Software Sales Manager Jobs in Ontario (NOW HIRING)

As an Account Executive, you will sell contact centre software (CCaaS) together with SIP-based telephony and connectivity, delivered through the cloud, to contact centres in the utilities, retail, insurance, credit union, and financial institution sectors. You will primarily be selling to Director and VP-level buyers through to the C-suite, with roughly four influencers involved per deal. This role is 75% new business development and 25% account management in Year 1. You will build your own prospect lists and pipeline from a standing start; roughly half of your pipeline is self-prospected, with the remainder split between company-supplied lists and warm leads. This is a newly created position, an addition to a three-person sales team, reporting to the Director of Client Development & Partnerships. The territory is North America (Canada and the United States), with client concentration across Ontario province-wide and the United States. The base salary is $85,000 – $100,000 CAD, plus uncapped commissions.

COMPENSATION & BENEFITS

• Base salary: $85,000 – $100,000 CAD
• Year 1 OTE: $170,000 – $210,000 CAD
• Year 2 OTE: $150,000 – $225,000 CAD
• Commission structure: Uncapped and residual. Paid quarterly.
• A separate annual performance bonus is available (capped).
• Top performer earnings: $300,000 CAD, reached within one to two years.
• Health benefits (partially company paid)
• Laptop, cell phone, and expense account provided
• Mileage reimbursed per trip (no company vehicle or car allowance)
• 15 vacation days, 10 sick days, 5 personal days, with additional flexibility
• Employee recognition, gifts, and rewards program
• President's Club trip
• Full-time work from home
• Career path: Sales Manager → Director → VP, with advancement possible within two years

THE COMPANY & CULTURE

Our client was founded in approximately 2004 (22 years in business), is structured as a partnership, and is an established, mature company with steady revenue growth, and an average employee tenure of 5–10 years. Headquartered in Richmond Hill, Ontario, they employ 60 people company-wide, with 20 based locally. They sell, implement, and support contact centre software (CCaaS) together with their own SIP-based telephony and connectivity, delivered through the cloud, allowing clients to purchase software and connectivity from a single vendor and retain managed services after the sale. Their target markets are utilities, retail, insurance, credit unions, and financial institutions, primarily large businesses (100–999 employees) across Ontario and the United States. Client relationships typically run 10 to 20 years, and the company reports 98% client retention. The culture is family-oriented: a small, intimate, flat environment where anyone can speak directly to the executive team, and leadership explains the company's direction rather than directing day-to-day activity.

OFFICE LOCATION & SALES TERRITORY

• Head Office: Richmond Hill, Ontario, Canada
• Work arrangement: Fully remote (work from home), with an optional hotel-style office meet-up approximately once per month. No required office days.
• Sales territory: North America (Canada and the United States); client concentration is Ontario province-wide plus the United States. One rep covers the full territory.
• Overnight travel: Approximately 5–10% (roughly 1–2 trips per month), primarily to meet Genesys representatives or attend industry conferences
• Hours: Monday to Friday, 40 hours per week. No regularly scheduled evening or weekend client calls.

EXPERIENCE, BACKGROUND & EDUCATION REQUIREMENTS

• 5–15 years of B2B sales experience, hybrid inside and outside, consultative and relationship-led
• Must have carried long, multi-stakeholder sales cycles, built business cases, and created their own outbound pipeline
• Industry experience is preferred, not required. Telecom and contact-centre-software experience is the strongest fit; also transferable: cybersecurity, SaaS, CRM, infrastructure software, and other software sales backgrounds
• Experience selling to Director and VP-level buyers through to the C-suite, navigating roughly four influencers per deal
• An established book of business or professional network is an asset, though not a stated requirement
• No degree or formal education requirement
• No driver's licence or vehicle required
• Bilingualism is not required

TECHNICAL SKILLS

• CRM software (HubSpot or comparable) – Intermediate
• Microsoft PowerPoint – Intermediate
• Google Drive / Docs – Intermediate
• Microsoft Excel – Basic
• Microsoft Word – Basic
• Comfortable communicating over video, phone, and email; online product demos are not required

THE PRODUCT / SERVICE / SOLUTION

PROSPECTIVE CUSTOMERS / INDUSTRY FOCUS / DECISION MAKER(S)

• Industries: utilities, retail, insurance, credit unions, and financial institutions
• Company size: primarily large businesses (100–999 employees)
• Geography: Ontario province-wide and the United States
• Decision-makers: Director and VP-level buyers through to the C-suite; approximately four influencers are typically involved per deal

SALES CYCLE / ORDER VALUE / ACCOUNT SIZE

• Average sales cycle is approximately 12 months, with a typical range of 6 to 24 months depending on deal size
• Mid-market opportunities (roughly $125,000–$150,000) tend to close closer to 6 months; enterprise engagements typically run 12–24 months
• Target order size is approximately $250,000
• It typically takes 8–10 sales calls or visits after initial interest to reach a first order

COMPETITIVE ADVANTAGES

• One of very few vendors in the space that can sell both the software and the underlying telecom connectivity from a single source
• Deep specialization in this specific contact-centre-and-telecom niche, drawing clients who were previously oversold by a generalist provider
• 98% client retention, with relationships that commonly run 10 to 20 years
• Recurring, residual revenue model: account ownership continues after the initial sale, with upsell opportunities in usage, implementation, and additional users

TYPICAL DAY & DUTIES

• 75% New Business Development
• 25% Account Management

On a typical day you will build and manage your own prospect lists (the largest single time commitment in the role), run consistent outbound activity against those lists, and work to develop relationships within the Genesys partner channel. You will sell to multiple executive stakeholders, build the business case for long sales cycles, and, once an account is won, continue to own and grow it.

LEADS

• Approximately 50% self-prospected pipeline that you build yourself
• Approximately 25% from company-supplied lists
• Approximately 25% from warm leads supplied by the company

This is a new-business-focused role: you are expected to build your own funnel from a standing start rather than working from an existing territory book or inherited accounts. Lead flow can be uneven month to month, with some periods producing little and others producing several opportunities at once.

OVERNIGHT TRAVEL

• Approximately 5–10% (roughly 1–2 trips per month)
• Travel is primarily to meet Genesys representatives or attend industry conferences, not required for day-to-day selling

SUPPORT & TRAINING

• Approximately 60 hours of structured product training, delivered remotely over roughly 1.5 to 2 weeks with no requirement to be in the office
• A hands-on manager who joins customer calls, runs ride-alongs, and uses a lead-and-follow approach until you are comfortable running calls independently
• Solution engineers and consultants are available to support calls
• Selling activity begins after approximately two weeks of training; established pipeline is expected within roughly 3 months for a rep at the top of the base range, or 3 to 6 months for a rep at a lower base

WHY YOU SHOULD APPLY

• Uncapped, residual commission structure: earn ongoing trailer commissions for as long as an account you won continues to be invoiced and paid
• A genuinely hands-on manager who joins your calls, runs ride-alongs, and gives you a director in the room when you ask for one
• A small, flat, family-oriented culture where anyone can speak directly to the executive team
• An established, stable company: 98% client retention, relationships that typically run 10 to 20 years, and average employee tenure of 5 to 10 years
• Fully remote work, genuine flexibility once you are hitting your numbers, a President's Club trip, and a defined path to Sales Manager, Director, or VP

Equal 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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