Sales Manager – Commercial Expansion Lead Confidential Software Enterprise | Fully Remote (U.S. & Canada) Comp: $160,000++ Base | $50,000+ Bonus (Uncapped Upside) | Exceptional Benefits

The Chance: Build the Machine, Don't Just Run It

Most software sales roles force a trade-off: join an unproven startup with zero pipeline and high burn, or take a seat at a mature corporate giant maintaining a tired territory.

This is the rare third option. We are a highly stable enterprise operating for over 40 years. We’ve spent the last several years secretly building and perfecting a next-generation, cloud-based ERP and integrated business operations platform. The software solves legacy issues faced by all other competitors in the market it serves. The technology is unmatched and places far ahead of any other user platform for features, user interface and functionality not available in any other product. You will inherit an established customer base, active relationships, and warm, inbound demand from existing accounts eager for this upgrade / launch. Your job is to convert that initial momentum into closed business, chart the go-to-market playbook, and expand into an untapped blue-ocean market.

What Makes This Role Different

- Warm Runway: No cold territory, no blank CRM. You’ll begin with warm prospects, existing accounts, and warm leads ready for conversion.
- Blue-Ocean Potential: You won't fight for scraps in an over-saturated market. You will introduce a differentiated solution backed by 40 years of vertical expertise.
- Unmatched Autonomy: Report directly to executive leadership. As head of the sales group, you will shape our sales messaging,



discovery framework, objection handling, and pricing structures.
- Upward Trajectory: As you establish a repeatable sales engine, you will have the first right of refusal to build and lead the expanded sales team.

The Platform You’ll Sell

A sophisticated, next-generation SaaS platform designed to streamline complex administrative, financial, and multi-entity operations. It unifies:

- Financial management, automated accounting, and bank reconciliation
- Multi-entity consolidation and automated workflows
- Integrated payroll and HR operations
- Real-time executive reporting and cloud-based visibility

This product is fully built, market-tested, and supported by a robust implementation and technical infrastructure. You don't need to sell roadmap promises—the solution exists, and the demand is already present.

Your First-Year Objectives

- Convert Momentum: Work through warm accounts and existing relationships to secure early wins.
- Own the Cycle: Manage complex, value-driven sales cycles end-to-end—from deep discovery and executive demos to final negotiations and closing.
- Scale the Footprint: Drive net-current customer acquisition across the North American market, targeting ‘X’ new customer closes in Year 1.




- Establish the Playbook: Codify the commercial sales process, document market feedback, and optimize the buyer’s journey for future team expansion.

Who You Are

- Proven Closer: 5+ years of direct SaaS, ERP, or enterprise business software sales experience with a documented track record of exceeding quota.
- Consultative Strategist: You uncover core business pains rather than feature-dumping. You navigate multi-stakeholder deals, handle complex objections, and sell on business value.
- Self-Directed Builder: You thrive when given ownership. You prefer autonomy, high visibility, and direct influence over your trajectory.
- Commercial Curiosity: High EQ, strong business acumen, and the ability to build trust with senior executives.

Why We Are Keeping This Search Confidential

We are deliberately keeping our company identity and product details confidential during this initial recruitment phase to protect our market position while finalizing our commercial rollout. Qualified candidates will receive full details regarding the platform, market data, and complete compensation details during initial discussions.

How to Apply

If you are a proven software sales closer looking for enterprise stability combined with greenfield expansion potential, submit your resume along with a brief overview detailing:

- The software applications you have sold
- Your average deal size and typical sales cycle duration
- Your career track record against quota

Pay: $150,000.00-$200,000.00 per year

Work Location: Hybrid remote in Toronto, ON (Toronto District)

📌 Sales Manager - Remote - Saas (Toronto)
🏢 Leading
📍 Toronto