Original job description
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?
