How Tom Amos Built Sidekicker: Turning Real Frustrations Into an SMB Hiring Powerhouse

Solving a Real Problem: The Sidekicker Journey

In 2013, Tom Amos was juggling work at Deloitte, golf, and university. Like most busy people, he needed a hand with everyday tasks, a solution just wasn’t there. Yes, TaskRabbit in the US had some buzz, but the Australian market? Hardly touched. It wasn't only Tom's to-do list that suffered; in his consulting roles, he saw small businesses (SMBs) constantly struggle with unreliable temp agencies, slow recruitment, and too much paperwork. There had to be a better way.

From Personal Annoyance to Entrepreneurial Spark

For Tom, the pain was personal. Leaning on his mum for errands, staring at a never-ending workload, he often thought, “I’d pay someone to help right now.” At the same time, he watched SMB clients pinched for time and labor, forced to work with old-fashioned temp agencies they didn’t trust.

Seeing TaskRabbit open a door, Tom realized the bigger opportunity wasn’t helping individuals, it was solving temp staffing frustration inside businesses. He saw first-hand: small enterprises, events teams, hospitality venues all struggled to maintain agile teams. Traditional agencies took too long, cost too much, and didn’t understand speed. “They want someone yesterday, not after 50 resumes.”

Industry Knowledge, Not Just Data

Many founders bury themselves in data. Tom did his homework, but more than that, he’d worked among SMBs, run consulting gigs, and felt the pain personally. He didn’t approach the staffing market as an outsider trying to disrupt for disruption’s sake. Instead, he started with one question: what do these business owners hate about temp agencies? The answer came quick: time, trust, hassle.

He also noticed early that most existing agencies made things harder, extra fees, waiting around, generic candidates. Smart business owners want candidates who fit, and they want to decide quick. Tom knew SMBs didn’t want another layer; they wanted less. This is how Sidekicker started drawing up a plan to cut out the middle step, connecting business and temp worker directly online, in real-time.

Bringing Passion and New Energy

But there was an extra gear: Tom’s personal “thing” was empowerment. The staffing business felt old. Intermediaries made decisions, not the people doing the work or the ones hiring. Tom wanted Sidekicker to shake that up, to give individuals more control, more dignity, and a shot at flexible income.

“You’ve got two people that matter: the job poster and the person doing the job, ” he’d say. “Everything else just slows them down.” Sidekicker’s technology would make sure they connected, no gatekeepers, no bottlenecks. Tech would handle contracts, payments, verification – all the messy stuff people hate.

Taking the Leap, and Sticking It Out

Tom saw opportunities but was still holding back. It was a trip to Wellington, New Zealand, to work with a friend’s upstart beer company that tipped him forward. If his mate could do it, why not him? Back in Melbourne, he dove in one coffee at a time, each conversation pulled him further until turning back wasn’t an option. It became a full-time focus.

Turning the Plan Into Tech, and Results

Sidekicker wasn’t “the Uber for everything” at launch. The founders zeroed in: make hiring temps for SMBs as fast and painless as ordering food. Building that required bringing in serious tech skills, co-founder Jackie Ellis came aboard, and they teamed up with development agency Loud and Clear. Sidekicker launched with a clean, direct platform staffed with real, verified “Sidekicks.”

What mattered most: speed, reliability, and clarity. No endless job ads, just matched connections. Business owners loved skipping the hassle. Workers loved the flexibility and fewer middlemen. Sidekicker started with events and hospitality, fast-changing industries desperate for agility. The formula worked. Word-of-mouth fueled early traction. Revenue started climbing as repeat business picked up.

Evolving With Feedback and Opportunity

Sidekicker never stayed still. Tom’s biggest advice? “Don’t hold your idea too tightly.” As the company grew, new customer problems appeared: candidates rejected from gigs had no path to improve, businesses started asking for workers in new industries, Sidekicker had unexpected access to rich hiring data. A chance conversation at an industry event led Sidekicker to partner with training organizations, launching upskilling programs for the large pool of rejected applicants.

Adaptability stayed key. Sidekicker leaned into rapidly changing business needs, launching in new verticals (such as aged care and logistics), scaling up alongside market demand. All the while, technology allowed them to move faster and cheaper than traditional agencies, passing savings to businesses and staff alike.

Impact and Scale

Today, Sidekicker is a household name in the flexible staffing game for SMBs in Australia and New Zealand, with offices in Melbourne, Sydney, Auckland, and beyond. The team has grown above 135, supported tens of thousands of job seekers and serviced thousands of businesses, from fast food chains to hospitals. The company continues to invest in its platform, now using automated vetting, real-time performance ratings, and integrated compliance checks for Australia and New Zealand’s evolving labor laws.

On a rough day, Tom still points to his original “why”, empowering people and solving the problems he hated most. In a crowded market, it’s knowing (and caring) about your end user that keeps Sidekicker winning.

Key Principles for Success

• Don’t obsess over inventing something never seen before, some of the best businesses take a real problem and fix it better than anyone else.
• Get closer to customers than the incumbents. Know their day-to-day, not just what the numbers say. Real empathy always wins out.
• Keep moving, your initial vision is a launchpad, not a blueprint carved in stone.
• Let feedback guide your features, new verticals, and growth plan.
• Don’t let gatekeepers slow you down. Use technology to remove friction wherever possible.
• Build a mission others care about. If you care on the tough days, your team and your users will too.

Final Thought

Sidekicker isn’t just another tech startup. It’s a business that took the stale world of temp staffing, a sector full of negativity, and injected speed, transparency, and directness. Want to replicate their journey? Focus on a pain you know is real, listen (and react) to customers, and leverage tech for better, faster, and more human outcomes. Also, be ready to change course when a new, better solution appears. That’s how you’ll stick around the long haul.