Account Executive (San Diego)

About ClearDesk

ClearDesk helps US small and mid-sized businesses hire and manage full-time Remote Team Members (RTMs) based in the Philippines. We place and support ~500 contractors today across home care, real estate, bookkeeping, and home services, on a simple flat-fee model with a US leadership team and Philippines-based operations managers behind every placement.

We are growing fast. Our 2026 goal is 100 new deals a month, and the Account Executive is the person who closes them. You will run a full calendar of qualified appointments set by our SDR team and turn them into signed clients who stay.

Role: Account Executive · Reports to: Head of Growth · Team: Sales (SDRs, AEs, Client Experience)

What you'll do

• Run 15–25 SDR-booked discovery calls a week with owners and operators of home care agencies, real estate teams, bookkeeping firms, and home services companies.
• Diagnose each business's staffing pain, map it to the right RTM role (scheduler, intake coordinator, bookkeeper, ISA, dispatcher), and present ClearDesk as the fix.
• Close new clients and expansions: proposals, pricing conversations, objection handling, and signed agreements, with a clean handoff to the Client Experience team.
• Own your pipeline in HubSpot: every call logged, every deal staged, forecasts you'd bet on.
• Follow up relentlessly on no-shows, stalled deals, and not yet prospects. A third of our booked meetings don't show the first time; the AEs who win here are the ones who get them back.
• Feed what you hear back to Marketing, SDRs, and Recruiting: which roles are in demand, which objections keep coming up, which verticals are heating up.
• Use AI tools daily (call notes, follow-up drafting, research) to spend more of your week in front of buyers.

Who you are

Must have

• 2+ years closing B2B deals to small-business owners (SMB SaaS, staffing, payroll, insurance, marketing services, or similar). You've carried a quota and hit it.
• Comfortable selling a consultative, high-velocity motion: short cycles, many conversations, a clear next step on every call.
• Proven discipline in a CRM (HubSpot preferred). Your pipeline is a tool you use, not a chore you dread.
• Clear, warm communicator on Zoom and phone. You make an agency owner feel heard in the first two minutes.
• Resilient and self-directed. No-shows and let me think about it don't slow you down.
• Curious about AI and already using it to work faster.

Nice to have

• Experience selling into home care, real estate, accounting, or home services.
• Background in staffing, outsourcing, or managing remote/offshore teams.
• Prior work in a startup or small team where you helped shape the playbook, not just run it.

Compensation, location, and how to apply

• Compensation: Base salary plus uncapped commission on closed deals and expansions. OTE discussed in the first conversation.
• Location: In-office in San Diego (UTC)
• Benefits: Health, PTO, 401(k), equipment
• Why this role: You'll sell a service that owners thank you for six months later, in a company small enough that your ideas change the playbook and growing fast enough that there's a clear path to senior AE or sales leadership.

To apply: Email a résumé and a short note (three sentences is fine) on the hardest deal you closed last year and how you did it. email: