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.

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.

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.

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.

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.

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.

• 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.

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…