Founding Sales Development Representative (SDR)

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 strong 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, opportunities, or pipeline through outbound prospecting
• Comfort handling rejection and continuing to call consistently
• The ability to take specific feedback and improve quickly
• The independence to manage prospecting, calling, follow-up, and CRM work without constant supervision

1+ years of meaningful B2B outbound experience is preferred, but we care more about evidence of strong performance than an exact number of years.

Experience with tools such as Apollo, ZoomInfo, Clay, HubSpot, LinkedIn Sales Navigator, or similar prospecting platforms is helpful but not required.

You do not need an American accent.

What Makes This Role Different

You won't be selling a generic nice-to-have product.

Our prospects operate emergency and after-hours teams where a missed call can create a serious operational problem — and in some industries can mean losing a job worth tens of thousands of dollars.

That makes good discovery important.

We don't want someone simply reading a script and trying to book a meeting with everyone who answers.

We want someone who can have an intelligent conversation, uncover how the prospect's current process works, recognize a meaningful problem, and earn the next conversation.

Hours

This is a full-time role. You must reliably work our primary U.S. calling window:

8:30 a.m.–2:30 p.m. Central Time

Most of this period will be active calling. The rest of your workday can include prospect research, list building, CRM updates, follow-up, call review, and outbound experiments.

Growth

This is a founding role in an established company with tons of growth opportunities for the right individual. This is initially a hands-on SDR role, but there is substantial room to grow.

As you succeed, you can take increasing ownership of:

• ICP and account targeting
• Messaging and talk tracks
• Outbound experiments
• Prospecting systems and automation
• Qualification standards
• SDR processes
• Future SDR coaching and leadership

We're a small team, so strong performers can earn meaningful responsibility quickly.

Our Hiring Process

We try to evaluate candidates based on the work itself.

During the process, we'll ask about the U.S. businesses you've personally prospected, the calls you've made, the meetings you've generated, and what you've learned from real conversations.

Later-stage candidates will complete a short cold-call role-play, receive feedback, and get another attempt.

• We're looking for judgment, curiosity, consistency, coachability, and the ability to create genuinely qualified conversations.