Why Evolution is Key for Startups - Kate Claringbold - Leading the Product

Why evolution is key for startups – Kate Claringbold, Sidekicker

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Kate Claringbold Leading the Product

Chief Product Officer for on-demand workforce startup Sidekicker, Kate Claringbold, explains why you have to evolve to meet the demands of your customer base.

Sidekicker is a curated, two-sided marketplace that works with more than a thousand businesses in Australia and New Zealand, allowing them to hire waiters, bar staff, promo staff and business administrators. At the 2016 Leading The Product conference, Kate Claringbold explained the backstory of Sidekicker and outlined how the business has evolved its strategy.

Kate explains the startups most likely to succeed are the ones that drastically change their plans along the way.

“It’s not about having the perfect vision from the beginning. It’s about everyone having the grit, the determination and the mindset to reach your goal.”

The Sidekicker story

The founders of Sidekicker saw a gap in the contingent workforce space (i.e. the people who do one-off jobs such as bartending events, taking on temporary contracts or even filling in for a receptionist). After some original pivots the company hit its stride in 2015, with employment website SEEK coming on board as an investor not long after.

The company’s clear focus was to achieve greater net revenue than its competitors by delivering a product that cost clients less and had minimal operational costs to run.

In the early days, Sidekicker’s main goal was to establish itself as a brand and earn the trust of its customers. From there, the business discovered that to maximise profits, certain types of jobs and workers made more sense than others. For example, Sidekicker came to focus on jobs that were between 4 – 8 hours, within a specific range of job requirements.

To become the most reliable short term worker platform, Sidekicker only accepts 100 out of 1000 applications from people wanting to be on its books as workers.

Lean Canvas

As Kate explains, Sidekicker’s path to product market fit wasn’t smooth. They used the lean canvas to help find product market fit.

“When finding product market fit,” says Kate, “you can brainstorm versions of the lean canvas. You can explore models and work through the ones that don’t work. This approach allows people to be wrong. There are so many decisions and moving parts that you can’t expect to get everything right from day one.”

Kate Claringbold Product Market Fit Iteration

Sidekicker uses the lean canvas to test out things until they find what works. “When things don’t work, it is simple to review the pieces of your puzzle and look at different combinations,” clarifies Kate.

Evolving the product

Once the product fit began to take shape, the next challenge for Sidekicker was scale, sales and marketing. With a small segment of the market nailed, it was time to expand.

To do this, Sidekicker had to continue its evolution, but also iron out ‘kinks’ in the hiring process.

One of these kinks included ‘defective jobs’, those which required intervention from the support team at Sidekicker before a workers was placed. 30% of jobs were initially ‘defective’. After 3 weeks of focusing on top issues Kate and the product team got it down to 22%. The end goal for Sidekicker is to only have a 5% rate of defective jobs.

Some examples that Kate shared of reducing defective jobs include:


Key problem: Workers pulling out at the last minute

Solution: Reminding workers via an SMS that they had a shift coming up and asking them to confirm attendance.

Result: Pullouts reduced by half

Tweak – A second text message to the worker reminding them to reply and confirm their intentions surrounding the job reduced pull-outs to just 1 in 100


Key problem: Filling jobs within 4 hours

Solution: The Sidekicker team starts contacting applicants after a job has been live for 3 hours to hustle along responses.

Result: This remains work in progress. Sidekicker has discovered that Sidekicks want a text for a job that is on that day. They want an email if it is next week. All this feedback has been valuable to improving the user experience for all.


Key problem: Businesses taking too long to choose applicants

Solution: Sidekicker has a campaign focused at educating the employee-seeking side of the market. It is also providing more engaging user profiles, complete with reviews from past employers to help businesses make decisions more rapidly.

Result – TBC!


Key problem: Getting workers onto the platform

Solution: Kate and her team gathered information from current Sidekickers about how they found out about the business. They realised referral from an existing ‘Sidekick’ was an indicator of good candidates. They also realised people in different metropolitan centres had different expectations of what the onboarding process should involve.
Result: Sidekick now uses different onboarding processes in Sydney, Melbourne and Auckland, to better suit the people who want to become Sidekicks.


Future challenges

The next round of obstacles that Sidekicker faces is improving the dynamic of their marketplace to create a faster, more efficient experience for employers as well as workers.

For anyone thinking of joining a startup, Kate’s advice is: “Be adaptable! Expect the product market fit journey to be a true experiment that requires you to be open to change.” 

kate claringbold
Leading the Product 2016 Sketch by Rebecca Jackson

About Kate Claringbold

Kate has spent the past six years in product management and product leadership positions, working at SEEK, SEEK Learning and now Sidekicker. Her diverse career has taken her all over the world, including Japan and Barcelona. Kate has launched startups and has also been instrumental in driving product growth and evolution.

Read more:

Driving your product management career – Victoria Butt, Parity Consulting

Creating value for customers – Dan Olsen, Author

Iterating a new product culture – Lucie McLean, BBC

Details are the difference – Ash Donaldson, Tobias & Tobias

Life after launch – Cameron Adams – Canva