Full-Cycle Account Executive

About Proper

We're rebuilding accounting from the ground up.

Proper is building a complete, AI-native accounting system for growing businesses. Our ambition goes beyond faster bookkeeping: a system that takes on the routine work, helps people understand what the numbers mean, and gives finance teams more time to guide the business.

Our founders bring deep knowledge of the accounting industry and a proven track record of building and scaling successful accounting technology. We know this space, and we're coming together to build something fundamentally better.

Our full-stack approach brings every accounting function into one connected platform—including capabilities such as payroll that businesses often have to bolt on separately. Rather than adding another tool to a fragmented back office, we're bringing the work, the data and the controls together to rethink what an accounting system can do.

This is not a traditional startup. We're building a small team by design, with substantial ownership and AI at the heart of how we work—not just what we build. We're looking for people who are already proficient with AI, committed to mastering its use in their craft, and excited to redefine what a small, exceptional team can achieve.

We believe the strongest endorsement is a CFO putting their reputation behind a recommendation. Earning that trust is the standard we're building toward.

Our mission: to become the accounting system CFOs recommend most, anywhere in the world.

The opportunity

Own the sale from the first conversation to the signed agreement.

You’ll identify the right businesses, create your own opportunities, understand how their finance teams work, and guide them through a buying decision. Prospecting is a core part of this role—not something handed off to someone else. You’ll also help shape our messaging and sales approach as we learn what earns customers’ trust.

You may already be closing deals, or you may be a proven prospector ready for your first closing role. What matters is your prospecting track record, accounting knowledge and willingness to own the outcome.

What you’ll own

• Build your pipeline. Research target accounts and create qualified opportunities through thoughtful phone, email and social outreach.
• Run meaningful discovery. Understand the customer’s workflows, current systems, business impact, decision process and reasons to change.
• Make the case for Proper. Lead tailored product conversations and demos, involving accounting and product specialists where needed. Connect capabilities to outcomes—not a feature checklist.
• Own the close. Manage stakeholders, next steps, proposals, negotiations and agreements, then coordinate a clear handoff for implementation.
• Build a repeatable approach. Keep accurate CRM records and forecasts. Use AI to improve research, preparation, outreach and follow-through, and bring customer insight back to the team.

What you’ll bring

• At least two years in a prospecting sales role. Show that you can identify the right accounts, earn conversations and create qualified opportunities.
• Strong accounting-domain knowledge. You must understand accounts payable, accounts receivable, payroll and accounting systems well enough to have credible conversations with CFOs, controllers and finance teams about workflows, controls and day-to-day challenges.
• Practical AI proficiency. You already use AI effectively in your work, check the quality of its output and are committed to mastering it as part of your sales craft.
• Ownership and coachability. You follow through, communicate clearly, seek feedback and keep improving. You are comfortable building the approach, not just following an established playbook.

Preferred, not required: Closing experience or previous ownership of a full sales cycle.

What success looks like

Success is measured by the qualified pipeline you create, the new business you close and the accuracy of your forecasts—not activity for its own sake.

Compensation

Annual on-target earnings range from CAD $125,000 to $150,000.

Apply

Apply with your resume and a short note about the pipeline you’ve generated, your knowledge of accounting workflows and how you use AI in your work. Tell us why you’re ready to own the full sales cycle.

We welcome different backgrounds, experiences and perspectives. Please let us know if you need an accommodation during the hiring process.