About Rentsync
Rentsync is a leading marketing and technology partner serving the rental housing industry. We help property owners and operators generate high-quality leads, improve leasing performance, and drive measurable ROI through marketing, data, and technology solutions.

As we expand beyond our core offerings, Rentsync is investing in new growth areas — including real estate data products and commercial listing marketing solutions. These emerging business lines represent significant long-term expansion opportunities and require dedicated leadership to scale.

About the Role

The Director, Emerging Data & Market Expansion will lead the growth, market development, and operational scaling of Rentsync's emerging data and commercial listing business lines.

This is a highly strategic and entrepreneurial role responsible for building and executing go-to-market strategy, standardizing sales processes post-acquisition, driving geographic expansion, and owning revenue growth.

You will operate as the business lead for this emerging division — responsible for revenue targets, sales execution, market validation, and cross-functional alignment — while also remaining hands-on in direct enterprise selling.

This role will manage one Business Development Representative initially and works closely with Sales, Marketing, Product, and Leadership to build a scalable and repeatable growth engine.

This is a hybrid position, candidates must be able to report to Rentsync's Toronto or Montreal office 2 days per week on average.

Duties & Responsibilities

Business Line Growth & Revenue Ownership

•         Own annual revenue targets and growth strategy for emerging data and listing-related products

•         Build and execute GTM plans across target verticals and geographies

•         Develop pipeline strategy and personally close key mid-market and enterprise accounts

•         Contribute to annual budgeting and forward-looking revenue planning

•         Establish scalable growth plans for future-year expansion

Sales Process Design & Integration

•         Lead the standardization of sales processes for newly acquired business lines

•         Align sales methodology, CRM usage, reporting, and forecasting with Rentsync's existing systems

•         Implement structured pipeline management and performance tracking

•         Develop training materials and onboarding processes to enable future team growth

•         Build a repeatable sales playbook for scaling beyond the initial phase

Market Expansion (Vertical & Geographic)

•         Identify and validate new geographic markets for expansion

•         Assess vertical-specific opportunities within real estate data and commercial listing ecosystems

•         Develop entry strategies, pricing frameworks, and positioning for new markets

•         Evaluate competitive landscape and differentiation strategy

Enterprise Sales & Client Engagement

•         Lead complex, strategic sales conversations with enterprise clients

•         Navigate multi-stakeholder buying processes

•         Act as senior executive presence in key deals

•         Support BDR with inbound lead qualification and conversion strategy

Product Feedback & Market Validation

•         Serve as the primary commercial feedback loop to Product and Leadership

•         Deliver structured market insights, feature validation, and competitive intelligence

•         Identify gaps in product-market fit and recommend roadmap enhancements

•         Provide ongoing client feedback to ensure offerings remain competitive and scalable

Team Leadership

•         Directly manage one Business Development Representative

•         Coach and support pipeline generation and inbound qualification

•         Build hiring plan recommendations as the business scales

Requisite Knowledge, Skills & Abilities

•         Demonstrated ability to balance strategy with hands-on execution

•         Strong financial and commercial acumen, including forecasting and budget planning

•         Comfortable operating with autonomy in an entrepreneurial environment

Essential Qualifications

•         7–10+ years of B2B sales, business development, or GTM leadership experience

•         Proven track record of building or scaling a new business line, product, or market

•         Strong enterprise sales background with experience closing complex, high-value deals

•         Bachelor's degree in Business, Commerce, Marketing, or a related field, or an equivalent combination of education and experience

Additional Preferred Qualifications

•         Experience integrating or operationalizing post-acquisition sales processes

•         Experience in real estate data, commercial listings, proptech, SaaS, or related industries

Measuring Year 1 Success

•         Revenue targets met or exceeded for emerging business lines

•         Full integration of newly acquired sales processes into Rentsync's CRM and systems

•         Clear enterprise pipeline established across prioritized markets

•         Defined expansion strategy for at least 1–2 new geographic regions

•         Repeatable sales motion documented and operationalized

•         Strong product feedback loop influencing roadmap decisions

Rentsync is an equal opportunity employer. If you are selected to participate in the interview process and require unique accommodations, please don’t hesitate to let us know. 

Successful candidates may be required to complete a criminal background check and employment reference check in the final phase of the interview process.