AI Sales Executive

Job Context

Senior AI Sales Executive - 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.

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

What We Can Offer You

Responsible Time Off

Comprehensive medical, dental, vision package with 100% employer paid options

Additional benefits including Health Savings Account; Flexible Spending Account; Critical Illness Insurance; Hospital Insurance; Accident Insurance; Life Insurance and AD&D; and Disability Insurance available to purchase.

Wellness Challenge App, Diabetes Prevention App, and Health Hub App

401k/Retirement Plan with 6% employer match

Generous Parental Leave Program

Paid Volunteer Leave Days

Public Holiday Exchange Scheme

Talent Referral Program – get rewarded for referring a friend to join our team!

Diverse training & internal networking opportunities across all of our product lines

Opportunities for career progression and development

Service recognition awards

Click here to find out more about working at Simpro Group!

Our Core Values

We Are One Team

We Are Customer Centric

We Are Growth Minded

We Are Accountable

We Celebrate Success

Please note, no agencies will be accepted in the recruitment of this role.