Account Executive

Propra; Winnipeg; On-site; CAD 90,000 - 130,000; Full time

Job summary

Propra is hiring a Full-Stack Account Executive to own the end-to-end sales cycle for our autonomous property management platform. You’ll prospect, qualify, demo, negotiate, and close multi-family real estate software deals in a fast-growing startup.

The role requires a strategic, self-starter mindset with deep SaaS sales experience and a track record of closing 6-7 figure deals. Travel may be required for client meetings and industry events.

Qualifications

• Minimum of 5+ years in a high-level strategic sales, advisory, or operational role within multi-family real estate or related field.
• Proven track record of building and closing a strong pipeline.
• Experience selling property management software, fintech, or automation-driven solutions is a bonus.
• Strong communication, interpersonal, presentation, and negotiation skills with discovery calls.
• Expert understanding of institutional multi-family business models, including financial drivers and operations.

Responsibilities

• Lead generation and prospecting aligned with ICP; build targeted lead lists.
• Research and qualify leads in property management and real estate tech to build a pipeline.
• Execute multi-channel outreach (email, calls, LinkedIn).
• Identify decision-makers and tailor messaging to pain points.
• Conduct discovery calls to understand needs and position Propra’s value.
• Provide product demonstrations and guide the buying process.
• Collaborate with marketing and product to refine messaging.
• Own end-to-end sales cycle from discovery to close and negotiation.
• Use CRM (HubSpot/Salesforce) to track activities and data.
• Analyze performance metrics and optimize strategies.

Skills

Strategic sales

Pipeline development

Discovery calls

Negotiation

Communication & presentation

Multi-channel outreach

Tools

HubSpot

Salesforce

Job description

Propra is reimagining property management technology with a focus on building simple, modern, 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.

Job Description

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.

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.

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.

Successful candidates for this position may be required to undergo a security screening, including a criminal records check.