Job Description

Clearing is looking for a Sales Development Representative (SDR) to help generate new opportunities and bring new customers onto our platform as we continue to grow.

This role is primarily focused on outbound prospecting (roughly 85%), with the opportunity to close smaller accounts directly (about 15%). It’s an ideal position for someone who wants meaningful ownership, direct exposure to the sales process, and a clear path toward a larger sales role as the company expands.

AI-powered platform. High-value SaaS product. Real customers managing real money.

About Clearing

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

Property managers handling funds on behalf of owners face complex financial workflows — reconciliation, expense allocation, owner statements, and payouts all need to be accurate and transparent. Clearing helps operators replace spreadsheets, fragmented systems, and manual processes with a platform designed to automate these workflows and bring clarity to their financial operations.

As the short-term rental industry grows, the need for purpose-built financial infrastructure continues to increase — and Clearing is positioned at the center of that shift.

About the Role

We are hiring a Sales Development Representative (SDR) to help expand our outbound pipeline and convert new customers onto the platform.

This role works closely with sales leadership, marketing, partnerships, and product teams. You will help identify the right prospects, initiate conversations, run discovery calls, and bring smaller opportunities through to close while partnering with senior team members on larger deals.

You’ll also contribute to refining messaging, experimenting with outreach strategies, and helping shape how outbound sales evolves as the company grows.

This position is well suited for someone who is motivated, proactive, and interested in building their career in SaaS sales within a high-growth company.

What You’ll Do

• Identify and qualify short-term rental operators, property managers, and co-hosts as potential customers
• Run outbound prospecting campaigns using email, LinkedIn, phone, and other channels
• Craft thoughtful, relevant messaging that speaks to real operational and financial challenges
• Conduct discovery calls to understand how prospects currently manage financial workflows
• Close smaller accounts independently and collaborate with the team on larger opportunities
• Schedule qualified meetings and ensure smooth transitions when deals move upmarket
• Work with sales leadership to refine ICP targeting and outbound strategy
• Assist with partner-driven outreach and follow-up communications after events or introductions
• Keep CRM records accurate and maintain visibility into pipeline activity using Salesforce
• Develop deep familiarity with the short-term rental ecosystem and Clearing’s financial platform

Who You Are

• You see sales as a craft that can be learned and improved over time
• You enjoy having real conversations with business operators and understanding how they work
• You are competitive, driven by progress, and motivated to improve
• You are comfortable taking initiative and owning your responsibilities
• You communicate clearly and confidently in both writing and conversation
• You are willing to pick up the phone and engage prospects directly
• You welcome feedback and are committed to continuous improvement
• You enjoy learning complex products and the workflows behind them

You also have:

• Experience or familiarity with the short-term rental or property management industry
• A basic understanding of financial or accounting concepts
• Interest in fintech or financial operations software

Nice to Haves

• Experience in SaaS sales, BDR/SDR roles, or other customer-facing positions
• Academic or practical background in business-related disciplines
• Exposure to accounting, bookkeeping, fintech, or financial operations
• Experience working within startup or high-growth environments
• Comfort working in distributed or remote teams
• Experience using Salesforce or other CRM platforms
• Strong writing ability and creative outbound approaches

Why Join Clearing

Meaningful product, real impact
Help businesses manage millions of dollars in owner funds with greater accuracy and transparency.

High-value sales conversations
You’ll sell into complex operational problems rather than pushing commodity software.

Ownership and growth
You’ll play an important role in shaping how outbound sales operates as the company grows.

Career development
Strong performers will have opportunities to grow into AE or broader go-to-market roles.

Collaborative team environment
Work alongside experienced operators, builders, and leaders across the business.

How to Apply

Applications can be submitted through Wellfound. If you want to stand out, we encourage creativity. Optional additions include:

• A short note explaining why this role and Clearing interest you
• An example of outbound messaging you’ve written (email, LinkedIn message, or call script)
• A short Loom video demonstrating how you would run a discovery or cold call

The more authentic and thoughtful your approach, the better.

We receive many applications, and we’re looking for candidates who show initiative and originality.

If screening answers appear heavily AI-generated without personal context or creativity, this role may not be the best fit.

Location: United States or Canada

For questions, reach out to hiring@getclearing.co

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