Sidekick Training

What Sidekick Training does

Sidekick Training is a Canadian SaaS company headquartered in Milton, Ontario, that builds a live learning engagement platform designed to augment video conferencing — primarily Zoom — with gamification, structured event templates, and real-time engagement analytics for virtual, in-person, and hybrid training. The platform combines three components: the Sidekick Live Learning Platform (with feature modules branded as Playbooks, Games, and a Data Dashboard that surfaces a proprietary 'Learning Engagement Score' and Attendance Timeline), Sidekick Course Development (custom content authoring by Sidekick's Learning Experience Design team), and the Sidekick Facilitator Hero Program (train-the-trainer support). The technology is built on adult learning principles and is differentiated by click-of-a-button clonable event templates, embedded games such as Escape Rooms and Brick Breaker, and per-presenter analytics that surface participation, poll accuracy, and attendance patterns across live sessions.

The company monetizes through a two-tier subscription model: a Team tier at $99 per presenter per month (minimum 3 presenters, unlimited participants, monthly billing) with self-serve demo booking, and an Enterprise tier with custom pricing for deployments above 25 presenters sold via a sales-assisted quote motion. A Custom Learning Design professional-services stream supplements subscription revenue. Customer segments disclosed are mid-sized scale-ups without dedicated L&D resources (primary), nonprofits and volunteer organizations (Engineers of Tomorrow, Ontario Ethics Bowl, FIRST LEGO League, Haltech), EdTech companies (CPET Columbia, Littératout), sales enablement teams, and customer education programs (Hello Hair). GTM mixes PLG (free trial signup, Sidekick Challenge campaign) with event-driven demand generation (Collision 2022, innovation roundtables with Canadian government officials).

Founded in 2021 as a spin-off from Enable Education and officially launched in February 2022, Sidekick remains privately held with no disclosed institutional funding, no disclosed revenue, and a headcount in the 11-50 range. The leadership team is anchored by co-founders Ben Zimmer (CEO) and Amy Leask, who also founded Enable Education 16 years earlier and serve as the strategic content partner via a formalized December 2022 partnership. Reported customer outcomes include a 200% increase in volunteer participation for Engineers of Tomorrow and a 76-percentage-point jump in participant preparedness for the Ontario High School Ethics Bowl, supplying the load-bearing claims in the company's narrative around the $13,000-per-employee annual training waste problem.

Name

Sidekick Training

Legal name

Sidekick Training

Website

https://sidekicktraining.com

Company type

Private

Founded year

2022

Operating status

Operating

Headcount range

11–50 employees

Short description

Sidekick Training is a Canadian SaaS company that augments Zoom with gamification, structured event templates, and real-time engagement analytics to help mid-sized businesses, nonprofits, EdTech firms, and sales teams deliver live, hybrid, and virtual training without dedicated L&D staff.

Ownership category

akta.pro rank

Product category

Corporate Live Learning Platform

NAICS

Professional and Management Development Training (611430), Educational Support Services (61171)

SIC

Services-Educational Services (8200)

akta.pro primary industry

Training Delivery Services (Onsite/Virtual Instruction, Workshops, Coaching) (BPAEANAN)

akta.pro secondary industries

Training Delivery Providers (In-Person, Virtual, Train-the-Trainer) (BPACANAM), Train-the-Trainer & Instructor Enablement Services (BPAEANAL)

Keywords

• Virtual training platform
• Live learning software
• Learning engagement tools
• Gamified training solution
• Corporate learning platform

Headquarters

HQ city

Milton

HQ country

Canada

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Software

Cost components

Personnel, Technology or R&D, Marketing or Sales, Operations

Revenue model

1. SaaS Platform Subscription: Monthly subscription model with per-presenter pricing. Team tier at $99/presenter/month with minimum 3 presenters. Includes onboarding support, Learning Experience Design support, and unlimited participants. Enterprise tier offers custom pricing with >25 presenters and custom instructional design services.
2. Custom Learning Design Services: Professional services for transforming company content into engaging learning experiences. Includes needs analysis, upgrading learning materials (slides, worksheets, assessments), and facilitator support. Clients own and can reuse the end result.

Pricing tiers

Go-to-market motion3 records

Distribution channels4 records

Marketing channels6 records

Core offering

Sidekick Training is a SaaS learning engagement platform that augments video conferencing tools (primarily Zoom) with gamification, engagement features, and real-time data analytics for live virtual, in-person, and hybrid training events. The offering combines a self-serve software platform with optional course development and facilitator training services, enabling subject matter experts to deliver structured, repeatable learning experiences without dedicated L&D staff.

