Founding Sales Development Representative (B2B Outbound)

Remote Worldwide | Full time | U.S. B2B Sales
$12,000–$20,000 USD base | $18,000–$30,000+ OTE
Helpline Software builds mission-critical software for organizations that operate 24/7 hotlines, emergency lines, and after-hours teams.

When an important call comes in, our software helps make sure it reaches the right on-call person — and automatically escalates when someone doesn't answer.

We're looking for a Sales Development Representative to help us grow in the U.S.
This is a great role for someone who enjoys cold calling, talking with real decision-makers, figuring out how businesses currently operate, and turning genuine problems into qualified sales opportunities.
You'll work closely with our founder and have significant ownership over how our outbound motion develops.

What You'll Do
- Personally cold-call U.S. businesses during U.S. business hours
- Speak with owners, executives, Operations leaders, and Customer Service leaders
- Research accounts and identify the right people to contact




- Navigate gatekeepers and common objections
- Ask thoughtful discovery questions and understand how prospects handle after-hours calls today
- Identify genuine pain, fit, urgency, decision ownership, and timing
- Book qualified meetings when there is a real reason for the conversation to continue
- Keep clear CRM notes and manage follow-up
- Review your calls and improve through direct coaching
- Help us refine targeting, messaging, scripts, and qualification based on what you learn from the market

What We're Looking For

We care more about what you can actually do on a cold call than an impressive résumé.
You'll likely be a robust fit if you have:
- Experience personally cold-calling U.S. businesses in a B2B environment
- Clear, natural spoken English and confidence speaking with U.S. decision-makers
- Strong listening skills and the ability to ask useful follow-up questions
- Experience generating meetings, opportuni

📌 Founding Sales Development Representative (Vapi)
🏢 Helpline Software
📍 Vapi