Compensation Notice — Please Read Before Applying

This is a 100% commission-only independent contractor opportunity. There is no base salary, hourly wage, draw, retainer, sign-on bonus, employee benefits, equity or guaranteed income. Commission is earned only after eligible client payments have been received and cleared by Miles Ahead Hosting. Estimated earning potential is CAD $120,000–$250,000+, depending on closed revenue, deal size, client payment, sales activity, follow-up discipline, team performance, project margins and execution. This is not a guaranteed salary or guaranteed income range. Please apply only if you fully understand and are comfortable with a performance-based contractor opportunity.

About Miles Ahead Hosting

Miles Ahead Hosting is a Canadian digital infrastructure, technology, marketing and business-growth company. Our services include domain registration, business email, web hosting, website design and development, SEO, branding, social media marketing, digital advertising, custom applications, CRM systems, business automation, lead generation, sales infrastructure, website maintenance and ongoing digital support. We help businesses connect their brand, website, marketing, technology, operations and sales process into one stronger growth system. We already have existing customers, active opportunities, a sales team, marketing and creative support, CRM activity and thousands of generated business leads. We now need an experienced sales and commercial leader who can turn that activity into organized, consistent and paid revenue.

The Opportunity

The Head of Sales & Commercial Operations will lead the sales function, strengthen CRM and pipeline discipline, coach the team, improve conversion, support major closes and help build the company’s commercial and financial operating systems. This is not a title-only management position. You will operate as a player-coach: leading the team while remaining directly involved in qualification, discovery, proposals, negotiations, stalled opportunities and important closes. This role is suited to someone who understands B2B sales, high-ticket digital services, CRM discipline, sales forecasting, team accountability, proposal strategy and commercial decision-making. The goal is simple: turn leads, conversations, follow-ups, proposals and existing customer relationships into paid revenue.

What You Will Own

Lead, coach and organize SDRs, lead generators, appointment setters, account executives and closers Assess team performance and recommend training, reassignment, hiring or removal Ensure every viable lead has an owner, stage, value, notes, next action and follow-up date Run pipeline reviews, call reviews, sales training and individual coaching Improve outreach, qualification, discovery, follow-up, objection handling, proposals and closing Build a reliable handoff between lead generation and sales Personally support major, complex or stalled opportunities Create weekly forecasts and report paid revenue, pipeline, proposals, risks and next actions Review existing customer relationships for retention, hosting, SEO, marketing, CRM, automation, applications and account growth Coordinate with marketing, strategy, design, development and delivery teams Protect pricing, delivery capacity, project scope and commercial margins Build repeatable sales processes, scripts, call structures and follow-up systems Make sure strong leads do not sit untouched Create a sales culture where the team acts with ownership instead of waiting for direction

Commercial and Finance Responsibilities

You will help the Founder build and maintain practical commercial and financial systems, including: Project budgets and margin calculations Delivery, software and third-party cost tracking Pricing, discounts and payment schedules Invoice and payment-status tracking Accounts-receivable and collections follow-up Commission records and contributor splits A 13-week cash-flow forecast Revenue forecasting and management reporting Sales-tax reserve records Organized banking, incorporation, contract and compliance files Accountant-ready records for T2, GST/HST, PST and other applicable filings You will not be expected to act as the company’s accountant, lawyer or tax adviser. Your role is to maintain organized records, make the company’s commercial position visible, identify missing information and coordinate with the Founder, delivery team and qualified professionals.

Commission Structure

The standard commission pool is 25% of eligible client revenue after payment has been received and cleared. If you are the sole material sales contributor, you may be eligible for the full approved commission pool. When lead generators, appointment setters, account executives, closers or other contributors participate, you will determine the proposed internal split based on documented contribution. For projects above CAD $10,000, an enhanced commission pool of up to 35% may be proposed, subject to project margins and written Founder approval. There is no automatic leadership override on every team-generated deal. Commission participation must reflect documented involvement unless an additional written incentive has been approved. Commission terms, contributor splits and any enhanced commission pool must be agreed in writing before work begins.

First 30 Days

During your first month, you will be expected to: Audit the CRM, lead inventory, active proposals and overdue follow-ups Meet individually with current sales and lead-generation team members Assess each person’s activity, reliability, CRM discipline, strengths and best role Establish clear pipeline, reporting, meeting and follow-up standards Create a lead-prioritization and conversion plan Improve scripts, discovery questions, proposal flow and closing practices Personally engage important or stalled opportunities Review current customers for retention and expansion Identify immediate revenue opportunities from existing customers, warm leads and active proposals Begin building budget, invoice, collections, commission and cash-flow tracking Deliver a written 30-day report covering revenue, pipeline, team recommendations, commercial risks and the next 60-day plan

Must-Have Qualifications

Proven B2B sales leadership experience Experience managing, coaching and holding salespeople accountable Strong CRM, pipeline and forecasting discipline Experience personally closing complex or high-value deals Ability to build sales processes, playbooks and reporting systems Commercial understanding of pricing, costs, margins and payment structures Experience with budgeting, invoicing, commissions, collections or financial reporting Ability to work independently and make commercially sound decisions Comfortable working hands-on in a startup or growth-stage environment Fully comfortable with commission-only compensation Strong written and verbal communication Ability to work with founders, salespeople, marketers, designers, developers and delivery teams Experience selling websites, hosting, SEO, SaaS, applications, CRM systems, automation, marketing or related digital services is strongly preferred.

This Role Is Not For Someone Who

Needs guaranteed income Wants a title without direct involvement Avoids follow-up Does not update CRM Needs constant direction Cannot coach or hold salespeople accountable Is uncomfortable with commission-only compensation Talks about sales but does not drive revenue Only wants to manage from a distance Lets strong leads sit untouched Cannot work in a startup or growth-stage environment

Location and Working Arrangement

This opportunity is open to qualified candidates worldwide. The role is remote and can be performed from Canada or internationally, provided the contractor can communicate reliably, work independently, meet agreed standards and attend scheduled meetings when required. Candidates based in Metro Vancouver or on British Columbia’s Sunshine Coast may participate through a hybrid arrangement involving scheduled team meetings, customer meetings, planning sessions or business events. Daily office attendance is not required. The contractor will generally manage their own working methods and schedule, provide their own equipment and may serve other non-conflicting businesses. Availability is required for scheduled meetings, including some meetings within the 9:00 a.m.–1:00 p.m. Pacific Time collaboration window.

Why Join Miles Ahead Hosting

Existing customers and active opportunities already exist Thousands of business leads and prospects have already been generated Sales, marketing and creative support are already in place High-ticket digital services create strong commission upside Recent client opportunities have reached CAD $40,000+ Direct access to the Founder Remote worldwide opportunity Hybrid option for Metro Vancouver and Sunshine Coast candidates Opportunity to build the sales system, not just inherit one Potential to grow into a senior VP-level commercial leadership role as revenue and team structure scale

How to Apply

Please include: The largest sales team you have directly managed The largest deal you have personally sourced, closed or helped close Your experience with CRM, forecasting and pipeline management Your experience with budgets, margins, invoicing, commissions or commercial controls Your experience selling websites, hosting, SEO, SaaS, applications, CRM systems, automation, marketing or related digital services What you would audit and improve during your first 30 days Confirmation that you understand this is a commission-only contractor opportunity with no guaranteed income