Overview
Head of Sales Jobs in Canada at Empowerists
About Citadelis
Citadelis – A brand of Empowerists is an AI-native managed IT and cybersecurity company serving professional services firms across Canada. We combine managed IT operations, 24/7 security monitoring, compliance support, and fractional vCISO/vCIO advisory under one integrated model.
The Opportunity
We are looking for a commercially strong sales leader who can build pipeline, close strategic deals, and help scale the business across Canada and USA. This is a hands-on role. You will own revenue generation, outbound motion, referral partnerships, and client acquisition while helping shape the long-term go-to-market strategy.
The right person is comfortable operating in growth-stage environments, building from zero, and leading from the front.
What You’ll Own
- Own and deliver new business revenue and pipeline targets
- Build pipeline across outbound, referral, networking, and partner-led channels
- Develop strategic relationships with referrals partners
- Lead the full sales cycle from prospecting and discovery through proposal, negotiation, and close
- Sell cybersecurity and managed services solutions in business and risk-impact language
- Target professional services firms across Canada, including legal, accounting, consulting, and PE-backed organizations
- Build structure across CRM management, pipeline visibility, forecasting, and reporting
- Work closely with technical teams during solution scoping and pre-sales conversations
- Represent Citadelis through industry events, webinars, networking forums, and executive discussions
- Help build scalable sales processes and support future team expansion
What Success Looks Like
- Strong outbound pipeline and referral ecosystem established within the first 90 days
- Early customer wins and repeatable sales rhythm established within the first 6 months
- Consistent ARR contribution and scalable GTM structure built within the first 12 months
- Expansion into broader commercial leadership responsibility as the business grows
What We’re Looking For
- Proven experience selling managed IT services, cybersecurity services, SaaS, or related B2B technology solutions
- Strong track record independently building pipeline and closing complex multi-stakeholder deals
- Experience operating within growth-stage or entrepreneurial business environments
- Ability to engage confidently with founders, CFOs, COOs, and senior decision-makers
- Strong commercial judgement and ability to position technical solutions through business value
- Excellent communication, relationship management, and negotiation skills
- High ownership mindset with strong execution capability
Preferred Experience
- Experience building or mentoring sales teams
- Exposure to cybersecurity, compliance, managed services, or consulting industries
- Existing relationships within Canadian professional services ecosystems
- Bilingual English/French capability
Why Join Citadelis
- Opportunity to help shape the commercial growth journey of a scaling business
- Direct exposure to leadership and strategic decision-making
- High ownership and visibility from day one
- Strong long-term growth potential as the organization expands
Title: Head of Sales
Company: Empowerists
Location: Canada