B2B Software SaaS Sales Expert - Cold Calling - USA

JOB TYPE: Part-time (20–25 hrs/week), OR full-time 40 hours per week

SALARY: $7 - 8/hour paid + commission (20,000–100,000 per closed sale) HOURS: US Eastern Time business hours

Read this whole post before applying. Applications that skip the instructions at the bottom will not be opened.

What this is

We are a small US software company. We built a Windows application that completely automates the billing and paperwork for a very specific American professional: an independent vocational rehabilitation case manager who helps injured workers return to work, and who bills the state workers' compensation system for her time.

Right now she types the same information four separate times — into a daily spreadsheet, a weekly written report, a claim form, and a payment tracker — then faxes it. Our software means she types it once and everything else generates automatically. Our first customer went from losing entire mornings on paperwork, to just being able to complete it all in minutes.

Nobody else has built this. There is no competitor. She has never had a software company understand her job.

Your job is to find these people, get them on the phone, and get them to look at it.
Why this role is unusual — please read carefully

This is not a volume dialing job. If you are looking for a job where you make 80–150 calls a day, this is the wrong post and you will hate this work.

There are only about 100–150 of these professionals in the state we're starting with. That is the entire market. We cannot buy more of them.

That means every single call matters. Burning through the list with a rushed pitch destroys the campaign permanently. We need someone who will make 40 excellent calls a week, not 400 mediocre ones.

You will spend as much time researching who these people are as you will spend calling them.

Who you'll be calling

Typically a woman, 45 to 65 years old, who has run her own practice for 15 to 30 years. She works alone, often from home. She has a master's degree and professional certifications. She handles confidential medical information. She is not technical and does everything in Word and Excel by choice. She has almost no online presence.

She has never been called by a software company that understood her job.

High-energy, high-pressure selling will fail instantly with this person. She responds to someone who has clearly done their homework, asks good questions, and is patient. Your credibility comes entirely from sounding like you understand her work.

You will need to learn the US workers' compensation vocabulary — BWC, MCOs, W-codes, CMS-1500 forms. We'll train you and pay you while you learn it. But you have to be the kind of person who can absorb a technical subject and speak about it confidently within a week.

What you'll actually do

Research and verify who is genuinely still practising (many public listings are outdated)
Manually dial — no auto-dialers, for US legal compliance
Have real conversations: ask about their process, find where the pain is
Book demos for our team
Ask for referrals — this community is invisible online and they all know each other
Keep detailed notes; with a list this small, everything you learn is valuable
Report back on what you're hearing so we can improve the approach

The first week is genuinely exploratory: validating the list, testing angles, and learning what actually resonates. We're not expecting sales in week one. We're expecting intelligence.

Requirements — please be honest with yourself

You must have:

3+ years of B2B outbound phone sales to the US market
Experience selling software or SaaS to small businesses or solo professionals (not enterprise, not consumers)
Experience representing a company the prospect has never heard of
A track record of learning a technical or regulated field (healthcare, insurance, legal, finance, compliance)
Genuinely consultative style — you ask questions before you pitch
Clear, calm, natural English. Warmth matters more than a perfect accent.
Reliable internet, quiet workspace, good headset
Ability to work US Eastern Time business hours

Big plus:

Sold into US healthcare, medical billing, insurance, or workers' compensation
Have done customer discovery or research interviews for a startup
Have built your own prospect lists
Have worked a niche market with under 1,000 total possible customers

Please do not apply if:

Your background is only inbound sales and customer service
You measure your work in calls per day
Your experience is only for generic lead generation (SEO, web design, solar, insurance, credit repair)
You need a script to have a conversation
You would describe yourself as "money hungry" — this list needs patience, not hunger
Compensation

Paid pilot week: $7–8 USD/hour for 20–25 hours, based on experience. No sales targets. You'll research, call, explore, and write up what you learn.

After the pilot, for the right person:

Base: $7–8 USD/hour
2,500 per demo booked that actually happens
20,000 per closed solo customer
35,000 per closed professional-tier customer
75,000–100,000 per multi-user practice customer

This can be a short project or a long-term role. That depends on results, and honestly, on whether you enjoy it. If this campaign works, there are five more US states behind it.

How to apply — follow this exactly

1. Subject line must be exactly: VOCREHAB SPECIALIST — [Your Name]

2. In your message, answer these three questions briefly:

What software or SaaS product have you sold to US small businesses, and what did it do?
What is the most technical or complicated subject you've had to learn in order to sell something?
Why does a market with only 150 possible customers require a different approach than a big one?

3. Record a voice message at ---------- and paste the link in your application.

Go to ---------- , click record, speak for 5 to 10 minutes, then paste the share link into your application.

Please speak naturally. Do not read from a script or from anything AI-written — we can tell immediately, and it's an automatic no. We want to hear how you actually talk on a call.

Cover these four things, in order:

(a) Walk us through one specific B2B deal you sold. Name the company, what they did, what they were using before, what their objection was, and what changed their mind.

(b) Tell us about a product you had to learn from scratch. How did you learn it, and how long before you were comfortable talking to prospects about it?

(c) Answer this out loud, exactly as you would on a real call:

You've called a 55-year-old woman in Ohio who has run her own vocational rehabilitation practice for 25 years. She does all her billing by hand in Word and Excel. She's never heard of you or our company. Thirty seconds into the call she says:

"I've been doing this for 25 years. I don't need software."

Say word for word exactly what you would say next.

(d) Tell us about a deal you lost, and what you would do differently now.


**Applications missing the Vocaroo link will not be reviewed. Applications with the wrong subject line will not be opened.

We're looking for one person. We'd rather wait for the right one.