Founding Commercial Partner (Enterprise AE for B2B SaaS, Independent Incorporated Contractor)

Description

About Digi Cosmos

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.

Our Portfolio Includes Two Core Platforms

• 🔹 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.
  
  

🌐 Learn more at: DigiAudit.ai

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

Market Validation → First Customers → Repeatable GTM → Scale

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
• Close initial sales
  
  

Days 61–90

• Close 3–5 sales
• 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 strong 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
  
  

Requirements

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

• No contribution → no meaningful equity.
• Revenue → commission.
• 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 good 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
  
  

How to Apply

If you're a closer who thrives on autonomy and high-value enterprise deals — this is your arena.

Please apply on our portal & include with your resume:

• A brief cover note summarizing your recent enterprise deals closed
• A link to your business profile or corporate registration
• Verifiable examples of recent enterprise deals closed
  
  

Next Steps: Shortlisted applicants will be asked to complete an 'AE Assessment' online and provide documentation to verify identity and sales performance, and to execute a standard Independent Contractor Agreement and Performance & Reliability Addendum prior to commencing work.

LEGAL DISCLOSURES & DISCLAIMERS FOR APPLICANTS

• Governing Law Ontario, Canada
• 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.