Product overview

Sidekick Training offers a unified live learning solution comprising the Sidekick Live Learning Platform as the core product, supplemented by Sidekick Course Development services and the Sidekick Facilitator Hero Program. The platform integrates with Zoom to transform it into a training-focused tool with gamification (Sidekick Games including brick breaker, escape room, and side scroller games), structured event templates (Sidekick Playbooks), and real-time analytics (Sidekick Data Dashboard featuring Learning Engagement Score and Attendance Score). Custom Learning Design services provide instructional design support for creating hybrid learning, workshops, and courses. The solution targets mid-sized businesses, nonprofits, EdTech companies, and sales organizations needing to scale training without dedicated L&D resources.

Differentiator

Problem solved

Functional benefit

Products and services

• Sidekick Live Learning Platform Core SaaS platform that pairs with Zoom to add gamification, engagement features (polls, quizzes, breakout groups, spinner), and real-time data analytics (Learning Engagement Score, Attendance Score) for live virtual training events. Sold on per-presenter monthly subscription to businesses and organizations running training programs.
• Sidekick Course Development Custom course development service where the Sidekick team builds new courses and virtual instructor-led workshops for clients using their existing content and subject matter expertise. Delivered alongside platform subscription, primarily to Enterprise tier customers.
• Sidekick Facilitator Hero Program Facilitator training program that provides pro-tips and support to help employees become effective trainers using the Sidekick platform, enabling subject matter experts to deliver high-quality training without prior instructional design experience.
• Custom Learning Design Learning Experience Design service for creating new hybrid learning programs, onboarding, workshops, courses, lunch + learns, and blended learning experiences. Includes needs analysis, upgrading of slides/worksheets/assessments, and first-event facilitator support. Clients own the end result and can reuse it.

Quantifiable outcome

• 200% increase in volunteer participation (Engineers of Tomorrow)
• +4 more outcomes

Named customers7 records

Segments5 records

Ideal customer profiles4 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration1 record

Feature7 records

Partnerships

One partnership is on record.

• Enable EducationcoreStrategic or Co-development Partner · 1 December 2022Sidekick Training and Enable Education became partners in digital learning. Sidekick pairs its live learning platform with Enable's 16 years of expertise in custom digital learning content - from games to augmented and virtual reality simulations. Enable provides custom course content development, learning experience design, and tools bridging gap between learning and doing. Founded by Ben Zimmer and Amy Leask who also co-founded Sidekick Training.

Scale indicators11 records

Recent moves7 records

Expansion highlights5 records

Direct peers

• Kahoot!: Kahoot! offers a gamified live learning and audience engagement platform used in classrooms and corporate training, with quizzes, polls, and leaderboards that overlap directly with Sidekick's Games and Playbooks features. Both target the same mid-market training buyer.
• Mentimeter: Mentimeter is an audience engagement platform for live presentations and training sessions, offering polls, quizzes, and interactive slides that closely mirror Sidekick's polling, spinner, and engagement features. It serves both education and corporate training buyers.
• Slido: Slido (owned by Cisco/Webex) provides Q&A, polling, and quizzes for meetings and training events, integrating natively with video conferencing platforms — a near-direct functional overlap with Sidekick's Zoom-augmented engagement layer.
• 360Learning: 360Learning is a collaborative learning platform for businesses that combines course authoring, in-session engagement, and analytics — competing with Sidekick for the same mid-market L&D buyer seeking faster, more interactive live training.
• Thought Industries: Thought Industries is a customer and partner education platform with strong live learning and engagement capabilities, directly overlapping Sidekick's Customer Education vertical use cases.

Broad incumbents

• Workramp: Workramp is an all-in-one LMS and training platform used by mid-market and enterprise sales and customer teams, with live training features that overlap Sidekick's Sales Enablement and Customer Education verticals but as part of a broader LMS suite.
• Lessonly by Seismic: Lessonly (now part of Seismic) is a sales training and enablement platform with interactive practice and lesson delivery that competes with Sidekick's Sales Enablement vertical but from a broader LMS-style product suite.
• Docebo: Docebo is a global enterprise LMS with growing live learning, AI, and engagement capabilities, competing with Sidekick at the high end of the mid-market and enterprise L&D segment from a much broader product footprint.

Emerging players

• Skilljar: Skilljar is a customer education platform with authoring and engagement tools aimed at SaaS companies — a partial overlap with Sidekick's Customer Education vertical, focused more on self-paced content but increasingly adding live features.
• Spekit: Spekit delivers just-in-time learning and enablement content surfaced inside sales and productivity tools, intersecting Sidekick's Sales Enablement and live training use cases from a content-distribution rather than live-session angle.

Market position

Strengths5 records

Weaknesses3 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

• YouTubeyoutube.com/channel/UCNz12j_8R8Hko_ni9YT2pOA
• LinkedInlinkedin.com/company/sidekick-training

Revenue estimate

Valuation estimate

Number of profiles

Profiles5 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Sidekick Training