Founding Business Development & GTM Manager Short-Term Rental SaaS | One-Year Full-Time Contract Employment Type: One-year full-time fixed-term contract Hours: Up to 40 hours per week Hourly Rate: C$50 per hour Work Arrangement: Flexible and results-driven, with in-office attendance as needed About RentUP RentUP is a SaaS platform developed from the real-world operating experience of Nova Vacation Homes, a vacation rental management company managing approximately 250 properties. The platform helps short-term rental property managers improve guest communications, digital guidebooks, upsell opportunities, field operations, owner communications, and other key operational workflows. We are now preparing RentUP for broader market adoption and building our first repeatable go-to-market and customer-acquisition process.

About the Role
We are seeking a hands-on and entrepreneurial Founding Business Development & GTM Manager to become RentUP’s first internal commercial leader. This is a phased role. During the initial market-validation stage, you will work closely with an experienced external full-cycle sales team responsible for prospecting, outreach, discovery, demonstrations, proposals, negotiation, and early customer acquisition. During this period, you will represent RentUP internally, support and oversee the external team, participate directly in the sales process, and ensure that the market knowledge, customer relationships, sales processes, and playbook developed through the engagement are successfully transferred to RentUP. As the commercial model is validated, you will progressively take ownership of RentUP’s business development and sales execution. This will include managing the pipeline, developing customer relationships, closing current business, refining the sales playbook, and helping build an internal sales function. This is not solely a vendor-management or coordination position. The successful candidate will be expected to learn from the external sales team during the initial stage and then assume increasing responsibility for RentUP’s sales and go-to-market activities during the remainder of the contract.

Key Responsibilities
Phase 1 – Initial 90 Days: Market Validation and Knowledge Transfer
- Serve as RentUP’s primary point of contact for the external go-to-market and full-cycle sales team.
- Coordinate priorities, product information, approvals, meetings, deliverables, and follow-up activities.
- Participate in customer discovery calls, product demonstrations, proposal discussions, and important commercial conversations.
- Provide the external team with accurate product knowledge, short-term rental industry context, approved pricing, sales materials, and demonstration access.
- Review prospecting activity, qualified opportunities, demonstrations, proposals, pipeline progress, and customer feedback.
- Ensure that the external team accurately represents RentUP’s capabilities, limitations, pricing, and implementation requirements.
- Work alongside the external team to understand and document its targeting, outreach, qualification, demonstration, objection-handling, negotiation, and closing methods.
- Ensure that prospect data, CRM history, sales materials, customer feedback, outreach sequences, and active opportunities are retained by RentUP.




- Take ownership of the completed sales playbook and prepare for an orderly transition to internal sales execution. Phase 2 – Remainder of the Contract: Direct Sales and Business Development
- Gradually assume responsibility for RentUP’s sales pipeline and customer-acquisition activities.
- Identify and develop relationships with qualified property management companies and industry decision-makers.
- Conduct discovery calls, product demonstrations, commercial presentations, and customer follow-ups.
- Prepare proposals, handle objections, negotiate commercial terms, and close new customers.
- Maintain accurate CRM records, pipeline stages, next steps, and sales forecasts.
- Continue testing and improving RentUP’s ideal customer profile, sales messaging, pricing, commercial offer, and acquisition channels.
- Develop relationships with PMS providers, industry associations, consultants, technology partners, and other members of the short-term rental ecosystem.
- Represent RentUP at relevant industry events, conferences, webinars, and partner meetings. Sales Team Development and Leadership
- Assess future internal sales staffing needs based on validated customer demand and pipeline activity.
- Help design the structure of RentUP’s internal sales organization.
- Where approved during the contract term, assist with recruiting, onboarding, training, and managing additional sales team members.
- Help establish individual and team targets, KPIs, commission structures, and performance expectations.
- Establish a consistent cadence for pipeline reviews, coaching, performance tracking, and forecasting.
- Develop repeatable sales scripts, training materials, demonstration standards, and sales processes. Product and Internal Coordination
- Develop a strong understanding of RentUP’s product, workflows, integrations, pricing, implementation requirements, and competitive positioning.
- Work closely with product, technical, operations, finance, onboarding, and customer support teams.
- Coordinate responses to technical, integration, security, pricing, and implementation questions from prospects.
- Ensure that sales materials and commercial claims accurately reflect current product capabilities.
- Translate customer objections, feature requests, competitive information, and market feedback into structured product recommendations.
- Help prioritize product improvements based on customer demand, revenue potential, and implementation feasibility.
- Ensure that commitments made during the sales process are properly reviewed and communicated internally. Customer Onboarding and Activation
- Coordinate the handoff from signed customer to implementation, onboarding, training, and ongoing support.
- Work with internal teams to establish a explicit and repeatable onboarding process.
- Monitor whether new customers are successfully activated and using the agreed workflows.




- Identify onboarding obstacles and coordinate their timely resolution.
- Gather early customer feedback and help improve adoption, retention, and time to value. Reporting and Commercial Analysis
- Maintain clear visibility into the CRM, sales pipeline, active opportunities, customer status, and next steps.
- Track qualified conversations, demonstrations, proposals, paying customers, recurring revenue, onboarding progress, and product adoption.
- Prepare concise commercial updates and forecasts for company leadership.
- Evaluate the effectiveness of customer segments, acquisition channels, messages, offers, and partnerships.
- Use actual market evidence to recommend changes to RentUP’s go-to-market strategy. Qualifications
- 5+ years of experience in B2B SaaS sales, business development, go-to-market, or a related commercial role.
- Proven full-cycle sales experience, including prospecting, discovery, demonstrations, proposals, negotiation, and closing.
- Experience launching a SaaS product, developing a new market, or building an early-stage sales function.
- Ability to work with an external sales partner and progressively take over internal sales execution.
- Strong communication, organization, project-management, and cross-functional collaboration skills.
- Proficient in using CRM, sales automation, prospecting, data-analysis, and AI tools for research, outreach, meeting preparation, follow-up, content creation, and reporting.
- Able to learn new products, technologies, and workflows quickly.
- Bachelor’s degree in Business, Marketing, Hospitality, Technology, or a related field is preferred but not required. Preferred Qualifications
- Experience in short-term rentals, vacation rentals, property management, hospitality technology, or PropTech.
- Familiarity with PMS platforms such as Guesty, Streamline, Track, Hostaway, or Hostfully.
- Existing relationships within the vacation rental or property management industry.
- Experience building, training, or managing a SaaS sales team. Work Arrangement This is a full-time, flexible, and results-driven position.
- Regular daily office attendance is not required.
- In-office attendance is required when needed for product learning, team collaboration, or important customer meetings.
- Occasional business travel may be required. Compensation & Growth
- One-year full-time fixed-term contract
- Hourly rate: C$50 per hour, based on up to 40 hours per week
- No employer-sponsored health, dental, retirement, or other supplemental benefit plan
- Statutory entitlements will be provided as required by applicable law
- Flexible, results-driven work arrangement with in-office attendance as needed
- Sales commission eligibility begins once RentUP transitions primary sales execution from the external sales team to the internal function
- Commission applies only to qualifying sales personally led and closed by the employee; no commission will be paid on sales generated or closed by the external sales team
- The commission structure, eligibility requirements, and payment terms will be documented before the employee assumes direct sales responsibility Pay: Up to $50.00 per hour Expected hours: 30.0 – 40.0 per week

Benefits:
- Flexible schedule Work

Location:
Hybrid remote in Richmond Hill, ON L4B 4W5

📌 Founding Business Development (Richmond Hill)
🏢 Nova Vacation
📍 Richmond Hill