As Director of Sales, you will own and drive the sales strategy for a boutique IT staffing and technical recruitment firm — selling permanent and contract IT talent placement to companies hiring technology professionals across Canada. This is a hands-on, player-coach leadership role, weighted toward leadership: you will lead from the front while still carrying a desk. Your personal desk is tilted toward customer success — expanding and re-activating the strong base of existing and dormant client relationships built since 2017 — alongside select net-new business, while a Business Development Representative owns net-new cold outreach under your direction. You will run Ontario like a region — a business within a business — owning the strategy, the system, and the full sales lifecycle, coaching and scaling the sales team, owning HubSpot, and partnering closely with marketing. You will sell to relationship-driven HR and talent acquisition leaders and to skeptical, time-poor C-suite technology executives. This senior leadership role reports directly to the Founder and CEO. The base salary is $100,000 – $120,000 CAD, plus a performance incentive.
COMPENSATION & BENEFITS
- $100,000 – $120,000 CAD base salary; final base depends on experience, leadership track record, and demonstrated new-business and account-growth results
- Year 1 OTE: $150,000 – $190,000 CAD (base plus variable at plan), tied to personal account growth and select net-new production plus overall sales-team results
- Performance incentive with accelerators and upside above OTE for over-achievement
- Company-paid health benefits
- Laptop and full work-from-home setup provided
- 15 vacation days, 5 sick days, 5 personal days, and your birthday off
- Quarterly in-person team events
- Employee recognition program
- Clear path to grow into a Head of Sales / VP of Sales role as the team and revenue scale
THE COMPANY & CULTURE
Our client was founded approximately eight years ago and is a privately owned, single-owner company. After building an established operating base, they are now in an active scaling phase, with annual revenue growth tracking between 75% and 100% and recent investment in brand, marketing, and HubSpot infrastructure. They are a team of six, based in the Greater Toronto Area, headquartered in Mississauga, Ontario.
The company is a boutique IT staffing firm that places permanent and contract technology talent for clients across Canada. They operate a high-touch, consultative, white-glove model — delivering small batches of curated candidates rather than high-volume resume submissions. They serve clients across retail, manufacturing, fintech, SaaS, edtech, hospitality, logistics, food and beverage, managed service providers, and IT consulting. Clients include Danby Appliances, Service Inspired Restaurants, First National Financial, Eckler Ltd, JIG Technologies, and Pearle Hospitality.
The culture is collaborative, agile, and entrepreneurial — a wears-many-hats start-up environment with low micromanagement. The team runs daily morning calls and holds quarterly in-person events. Leaders are accessible and open to feedback. This is not a fit for someone who wants to stay strictly in their lane.
OFFICE LOCATION & SALES TERRITORY
- Head office: Mississauga, Ontario, Canada
- Work arrangement: Fully remote (work from home); open to candidates across Canada — GTA-based is an asset given the team-leadership nature of the role and periodic in-person events, but is not required
- Territory: Canada-wide ownership of the outbound and account-growth strategy, with primary front-line ownership of Ontario while the CEO expands into new regions such as British Columbia
- This is primarily a desk-based leadership and selling role; occasional client-facing involvement may be expected as you lead from the front
- Hours: Monday to Friday, standard business hours, approximately 40 hours per week — no evening or weekend requirement
- Overnight travel: None — occasional travel only for quarterly team events
EXPERIENCE, BACKGROUND & EDUCATION REQUIREMENTS
- A career built through the ranks — progressing from BDR/SDR to Account Manager to sales leadership or team-lead, with each step earned through results
- A modern, consultative B2B sales background in IT, technology, SaaS, cybersecurity, managed services, software development, or enterprise software
- A proven, hands-on track record of personally winning and growing business — including expanding and re-activating existing and dormant client relationships, not only chasing cold net-new
- Demonstrated experience building and developing reps or a sales team — coaching, mentoring, and lifting performance
- Experience owning or materially shaping a sales strategy and process — building the engine, not just running someone else’s
- Technically literate — comfortable enough with IT concepts (infrastructure versus development roles, the software-development lifecycle) to assess client need and sell consultatively from the first call; a business-analyst-style mindset is sufficient — deep technical depth is not required
- HubSpot fluency — has personally built and optimized sequences, dashboards, reporting, and process; strong proficiency in another modern CRM is acceptable if HubSpot can be mastered quickly
- A marketing mindset or background is a strong asset
- Some exposure to enterprise selling and the RFP/RFQ process is a nice-to-have — the core audience is SMB
- Strong tenure and stability — ideally that progression within one organization or very few, showing commitment rather than job-hopping
- Self-driven and fully remote-capable
- Education: post-secondary preferred but not required — track record outweighs credentials
- A driver’s licence is not required for this role
TECHNICAL SKILLS
- HubSpot CRM — hands-on ownership: building and optimizing sequences, dashboards, reporting, pipeline hygiene, and team-wide adoption (current system of record)
- Modern sales-engagement, sequencing, and prospecting tools — including LinkedIn and AI-assisted prospecting
