Head of Revenue & Business Operations — 100% Commission-Only

IMPORTANT COMPENSATION DISCLOSURE — READ BEFORE APPLYING

This is a 100% commission-only independent contractor opportunity. There is no salary, hourly wage, retainer, draw or guaranteed compensation. Commissions are paid only after the client’s payment has cleared. If you require guaranteed income, please do not apply.

Standard commissions generally range from 10% to 25% of collected deal value, depending on your sourcing, qualification and closing contribution.

For projects with an approved client budget above CA$25,000, commission may exceed 25% when:

You personally sourced and materially contributed to closing the opportunity.
The project’s delivery costs and approved profit margin support the higher rate.
The enhanced commission is documented in writing before the client accepts the proposal.

A commission above 25% is negotiated individually and is not guaranteed.

About Miles Ahead Hosting

Miles Ahead Hosting Inc. is a Canadian digital solutions company helping businesses move from domain to sales.

Our services include domains, professional email, high-performance hosting, websites, e-commerce, custom applications, SEO, digital marketing, CRM systems, AI automation, lead generation and sales infrastructure.

We are rebuilding our commercial operation and need a hands-on revenue leader who can create structure while personally generating and closing business.

The Role

This is not a passive management or title-only position.

You will own revenue execution and business operations while working directly with the Founder. You must be equally comfortable selling, managing a pipeline, improving processes and keeping business records organized.

A successful person may eventually be considered for a Chief Revenue Officer position as Miles Ahead grows, but progression will depend entirely on measurable performance.

Responsibilities

• Personally source, qualify and close B2B opportunities.
• Sell websites, hosting, SEO, marketing, applications, CRM and AI automation services.
• Lead discovery calls, proposals, negotiations and payment discussions.
• Manage lead-generation contributors, closers and assigned salespeople.
• Maintain accurate opportunities, stages, values and next actions in Pipedrive.
• Produce reliable weekly pipeline and collected-revenue forecasts.
• Establish clear deal-ownership and commission rules.
• Protect pricing, project margins and scope.
• Track proposals, contracts, invoices, deposits, outstanding payments and commissions.
• Coordinate client handoffs between sales and technical delivery.
• Organize receipts, agreements and transaction records so the company remains audit-ready.
• Maintain a calendar for GST/HST, corporate filings, renewals and other business deadlines.
• Coordinate accounting, tax and legal matters with qualified Canadian professionals.
• Support future U.S. expansion—including potential operations or registration in Florida and Texas—by coordinating with qualified Canadian and U.S. tax and legal advisors.
• Work with marketing to improve lead quality, messaging and conversion.

You will not be expected to provide legal or tax advice unless you hold the required professional qualifications. Your responsibility is ensuring records, deadlines and professional coordination do not fall through the cracks.

Requirements

• At least five years of B2B sales, revenue operations or business operations experience.
• Verifiable experience personally sourcing and closing digital-service or technology deals.
• Experience managing salespeople, closers or lead-generation contributors.
• Strong knowledge of Pipedrive, HubSpot, GoHighLevel or a comparable CRM.
• Experience with proposals, pricing, negotiation, invoicing and payment collection.
• Familiarity with bookkeeping workflows and tools such as QuickBooks.
• Ability to maintain confidential, accurate and audit-ready business records.
• Strong spoken and written English.
• Consistent overlap with Pacific Time business hours.
• Comfortable working directly with the Founder in an early-stage environment.
• Able to begin quickly and produce measurable results.

First 90 Days

You will be expected to:

• Audit and organize the active sales pipeline.
• Identify and reactivate the strongest warm opportunities.
• Implement clear deal-ownership and follow-up standards.
• Establish accurate weekly revenue forecasting.
• Personally generate and close new opportunities.
• Organize proposal, invoice, payment and commission tracking.
• Build an audit-ready records and compliance system.
• Create a practical plan for future Canadian and U.S. business requirements.

This Role Is Not Suitable If You

• Require guaranteed compensation.
• Want only a leadership title without personally selling.
• Avoid cold outreach, discovery calls, negotiation or closing.
• Do not consistently update CRM records.
• Are uncomfortable with direct accountability for collected revenue.
• Cannot reliably overlap with Pacific Time.

To apply, provide specific and verifiable examples of deals you personally sourced and closed, revenue systems you improved and teams you managed.