Founding Commercial Partner (Enterprise AE for B2B SaaS, Independent Incorporated Contractor)
Sales & Business Development Toronto, ON Contract Permanent Hybrid

Description
Digi Cosmos (operated by HealthCart Inc.) is a Canadian technology pioneer building the digital & AI transformation and governance ecosystem for SMEs, agencies, and consultancies. We fuse Digital Transformation, Growth, Governance, and Risk Intelligence to help organizations scale with algorithmic certainty, compliance execution, and auditable readiness.

DigiAudit AI Engine - Assesses digital maturity, identifies opportunities, prioritizes investments, and creates actionable Fortune 500-grade transformation roadmaps.

Smart RMOS - An AI-powered Governance Office as a Service that helps organizations manage the growing complexity of AI, privacy, compliance, technology, and digital risk.

Important: Digi Cosmos is currently a pre-revenue startup. Please review the qualifications carefully before applying to ensure your background aligns with our core needs and long-term vision.

About the Role
We have built the technology, methodology, and commercial foundation for an emerging AI and digital transformation business. We are now looking for an experienced commercial partner to help turn that foundation into a growing Canadian enterprise.

This is not a traditional sales job or a conventional salaried position. This is an opportunity to join an early-stage, pre-revenue startup as an independent Founding Commercial Partner - with uncapped commission upside, a performance-based equity opportunity, and the potential for a deeper long-term co-founder relationship.

There is no established Canadian sales machine waiting for you - you would help build it. You will identify the right ICP, open executive relationships, test positioning, develop partnerships, win early customers, and establish a repeatable commercial model across our digital transformation and AI governance portfolio.

Our growth trajectory is clear:

Key Responsibilities
As our Canadian Founding Commercial Partner , you will own the full commercial motion from the ground up:

Refine the Canadian Ideal Customer Profile (ICP) and market strategy

Identify and develop target accounts across Canada and the U.S.

Generate qualified, executive-level opportunities through outbound prospecting

Own the full sales cycle - from lead generation through to close

Build channel and referral partnerships

Lead discovery sessions, proposals, and negotiations

Close new business and secure collected revenue

Manage post-sales relationships and identify expansion opportunities

Convert early customers into referenceable accounts

Establish a repeatable Canadian Go-to-Market (GTM) model

Identify cross-portfolio opportunities across DigiAudit AI Engine and Smart RMOS

Provide market intelligence that informs product development and positioning

Digi Cosmos provides: technology platforms, product expertise, sales enablement, demonstrations, technical support, proposals, delivery capability, and founder-level support.

You bring: enterprise sales experience, commercial relationships, market access, and the ability to close.

What You'll Do — Measurable Outcomes
This engagement is measured against objective, contractually agreed performance outcomes - not time controls. Typical deliverables include:

Product Readiness - Rapidly learn our tools and services; be demo-ready from the outset

Pipeline Generation - Achieve a minimum number of qualified meetings per week (to be specified in the services agreement)

Opportunity Progression - Maintain pipeline value and advance deals through defined stages with accurate forecasting

Closed Revenue - Meet quota targets and close deals per the commission schedule

CRM Hygiene - Deliver timely, accurate CRM updates and sales documentation

Customer Engagement - Attend scheduled prospect and customer meetings; support onboarding and expansion as required

30-60-90 Day Success Plan
First 30 Days

Confirm our target ICP: $10M-$500M mid-market companies actively adopting AI and pursuing digital transformation

Develop a Canadian target-account universe

Identify decision-makers and potential introductions





Test positioning and messaging

Begin executive conversations

Generate and qualify opportunities

Establish a disciplined sales pipeline

Days 31-60

Develop channel and referral relationships

Conduct discovery meetings

Develop initial proposals and pilots

Advance qualified opportunities

Lead negotiations and overcome objections

Days 61-90

Build case studies and secure customer testimonials

Establish reference opportunities

Manage post-sales relationships and identify expansion potential

Build measurable Canadian pipeline

Identify the most repeatable GTM motion

Service Levels & Availability

You determine your own schedule and working methods

Reasonable availability during North American business hours for mutually pre-scheduled prospect and customer calls

Timely response to inbound qualified leads within agreed lead response timeframes

If unable to attend a scheduled meeting: provide timely notice, assist with rescheduling, and arrange an appropriate delegate

This Role Is Probably NOT For You If…

You are looking for a conventional salaried sales position

You have not managed a full enterprise sales cycle from lead generation through post-sales relationship management

You are primarily an appointment setter, lead generator, or relationship manager without solid closing experience

You require guaranteed income unrelated to commercial outcomes

You need a manager to direct your daily activities

You do not have meaningful enterprise relationships or market access

You are looking for a casual side project without measurable commercial commitment

You are uncomfortable joining a pre-revenue startup and helping create the market

Why Join Us

High-impact engagement with a fast-moving AI and digital transformation startup at the frontier of GRC and enterprise technology

Uncapped earning potential tied directly to your performance - the more you close, the more you earn

