Sales Business Development Representative

Business Development Representative

Location: Remote (US & Canada)
Salary $50,000 base annually + Commission ($65,000 OTE)
Department: Business Development
Employment Type: Full-time

Description:
Clearing is hiring a Business Development Representative (BDR) to help drive outbound growth and net new business for a fast-growing SaaS platform serving the Short-Term Rental (STR) industry.

AI-powered platform. Quick B2B SaaS sales cycles. Real customers managing real money.

About Clearing
Clearing is an AI-powered trust accounting and financial operations platform built specifically for Short-Term Rental (STR) property managers.

We help operators replace spreadsheets, manual reconciliations, and error-prone workflows with automated trust accounting, booking-level financials, clean owner statements, and streamlined payouts. Our customers manage money on behalf of others: accuracy, compliance, and clarity are non-negotiable.

Clearing is experiencing strong momentum as demand grows for purpose-built financial infrastructure in the Short-Term Rental industry.

About the Role
We’re hiring a Business Development Representative (BDR) to help accelerate pipeline growth, support outbound sales, and close accounts as we continue to scale our go-to-market motion.

Clearing operates with close collaboration across sales, marketing, partnerships, and leadership. In this role, you’ll play an active part in shaping and scaling outbound sales, contributing to messaging, supporting partnership and event-related functions, and developing a strong understanding of how our GTM strategy drives growth.

This role is ideal for someone who is highly motivated, self-directed, and eager to take ownership in a company entering its next phase of growth.

What You’ll Do

• Source and qualify short-term rental operators, property managers, and co-hosts
• Own outbound prospecting across email, calls, social media, and other channels
• Write clear, compelling outbound messaging focused on financial and operational pain points
• Lead discovery/cold-call conversations to understand portfolio size, workflows, and trust accounting needs
• Partner on opportunities with AE and leadership to increase net new recurring revenue
• Book high-quality meetings and ensure a smooth, thoughtful handoff with sales reps
• Collaborate with sales leadership & marketing on ICP refinement, messaging, and outbound experimentation
• Support partnership- and event-driven outreach through targeted correspondence
• Maintain accurate CRM records and pipeline visibility in Salesforce
• Build deep fluency in trust accounting, STR financial operations, and Clearing’s product and positioning

Who You Are

• A driven SaaS sales professional with 2+ years of experience, strong in outbound prospecting and cold outreach
• Comfortable operating in high-volume, high-rejection environments, with a track record of hitting activity and pipeline goals
• A clear and confident communicator, able to lead cold calls, handle objections, and run thoughtful discovery conversations
• Organized and process-driven, with experience using modern sales tools (Salesforce, Sales Engagement tools, LinkedIn Sales Navigator, etc.)
• Competitive, curious, and motivated by growth, performance, and continuous improvement
• Proactive and accountable. You take ownership and don’t wait for direction
• Coachable and self-aware, with a genuine desire to improve your craft in sales

Nice to Have

• Additional languages
• Experience in SaaS-adjacent domains such as fintech, AI, accounting, or financial workflows
• Familiarity with the short-term rental or property management space
• Experience working in fast-growing, startup, or remote environments
• Proficiency with Salesforce or similar CRM tools
• Strong writing skills or experience with creative outbound prospecting
• Solid business acumen or relevant academic background

Why Clearing

• Meaningful product, real impact - Help operators manage millions in owner funds with accuracy and confidence
• Challenging, high-impact sales - Sell into complex, high-stakes financial workflows where the value is clear
• Ownership and influence - Play a key role in shaping outbound as the company scales
• Career growth - Clear progression paths into AE and broader go-to-market roles
• Strong team and culture - Work alongside experienced operators and builders who move fast and support each other

What Success Looks Like

• Consistently hit or exceed activity, pipeline, and revenue targets
• Generate high-quality pipeline through outbound (cold calls, email, and creative prospecting)
• Communicate clearly and confidently, leading effective discovery and business conversations
• Build urgency and align stakeholders to drive deals forward
• Maintain accurate pipeline management and forecasting in CRM
• Thrive in a fast-paced environment with strong ownership and accountability
• Quickly learn new tools, adapt to feedback, and continuously improve your approach

How to Apply
If you’re serious about this role, apply through Wellfound.

To stand out, we encourage creativity:

• Send a short note on why this role and Clearing interest you, and what excites you about selling into the STR space
• Include an example of outbound you’re proud of (email, LinkedIn message, or call script)
• Share a Loom video showcasing a discovery or cold call

The more creative, the better. This is preferred, not required.

We receive a high volume of applications and are looking for candidates who stand out. If you’re using AI to answer screening questions, make sure your responses are thoughtful and distinctive; otherwise,
this may not be the right fit.

Questions? Reach out to [email protected]