Experienced U.S. B2B Cold Caller / Appointment Setter

Full-Time | Remote | Philippines | U.S. Business Hours / Philippine Night Shift

Base Salary: $1,000–$1,333 USD/month
Target Total Compensation After Ramp: $1,417–$1,833 USD/month

This Is a Phone-First Sales Job

Helpline Software is hiring an experienced U.S. B2B cold caller / Sales Development Representative.

You will spend several hours every working day making outbound cold calls to U.S. businesses.

This is not an entry-level sales role.

Please do not apply if your experience is primarily:

Customer service
Inbound sales
Email or LinkedIn outreach
Lead generation without personally making the calls
B2C telemarketing
Reading a script to a list without conducting real discovery

We are looking for someone who has already spent significant time calling U.S. business prospects and knows how to create real conversations with skeptical, busy decision-makers.

You should be comfortable making 60+ outbound calls in a working day when the list and contact data support it, while still prioritizing conversation quality over meaningless dial volume.

What You'll Do

Your primary job is to create qualified sales conversations through cold calling.

You will:

Cold call U.S. businesses during U.S. business hours
Reach decision-makers through direct numbers, company lines, gatekeepers, branches, and other appropriate channels
Open conversations naturally without sounding robotic or overly scripted
Ask intelligent discovery and qualification questions
Understand the prospect's current process and determine whether there is a real problem we can solve
Identify pain, urgency, decision ownership, timing, and fit
Handle objections such as "not interested," "send me information," "we already have something," and "I'm busy"
Book qualified meetings when there is a legitimate reason for a prospect to speak with us
Leave useful voicemails and complete appropriate follow-up
Record accurate notes, objections, qualification information, and next steps
Review your own calls and improve based on feedback

You will also help with prospect research and list building.

We will teach you our Ideal Customer Profiles and provide access to appropriate tools. You should be capable of using sources such as Apollo, LinkedIn, company websites, Google, directories, and other data tools to identify good accounts, decision-makers, and phone numbers.

If the obvious phone number is unavailable, we expect you to be resourceful rather than simply giving up.

What We Care About

We do not want someone whose only goal is to maximize the number of dials or put unqualified meetings onto the calendar.

We care about:

Meaningful conversations with the right prospects
Qualified opportunities
Qualified meetings that actually happen
Strong call quality
Accurate qualification
Good prospect selection
Consistent follow-up
Accurate CRM notes
Resourcefulness
Coachability
Improvement over time

We look closely at results, not just activity.

Requirements

You should apply only if you meet the most important requirements below.

1. Real U.S. B2B Cold-Calling Experience

You have at least 3 years of meaningful experience personally cold calling U.S. B2B prospects.

We will ask you specifically about:

Calls made per day
Decision-makers reached
Conversations generated
Meetings booked
Meetings that actually showed
The products or services you sold
The types of businesses and buyers you called

Please be prepared to provide real numbers.

2. Excellent Spoken English

Your spoken English must be immediately understandable to U.S. business buyers over the phone.

You should sound:

Natural
Confident
Credible
Conversational
Calm under pressure

Perfect grammar is less important than being easy to understand and sounding comfortable in a real business conversation.

3. Strong Discovery Skills

We do not want someone who races through a script.

Strong callers listen.

You should be able to hear something unexpected from a prospect, ask a useful follow-up question, and adapt the conversation.

4. Objection Handling

You should be comfortable when someone says:

"I'm not interested."
"Just send me something."
"We're happy with what we have."
"Who are you?"
"How did you get my number?"
"I'm busy."
"We don't need this."

We are not looking for aggressive objection handling.

We want someone who stays composed, gets curious when appropriate, and knows when there is—and is not—a useful conversation to pursue.

5. Prospecting Resourcefulness

You have experience identifying companies and decision-makers instead of relying exclusively on perfectly prepared lists.

Experience with tools such as these is helpful:

Apollo
LinkedIn Sales Navigator
ZoomInfo
RocketReach
Lusha
Clay
Other prospecting or contact-data platforms

You should also be comfortable researching companies using Google, company websites, directories, and other public information.

6. Ownership and Honesty

You take responsibility for your:

Calls
Follow-up
Prospect research
CRM notes
Commitments
Working hours
Results

We have zero tolerance for fabricated activity, fake research, misleading prospects, fake call numbers, or dishonest reporting.

If something is not working, we want you to say so and help us figure out why.

Working Hours

This is a full-time remote position.

Our 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 period is active calling.

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

You must be able to work this schedule consistently.

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 operate services where missed calls 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 demonstrated experience and ability.

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

Variable compensation is based primarily on performance factors such as:

Qualified held meetings
Call quality
Qualification accuracy
Reliable execution
Prospect quality
Follow-up quality
Continuous improvement

We do not reward people simply for maximizing dial counts or filling the calendar with bad meetings.

Growth Opportunity

This is intended to be a long-term role.

Initially, you will spend most of your time executing:

Research → Call → Discover → Qualify → Follow Up → Document → Learn

Strong performance can lead to greater ownership of:

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

We want someone who can become increasingly independent as they demonstrate good judgment.

How We Hire

We do not hire someone merely because they interview well.

Strong candidates should expect to:

Submit a short, unedited voice recording
Discuss cold-calling work they personally performed
Provide specific historical performance numbers
Explain how they researched prospects
Complete a live cold-call role-play
Handle realistic objections
Repeat part of the role-play after receiving feedback so we can evaluate coachability
Share previous cold-call recordings when available, with confidential information removed
Complete a short paid work sample or trial when appropriate

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

How to Apply

Do not send us a generic cover letter.

Begin your application with exactly:

I READ THE FULL JOB DESCRIPTION

Then answer the questions below.

1. Your Most Recent U.S. B2B Cold-Calling Role

Tell us:

What were you selling?
What types of companies were you calling?
Which job titles were you trying to reach?
How long did you personally perform this role?
2. Your Actual Calling Numbers

For a typical week in your most recent cold-calling role, approximately:

How many outbound calls did you personally make per day?
How many live conversations with decision-makers did you have per day?
How many qualified meetings did you book per week?
Approximately how many of those meetings actually showed up?

Please give numbers, not general statements such as "I consistently exceeded quota."

3. Prospect Research

Were you given a completed calling list, or did you personally help decide who to contact?

If you did prospect research yourself, explain:

How you identified companies
How you found decision-makers
How you found phone numbers
Which tools you used
4. Tell Us About One Real Cold Call

Describe one U.S. B2B cold call that resulted in a genuinely qualified opportunity.

Tell us:

How you opened the call
What the prospect initially said
What questions you asked
What problem you discovered
Why the prospect agreed to the next step
What ultimately happened with the opportunity
5. What Did the Market Teach You?

Give one example of something you learned from actual cold calls that caused you to change your:

Targeting
Talk track
Qualification
Prospecting approach
6. Voice Recording

Include a link to a 60–90 second unedited voice recording.

Pretend you have just reached the Operations Director of a U.S. organization after making a cold call.

Introduce yourself and explain why you are calling.

Do not use AI-generated audio. Do not add music. Do not heavily edit the recording. We want to hear how you naturally sound.

7. One Objection

Finally, write what you would say next if the prospect interrupted you and said:

"We're not interested. We already have a system for this."

Do not give us the answer you think appears in a sales textbook.

Write what you would actually say on the phone.

We would rather receive a precise, honest application from someone who has done this work than an impressive but vague application from someone who has not.