Sales Development Representative — Founding SDR
Yourco · Chicago, IL (In-office Tues–Thurs)
Read this first
This is a founding sales team seat. You’d be our first Sales Development Rep, the person who builds the top of the funnel from the ground up.
We’ve hit product-market fit, we just closed our $6M Series A led by High Alpha, and we’re ready to scale into our massive Total Addressable Market (TAM), which means there is no ceiling but the ground floor is still being poured. There is no formal training program. There is no onboarding script waiting for you. You will own your ramp the way you’ll own everything else here: by figuring it out, moving fast, and building the thing while you run it.
Here’s the part that matters just as much: you won’t be doing it alone. You’ll have an amazing team behind you people who will back you, share what they’re learning, and help you win. We have a seasoned Head of Revenue and an already successful Founding Account Executive (and currently hiring more). We’re builders who support each other. So while you’ll own your number and your ramp, you’ll never be without people in your corner.
This is a rare opportunity, especially if you love to build. If that excites you, keep reading. If it worries you, this isn’t the seat.
About Yourco
Yourco is the SMS-based frontline employee platform built for deskless workers: ~80% of the global workforce who don’t sit at a desk, don’t have a work email, and won’t download another app. We reach them where they already are…text.
From small businesses to Fortune 500 enterprises, organizations across manufacturing, construction, hospitality, transportation, warehousing, retail, and healthcare trust Yourco to connect, engage, and grow their frontline workforce. The platform supports 135+ languages, syncs with 240+ HRIS and payroll systems, and customers see 86% two-way frontline employee engagement on average within their first 90 days.
With the launch of Frontline Intelligence, our AI-native capability that turns everyday frontline communication into real-time operational insight, we’re defining a new category. This is the wedge and you’ll be selling it at the moment it’s breaking out.
What this role is
You are the tip of the spear. You research target accounts, run creative outbound across phone, email, and social, and turn cold accounts into qualified meetings for our Account Executives — while also being the first to respond to and qualify inbound interest. You’re the first impression prospects have of Yourco, and the engine that keeps pipeline flowing. You’re not inheriting a sequence library and a list. You’re helping build the outbound motion from scratch.
What you’ll do
Generate pipeline
- Book 5 qualified meetings per week through outbound prospecting, the core of the role
- Own inbound response and qualification, be fast, sharp, and the reason a curious lead becomes a real opportunity
- Follow up and own the event leads to pipeline conversion
- Research target accounts and decision-makers across HR, IT, and Operations, and craft personalized outreach that actually gets replies
Run a high-quality outbound motion
- Prospect across phone, email, and LinkedIn with a creative, multi-channel approach, not spray-and-pray
- Qualify thoughtfully so every meeting you pass to an AE is worth their time
- Help build and refine the outbound playbook, sequences, messaging, and target lists as we learn what works
Operate with discipline
- Keep clean, accurate activity and pipeline data in HubSpot, next steps and notes that reflect reality
- Operate effectively in a fast-growing, high-ambiguity environment, using creative problem-solving to uncover and address customer pain
Your path forward
This is a launchpad, not a holding pattern. Once you’re consistently hitting your meeting quota, you’ll earn the chance to work some smaller deals end-to-end, your first reps as a closer, with the support of the team. Do that well, and the path to a full Account Executive seat is right in front of you. We’re building the sales org, and we’d much rather grow our next AEs than go hire them.
What we’re looking for
- 1–2 years of business, sales, or SDR experience, you’ve carried a number or done the work to know you want this role
- An entrepreneurial mindset, you see ambiguity as opportunity, not obstacle
- A self-starter who hears “there’s no formal onboarding” and thinks good, you’ll own it
- Someone who genuinely loves the startup environment: the speed, the ownership, the build
- Comfortable picking up the phone and reaching out cold…you don’t wait for warm
- Hungry to grow into a closing role and willing to put in the reps to get there
- Experience selling to or prospecting HR professionals a plus
- Familiarity with one or more of these industries: Manufacturing, Hospitality, Construction, Transportation & Warehousing, Retail, Real Estate, or Healthcare a plus
The traits we hire for
- Coachability — You actively seek feedback, take it without ego, and apply it fast. You treat every call, demo, and lost deal as a chance to get sharper.
- Resilience & Grit — You push through rejection, ambiguity, and the inevitable hard stretches without losing momentum. When a quarter gets heavy, you lead from the front instead of looking for cover.
- Collaborator — You win as a team. You share what’s working, ask for help when you need it, and make the people around you better — because a founding team only scales if everyone lifts.
- Genuine Curiosity — You’re relentlessly interested in your customers’ world: how frontline work actually happens, where the pain lives, and why. You ask better questions because you genuinely want the answers.
- Consistency Day to Day — You show up and do the work when no one’s watching. Your activity doesn’t spike before a forecast call and crater after — you build pipeline at a steady, reliable clip.
- Confidence — You make tough calls and stand behind them. You can pick up the phone, challenge a prospect’s thinking, and earn a busy executive’s attention without flinching — because you know your value and you’ve done the work to back it up.
Tools you’ll use
HubSpot · Fathom · Zoom · LinkedIn Sales Navigator · Clay · ZoomInfo
Why Yourco
- A real, differentiated wedge (SMS) into a market everyone else struggles to reach
- A new category (Frontline Agents & Frontline Intelligence) breaking out at exactly the right moment
- Product-market fit behind you, fresh Series A capital in the bank, and scale ahead of you
- A founding seat with a clear path to AE for those who earn it
- A team that backs each other and wins together
Logistics, comp & benefits
- Location: Chicago, IL (in-office Tuesday through Thursday)
- Travel: ~25% for events
- Compensation: Base salary plus variable (OTE based on meeting and pipeline targets)
- Benefits: Competitive compensation, medical, dental, and vision coverage, WFH stipend, Apple laptop, PTO, and Stock Options
