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Remote (U.S.-based) Type: Full-Time or Part-Time, 1099 Independent Contractor — depending on experience Earnings Potential: $70,000–$100,000+ annually based on performance Apply To: resumes@customaisoft.com Website: customaisoft.com
About Us
We’re a fast-growing, revenue-generating AI startup that builds Voice AI Intelligent Virtual Assistants (IVAs) for transportation dispatch software platforms. Our technology answers inbound calls, books rides, handles routine customer service, and integrates directly into the dispatch systems our partners already use — replacing expensive call center labor with always-on automation.
We already serve a national client base. Now we’re scaling, and we’re ready to hire the right person to help us open the next set of doors.
The Role
We’re hiring our first dedicated Sales Development Representative to drive top-of-funnel outreach into the Non-Emergency Medical Transportation (NEMT) industry and adjacent transportation verticals.
You won’t be closing deals. Your job is to find the right people, get them on the phone, walk them through a high-level overview deck, and book a discovery call between them and our Account Executive — who runs the live demo and moves the conversation toward a partnership.
This role is fully remote and structured as a 1099 contract. We’re flexible on full-time vs. part-time depending on your experience and what you’re looking for.
Career Path
This is a true growth seat, not a dead-end SDR slot. The trajectory we’re hiring for is:
SDR → Account Executive → Enterprise Sales Manager
You’ll be in a room with the C-suite from day one, building the playbook with us. As we scale, the people who built the motion get first crack at running it.
Who You’ll Be Calling
Your initial focus is the NEMT ecosystem:
- NEMT dispatch software companies and SaaS platforms
- NEMT brokers (regional and national)
- NEMT transportation providers and agencies
- Healthcare systems, MCOs, and government entities operating their own patient-transportation fleets (think large integrated delivery networks running internal shuttles for members)
Once we’ve worked through that list, you’ll expand into adjacent transportation verticals: paratransit, senior transit, non-emergency fleet operators, and beyond.
What You’ll Do
- Make a minimum of 100 outbound cold calls per day using our Dialpad VoIP account
- Send personalized email and LinkedIn outreach to decision-makers
- Follow up consistently and systematically — the deals live in touches 5 through 10, not touch 1
- Present our overview deck via screen-share to qualified prospects
- Book live demos with our Account Executive
- Log activity, contacts, and pipeline in HubSpot CRM
- Report your daily activity in MS Teams or Slack
- Work directly with our C-suite to refine messaging, scripts, and process
Compensation Structure
- Monthly base retainer, paid twice per month — negotiable based on experience
- Per-appointment bonus for every qualified meeting booked, paid monthly
- Partnership commission for every new integration partnership your outreach helps generate, paid monthly
- Total earnings potential: $70,000–$100,000+ depending on performance
Full Disclosure (Because We Respect Your Time)
We’re early enough that our outbound playbook isn’t fully proven yet, and our sales cycle for partnership deals isn’t fully mapped. That means commission ramp on closed partnerships may take a few months as we figure out our pipeline together. Appointment-setting bonuses, however, can start the moment you start dialing — so the activity-driven side of your earnings is in your hands from day one.
If you want to be part of building the sales motion at a real, revenue-generating AI company — not just executing someone else’s playbook — this is the room.
What You Need
Mindset and habits:
- Disciplined and self-managed — you don’t need to be told to pick up the phone
- Resilient with rejection — you treat “no” as routing data, not a personal verdict
- Organized and consistent with follow-up
- Professional, articulate, and high-integrity
- Comfortable working fully remote and accountable to your numbers
Equipment (you provide):
- Reliable computer or laptop
- Quality microphone and speakers (or a good headset)
- Stable internet
- A quiet, professional environment for calls
Tools we provide:
- HubSpot CRM
- Dialpad VoIP and call logging
- Sales deck and outreach assets
- Direct collaboration with founders to develop scripts and process
- MS Teams or Slack for daily communication
Background We’re Looking For
We’re open on background, but the ideal candidate fits one of these profiles:
- Recent college graduate looking to break into tech sales and start a real career — strongly encouraged to apply
- 1–3 years of B2B sales, SDR/BDR, or telemarketing experience
- Anyone with proven phone chops and the hunger to grow
A degree is not required. Experience in transportation, healthcare, SaaS, or call center industries is a plus but absolutely not a requirement.
Why This Role Is Worth Your Look
- Get in early at a profitable, fast-growing AI startup with a real national client
- Help build the outbound sales motion from the ground up
- Direct mentorship from the C-suite — not a 3-tier SDR org chart
- Real path from SDR to AE to Enterprise Sales Manager as we scale
- Fully remote, flexible hours
- Sell technology that’s already deployed and working at scale
How to Apply
Email your resume to resumes@customaisoft.com.
To stand out: include a 60-to-90-second Loom video introducing yourself and telling us why you’d be great in this role. Selling yourself in your application is the first cold pitch we’ll evaluate — and we pay close attention to it.
We respond to every applicant. We are ready to hire the right qualified individual.
- Custom AI Solutions is an equal opportunity employer. We celebrate diverse perspectives and are committed to building an inclusive environment for all team members and contractors.
