Business Development Representative (BDR)

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

This is a hybrid outbound (80%) + light closing role (20%) for someone who wants ownership, real responsibility, and the opportunity to grow into a senior sales role as the company scales.

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 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, LinkedIn, phone, and other channels
• Write clear, compelling outbound messaging focused on financial and operational pain points
• Lead discovery conversations to understand portfolio size, workflows, and trust accounting needs
• Close smaller SMB accounts directly and partner on larger opportunities
• Book high-quality meetings and ensure a smooth, thoughtful handoff when deals move upmarket
• Collaborate with sales leadership 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

• You view sales as a skill to develop and master, not just a set of tasks
• You’re confident, curious, and comfortable having real business conversations with operators
• You’re competitive and motivated by improvement, outcomes, and momentum
• You take initiative and ownership without needing constant direction
• You communicate clearly and thoughtfully, both written and verbal
• You’re comfortable picking up the phone and leading discovery conversations
• You’re coachable, self-aware, and driven to get better over time
• You enjoy learning complex products and understanding nuanced workflows
• You have previous experience in the Short-Term Rental or property management space
• You have an understanding of accounting and financial concepts
• You have interest or previous experience in fintech software

Nice to Haves

• Experience in SaaS sales, BDR/SDR roles, or customer-facing positions
• Business acumen or background education in business related studies
• Exposure to accounting, bookkeeping, fintech, or financial workflows in practice
• Experience working in fast-growing or startup environments
• Experience working in remote environments
• Experience with Salesforce CRM
• Strong writing or creative outbound experience

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.

Growth and ownership - Play a meaningful role in shaping how outbound works as the company scales.

Career progression - Clear paths into AE or other go-to-market roles over time.

Strong team and culture - Work closely with experienced builders and leaders across the business.

How to Apply

If you’re serious about this role you can apply through Wellfound.

To stand out, we encourage creativity:

• Send a short note explaining why this role and Clearing interest you, and what excites you about selling into the STR space
• Include an example of outbound messaging you’re proud of - an email, LinkedIn message, or call script
• Create a loom video showcasing a discovery or cold call
• the more creative the better - preferred, not required

Most companies recieve a high volume of applications - we are looking for someone to stand out - if you're using AI to fill in screening questions or provide reasoning for "why you?" without something unique, we likely won't be a great fit.

Only hiring in USA and/or Canada.

Inquiries can be sent to [email protected]