Sales Development Representative (SDR) — Voice AI Startup

Location: Remote (U.S.-based) Type: Full-Time or Part-Time, 1099 Independent Contractor — depending on experience Schedule: Flexible — set your own hours Earnings Potential: $70,000–$100,000+ annually based on performance Apply with Loom video and resume To: resumes@customaisoft.com Website: customaisoft.comAbout UsWe'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 bring on the right person to help us open the next set of doors.The RoleWe're engaging 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 independent contractor engagement. We're flexible on full-time vs. part-time depending on your experience and what you're looking for. You set your own schedule and work the hours that allow you to hit your targets.Career PathThis is a true growth seat, not a dead-end SDR slot. The trajectory we're hiring for is:SDR → Account Executive → Enterprise Sales ManagerThe people who help us build the playbook get first crack at running it as we scale.Who You'll Be CallingYour initial focus is the NEMT ecosystem:NEMT dispatch software companies and SaaS platformsNEMT brokers (regional and national)NEMT transportation providers and agenciesHealthcare systems, MCOs, and government entities operating their own patient-transportation fleets (think large integrated delivery networks running internal shuttles for members)Once you've worked through that list, you'll expand into adjacent transportation verticals: paratransit, senior transit, non-emergency fleet operators, and beyond.What You'll DoConduct outbound calls at a volume consistent with meeting monthly appointment targetsSend personalized email and LinkedIn outreach to decision-makersFollow up consistently and systematically — the deals live in touches 5 through 10, not touch 1Present our overview deck via screen-share to qualified prospectsBook live demos with our Account ExecutiveLog activity, contacts, and pipeline in HubSpot CRMSubmit results-based updates (appointments set, pipeline status) on an agreed cadenceCollaborate with our team to refine messaging and outreach strategy based on what's working in the fieldCompensation StructureMonthly base retainer, paid twice per month — negotiable based on experiencePer-appointment bonus for every qualified meeting booked, paid monthlyPartnership commission for every new integration partnership your outreach helps generate, paid monthlyTotal earnings potential: $70,000–$100,000+ depending on performanceFull 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 the 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 NeedMindset and habits:Comfortable operating as an independent contractor, managing your own time and workflow to deliver resultsSelf-motivated and disciplined — you don't need to be told to pick up the phoneResilient with rejection — you treat "no" as routing data, not a personal verdictOrganized and consistent with follow-upProfessional, articulate, and high-integrityComfortable working fully remote and accountable to your numbersEquipment (you provide):Reliable computer or laptopQuality microphone and speakers (or a good headset)Stable internetA quiet, professional environment for callsTools we provide:HubSpot CRMDialpad VoIP and call loggingSales deck and outreach assetsMS Teams or Slack for ongoing communicationBackground We're Looking ForWe'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 apply1–3 years of B2B sales, SDR/BDR, or telemarketing experienceAnyone with proven phone chops and the hunger to growA 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 LookGet in early at a profitable, fast-growing AI startup with a real national clientHelp build the outbound sales motion from the ground upReal path from SDR to AE to Enterprise Sales Manager as we scaleFully remote, flexible scheduleSell technology that's already deployed and working at scaleHow to ApplyTwo items are required to be considered. Applications missing either will not be reviewed.Your resumeA 60-to-90-second Loom video introducing yourself, telling us why you'd be great in this role, and giving us a 30-second cold pitch as if you were calling one of our prospects.Email both to resumes@customaisoft.com in the same message, with the Loom link in the body.Loom is free at loom.com — install the Chrome extension, hit record, paste the link in your email.Why we require this: selling yourself in your application is the first cold pitch we'll evaluate. We pay close attention to it. Candidates who skip this step won't move forward — no exceptions.We respond to every complete application. 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.