Account Executive

Mid-Market Account Executive — Founding Sales TeamYourco · Chicago, IL (In-office Tues–Thurs)Read this firstThis is a founding sales team seat. We have one founding AE today (who is already making a big impact). You’d be the next.

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 hired a seasoned Head of Revenue and will be adding a Founding SDR to the team as well. 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 YourcoYourco 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 isYou own the pipeline, prospect to close. You self-source the majority of your opportunities, multi-thread into power, and close, including Enterprise Bridge deals, where you land a few locations and expand into the broader enterprise relationship. You run a high-activity motion, keep a clean pipeline, and bring a hunter’s creativity to a segment that’s still being defined.

You’re not inheriting a playbook. You’re helping write it.

• What you’ll do
• Close
• Close $200K in ARR per quarter once fully ramped
• Own full-cycle sales from prospect to close, you will own your pipeline.
• Create & Advance
• Run a minimum of 10 meetings per week, split across creating new opportunities (with inbound sprinkled in) and advancing your existing pipeline opportunities.
• Self-source the majority of your pipeline through targeted outbound, account research, and creative prospecting
• Build and maintain a healthy pipeline with the right mix of deals and dollars to consistently hit number
• Multi-thread to power
• Navigate complex, multi-stakeholder deals across HR, IT, Operations and Internal Communications
• Gain access to economic buyers and decision-makers to close Mid-Market & Enterprise Briddeals, start with a few locations, bridge to the enterprise
• Operate with discipline
• Maintain a clean, accurate pipeline at all times: stages, next steps, and close dates that reflect reality
• Operate effectively in a fast-growing, high-ambiguity segment, using creative problem-solving and a proactive approach to uncover and address customer pain
• What we’re looking for2–4 years of full-cycle sales experience with a track record of exceeding targets at an early-stage company
• 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
• Demonstrated ability to self-source pipeline, you can point to deals you built from cold, not just closed from inbound
• Proven multi-threading skills and the ability to navigate complex B2B sales cycles to power
• Experience selling to HR professionals is a plus
• Experience selling into one or more of these industries: Manufacturing, Hospitality, Construction, Transportation & Warehousing, Retail, Real Estate, or Healthcare is 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 and move deals at a steady, reliable clip.

Confidence — You make tough calls and stand behind them. You can challenge a prospect’s thinking, hold your price, and walk a C-level executive through a decision without flinching because you know your value and you’ve done the work to back it up.

• Tools you’ll useHubSpot
• Fathom
• Zoom
• LinkedIn Sales Navigator
• Clay
• Zoom
• Info
• 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 the ownership and upside that comes with being early
• A team that backs each other and wins together
• Logistics, comp & benefits
• Location: Chicago, IL — in-office Tuesday through Thursday
• Travel: ~25% for events and customer meetings
• Compensation: Base + Variable
• Benefits: Competitive compensation, medical, dental, and vision coverage, WFH stipend, Apple laptop, PTO, and Stock Options