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TYPE OF WORK
Full Time
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SALARY
N/A
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HOURS PER WEEK
40
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DATE UPDATED
Sep 18, 2026
Head of Sales – North America
Remote | Philippines-based | Full-time | North American business hours
We are looking for a Head of Sales – North America to work directly with our Founder and
help build a scalable sales organization.
This is a hands-on player-coach role. You will help shape the sales strategy, personally participate in selling, build outbound systems, recruit and coach the sales team, manage pipeline, and progressively take ownership of day-to-day sales execution.
You are not inheriting a mature sales department. You are helping build it.
What You’ll Own
• Develop and execute the sales strategy for Canada and the U.S.
• Refine our ideal customer profile, priority industries, and target segments
• Build and improve outbound prospecting systems
• Develop messaging, scripts,
• Participate directly in prospecting, discovery calls, proposals, negotiations, and closing
• Build strong CRM discipline, pipeline stages, KPIs, dashboards, and forecasting
• Recruit, onboard, coach, and manage SDRs, BDRs, AEs, and future sales hires
• Run pipeline reviews, call coaching, and performance management
• Establish quotas and sales incentives
• Improve conversion rates across the sales funnel
• Work closely with internal teams to ensure sales commitments are realistic and deliverable
• Progressively reduce dependence on founder-led sales
Who We’re Looking For: We care more about what you have actually built and sold than the titles you have held.
You should have:
• Proven experience selling B2B services into the U.S. and/or Canada
• Experience personally carrying and achieving quota
• Experience hiring and managing SDRs, BDRs, AEs, or full-cycle sales reps
• Experience building or materially improving an outbound sales motion
• Strong pipeline-generation experience
• Strong discovery, negotiation, objection-handling, and closing skills
• Experience managing CRM, KPIs, forecasting, and team performance
• Excellent written and spoken English
• Strong commercial judgment
• High ownership and accountability
• Comfort operating in an environment where the sales system is still being built Experience in BPO, outsourcing, professional services, managed services, SaaS, HR technology, agencies, or other B2B services is highly valuable.
This Role Is Not For You If
• You only want to manage an established sales team
• You rely primarily on inbound leads
• You are uncomfortable selling personally
• You have managed sales activity but never owned revenue
• You have never built or materially improved a sales process
• You prefer maintaining an existing system rather than creating one
We are looking for someone who can build, sell, coach, and lead. What Success Looks Like In your first 90 days, you should be able to:
• Learn the business, clients, pricing, and current sales motion
• Work alongside the Founder on active opportunities
• Refine ICPs and priority verticals
• Improve outbound messaging and sales processes
• Establish strong CRM discipline and reporting
• Begin generating qualified pipeline
• Build the initial sales hiring plan
Within 6–12 months, we expect you to:
• Build a repeatable outbound sales engine
• Recruit and manage a growing sales team
• Establish more predictable pipeline and forecasting
• Improve conversion rates
• Increase new client acquisition
• Establish clear team performance standards
• Progressively take ownership of day-to-day sales management
Compensation
This role includes a competitive Philippines-based base plus meaningful performance upside.
Target OTE: CAD $60,000–$75,000+ annually
Top performers: CAD $90,000+ potential
Performance compensation will be tied to measurable sales and team results.
The detailed compensation structure will be discussed with shortlisted candidates.
Working Hours
• This is a full-time remote role based in the Philippines.
• You must be available during significant North American business hours, primarily Eastern Time.
• Flexibility around prospect and client schedules is required.
Growth Opportunity
• This is an opportunity to build the sales organization, not simply join one. For the right person, there is a clear path toward increased executive responsibility and senior revenue leadership as the company scales.
How to Apply
Please use the following subject line:
ROCKSTAR HEAD OF SALES – [Your Full Name]
Then answer:
1. What experience do you have selling B2B services into the U.S. and/or Canada?
2. Tell us about a sales team or sales process you personally helped build. What
existed before, what did you change, and what measurable results did you produce?
Please be specific. We are most interested in what you have personally built, managed, and
improved.
