Company Description

Propra is reimagining property management technology with a focus on building simple, contemporary, and easy-to-use tools to improve efficiency, communication, and cost-savings – all to elevate the resident and landlord experience. Since we are an early-stage startup, you can get in on the ground floor and make a lasting impact. Our team is highly collaborative and customer-obsessed, often stretching outside traditional roles' boundaries to help move things forward and leave things better than they found them.

About the Role As a Full-Stack Account Executive at Propra, you’ll own the end-to-end sales cycle, from prospecting to closing, while leveraging data-driven insights to scale outreach efforts effectively. This role requires a strategic, self-starter mindset with a deep understanding of property management software and SaaS sales. You’ll play a critical role in driving Propra’s expansion, helping real estate operators streamline their business with our autonomous property management platform.

We’re a fast-growing, high-performance startup, and we’re looking for sales leaders who can think beyond traditional sales tactics and contribute to our growth strategy. If you thrive in a dynamic environment and love selling innovative solutions, we want to hear from you.

Key Responsibilities

Lead Generation & Prospecting

- Build and manage targeted lead lists aligned with our Ideal Customer Profile (ICP).
- Research and qualify leads in the property management and real estate tech space to build a high-quality sales pipeline.

Sales Outreach & Relationship Building

- Execute multi-channel outreach strategies (personalized emails, calls, LinkedIn,



etc.).
- Identify key decision-makers within target accounts and tailor messaging to their pain points.
- Conduct discovery calls to understand prospects’ needs and position Propra’s value proposition effectively.
- Provide product demonstrations and guide prospects through the buying process.
- Collaborate with marketing and product teams to refine sales messaging and approach.

Pipeline & Deal Management

- Own the entire sales cycle from discovery to contract negotiation and close.
- Use CRM software (HubSpot, Salesforce, or similar) to track sales activities and maintain accurate deal data.
- Regularly analyze performance metrics (e.g., lead-to-meeting, meeting-to-close conversion rates) and optimize strategies accordingly.

Ad Hoc Projects

- Be prepared to wear many hats! In a startup environment, you'll be expected to handle ad-hoc tasks and projects as assigned by the co-founders, in addition to your core responsibilities.

Qualifications

Ideal Candidate Profile

Experience

- Minimum of 5+ years in a high-level strategic sales, advisory, or operational role within the multi-family real estate or a related role.
- Proven track record of building and closing a strong pipeline.
- Bonus: Experience selling property management software, fintech,



or automation-driven solutions, and/or property management operations.

Skills & Tools

- Proficient in CRM management and reporting (HubSpot, Salesforce, etc.).
- Strong communication, interpersonal, presentation, and negotiation skills including ability to conduct effective discovery calls and articulate a clear value proposition.
- Proven history of navigating and successfully closing large, complex enterprise sales/partnership agreements (typically 6-7 figures annually).
- Expert-level understanding of the institutional multi-family business model, including financial drivers, property operations, investment cycles, and the role of legacy PropTech systems.

Personal Attributes

- Self-starter with a proactive, problem-solving mindset results-oriented approach to achieving goals
- Exceptional presence, communication skills, and the ability to articulate a high-level vision to skeptical or highly analytical executive audiences.
- Ability to thrive in a fast-paced startup environment.
- Growth-oriented, always looking for ways to improve and scale.
- Strong time management and organizational skills
- Ability to analyze market trends and adapt sales strategies accordingly
- Willingness to travel as needed for client meetings and industry events

Additional Information

Propra is an equal opportunity employer. We appreciate your interest in working with us; however, only those applicants selected for interviews will be contacted. Successful candidates for this position may be required to undergo a security screening, including a criminal records check.

📌 Account Executive (Winnipeg)
🏢 Propra
📍 Winnipeg