Full autonomy over how and when you deliver your services

Differentiated, AI-native products in a rapidly expanding market with genuine enterprise demand

Full sales enablement support - digital marketing assets, ICP lists, messaging frameworks, demo structure, and AI-native CRM access

A clear path to equity and leadership for exceptional partners who demonstrate sustained contribution and commitment

Commercial Package

$2,000/month professional-services retainer

Realistic $120,000 OTE in your first year

15% commission on qualifying revenue from opportunities you originate and successfully close

12% commission on qualifying revenue from Digi Cosmos-generated opportunities that you successfully close

Performance-based equity opportunity after the initial six-month period, subject to mutually agreed milestones and formal documentation

Potential long-term path to a Co-Founder / CRO-level relationship for an exceptional partner who demonstrates sustained contribution, leadership, and commitment

Equity is not granted automatically. It is earned through measurable contribution and continued alignment with the business.

The philosophy

Sustained contribution - equity opportunity.

Exceptional contribution + long-term commitment - potential Co-Founder relationship.

We are not looking for someone to simply sell two products. We are looking for someone who wants to help build the Canadian commercial engine for an emerging AI and digital transformation company, from first prospecting activity to closed revenue and long-term customer relationships.

Contractor Onboarding Requirements
To engage with Digi Cosmos, all contractors must:

Operate as an Independent Incorporated Business and invoice Digi Cosmos for services rendered

Use and maintain their own laptop, mobile, hardware equipment and high-speed internet connection

Maintain all required tax registrations,



insurance, and licenses ; be solely responsible for tax, CPP, EI, HST/GST, and all other statutory obligations.

Provide government-issued ID, proof of address , and verifiable proof of sales performance as part of onboarding.

Consent for a background check.

Perform all services professionally, ethically, and in positive faith , consistent with industry standards.

Review DigiAudit.ai and all provided product materials prior to commencing the engagement .

Legal, IP & Compliance

Independent Contractor Relationship: Nothing in this posting creates employment, partnership, or agency. Digi Cosmos will not control the contractor's methods, schedule, or tools.

Confidentiality & IP: The services agreement will include confidentiality and IP assignment provisions ensuring work product created under the engagement is assigned to Digi Cosmos, consistent with applicable law.

Non-Solicit / Non-Compete: Reasonable non-solicit and limited restrictive covenants may be included, subject to negotiation and applicable law.

NDA, Data Protection & Security: Contractors must comply with Digi Cosmos' reasonable privacy, security and data handling requirements when accessing customer or company data.

Background & References: Digi Cosmos may require references, identity verification, and proof of prior sales performance as part of onboarding.

Insurance & Indemnity: Contractors should maintain appropriate professional liability and cyber insurance where applicable; indemnity and limitation of liability clauses will be included in the services agreement.

Performance Management & Termination
To protect clients and ensure business continuity, the services agreement will include enforceable, contractor-safe remedies for non-performance or misconduct:

Objective performance metrics and a regular reporting cadence

Service Level & Reliability Clause: Repeated missed meetings, failure to meet agreed service levels, or conduct materially detrimental to Digi Cosmos' business constitutes a material breach

Remedies: Right to suspend commission payments, place payments on hold, require corrective action plans, or impose reasonable callbacks for fraudulent or materially negligent conduct where lawful

Termination: Digi Cosmos may suspend or terminate the engagement for material breach or sustained non-performance with short notice as specified in the services agreement (e.g., 7 days' notice for failure to meet agreed metrics; immediate termination for fraud or gross misconduct)

Dispute Resolution: Commercial dispute resolution process - negotiation, then mediation, then arbitration - as set out in the services agreement

LEGAL DISCLOSURES & DISCLAIMERS FOR APPLICANTS

Location : Remote within Toronto - prospects across Canada & the U.S.; travel in Toronto & GTA for client meetings as required.

Digi Cosmos is an equal opportunity organization. We welcome applications from diverse backgrounds and encourage all qualified contractors to apply.

By submitting an application for this position, you acknowledge and agree that:

The relationship resulting from a successful application will be that of an independent contractor and business-to-business vendor, not an employer-employee relationship.

You will not be covered by Ontario's Employment Standards Act (ESA), will not accrue vacation pay or overtime, and will not participate in employee benefit plans.

You are solely responsible for remitting your own income taxes, Canada Pension Plan (CPP) contributions, Employment Insurance (EI) premiums, and Workplace Safety and Insurance Board (WSIB) coverage or private equivalent.

In compliance with Ontario regulations, all candidates who participate in a formal interview for this posting will be notified of their final hiring status within 45 days of their interview.

AI SCREENING DISCLOSURE: In compliance with Ontario employment transparency standards, please note that this recruitment process uses an automated artificial intelligence (AI) screening tool to assist our team in reviewing, scoring, and sorting initial application submissions based on objective professional criteria. A human reviewer evaluates all shortlisted candidate profiles prior to final selection.

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📌 Sales & Business Development (Ontario)
🏢 Digi Cosmos
📍 Ontario