Mid-Market Account Executive

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.

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 what great selling at UpSmith looks like.

You'll close business.

You'll help shape the playbook.

You'll influence how SDRs are developed into future Account Executives.

You'll help establish the standards future sellers are measured against.

And if you perform, you'll have the opportunity to grow with the sales organization you helped build.