Head Of Sales (founding Hire / Player - coach) - Remote Eligible

Head Of Sales

Location: Remote (Canada, preference for Ottawa or EST timezone) Type: Full-time

Compensation: OTE: $140K–$150K CAD with accelerators for overperformance, structured as a 50/50 base-to-variable split. Equity is also available for the right candidate, tied to proven success and scaling the sales function.

Reporting to: CEO / CTO, Co-founder

About ZeroTek

ZeroTek is a fast-growing SaaS platform that helps Managed Service Providers (MSPs) deliver secure, scalable Identity and Access Management solutions powered by Okta. We're employee-owned, profitable, and committed to remote work. Our partners rely on us to simplify and monetize IAM at scale — and we're just getting started. In 2024, the Ottawa Business Journal recognized ZeroTek as the 2nd fastest growing company in Ottawa.

Location & Work Environment

This is a fully remote role open to candidates in Canada. Some travel may be required for team meetups, channel events, or major conferences.

The Opportunity

This is ZeroTek's first dedicated sales hire. You'll build, sell, and lay the foundation for our sales function, with a path to grow into VP Sales.

To date, ZeroTek has grown successfully through referrals and inbound channels. Now we're ready to build and scale outbound capacity — creating a repeatable engine that accelerates growth and expands our MSP footprint.

While the title is Head of Sales, this is very much a player-coach role: you'll be prospecting, closing deals, testing outbound plays, and proving what repeatable sales looks like. This is not a volume play — you'll focus on quality over quantity, building strategic relationships with right-fit MSP partners who can scale with us long-term.

If you've been the first salesperson or a founder-AE before, and you want the thrill of building sales foundations with the upside of equity and leadership growth, this is the role.

Reporting:

Directly to the CEO. You'll also work closely with Partner Success and Technical Solutions teams, supported by RevOps.

What You'll Do

• Own the full sales cycle: prospect, cold-call, email, LinkedIn — get meetings and close MSP partners
• Hone our outbound messaging and test new plays until we find repeatability
• Partner with leadership to shape GTM, but drive outbound yourself without waiting on marketing leads
• Prove the model, then help us scale: document what works, hire the next reps, and build the function into a team
• Serve as the voice of sales: bring feedback on what lands, what stalls, and where we win to shape our GTM
• Leverage our sales tools — HubSpot Sales Enterprise, ZoomInfo, Arrows (sales rooms), and integrated workflows with Fellow AI Notetaker — to manage pipeline, engagement, and collaboration.

What We're Looking For

• 5–10 years in SaaS/IT sales, with hands-on prospecting experience
• Experience as a founding AE / first sales hire / player-coach in an early-stage company
• Comfortable with ambiguity: you'll be experimenting as much as you're closing
• Strong understanding of MSPs (bonus if you've sold into or through them before)
• Relentless drive — you're not afraid to pick up the phone, test ten new messages, and learn fast

Success in the First 6 Months

Our enablement model follows the principles of Training, Coaching, and Roleplay, with activities prioritized early and outcomes ramping over time. These KPIs reflect both leading and lagging indicators of AE success — they are ambitious goals we'll coach you toward, not sink-or-swim gates:

• New Partner Conversations per Week: Minimum of 10 net-new MSP conversations generated through outreach, resulting in 3 meetings per week and 1 identified ICP.
• Pipeline Coverage: Maintain at least 3x quota pipeline by Day 60.
• Demo-to-Opportunity Conversion Rate: 40%+.
• MSP Signups (Closed-Won): 3+ in the first 90 days.
• Referral Loops Activated: 1 new loop per month (Okta or MSP-sourced).
• CRM Hygiene & Process Adherence: Accurate and complete HubSpot records.
• Partner Handoff: 100% of closed MSPs transitioned to Partner Success.
• Time to First Closed-Won: Within first 45 days.

• By 90 days: Running consistent demos, closing new MSPs, and feeding insights back into the playbook.
• By 6 months: Driving repeatable outbound success and building sustainable pipeline coverage.

Our Company Values

At ZeroTek, our culture drives everything we do. We live these values daily with our team and our partners:

• Ownership & Trust – We act with fairness, transparency, accountability, and build lasting trust.
• Fast, Smart, & Exceptional – We learn continuously, move quickly, think intelligently, and hold ourselves to high standards.
• Customer-First Partnership – We prioritize our partners' success with helpful, flexible, cost-effective solutions.
• Hardworking, Authentic & Fun – We work hard but bring approachability and a sense of fun to make collaboration rewarding.
• Learn, Grow, Adapt – We embrace change, encourage new ideas, and create opportunities for growth and improvement.

Why Join ZeroTek

• Founding role: You'll shape the DNA of our sales org
• Equity upside: If you prove the model and grow it, you'll scale into a Head of Sales / VP role with meaningful ownership
• Early-stage comp model with meaningful equity: ~$140K–$150K OTE to start (50/50 base-variable split) with upside to grow into $200K+ OTE as the team scales
• Impact: Your fingerprints will be on every playbook, every process, and every deal in our next phase of growth
• Ownership mentality: we're building something meaningful, and everyone plays a part
• Modern tech stack to empower high-impact work
• Direct mentorship from the CEO and exposure to executive-level decision-making
• A seat on the rocket ship — buckle up!