B2B Sales Development Representative

U.S. Cold Calling, Prospect Research & List Building

Full-Time | Remote | Philippines | U.S. Business Hours

Helpline Software is looking for an unusually strong B2B Sales Development Representative who can find the right prospects, research them intelligently, and cold call them confidently.

This is not a scripted telemarketing job.

This is not a role where someone gives you 200 phone numbers and asks you to dial through them.

You will learn our Ideal Customer Profiles (ICPs), use tools such as Apollo, LinkedIn, company websites, Google, and other research sources to identify good accounts and decision-makers, find workable phone numbers, and then call those prospects yourself.

Your job is to create qualified sales conversations, learn from the market, and continuously improve who we target and how we approach them.

We are looking for someone who wants substantial ownership and a long-term role.

What You Will Own

You will be responsible for the complete outbound prospecting loop:

Understand the ICP ? find accounts ? research them ? identify the right people ? find phone numbers ? cold call ? qualify ? document ? learn ? improve the next list.

Your responsibilities will include:

Build your own high-quality cold-call lists based on our ICP criteria
Research companies to determine whether they are genuinely worth contacting
Use Apollo, LinkedIn, Google, company websites, directories, and other tools to identify prospects
Find accurate direct dials, mobile numbers, company numbers, branch numbers, or other useful ways to reach the right person
Identify likely decision-makers such as Operations leaders, Customer Service leaders, executives, and other relevant roles
Spend most of the core U.S. business-hours overlap actively cold calling carefully selected prospects
Open conversations naturally and explain why you are calling
Ask thoughtful discovery questions to understand the prospect's current process
Identify pain, urgency, decision ownership, and ICP fit
Handle resistance without becoming aggressive, defensive, or robotic
Record accurate call notes, objections, qualification information, and follow-up steps in our CRM
Review your own call recordings and improve through coaching and repetition
Notice patterns in the market and recommend improvements to targeting and messaging

We do not want someone who says:

"Apollo didn't have a phone number, so I couldn't call them."

We want someone resourceful enough to find another sensible way to reach the organization.

About Helpline Software

Helpline Software provides mission-critical software for organizations operating 24/7 hotlines, emergency lines, and after-hours support systems.

Our software helps organizations route calls to the correct on-call responder based on the live schedule, escalate when someone does not answer, and give management visibility into what happened.

Our customers include organizations operating services where a missed call can have serious consequences.

We already support paying customers across the United States and are expanding into additional markets where reliable after-hours communication matters.

Compensation

Base salary: $1,000–$1,333 USD per month, depending on experience and demonstrated ability.

Target total compensation after ramp: approximately $1,417–$1,833 USD per month.

Variable compensation is based primarily on:

Qualified held meetings
Call quality
Accurate qualification
Reliable execution
Good prospect selection
Follow-up quality
Continuous improvement

We do not reward people simply for maximizing dial counts or putting unqualified meetings onto the calendar.

Working Hours

This is a full-time remote role.

The core calling window is:

8:30 a.m.–2:30 p.m. U.S. Central Time

For candidates in the Philippines, this is generally:

9:30 p.m.–3:30 a.m. Philippine Time while U.S. daylight saving time is in effect
10:30 p.m.–4:30 a.m. Philippine Time during U.S. standard time

Most of this six-hour window is active calling.

Prospect research, list building, preparation, CRM work, follow-up, and call review happen around the core calling block.

You must be able to work this schedule consistently.

Requirements

You should apply only if most of the following describe you:

You have at least 3 years of meaningful experience cold calling U.S. B2B prospects.
Your spoken English is excellent and immediately understandable to U.S. business buyers over the phone.
You sound natural, credible, confident, and conversational—not rushed, robotic, or overly salesy.
You have experience finding your own prospects, not only calling lists prepared by someone else.
You can research companies and decide which accounts are genuinely worth calling.
You have used tools such as Apollo, LinkedIn Sales Navigator, ZoomInfo, RocketReach, Lusha, Clay, or similar prospecting/data tools.
You are comfortable using online research to identify decision-makers and find ways to contact them.
You listen carefully and ask intelligent follow-up questions rather than racing through a script.
You take ownership of your calls, research, follow-up, CRM notes, commitments, and working hours.
You are highly coachable and willing to review recordings of your own calls.
You can receive direct feedback, change your approach, and demonstrate improvement quickly.
You remain composed when prospects are busy, skeptical, dismissive, or difficult to reach.
You are resourceful. When one approach fails, you intelligently try another.
You are honest. We have zero tolerance for fabricated activity, misleading prospects, fake research, or dishonest reporting.
What Success Looks Like

We are a quantitative team.

We track things such as:

Meaningful conversations
Qualified opportunities
Held meetings
Qualification accuracy
Account quality
Prospecting quality
Follow-up completion
CRM accuracy
Call quality
Objection patterns
Improvement over time

Raw dial volume matters, but it is not the goal.

High-quality conversations delivered consistently are the goal.

Growth Opportunity

You will initially spend much of your time executing: researching prospects, building lists, making calls, following up, and learning our markets.

If you perform well, we want you to become increasingly independent.

Over time, you may take greater ownership of:

ICP refinement
Account selection
Prospecting strategy
Talk tracks
Qualification standards
Outbound experiments
Coaching additional callers
Sales development performance

There is significant room to grow with the company.

How We Hire

We do not hire based on interviews alone.

Strong candidates should expect to:

Submit a short unedited voice recording so we can evaluate spoken English and communication
Walk us through previous cold-calling work they personally owned
Explain how they built or researched prospect lists
Complete a live cold-call role-play
Repeat part of the exercise after receiving feedback so we can evaluate coachability
Share prior cold-call recordings when available, with confidential information removed
Complete a short paid work sample or trial before a long-term offer when appropriate

We care much more about evidence of work you personally performed than impressive-sounding claims.

Culture

We want someone who could work with us for many years.

That requires both high standards and a healthy working relationship.

We give regular, direct feedback.
You are encouraged to give us feedback as well.
We expect people to honor their commitments.
We value independent thinking and intellectual honesty.
We want people who admit when something did not work and learn from it.
You will receive regular written and verbal performance feedback.
Strong performance leads to greater responsibility and autonomy.
Final Application Instruction

Please read this carefully.

Do not send us a generic cover letter.

Instead, begin your application with the words:

I READ THE FULL JOB DESCRIPTION

Then answer this question:

Tell me about one U.S. B2B prospecting campaign where you personally helped decide who to contact AND personally made the cold calls.

Please explain:

What were you selling?
Who was the Ideal Customer Profile?
How did you find companies that matched the ICP?
How did you identify the people you wanted to call?
What tools did you use to find their phone numbers?
Approximately how many calls were you making?
Walk me through one call that resulted in a genuinely qualified opportunity.
What did you learn from the calls that caused you to change your targeting or approach?

Please be specific.

We would rather read a precise answer about work you actually performed than an impressive but vague answer.