B2B Sales Manager — Web, Marketing & AI Services — Commission-Only

Remote Worldwide | 100% Commission-Only | Immediate Start Important Compensation Disclosure This is a 100% commission-only independent contractor opportunity. There is: No base salary No hourly wage No retainer No guaranteed compensation No draw No benefits package No relocation package No equity included at this stage Commission is paid only after the customer’s payment has been received and cleared. Please apply only if you are genuinely comfortable leading and selling within a performance-based startup environment. About Miles Ahead Miles Ahead Hosting is building a full digital growth company supporting businesses from domain to sales. Our capabilities include: Domain registration and business email High-performance hosting Website and e-commerce development Custom applications SEO and local visibility Branding and social media Digital advertising CRM systems AI and business automation Lead generation Sales infrastructure Ongoing technical and growth support We work with businesses ranging from local companies and growing brands to larger organizations requiring websites, applications, automation, marketing and connected digital systems. Projects can range from focused website engagements starting around CA$2,000 to larger website, application, CRM, automation and digital-transformation opportunities valued at CA$10,000–CA$1,000,000+. The Opportunity We are looking for a hands-on Sales & Commercial Manager to help build, organize and lead the commercial function at Miles Ahead. This is broader than a traditional sales-management position. You will be responsible for bringing structure to the sales team while also helping manage the wider commercial process—from lead ownership and qualification through pricing, proposals, negotiation, payment and handoff to delivery. You will work directly with the Founder and CEO. This is not an advisory role, and it is not a position for someone who wants only a management title. You must be willing to operate inside the pipeline, support important conversations and help move opportunities toward collected revenue. What You Will Own Sales Leadership Coordinate and lead the remote sales team Assign leads and confirm clear opportunity ownership Run focused sales meetings and pipeline reviews Establish daily and weekly follow-up expectations Coach salespeople on discovery, qualification, objections and closing Support difficult or high-value opportunities Identify performance gaps and recommend corrective action Help recruit and onboard additional salespeople when required Pipeline and CRM Management Take ownership of Pipedrive discipline Review active, warm, stalled and unassigned opportunities Ensure every opportunity has an owner, stage, value, next action and next date Improve lead qualification and pipeline accuracy Remove duplicated, dead or unclear records Build reliable follow-up systems Produce clear weekly pipeline and revenue forecasts Commercial Management Help shape project scope before proposals are issued Coordinate pricing discussions with the Founder and delivery team Protect company margins and pricing floors Review commercial viability before commitments are made Support proposal development and negotiation Track proposals, invoices, payments and collected revenue Improve the transition from sales into project delivery Identify upsell, cross-sell and recurring-revenue opportunities Help develop partnerships and larger strategic accounts Connect sales activity with marketing, content and lead-generation campaigns Final approval of pricing, contracts, discounts, payment terms, major promises and compensation structures remains with the Founder and CEO. The Existing Team You will not be starting from zero. The current structure includes: Full-cycle sales closers Lead-generation support A substantial existing lead bank A Strategic Business Development Partner focused on relationship-led opportunities, partnerships and higher-value conversations A Brand, AI and Content-Led Growth Partner creating visibility, authority and warm business opportunities An established marketing and creative team Your First 30 Days Your first month will be focused on execution. You will be expected to: Meet the team and understand each person’s strengths. Audit the current sales pipeline. Confirm ownership of every viable opportunity. Review active, warm and stalled conversations. Clean and organize Pipedrive. Establish follow-up and reporting standards. Improve discovery and qualification. Support the closers with priority opportunities. Review how leads are assigned across the team. Connect marketing-generated opportunities to sales. Build a realistic weekly forecast. Identify immediate revenue opportunities. Recommend improvements to pricing, proposals and commercial workflow. Move credible opportunities toward proposals, invoices and payment. By the end of the first 30 days, Miles Ahead should have: A cleaner and more accurate pipeline Stronger lead ownership Better follow-up Clearer accountability More qualified conversations More opportunities moving toward proposals and payment A commercial process that can scale Who We Are Looking For You may be a strong fit if you: Have personally closed meaningful B2B revenue Have managed or coordinated