Sales Account Executive

Account Executive

Location: Remote (US & Canada)
Employment Type: Full-time

Description:
Clearing is hiring an Account Executive (AE) to own pipeline generation and close new business for a fast-growing SaaS platform serving the Short-Term Rental (STR) industry.
This is a full-cycle sales role combining outbound prospecting, discovery, and closing. You’ll work alongside a BDR and sales leadership, while owning your own pipeline and driving net new revenue.
AI-powered platform. High-value SaaS product. 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 an Account Executive (AE) to drive new revenue and help scale our go-to-market motion.

This is a hands-on, full-cycle sales role where you will:

• Own pipeline generation across both outbound and inbound channels
• Partner closely with a BDR on prospecting and qualification
• Lead discovery, position the product effectively, and close new business
• Collaborate with sales leadership on larger or more complex opportunities

Clearing operates with strong cross-functional alignment across sales, marketing, partnerships, and leadership. In this role, you’ll contribute beyond just closing — helping refine messaging, improve sales processes, and shape how we scale revenue as a team.

This role is ideal for someone who thrives on ownership, is comfortable carrying a quota, and enjoys hunting for new opportunities while closing high-quality deals in a fast-moving SaaS environment.

What You’ll Do

• Own the full sales cycle from prospecting through close
• Generate pipeline through outbound (email, LinkedIn, phone) and inbound channels
• Partner with a BDR to drive top-of-funnel activity and conversion
• Lead structured discovery and demos to uncover financial workflows and operational pain points
• Clearly position Clearing’s value and tie it to measurable business outcomes
• Close SMB and mid-market deals, and support larger opportunities as you grow domain expertise
• Manage pipeline, forecasting, and deal progression in Salesforce
• Navigate objections and guide prospects through complex decision-making processes
• Collaborate with sales leadership on messaging, ICP refinement, and overall sales strategy
• Develop deep expertise in trust accounting, STR operations, and Clearing’s platform

Who You Are

• Experienced in closing new business in a SaaS environment, ideally in a full-cycle role
• Comfortable generating your own pipeline and operating with a high degree of ownership
• Strong at discovery, qualification, and running a consultative sales process
• Confident handling objections and asking for the close
• Competitive, driven, and motivated to consistently hit and exceed targets
• Organized and disciplined in managing pipeline, forecasting, and sales processes
• Clear, effective communicator with strong written and outbound messaging skills
• Coachable, self-aware, and committed to continuous improvement
• Curious and interested in learning complex products, workflows, and industries

Nice to Have

• Experience in fintech, SaaS, AI tools, or financial/accounting workflows
• Familiarity with the short-term rental, property management, or hospitality space
• Experience working in startup, high-growth, or remote environments
• Proficiency with Salesforce or similar CRM tools
• Strong business acumen or relevant academic background
• Creative outbound or strong copywriting skills

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 meet or exceed quota across pipeline generation and closed revenue
• Build and convert a high-quality pipeline through outbound and inbound efforts
• Run effective discovery and sales processes that uncover real business needs and drive strong close rates
• Create urgency and align multiple stakeholders to move deals forward efficiently
• Maintain accurate pipeline hygiene, forecasting, and deal progression in CRM
• Operate with a high degree of ownership in a fast-paced, evolving environment
• Ramp quickly on product, market, and tools, while continuously improving performance through feedback

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]