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Sydney Wingender

Tedy is a Lifestyle Spending Account that helps business owners boost hiring and retention by automating the implementation and management of lifestyle benefits.

We’re doing for lifestyle benefits what QuickBooks did for accounting by giving small businesses innovative ways to enhance their employer brand and maximize value for the employee, all the while keeping it budget-friendly.

Tell us about yourself?

I’ve done anything from speechwriting for federal politicians to coding an automated database for a research team and developing digital marketing strategies for big clients. I’m a Swiss Army Knife that stumbled upon a great team of cofounders with a great idea!

If you could go back in time a year or two, what piece of advice would you give yourself?

Execution is more important than the idea. Start building now, stay close to your users, and keep iterating.

What problem does your business solve?

Hiring and employee retention are harder than ever, especially for small businesses. Current solutions are either complex and expensive (group insurance) or have low perceived value by the employee (perks and rewards). Tedy’s Lifestyle Spending Account takes the best of both worlds.

What is the inspiration behind your business?

One of my co-founders was frustrated with how little group insurance was used by his employees – all the while having his premium raised by 30 per cent. Aside from basic group insurance (dental, disability and life insurance), why couldn’t the rest be put into an expense account that’s as easy as QuickBooks to implement?

What is your magic sauce?

We don’t take a commission on expenses. We used a monthly subscription model. Plus, amounts are charged in real-time: employers only pay for what employees actually spend.

What is the plan for the next 5 years? What do you want to achieve?

We want to become the de facto Employee Experience platform that manages flexible and traditional benefits and follows employees from one employer to another.

What is the biggest challenge you’ve faced so far?

Keeping up with the demand! We had to accelerate our product development in order to help our operations team.

How can people get involved?

You can sign up and start using Tedy today by visiting You can also reach us at