a remote sales team Understand consultative and solution-based selling Can work directly with a founder Can bring structure without creating unnecessary bureaucracy Know how to manage a CRM properly Can coach salespeople while still participating in deals Understand pricing, margins and commercial risk Can turn warm interest into a structured sales process Communicate clearly and follow through consistently Are comfortable operating in an early-stage environment Can work reliably during Pacific Time business hours Are genuinely comfortable with commission-only compensation Direct experience selling one or more of the following is strongly preferred: Websites Hosting SEO Digital marketing Applications CRM systems SaaS AI automation Business automation Technology services Professional services Digital transformation This Role Is Not Suitable for Someone Who Requires guaranteed salary Wants only a leadership title Avoids direct selling Does not want to support closing Needs a finished corporate department Refuses to maintain CRM records Waits to be chased for updates Measures performance only by call or message volume Cannot overlap consistently with Pacific Time Is uncomfortable being accountable for commercial results Compensation This is a commission-only position with no fixed earning ceiling. Compensation may include approved commission on: Personally sourced and closed opportunities Founder-sourced opportunities you materially help advance or close Team-generated opportunities you directly support Eligible management overrides on collected team revenue Approved strategic or partnership opportunities Exact commission splits will depend on your role in each opportunity and must be confirmed in writing before the deal closes. All commissions are paid only after the customer’s payment has been received and cleared. Why Join Miles Ahead Miles Ahead is not positioning itself as only a hosting provider, web-design company or marketing agency. We are building one connected digital growth company: Domain → hosting → website or application → SEO → marketing → CRM → automation → follow-up → sales The right Sales & Commercial Manager will have the opportunity to help shape the company’s commercial operating system at an early stage and become a central leader as the business grows. This role offers significant autonomy, direct access to the Founder and the opportunity to build a sales function around meaningful digital-service opportunities. It also requires initiative, resilience, accountability and the ability to produce results without waiting for perfect conditions. Application Questions Are you genuinely comfortable with a 100% commission-only independent contractor structure, with no salary, hourly wage, retainer, draw or guaranteed compensation? What Pacific Time hours can you consistently work, and how quickly could you begin? What is the largest B2B deal you personally sourced and closed? Include the value, sales cycle, service sold and your direct role. What direct experience do you have selling websites, hosting, SEO, digital marketing, applications, CRM systems, AI automation or other high-ticket digital services? Describe a sales team or pipeline you inherited that lacked structure. What did you change, and what measurable result followed? How would you manage the full-cycle closers, a lead-generation specialist without creating confusion over ownership or commission? What CRM systems have you managed, and how would you enforce accurate stages, next actions, follow-up dates, proposal tracking and revenue forecasting? What experience do you have with pricing, proposals, negotiation, margin protection, contracts, invoicing and collecting payment before commissions are released? What is your understanding of working as an independent contractor for a Canadian company, including business invoicing, GST/HST where applicable, contractor classification, privacy, anti-spam rules and knowing when qualified Canadian advice is required? What would your first 14 days at Miles Ahead look like, and what specific improvements would you expect to have completed by the end of your first 30 days?

The Sales & Commercial Manager will lead the remote sales team, manage the sales pipeline, and oversee the commercial process from lead qualification to payment. This role requires direct involvement in sales activities and supporting the team to achieve revenue goals.

Candidates should have experience in closing B2B sales and managing remote sales teams, with a strong understanding of consultative selling and CRM systems. The role demands comfort with a commission-only structure and the ability to work during Pacific Time business hours.

• Project managementPreferred

Identified from the job description. Confirm important requirements above.

• B2B Sales
• Sales Management
• Consultative Selling
• CRM Management
• Lead Generation
• Negotiation
• Pipeline Management
• Coaching
• Digital Marketing
• SEO
• AI Automation
• Business Automation
• Project Management
• Commercial Management
• Team Coordination
• Performance Analysis

• Sales
• Management & Leadership
• Technology
• Marketing

Minimum experience

5+ years

Posting language

English

Working hours

40 hours per week

Location requirements

Country, Canada

Application method

Direct apply is available