Mid-Market Account Executive

Join an early-stage AI company and help build the sales organization that scales it. UpSmith is building AI for the skilled trades — helping HVAC, plumbing, electrical, and other home-services businesses find and capture revenue already sitting inside their business. We're entering the next stage of growth, and we're building the sales team that will take us there. We're looking for Account Executives who want more than a book of leads and a quota. You'll own deals from first conversation through close, work directly with business owners and executives, help shape how we go to market, and have a direct impact on how the UpSmith sales organization is built. This is an opportunity to join early, sell a product with a clear financial impact, and grow alongside the company as we scale. The Opportunity As an Account Executive, your job is simple: Create pipeline. Understand the business. Build the case. Close the deal. You'll sell directly to owners and operators of home-services businesses across the country. These aren't abstract software conversations. You'll be talking about: Revenue sitting inside their existing customer database Open estimates that were never closed Aging equipment and replacement opportunities Cancelled and unbooked appointments Dormant customers Capacity and labor constraints Customer retention Revenue growth Profitability Your job is to understand where the business is losing opportunity, quantify the impact, and show how UpSmith can help capture it. Then close the business. Why Join UpSmith Now Join while the sales organization is being built You're not stepping into a sales machine where every territory, process, script, and decision was established years ago. We're building it now. You'll have the opportunity to influence messaging, discovery, qualification, demos, pricing strategy, territory design, sales process, and how future Account Executives are developed. We want sellers who can execute the playbook and help make the playbook better. Sell AI tied directly to revenue A lot of AI products sell productivity. UpSmith sells business outcomes. Our conversations center on revenue recovered, appointments booked, estimates closed, customers retained, and opportunities captured. That gives you the ability to sell around measurable ROI rather than vague technology promises. Sell directly to business owners You'll spend your time with entrepreneurs and operators running multimillion-dollar businesses. That requires more than delivering a polished demo. You need to understand how they make money, what is preventing them from making more of it, and why solving that problem matters now. You'll become a better business seller because of it. Your upside grows with the company We're building the team now. As the company grows, we expect opportunities to emerge across larger accounts, strategic sales, sales leadership, and other parts of the GTM organization. The people who join early, perform, and help us build the organization should be positioned to take on increasingly meaningful responsibility. What You’ll Own Own the sales process from qualified opportunity through closed-won Build additional pipeline through strategic self-sourced prospecting and account development Run discovery conversations with owners, executives, and senior operators Understand each prospect's business model, priorities, challenges, and financial drivers Identify and quantify the revenue opportunity UpSmith can address Deliver compelling product demonstrations tied to the prospect's specific business Build business cases around measurable ROI Navigate multiple stakeholders throughout the buying process Handle objections around AI, technology, implementation, pricing, and change Develop champions inside prospective accounts Create urgency without relying on artificial pressure Manage negotiations and commercial conversations Maintain accurate pipeline, forecasting, and next steps Work closely with SDRs to improve targeting, qualification, and handoffs Bring market feedback back to Product, Marketing, and leadership Consistently hit and exceed revenue targets You don't own demos. You own revenue. What Great Selling Looks Like Here We don't want feature dumping. We don't want generic demos. We don't want reps waiting around for perfect inbound opportunities. Great Account Executives at UpSmith understand the customer's business before prescribing a solution. They can move between operational problems and financial outcomes. They know how to ask difficult questions. They create urgency by making the cost of doing nothing visible. They understand who actually makes the decision. They know when to push and when to listen. And they take responsibility for moving the deal forward. What Success Looks Like First 30 Days You'll understand UpSmith's product, customers, ICP, competitive landscape, sales process, and the economics of a home-services business. You'll begin shadowing and participating in discovery calls, demonstrations, and active opportunities. You'll understand why our customers buy and what separates strong opportunities from weak ones. First 60 Days You'll independently run discovery and demonstrations. You'll be managing your own pipeline, progressing opportunities, building business cases, and demonstrating command of the sales process. You'll begin closing your first deals. First 90 Days You'll own your number. You'll independently manage opportunities from discovery through close, maintain an accurate forecast, consistently build pipeline, and demonstrate the ability to win business without requiring constant direction. From there, the expectation isn't simply to execute the sales process. It's to help us improve it. Who Thrives Here This role is built for someone who wants ownership. You'll likely thrive at UpSmith if: You have a track record of successfully selling B2B products or software You have experience owning a sales cycle from discovery through close You're comfortable selling directly to business owners and executives You can run discovery without turning it into a checklist You understand how to connect operational problems to financial outcomes You're comfortable discussing ROI and building a business case You can prospect and don't believe pipeline creation is someone else's job You're comfortable operating in an environment where the playbook is still evolving You want feedback and improve quickly from it You're competitive without needing to be managed through fear You're organized and disciplined about pipeline and forecasting You take ownership when deals stall instead of blaming the prospect You want your income and responsibility to be heavily influenced by your performance Experience selling SaaS, AI, ServiceTitan-related technology, home-services software, or products to SMB and mid-market owner-operators is valuable but not required. This Role Probably Isn't for You If You want to inherit a full calendar of inbound demos You believe prospecting stops when you become an AE You rely on product features instead of business discovery You need a rigid playbook before taking action You avoid difficult conversations around budget, decision-making, timing, or competition You're uncomfortable being directly accountable for a revenue number You prefer maintaining existing accounts to winning new business This is a closing role. We expect our AEs to hunt, diagnose, sell, negotiate, and close. How We Work Mission First Builders come first. Every decision runs through the mission: trades companies win, tradespeople thrive. Speed Wins Bias to action. Ship Monday over polished next month. Inaction is the only unforgivable mistake. Be an Owner See what needs doing and do it. Own your mistakes, fix them fast, share what you learned. Choose Greatness Hold a high rigor bar. Real businesses and real livelihoods deserve our best work. Location This is an in-person role at UpSmith's Dallas headquarters. We're building the company and the sales organization at the same time. We believe being together makes us faster — better coaching, faster feedback, stronger collaboration, and more learning from the wins and losses happening around you. What You're Joining This isn't a role where the sales organization has already been built and your job is simply to occupy a territory. You're joining early enough to help define #J-18808-Ljbffr