Head of Sales / Revenue Operator — COMMISSION ONLY

Compensation Disclaimer — Please Read Before Applying This is a commission-only contractor role. There is no base salary, hourly pay, retainer, or guaranteed income at this stage. Compensation is earned from closed client revenue after client payment is received, based on agreed commission terms. Please only apply if you fully understand and are comfortable with a performance-based sales leadership role. Recent client opportunities have reached $40,000+, creating strong commission upside for the right person. Earnings depend on closed revenue, deal size, follow-up, team performance, and execution. About Miles Ahead Hosting Miles Ahead Hosting is a growing web hosting, website, SEO, app development, automation, and digital infrastructure company helping businesses build stronger online systems. We help entrepreneurs, service businesses, agencies, and growing companies improve their online presence, generate leads, build better systems, and scale with stronger digital infrastructure. We already have a sales team, active outreach, CRM activity, and lead generators who have produced thousands of leads and prospects. The opportunity is there. Now we need a strong sales leader/operator who can bring structure, accountability, training, and closing discipline to convert that activity into paid revenue. The Role We are hiring a Head of Sales / Revenue Operator to lead the sales team, train closers, manage pipeline discipline, and turn active opportunities into paid clients. This is a leadership role, but it is also hands-on. Our lead generation team has already generated thousands of leads and prospects, and the pipeline is active. The next stage is not finding opportunity — it is creating stronger sales leadership, better qualification, cleaner CRM activity, better follow-up, stronger proposals, and more closed clients. We do not need someone who only wants a title. We need someone who can lead from the front, create momentum, coach the team, manage follow-up, and help convert existing lead flow into real revenue. What You’ll Own You will own the sales function and help build a repeatable revenue system. Responsibilities include: Leading, training, and managing the sales team Coaching SDRs, appointment setters, and closers Improving outreach, discovery, follow-up, objection handling, and closing Making sure every lead has a clear owner, status, next action, and next follow-up date Keeping CRM activity clean, updated, and useful Reviewing active deals and moving them toward booked calls, proposals, invoices, and payments Creating sales scripts, call structures, proposal flows, and follow-up systems Helping prepare higher-value proposals and RFP-style outreach Protecting pricing floors and deal margins Building weekly sales forecasts Reporting active deals, projected revenue, and next actions Making sure no strong lead sits untouched Creating a sales culture where the team acts with ownership instead of waiting for direction What Success Looks Like Success means the sales team becomes trained, organized, accountable, and revenue-focused. Every lead should have: A clear owner A status A next action A next follow-up date CRM notes A clear path toward a booked call, proposal, invoice, or closed deal A close means the invoice is issued and payment is received. Everything before that is pipeline. The goal is simple: turn lead activity, conversations, follow-ups, proposals, and outreach into real paid clients. Who We’re Looking For We are looking for someone proactive, experienced, and commercially sharp. You may be a strong fit if you have experience in: B2B sales leadership High-ticket service sales Website, SEO, hosting, SaaS, app, or digital marketing sales Managing SDRs, appointment setters, or closers CRM and pipeline management Sales coaching and team accountability Proposal strategy Commission-based sales environments Startup or growth-stage sales operations This Role Is Not For Someone Who Wants a guaranteed salary Needs constant direction Only wants a title Avoids follow-up Does not update CRM Cannot train or hold people accountable Is uncomfortable with commission-only compensation Talks about sales but does not drive revenue Compensation This is a commission-only role. There is no base salary, hourly pay, retainer, or guaranteed income. Commission is paid from closed client revenue after client payment is received, based on agreed terms. Because Miles Ahead Hosting sells websites, hosting, SEO, apps, automation, and digital growth services, deal sizes can be meaningful. Recent client opportunities have reached $40,000+, creating strong earning potential for the right sales leader/operator. Why Join Miles Ahead Hosting Thousands of leads and prospects have already been generated Active pipeline and opportunities already exist Sales team is already in place High-ticket digital services with strong commission upside Opportunity to lead and train the sales team Direct access to the founder Remote flexibility Leadership opportunity as the company scales Real ability to shape sales systems, training, and revenue process Growth Potential This role can grow into a senior VP-level position as revenue, team structure, and sales systems scale. Right now, the company needs a hands-on Head of Sales / Revenue Operator who can lead the team, train closers, build discipline, and turn pipeline into paid clients. Application Questions Please answer the following when applying: Do you understand this is commission-only with no base salary, hourly pay, retainer, or guaranteed income? Are you comfortable leading a sales team in a performance-based role? What experience do you have leading or training salespeople? Have you sold websites, SEO, hosting, SaaS, apps, or digital services before? How would you improve a sales team that already has thousands of leads but needs stronger follow-up and closing discipline? What CRM systems or sales tools have you used? What size deals have you personally closed or helped a team close? How would you keep a sales team accountable without micromanaging? Are you available to start immediately or within the next 1–2 weeks?

The Head of Sales / Revenue Operator will lead the sales team, train closers, and manage pipeline discipline to convert active opportunities into paid clients. This role requires creating stronger sales leadership and better qualification processes.

Candidates should have experience in B2B sales leadership and high-ticket service sales, particularly in digital services like websites and SEO. The role is suited for proactive individuals who can manage and coach a sales team effectively.

Identified from the job description. Confirm important requirements above.

• B2B Sales Leadership
• High-Ticket Service Sales
• Website Sales
• SEO Sales
• Hosting Sales
• SaaS Sales
• App Sales
• Digital Marketing Sales
• CRM Management
• Pipeline Management
• Sales Coaching
• Team Accountability
• Proposal Strategy
• Commission-Based Sales
• Startup Operations
• Growth-Stage Sales Operations

• Sales
• Management & Leadership
• Technology

Minimum experience

5+ years

Posting language

English

Working hours

40 hours per week

Location requirements

Country, Canada

Application method

Direct apply is available