Interview featurePublished August 29, 20261 hr 50 min

The MikeyG Podcast Experience

The work after the job title

Tessa JamesFounder, HireGains

Portrait of Tessa James

Tessa James has spent more than two decades trying to understand why people flourish in some kinds of work and disappear inside others. Now, after a life shaped by grief, motherhood and repeated reinvention across three continents, she is building HireGains, an unproven marketplace for domain experts who want a role in the development of AI.

The ferry out of Tasmania takes all night. James remembers the crossing as rough and miserable, but discomfort was not the part that stayed with her. She was heading for Victoria with a university course due to begin in two weeks, rent already owed and $50 in her pocket. A friend had a room for her. Everything after that would have to be found.

On the far side of the Bass Strait, the reassuring version of her plan ended. James needed work, so she walked Melbourne restaurant streets and asked at one door after another. Thirty-six restaurants said no. The thirty-seventh manager said yes. She left with a job, an apron and a waiter's corkscrew, then sent her mother an email home with photos of the apron and corkscrew.

That conversion, from panic into proof, runs through James's life. Before she became an executive or founder, she learned to make confidence out of completed work. HireGains is a larger and riskier version of the same experiment. One restaurant job will not settle this question.

The story of Tessa James

A household governed by weather

James grew up on a sheep farm in Tasmania, where work did not begin at nine and stop at five. Her father worked according to the animals, crops and weather. A good year might mean a family drive to the coast. A bad one could cancel even that modest holiday. The farm made effort visible, but it also taught her that effort did not control every result.

Her afternoons were spent running through paddocks, riding four-wheel motorbikes and towing a tire on a chain until trouble arrived. Before boarding school filled her days with other children, she made stories, games and private adventures around the farm. Her creative life began in that empty space.

At eight, she found a stacked stereo in a magazine, circled it and fixed the page to the refrigerator. To pay for it, she bagged 1,000 sacks of sheep manure, earning a dollar for each. The stereo sat in the family living room for roughly 15 years, a bulky record of what wanting something could require.

Leaving the village

At 11, James left the farm for boarding school. Her family treated boarding as the route to opportunities unavailable locally. Some people in her primary school community saw her as abandoning the village for somewhere fancy. At school she found close friendships, structure and a rowing routine that put her on the water before dawn.

Then, as she entered the final two years of school, her father died suddenly. James was about 16. Grief detached her from classmates and forced questions about death and time into an age that had little room for them. She sought help from both a psychologist and a spiritual counselor. She also chose a university degree on the Australian mainland, one that her previous grades would not make easy to enter.

She studied with new intensity. At night she listened to music on a Walkman and pictured another life in detail: leaving the island, working, becoming her own person. She later recognized the ritual as a form of visualization. At the time it was less mystical. The imagined future gave her a direction when the present had lost its shape.

An apron in Melbourne

Melbourne supplied the practical education. James worked about 40 hours a week in restaurants while completing her psychology studies on top. She is careful not to turn that schedule into advice. She missed much of the student social life and eventually deferred her third year because she was exhausted. The pause worried her mother, who feared she might never return. James worked, saved and went back to finish.

The restaurant work was humbling and repetitive, but it also put her in contact with a new person every few minutes. She had to notice moods, absorb rudeness and keep functioning. More important, it revised her idea of a safety net. Before the move, home was the place she could return if she failed. After she paid her rent and stayed in school, the fallback mattered less. She had evidence that she could solve the next problem because she had solved one already.

The limits of a good assessment

James began university convinced that she would become a therapist. The support she received after her father's death had given the profession moral weight. A week observing therapy sessions changed the plan. She respected the work, which her sister does as a clinical psychologist, but wanted to influence more people at a different pace. Occupational psychology offered a route into the workplace, where adults spend so much of their time.

For about five years, she helped organizations assess whether people suited particular roles. The tools could measure preferences and compare them with a job's demands. They could not control for the manager, the culture or the daily environment awaiting a candidate. In her team's own formulation, the assessment captured only about 20 percent of the story. James moved into corporate recruitment because she wanted to understand the missing 80 percent, not because she believed a test could erase it.

Her instinct for systems appeared early. Faced with a process tracked on a whiteboard, she taught herself Microsoft Access and built a database. She lost track of time while making a clumsy process work better. That appetite carried her from Melbourne to London, then Switzerland, and into senior talent roles.

The silence after the title

By the time James was living in Switzerland, she held a senior role at a large healthcare company, traveled often and had two children under two. Maternity leave produced a rupture she had not expected. One week, a large job consumed her hours and made her necessary. The next, the organization continued without her. She loved her new family and still found the severance from work disorienting. Guilt made the conflict harder to admit.

The experience gave personal force to a problem she had studied professionally. A job can supply purpose, status, routine and proof of usefulness, then withdraw them at once. James sees the same injury in layoffs, especially the damage to confidence. Her response is not that work should matter less. It is that one employer should not carry the full weight of a self.

In 2019, after climbing as far as she wanted inside corporate life, she left without a settled destination. A manifesto for her consulting website argued for judging people by future potential, remote work and room for gig or fractional assignments. COVID later accelerated remote work, an event she had not predicted. She now thinks permanent jobs may give way to portfolios of outcomes and projects. It remains a forecast, not a settled fact.

A marketplace that still has to work

HireGains is James's attempt to turn those ideas into infrastructure. Domain experts in fields such as insurance, finance and law apply through the platform and complete an AI-led process about their experience. The system is intended to match them with companies developing AI, either for fractional assignments or permanent roles. Matching is meant to consider skills, interest and the conditions in which a person does good work.

The proposition is that specialized human knowledge can improve AI systems built for specialized industries. Participating experts can learn how those systems are developed and add another source of work. James believes lean AI-native companies will still need judgment, empathy and context. She admits the boundary is uncertain and machines may acquire capabilities she cannot imagine.

At the time of the interview, the technology was in final testing. James and her team were fixing bugs and preparing an MVP, not operating a proven marketplace. Recruiting experts has little value without companies ready to hire them, while companies will not stay if the right experts are absent. Broad marketing may build supply. Demand, she expects, will depend on the founders' relationships and advisory board.

James expected the first three to six months after launch to bring grunt work and uncertainty. Product-market fit had not been established. HireGains asks people to trust a new category of work while its founder tests the mechanism. Her career has prepared her to study the match. It cannot guarantee that a market will appear.

The person outside the work

James has been mentally composing a novel for much of her life and trying to write it for several years. The detail complicates the professional identity she describes. The founder and occupational psychologist are not the whole person. Neither are the mother, cross-border professional, farm child or executive. A portfolio life already exists inside her before her forecast for work comes true.

Near the end of the conversation, she describes entrepreneurship without romance: building something that may fail, giving it time that might otherwise belong to family and periodically wondering what she is doing. Reflection is how she keeps that strain from becoming amnesia. On the ferry, $50 and a restaurant job were enough to prove she could continue. HireGains offers no such clean proof yet. The open question is whether she can preserve the self she has assembled while waiting for the market to answer.

Source note. This feature was reported from the complete recorded conversation. Episode moments link to the original video at the cited timestamps.

Three ideas

What stays with you

  1. 01

    Confidence is often retrospective. One completed hard thing becomes evidence for attempting the next.

  2. 02

    A job can provide meaning without becoming the sole container for identity, income and usefulness.

  3. 03

    HireGains is a thesis under test. The matching idea matters only if expert supply and company demand arrive together.