Head of Sales & Commercial Operations — COMMISSION ONLY

Head of Sales & Commercial Operations — COMMISSION ONLY Compensation Disclaimer — Please Read Before Applying This is a 100% commission-only independent contractor role. There is: No base salary No hourly pay No guaranteed income No retainer No draw against commission No employee benefits No equity currently included Compensation is earned only from successfully closed business after the client has paid Miles Ahead Hosting. Commission terms, deal ownership, team splits, payment timing, and responsibilities will be agreed upon before work begins. The advertised earnings range is an estimate based on potential deal volume, commission structure, and higher-value opportunities. It is not guaranteed compensation. Recent opportunities have exceeded $40,000, creating meaningful commission potential for the right sales and commercial leader. Actual earnings will depend on closed revenue, collected payments, deal values, execution, follow-up, team performance, and individual contribution. Please apply only if you fully understand and are comfortable with a performance-based, commission-only leadership role. About Miles Ahead Hosting Miles Ahead Hosting is a growing digital infrastructure and technology company providing: Website design and development Web hosting and domain services Search engine optimization App development Automation systems CRM solutions Digital strategy Sales and marketing infrastructure We help entrepreneurs, service businesses, agencies, and growing companies build stronger digital systems, improve their online presence, generate opportunities, and scale more effectively. We already have a sales team, active outreach, CRM activity, existing prospects, and lead generators who have produced thousands of leads. The opportunity is already there. What we now need is a commercially sharp leader who can create structure, improve follow-up, train the team, manage deal economics, protect margins, and convert sales activity into collected revenue. The Role We are hiring a Head of Sales & Commercial Operations to lead the sales function and manage the commercial side of active opportunities. This is not a passive management role. You will be expected to lead from the front, work directly with salespeople and prospects, review deals, improve proposals, support major negotiations, manage CRM discipline, and help move opportunities from first contact through payment. You will also help ensure that deals are commercially sound. This includes reviewing pricing, protecting margins, recommending commission splits, tracking projected revenue, coordinating invoicing, and making sure opportunities have a clear path toward payment. This role does not replace an accountant, bookkeeper, or CFO. You will not be responsible for company tax filings, bookkeeping, payroll accounting, bank reconciliation, or formal financial reporting. Your financial responsibility will focus on the commercial side of sales and revenue. What You Will Own Sales Leadership Lead, train, coach, and manage the sales team Support SDRs, appointment setters, account executives, and closers Improve discovery calls, follow-up, qualification, objection handling, negotiation, and closing Conduct regular sales meetings and individual coaching sessions Review salesperson performance and recommend changes where necessary Help recruit, assess, onboard, and develop future sales team members Build a culture of ownership, accountability, urgency, and consistent follow-through Pipeline and CRM Management Ensure every lead has a clear owner Ensure every opportunity has an accurate status Set clear next actions and follow-up dates Keep CRM records, notes, deal values, and contact history updated Review active opportunities and stalled conversations Make sure qualified leads do not sit untouched Improve speed-to-lead and follow-up consistency Build clear movement from outreach to call, proposal, invoice, payment, and account handoff Closing and Deal Management Personally support or lead important sales conversations Help close higher-value website, SEO, hosting, app, automation, and digital infrastructure opportunities Review discovery notes before proposals are created Improve proposal structure and commercial positioning Support negotiations and objection handling Help determine when an opportunity is qualified, unqualified, active, stalled, or closed Ensure commitments made during the sales process are realistic and documented Commercial Operations Review deal pricing and proposed discounts Protect minimum pricing and healthy project margins Recommend commission splits between lead generators, setters, closers, and sales leadership Review whether proposed deals are commercially worthwhile Track pipeline value and weighted revenue forecasts Help prepare project budgets and commercial summaries Coordinate with leadership and delivery teams before major commitments are made Confirm that invoices are prepared and issued at the correct stage Follow up internally and commercially until client payment is received Identify upsell, renewal, hosting, maintenance, and recurring-revenue opportunities Improve visibility into projected revenue, collected revenue, commissions, and outstanding opportunities Sales Systems and Process Create and improve sales scripts Develop discovery-call structures Build qualification standards Improve follow-up sequences Create proposal and approval workflows Develop objection-handling guidance Establish weekly sales reporting Build practical sales forecasts Create repeatable processes that can scale as the company grows What Success Looks Like Success means the sales team becomes organized, trained, commercially responsible, and focused on collected revenue. Every opportunity should have: A clear owner An accurate CRM status A documented deal value Clear notes A next action A next follow-up date A defined decision-maker A clear path toward a call, proposal, invoice, payment, or closed-lost outcome A verbal commitment is not a closed deal. A signed proposal alone is not collected revenue. For internal reporting purposes, a successful close means the required agreement has been completed, the invoice has been issued, and the agreed client payment has been received. The overall objective is simple: Turn leads, conversations, meetings, proposals, and