startup World Cup.

I've mentored more than 15 founders and mid-career professionals and, together with some friends, launched the Wellington Startup Collective to help do it at scale.

How I can help

I'm looking for the next thing to pour my energy into: a juicy problem, a great team, something that stretches me, and the chance to make a real difference. I like breadth too - my time at Trade Me taught me that I can effectively lead functions where I'm not the expert.

Stuff I'm good at

Governance

I've been a director for more than 20 years, across private companies, not-for-profits, council-controlled organisations, giving me a well-rounded perspective on governance challenges. Mostly these were New Zealand boards, but one was the Chicago-based Usability Professionals' Association, and another was our Australian subsidiary (2008–14). I was also on the Optimal Workshop board for its first five years. I chaired Summer of Tech through COVID, ran a business model review as a director at Creative HQ, and sat on the exec side of the board table for four-and-a-half years at Trade Me, so I know what good reporting looks like from both directions. I have a reputation for asking unexpected questions.

Customer

I've spent my career improving digital and in-person customer experiences, from building websites as a software developer, through a decade as a user experience researcher (where I personally consulted to about 90 clients such as Air NZ, Te Papa, ACC, most of the banks) to running the customer function at Trade Me: the contact centre, Trust & Safety (2,000 police enquiries a year, and the only private organisation with a letter of intent with NZ Police), marketing, comms and UX. I was also the exec sponsor of Trade Me's company-wide NPS rollout, and created a company-wide fix-the-friction month called Customer Aroha (one team member deleted 74% of help content, fixed 16K broken links, and got a 71-point NPS boost on help).

Product

I was the inaugural CPO at Vend and Trade Me. I built both product management practices from scratch: frameworks, metrics, roadmap reviews, and a product council to keep everyone honest.

Leading high-performing teams

I've built and led teams small and large, from a two-person startup to a 127-person division, and scored 86% and 100% Kenexa scores along the way. I've also been on an exec team that wasn't a high-performing team at all (it wasn't even a team), which taught me just as much.

Culture change

As CCO at Trade Me, I ran an entire programme to grow the customer intimacy of the business. Before that, I got 22 dotted-line product managers to follow a new (scary!) process armed with nothing but my high-falutin title, a clear vision, and some patience. I presented both stories at conferences in Australia.

Entrepreneurial grit

I've mentored dozens of founders and mid-career leaders across Australia and NZ (at places like Xero and Atlassian), through programmes like CreativeHQ, Kōkiri and Te Pūtahitanga o Te Waipounamu (supporting Māori entrepreneurs), and via the Wellington Startup Collective. I even taught half-day "How to Think Like an Entrepreneur" workshops to 80+ staff at Trade Me.

Systems and practices

Everywhere I go I install operating systems: product councils and metrics frameworks (Trade Me), 90-day KPIs and manifesto (Vend), CRM pipelines and brand refresh (SoT). I created a formal mentoring programme that produced 6 of Trade Me's then-current PMs, and monthly Product Performance Reports that closed the loop between what we promised and what actually happened. I dragged our sales pipeline out of a pile of spreadsheets and into a proper CRM.

My skills

Strategy

I've owned overall strategy as a CEO twice, owned the product and design strategy at Vend, and helped set company-wide strategy at Trade Me. I regularly facilitate strategy offsites and 'North Star' sessions with founders, including one memorable away day where the founder concluded the right answer was to quit. Most recently, I worked on a five-year strategy for the Samoa Business Hub, commissioned by MFAT. I also ran Optimal Workshop's acquisition of a US competitor.

Hiring (and firing)

The calendar of 277 interview invites

I've run 277 interviews and hired many dozens of people, from interns on the Living Wage to executives on $260K. I've run grad recruitment programmes at two companies, led the restructures and redundancy processes that nobody enjoys but everybody remembers how you handled, and dealt with underperformers, personality clashes, and all the usual issues.

Marketing

At Optimal, I led our marketing efforts including writing dozens of newsletters to our 2,000 subscribers, and hosting our popular breakfast briefings. I ran Trade Me's 23-person central marketing team with a $5.4M budget, a remit that included a Facebook page with 342K followers (the top 0.3% of NZ pages).

Sales

I doubled revenue at Summer of Tech, built Optimal's client base to 250+ organisations, and made the Deloitte Fast 50 twice along the way. Through the GFC we grew 25% a year. Our client NPS at Optimal was +65.

Presenting

I've presented workshops, keynotes and conference talks in seven countries. I've been a podcast guest, a panelist more times than I can count, and an MC, most recently for the 2025 Startup World Cup. I've even been grilled by Kim Hill (you can still look it up).

Communication

I lead by writing: 132 weekly newsletters to my teams at Trade Me, and these days Dear Sam, my Substack about early retirement (50 posts and counting).

Community building

I've been building communities since high school. As a graduate, I co-founded Unlimited Potential for young IT professionals and I've founded another three professional networks since: the Usability Professionals' Association (UXPA) - I then spent 3 years on its international board as Director of Marketing & Comms, ProductTank in 2016, and Wellington Startup Collective in 2023. At Summer of Tech, our scale was such that we had to hire a stadium to run our events.

Industries I know

• Marketplaces and online classifieds e.g. Trade Me.
• SaaS e.g. Vend, Optimal Workshop (where 98%+ of revenue is offshore, a proper NZ export story).
• Consulting and professional services. Obviously I built and exited a services business, but I've since consulted to many others in Australia and New Zealand.
• Banking and financial services. 35% of Optimal's revenue was in financial services, with almost all of the major NZ banks as clients.
• Public sector. 20% of Optimal's revenue, and I have recent experience with MFAT.
• Startups and venture. Startups are my people. I'm a two-time exited founder, have invested in a dozen startups, was in the first cohort of the Creative HQ business incubator (and later on its board) and even had a short stint inside the corporate venturing arm of Spark. I also started the Wellington Startup Collective with some friends, a "no advice" format where founders share problems and former founders just tell stories. We even won the Startup of the Year in the 2006 Incubator Awards.
• Not-for-profit e.g. Summer of Tech.

Beyond work

Tramping and mountaineering. I usually complete 4–10 overnight tramps a year, mostly in New Zealand (although I did spend 12 days walking across Corsica with some friends in 2025). I've done a bit of mountaineering too.

Mountain biking. We are very spoilt in Wellington with the number and variety of trails. I occasionally enter races to keep the skills sharp, like the TransNZ (an epic multi-day enduro race), the Whaka50 (50km through Rotorua's famous trails), and of course, the Karapoti Classic (why is this a race?).

Home brewing. I enjoying brewing and have won 10 medals at the Aotearoa Homebrew Competition, including a couple of gold medals (for a Bière de Garde and an English Barleywine). I also started the South Coast Brew Club with some fellow gentle brewers in the neighbourhood.

DJing. I play mostly old-school hip hop with a sprinkling of drum and bass.

Family. I have two teenage kids and a friendly Burmese cat named Richard Parker.

Reading. Every year I read (or listen to) somewhere between 35 and 50 books, a mix of non-fiction and novels.

Board games. My partner and I play board games most Monday nights, and when she's not around I play a lot of solo Spirit Island, a challenging strategy game (500 hours and counting).

Trail running. I've recently started running again.