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Smile.io logo

Smile.io

Smile.io is a Kitchener company whose points, referral and VIP software runs loyalty programs for e-commerce merchants. Co-founder and CEO Mike Rossi told TechWaterloo in 2017 it was already powering about 20,000 reward programs. It launched under the name Sweet Tooth.

E-commerceKitchenersmile.io
~20,000reward programs on the platform — TechWaterloo stage 2017-09, a dated figureTechWaterloo stage 2017-10-31
5 → 18headcount over three years, as described on stage in 2017TechWaterloo stage 2017-10-31

The people

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Working at Smile.io

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On the TechWaterloo stage

Every talk is searchable — ask the archive about Smile.io

About

Smile.io grew up in Kitchener-Waterloo and sells loyalty software to online merchants — points, referrals and VIP tiers that sit on top of a store. Co-founder Mike Rossi took the TechWaterloo stage in September 2017, when the team had gone from five to ten to eighteen people in three years, and used the talk to explain how he made those hiring calls.

Backers

Not verified for this page.

Some figures are founder-stated, not independently confirmed

Quick answers

What does Smile.io do?

It builds loyalty and rewards software for e-commerce merchants — points, referral programs and VIP tiers — from Kitchener, Ontario.

Was Smile.io called something else?

Yes, Sweet Tooth. Rossi mentioned the earlier name on stage in 2017, noting that the designer who created their logo had joined as a remote hire.

How does Smile.io interview?

Rossi described a two-step process: a first conversation, then a live project run inside the company Slack, so the team can see how a candidate writes, responds and works before hiring.

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Maintained by TechTO · facts sourced and dated · last reviewed Jul 30, 2026