AI Sales Executive - Voice CSR

Simpro Software

$80K — $95K *
Miami, FL 33186In-Person
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years in sales, preferably in tech or AI solutions.
  • Proven track record of closing deals in a fast-paced environment.
  • Strong understanding of the trade and field service industries.
  • Technical credibility to address product-related inquiries effectively.
  • Ability to cultivate relationships with business owners quickly.

Responsibilities

  • Drive the adoption of AI back-office solutions for existing customers.
  • Conduct 3-4 high-impact demos per day to convert leads.
  • Connect AI products to customer profit margins.
  • Self-source 30% of the sales pipeline through existing accounts.
  • Address technical questions and objections confidently during sales calls.
  • Build trust and long-term relationships with trade business owners.
  • Consistently close deals with a high volume of success.

Benefits

  • Strong base salary with uncapped commission opportunities.
  • Flexible work environment with a focus on results.
  • Potential for ongoing career development and training.
  • Opportunity to make a transformative impact on customer profitability.
Full Job Description

Job Context

AI Sales Executive (Voice CSR) — The Most Important Seat We’re Filling This Year

Read this twice, because we don’t write job postings like this often.

Many businesses in our customers’ world run on tight profit margins — on average around 5%.

We’ve built the AI back-office solution to change that, helping customers work toward margins several times higher than they’re used to. Sit with that for a second. We are not asking you to squeeze more money out of customers — we’re asking you to help our customers become significantly more profitable than they’ve ever been. That’s the job. That’s the mission.

This is not order-taking. This is providing real business solutions for our trades and field-service management customers that are grinding on thin margins, showing them what AI can do to their

bottom line. You’ll be the person who introduces a transformation most of these businesses don’t even know is possible — and the better you are at it, the more companies you help change.

What You’ll Do

What you'll own

You'll drive adoption of Simpro Group's AI back-office solutions across our existing customer base. This is a closing role — not a prospecting grind. The majority of your pipeline comes to you warm, handed off by Account Managers or triggered through marketing. Your job is to run tight, high-impact demos, connect our AI products to where a customer is losing margin today, and close.

You'll also self-generate 30% of your pipeline through your own outbound — but exclusively into our existing customer base. No cold outreach, no net-new logos. Just deeper penetration into accounts that already know and use Simpro.

What you will sell

You will be selling a revolutionary, AI-powered Voice CSR (Customer Service Representative) built exclusively for the trade and field service industries. Our technology integrates natively with Simpro, the leading global software that plumbing, electrical, HVAC, and fire protection contractors use to run their entire operations.Field service businesses lose thousands of dollars weekly because roughly 45% of inbound client calls go unanswered during busy hours or after-the-clock. Our hyper-realistic AI voice assistant solves this by answering calls 24/7. It qualifies leads, parses complex job types, matches appointments against real-time Simpro staff calendars, and books service jobs directly into their Simpro workflow on autopilot with zero manual data entry required

Day to day, you will:

  • Receive warm inbound leads from the Account Management team and marketing — 70% of your pipeline is already primed before you pick up the phone.
  • Run 3–4 demos per day with existing customers, moving deals through a short 1–2 call cycle from first conversation to closed.
  • Connect our AI products directly to each customer's business — translating technology into the number they care about most: profit.
  • Generate your own pipeline through self-sourced outbound into existing accounts, owning 30% of your book independently.
  • Handle technical questions and objections with confidence — you'll be the product authority in every conversation.
  • Build real relationships with trade business owners throughout the sales process, earning the trust that turns a demo into a done deal.
  • Close consistently and at volume — this role is built for someone who wants multiple wins per week.

Who we want

Someone who wants to close, not just converse. You thrive in a fast-paced, high-volume environment where the deals are real, the cycle is short, and the wins stack up quickly. You have the technical credibility to earn a customer's respect in the first five minutes and the drive to turn that respect into a signature.

The base is strong, the commission is uncapped, and the pipeline is real. If you have a proven track record of closing in a short sales cycle, apply here.

What You’ll Bring

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