Sales Director

About Software Answers:

At Software Answers, we develop software that powers the operations of the global corporate housing and serviced apartment industry. Our flagship platform, Oscar, is the category-leading solution trusted by industry leaders to streamline unit management, resident experience, and back-office accounting—all in one intuitive system. With offices in Orlando and Toronto, we are a growing team building the future of operational software for Corporate Housing and Service Apartment businesses.

The Role:

• Job Title: Sales Director (Individual Contributor)
• Location: Orlando, FL or Toronto, ON (Remote-friendly) Department: Sales

Role Overview

• We are seeking a high-performing, self-driven Sales Director to join our team as an individual contributor (IC). This role is perfect for an experienced SaaS Account Executive or Sales Representative who understands the nuances of operational software in real estate-related verticals—such as corporate housing, vacation rentals, property management, HOAs, hotels, and serviced apartments.
• You’ll own the full sales cycle—from prospecting and pitching to closing and account expansion. Your mission: generate new business, grow existing relationships, and drive revenue growth by helping property operators modernize their workflows with Oscar.

Key Responsibilities

• Full-Cycle Sales Execution Own the sales process end-to-end—from discovery and demo to proposal, negotiation, and close.
• Prospecting & Pipeline Development Identify high-potential leads through outbound efforts, strategic research, and industry engagement. Consistently maintain a healthy sales pipeline.
• Client Growth & Account Expansion Grow wallet share within existing accounts by cross-selling and upselling Oscar's platform and related services. With a particular emphasis on migration of legacy on-premises and managed hosted customers to our modern SaaS based product.
• Collaborative Handoffs Coordinate with onboarding and implementation teams to ensure a seamless customer transition post-sale.
• Performance Tracking & Reporting Deliver weekly pipeline updates and performance reports to senior leadership, highlighting key wins, risks, and trends.
• Industry Engagement: Represent Software Answers at industry events, tradeshows, and networking forums to build brand visibility and uncover new opportunities.

What Success Looks Like

• Achieve and exceed quarterly and annual revenue targets.
• Schedule and conduct a minimum number of sales demos per month.
• Maintain a high-quality, up-to-date CRM reflecting pipeline status, customer interactions, and forecasts.
• Consistently close new logos and expand existing customer accounts.
• Set and track quarterly sales objectives (ROCKS) with weekly progress updates.

Who You Are

• A driven sales pro with 3+ years of experience selling SaaS—preferably in property tech, real estate, or hospitality verticals.
• Proven success in consultative B2B sales, ideally to operational or finance decision-makers.
• Familiar with accounting systems, property operations workflows, or enterprise software for property management.
• A confident communicator with excellent negotiation and relationship-building skills.
• A self-starter with a bias for action, who thrives in a fast-paced, remote-first team environment.

Required Skills & Experience

• Domain Knowledge: Deep understanding of the property management industry, including operational and accounting workflows.
• Sales Acumen: Track record of exceeding quotas with strong demo, proposal, and closing skills.
• CRM Fluency: Experience using CRM tools to manage pipeline and forecast accurately.
• Industry Insight: Awareness of competitor platforms and ability to articulate differentiation.
• Tech Literacy: Proficient in tools like Microsoft Office, Teams, and CRM platforms.

Why You'll Love This Role

• You thrive on ownership and autonomy in your sales process.
• You love connecting with customers, solving problems, and closing deals.
•  You have insatiable curiosity and relentless persistence.
• You’re energized by new challenges and the fast-moving nature of SaaS.
• You want to grow with a company that’s winning—in a niche but global industry.
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Join us in shaping the future of corporate housing technology. Apply now and become a key driver of growth at Software Answers.

Diversity, Equity, Inclusion & Equal Employment Opportunity at Banyan: Banyan affirms that inequality is detrimental to our Global Teams, associates, our Operating Companies, and the communities we serve. As a collective, our goal is to impact lasting change through our actions. Together, we unite for equality and equity. Banyan is committed to equal employment opportunities regardless of any protected characteristic, including race, color, genetic information, creed, national origin, religion, sex, affectional or sexual orientation, gender identity or expression, lawful alien status, ancestry, age, marital status, or protected veteran status and will not discriminate against anyone on the basis of a disability. We support an inclusive workplace where associates excel based on personal merit, qualifications, experience, ability, and job performance.