The role involves rebuilding and leading the sales function by personally prospecting, qualifying leads, and closing high-ticket digital service deals. The candidate will also be responsible for improving CRM discipline, training sales contributors, and establishing a repeatable sales process.

Requirements

Requires a hands-on sales leader with experience in B2B digital agency or SaaS sales who is comfortable in a commission-only startup environment. Must be able to work independently, manage a pipeline from imperfect data, and lead from the front without a base salary.

Experience

5 to 10 years

Working hours

40 hours per week

Job type

Contract
Full-time

Work arrangement

Remote OK

Skills

B2B Sales Leadership
High-Ticket Service Sales
Digital Agency Sales
CRM Management
Pipeline Management
Lead Qualification
Closing
Sales Coaching
Proposal Strategy
Revenue Forecasting
Objection Handling
Negotiation
SDR Management
Sales Process Development
Business Development
Digital Marketing Sales

Minimum pay

80000

Maximum pay

160000

Pay currency

CAD

Pay period

YEAR

Visa sponsorship

Not detected in the job text

Keywords

WordPress
Shopify
SEO
Web Hosting
Digital Marketing
SaaS
CRM
Lead Generation
B2B Sales
Revenue Operations
Pipeline Review
Commission Only
Startup
High-Ticket Sales
Business Automation
AI
Branding
Social Media
Discovery Calls
Sales Scripts

Original job description

Commission Only - Startup Environment - Hands-On Role Important Compensation and Role Disclaimer Please read this section carefully before applying. This is a 100% commission-only independent contractor role. There is: No base salary No hourly pay No monthly retainer No guaranteed income No paid training No employee benefits No guarantee that existing leads will close No guarantee that you will earn money during your first weeks or months Commission is earned only when a client signs, is invoiced and Miles Ahead Hosting receives cleared payment. Commission percentages and payment terms will be agreed upon in writing before you begin working on opportunities. You must be financially comfortable working without guaranteed income. This is not a salaried management position disguised as a commission role. It is a performance-based opportunity for someone who is prepared to personally sell, follow up, close deals and help rebuild the sales operation The Reality of the Opportunity Miles Ahead Hosting is a growing digital services company, but we are still building a consistent and dependable sales operation. There are team members supporting areas such as lead generation, outreach, marketing, proposals and business development. However, you should not expect to inherit a mature, fully trained or consistently performing sales department. Some leads may be older, cold, unqualified, incomplete or require significant follow-up. Thousands of contacts in a database do not automatically equal qualified opportunities or revenue. The sales process, CRM discipline, scripts, accountability and closing systems still require improvement. You will be expected to help fix that. About Miles Ahead Hosting Miles Ahead Hosting provides: Website design and development WordPress and Shopify solutions Web hosting and domains Search engine optimization Digital marketing Lead generation Branding and social media Custom applications CRM systems AI and business automation Ongoing website and technical support Our services can range from smaller website projects to larger digital systems, applications and growth engagements. Deal values can be meaningful, but larger deal values do not guarantee easy or immediate sales. The Role We are looking for a hands-on Head of Sales / Revenue Operator who can help rebuild, organize and lead the sales function. This is not a role for someone who only wants to supervise other people. You will be expected to: Personally contact and follow up with opportunities Participate in discovery calls Prepare and improve proposals Handle objections Negotiate and close business Help train and manage sales contributors Improve CRM organization Create accountability across the pipeline Report honestly on activity, opportunities and expected revenue Help determine which leads are worth pursuing Build a repeatable sales process from an imperfect starting point You must be willing to lead from the front. What You Will Be Walking Into The successful candidate should expect: A founder-led growing business A mixture of cold, warm and older leads Team members with different experience levels Processes that still need documentation and enforcement Opportunities that may require long follow-up periods Pressure to turn activity into collected revenue Direct communication with the founder The need to create structure rather than wait for it You will have room to improve the operation, but you will also be accountable for producing measurable progress. Responsibilities You will help take ownership of: Sales strategy and execution Lead assignment and ownership SDR, setter and closer accountability Outreach quality Lead qualification Discovery calls Proposal development Follow-up systems Objection handling Negotiation and closing CRM accuracy Sales scripts and call structures Pipeline reviews Revenue forecasting Invoice and payment follow-up coordination Protecting pricing and project margins Weekly reporting to the founder Every active opportunity should have: A clear owner An accurate status CRM notes A next action A follow-up date A realistic estimated value A clear path toward a call, proposal, invoice or payment A conversation is not a sale. A proposal is not a sale. A verbal commitment is not a sale. A deal is considered closed when the agreement is confirmed, the invoice is issued and payment is received. What Success Looks Like During the early stages, success means: Reviewing and cleaning the existing pipeline Identifying real opportunities Removing or deprioritizing poor-quality leads Establishing consistent follow-up Improving discovery and proposal quality Creating accountability across the team Personally helping move opportunities forward Producing clear and honest forecasts Converting opportunities into collected revenue The long-term goal is to create a dependable sales department that does not rely entirely on the founder. Who May Be a Strong Fit You may be suitable if you have experience with: B2B sales leadership High-ticket service sales Digital agency sales Website, SEO, hosting, SaaS or software sales Building sales systems in startups Personally closing deals Managing SDRs, appointment setters or closers CRM and pipeline management Sales coaching Proposal strategy Commission-based environments Working with imperfect systems and limited resources This Role Is Not Suitable for Someone Who Do not apply if you: Require guaranteed income Need a base salary to participate Only want a management title Do not want to make calls or personally sell Expect qualified appointments to simply appear on your calendar Believe a large lead list guarantees easy sales Avoid difficult follow-up Refuse to update the CRM Need constant direction Blame marketing, leads or other team members without proposing solutions Are uncomfortable working directly with a founder Leave roles quickly when results are not immediate Cannot work responsibly in a startup environment. Compensation This is a commission-only contractor opportunity. Commission is paid from collected client revenue according to written commission terms. Earnings will depend on: Your personal sales activity The quality and value of opportunities Your ability to qualify and close Deal size Client payment Follow-up consistency Team performance Execution It is possible to earn significant commission from larger projects. It is also possible to earn nothing if no paid business is closed. We will not present hypothetical commission as guaranteed income. Growth Opportunity The position can develop into a senior sales or revenue leadership role when the company has: Consistent collected revenue A dependable sales process Reliable forecasting A productive sales team Sustainable operating margins Future titles, compensation structures or salaried arrangements are not guaranteed and will depend on actual business performance. *Application Questions * Please answer every question clearly: Do you understand that this role has no salary, hourly pay, retainer or guaranteed income? Are you financially able to accept a commission-only role? Are you prepared to personally prospect, follow up, attend calls and close deals? Have you previously worked in an early-stage company with incomplete systems? What commission-only experience do you have? What websites, SEO, hosting, marketing, SaaS, software or digital services have you sold? What is the largest deal you have personally closed? How would you approach an existing database containing a mixture of cold, old and potentially qualified leads? How would you rebuild a sales team after several previous sales hires did not remain in the role? What CRM systems have you used? How would you hold remote salespeople accountable without micromanaging them? What would you aim to accomplish during your first 30 days? Are you available for regular collaboration between 9:00 AM and 1:00 PM Pacific Time? Are you available to begin immediately or within the next two weeks? By applying, you confirm that you have read and understood the compensation disclaimer and the current stage of the sales operation.

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Details last changed Sep 16, 2026. About these details

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