- Working familiarity with IT concepts — infrastructure versus development roles and the software-development lifecycle (SDLC) — sufficient for consultative discovery
- Standard proficiency in Microsoft Office required
THE PRODUCT / SERVICE / SOLUTION
- Permanent IT and technical placement services
- Contract IT and technical placement services
- A high-touch, consultative recruitment model delivering small batches of curated, vetted candidates rather than high-volume resume submissions
PROSPECTIVE CUSTOMERS / INDUSTRY FOCUS / DECISION MAKER(S)
- Companies hiring technology talent across retail, manufacturing, fintech, SaaS, edtech, hospitality, logistics, food and beverage, managed service providers, and IT consulting
- Account size: organizations with approximately $5M – $500M in annual revenue; the core audience is SMB, with select enterprise opportunities where they fit
- Customers are located Canada-wide, with primary front-line focus on Ontario
- Primary decision-makers: relationship-driven HR and talent acquisition leaders who buy on credibility, and skeptical, time-poor C-suite IT executives — Directors of IT, CTOs, and software hiring managers
SALES CYCLE / ORDER VALUE / ACCOUNT SIZE
- A typical engagement is 2 – 3 simultaneous roles per client; the range can run from 1 to 12 roles
- Target accounts carry approximately $5M – $500M in annual revenue
- The Director of Sales personally carries a desk tilted toward expanding existing and dormant accounts (customer success), plus select net-new business
- Success is measured on revenue grown from existing and dormant accounts and select net-new, a functioning and scaling sales engine, the development and output of the BDR and team, and the quality of the strategy and process you put in place
COMPETITIVE ADVANTAGES
- Specialization in IT and technology roles — not a generalist staffing firm
- Deep market intelligence in the technology talent market
- Hands-on, consultative engagement — clients work directly with a small, senior team
- A curated process built around quality of fit rather than transactional, high-volume submissions
- An established base of client relationships built since 2017, ready to be re-activated and grown
- A well-invested HubSpot stack and an engaged marketing partner driving inbound demand
TYPICAL DAY & DUTIES
- 30% Strategic Selling — account expansion and customer success across existing and dormant relationships, plus select net-new (the “player”)
- 30% Team Leadership, Coaching, and Mentoring — including directing the BDR on net-new outbound (the “coach”)
- 25% Sales Strategy, Process, and HubSpot Ownership
- 15% Marketing Partnership, Reporting, and Forecasting
On a typical day you will personally work your account base — re-activating dormant relationships and expanding active ones with creative, brand-led outreach — while coaching and directing the BDR on net-new prospecting. You will be the face of the brand on discovery calls, asking the right questions and building rapport, trust, and credibility. You will build and document repeatable process and cadences, own and optimize HubSpot, partner with the fractional CMO on the sales deck, discovery-call format, messaging and campaigns, and own pipeline management, forecasting, and reporting to the CEO.
LEADS
- Your personal desk is led by an established base of existing and dormant client relationships to re-activate and expand — relationship-led and creative, brand-led outreach (broad mass-blast campaigns have already been tried and exhausted by the team)
- Select net-new business that you choose to pursue personally
- Net-new cold outreach is owned by the BDR under your direction — you set the standard, build the prospecting craft, and coach hands-on
- Warm inbound leads generated by marketing through Google Ads, SEO, and the website
OVERNIGHT TRAVEL
- None for day-to-day work — this is a fully remote role
- Occasional travel only, approximately quarterly, for in-person team events
SUPPORT & TRAINING
- Direct partnership with, and support from, the Founder and CEO — who has personally carried front-line selling and will hand the function to you to own and scale
- A well-invested, HubSpot-based sales stack that serves as the center of the sales process
- Close collaboration with an experienced fractional CMO on messaging, the sales deck, the discovery-call format, and campaigns
- Daily morning team calls and a collaborative, low-micromanagement environment with accessible leadership
- Latitude to build the engine your way — you own the strategy, the system, and the team you scale around you
WHY YOU SHOULD APPLY
- Own and scale a sales function as a true player-coach — run a region like a business within a business and build something over the next 3 – 5 years
- A clear path to grow into a Head of Sales / VP of Sales role as the team and revenue scale
- Join a scaling company growing 75 – 100% year over year, with an established base of client relationships ready to be re-activated and grown
- Fully remote, work-from-home role open to candidates across Canada
- A well-invested, modern sales stack — HubSpot plus an engaged marketing partner driving inbound demand
- Accessible, hands-on leadership and a collaborative, entrepreneurial culture with low micromanagement
- Competitive base plus performance incentive, with accelerators and upside above OTE for over-achievement
E qual Opportunity Employer
Just Sales Jobs and our clients are equal opportunity employers. We do not discriminate. All candidates are evaluated solely on performance merit and organizational fit.
Not the Right Fit? We May Have Other Roles for You.
If this particular role isn’t the right match, we encourage you to browse our other open positions at https://justsalesjobs.ca/jobs-opening/ and apply for any that interest you. Our recruiters review every resume we receive — and if we have another role that could be a great fit for your background, we will reach out to you directly.
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