follow-up activity into profitable, collected revenue. Who We Are Looking For We are looking for someone proactive, experienced, commercially intelligent, and comfortable operating inside a growing company. You may be a strong fit if you have experience with: B2B sales leadership High-ticket service sales Website, SEO, hosting, SaaS, app, automation, or digital marketing sales Managing SDRs, appointment setters, account executives, or closers CRM and pipeline management Sales coaching and accountability Proposal development and negotiation Revenue forecasting Deal pricing and margin protection Commission-based sales environments Startup or growth-stage commercial operations Personally closing deals while also managing a team You should be comfortable making decisions, identifying problems, taking ownership, and communicating clearly with the founder, sales team, delivery team, and prospects. This Role Is Not Suitable for Someone Who Requires a guaranteed salary Is uncomfortable with commission-only compensation Needs constant direction Only wants a leadership title Avoids direct sales conversations Does not follow up consistently Refuses to update CRM records Cannot coach or hold salespeople accountable Discounts services without understanding margins Makes promises without confirming delivery requirements Focuses only on activity instead of collected revenue Expects to inherit a finished sales system Is unwilling to work hands-on during the company’s growth stage Compensation This is a 100% commission-only independent contractor opportunity. There is no base salary, hourly wage, guaranteed minimum income, draw, stipend, retainer, or employee benefits. Commission is paid only from successfully closed and collected client revenue, based on the agreed commission terms for each deal or sales arrangement. Commission may depend on: Who generated the opportunity Who qualified the prospect Who booked the meeting Who managed follow-up Who prepared or supported the proposal Who closed the deal The level of sales leadership involvement The final project value The project margin Whether the client payment has been received The Head of Sales & Commercial Operations may recommend commission splits for the sales team, subject to final company approval where required. Larger or more complex opportunities may use deal-specific commission terms. No commission is considered payable until the related client payment has been successfully received and cleared, unless a different written agreement has been approved. Why Join Miles Ahead Hosting Thousands of leads and prospects have already been generated Active opportunities and client relationships already exist A sales team is already in place The company offers higher-value digital and technology services You will have direct access to the founder You will have authority to improve sales structure and accountability You can help shape pricing, proposals, forecasting, CRM standards, and sales systems You will have the opportunity to train and develop the team The position is remote There is significant room to influence how the commercial function grows Strong performance can create meaningful commission upside Growth Potential This role can grow into a more senior commercial leadership position as revenue, recurring income, team structure, and internal systems develop. Potential future progression may include: Sales Director Commercial Director Vice President of Sales Vice President of Sales and Commercial Operations Chief Revenue Officer Progression will depend on actual performance, collected revenue, leadership ability, system development, team results, and company growth. There is no guarantee of a future salary, equity, executive title, or employment arrangement. Any future compensation or title changes would require a separate written agreement. Working Arrangement Applicants must be able to overlap consistently with the stated Pacific Time collaboration window. Preferred Skills Sales leadership B2B sales Sales strategy Commercial operations Revenue operations CRM management Pipeline management Sales training High-ticket closing Negotiation Proposal strategy Forecasting Margin protection Commission planning Account growth Client retention Website and digital-service sales SaaS or technology sales Startup sales operations Application Questions Please answer all of the following questions when applying: Do you fully understand that this is a 100% commission-only contractor role with no base salary, hourly pay, retainer, benefits, or guaranteed income? What experience do you have leading, training, and holding a sales team accountable? What size deals have you personally closed or helped a team close? What experience do you have reviewing pricing, discounts, project margins, and commercial terms? How would you decide whether a proposed deal is commercially worthwhile for the company? How would you manage commission splits between a lead generator, appointment setter, closer, and sales leader? How would you improve a sales team that already has thousands of leads but needs stronger CRM discipline, follow-up, forecasting, and closing performance? What CRM systems have you used, and are you available to start immediately or within the next one to two weeks? Applications that do not clearly confirm acceptance of the commission-only structure may not be considered.

The Head of Sales & Commercial Operations will lead the sales function and manage the commercial side of active opportunities, ensuring that deals are commercially sound and revenue is collected. This role involves direct engagement with salespeople and prospects, improving sales processes, and managing CRM discipline.

Candidates should have experience in B2B sales leadership, high-ticket service sales, and managing sales teams. They must be proactive, commercially intelligent, and comfortable in a commission-only environment.

Identified from the job description. Confirm important requirements above.

• Sales Leadership
• B2B Sales
• Sales Strategy
• Commercial Operations
• Revenue Operations
• CRM Management
• Pipeline Management
• Sales Training
• High-Ticket Closing
• Negotiation
• Proposal Strategy
• Forecasting
• Margin Protection
• Commission Planning
• Account Growth
• Client Retention

• 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