Senior Account Executive

Senior Account Executive

Remote (Canada) │ Hybrid Available – Kitchener, ON

Reports to:

Manager, New Sales

$90,000–$100,000 CAD base

About Encircle
Encircle is leading the $1.6 trillion property insurance industry out of the dark ages of pen-and-paper processes, into the digital age of transparency and empowerment. Our easy-to-use software platform enables thousands of restoration contractors and insurance professionals around the world to process claims faster.

We're a remote-first company with a collaboration hub in downtown Kitchener — and we're growing.

About the Role
Restoration contractors choose Encircle because the first conversation feels different: people who know their industry, understand their business and show them exactly how Encircle makes them money. As Senior Account Executive, you'll own the full sales cycle - prospecting, discovery, demo, proposal and close - for a book of restoration, independent adjusting and multi-location accounts.

This is an end to end sales position. You’ll be held accountable to hunting your own deals, not just working the marketing funnel. You'll build pipeline of your own alongside meetings sourced by our BDR team, and you'll be coached to the same formula every AE runs on: discovery and demo, demo-to-proposal, proposal-to-close, sales cycle length and ACV, using the SPICED methodology and the documented playbook.

As a senior member of the team, you're expected to perform at or above benchmark, take on the more complex, multi-stakeholder deals — franchise locations, multi-site operators, independent adjusting relationships — and help sharpen the playbook for the reps coming up behind you.

You’ll work closely with Onboarding & Activation and Account Management so every new customer starts with a plan, and with our BDR team so sourced pipeline converts cleanly into revenue.

What You'll Be Doing
Own the full sales cycle

Prospect and build pipeline in your territory: self-sourced outbound plus inbound and BDR-sourced meetings, managed as one connected funnel

Run discovery, demo, proposal and negotiation using SPICED and the documented playbook, converting at or above benchmark at every stage

Build and defend a monthly forecast — pipeline coverage, stage conversion and deal velocity you can stand behind

Own deal strategy for complex, multi-stakeholder accounts: franchise and network structures, multi-location operators and independent restoration relationships

Be the trusted advisor restoration contractors remember

Diagnose the real business pain behind every conversation — tool consolidation, adjuster pushback, time lost in the field, missed revenue on jobs — and connect it to how Encircle solves it

Run demos and presentations tailored to the room, from field crews to owners and executive leadership

Build account-based plans for named target accounts, including multi-location and franchise prospects

Use real ROI data and customer proof points to build a business case that holds up to scrutiny

Close clean and hand off cleaner

Close deals with signed contracts and accurate CRM data that sets up a smooth transition

Partner with Onboarding & Activation on a mutual onboarding plan at the point of close, so every new customer starts strong

Partner with Account Management on account context and handoff for multi-location and franchise-influenced accounts

Maintain Salesforce hygiene so your pipeline and deal data are accurate and usable by the wider business

Raise the bar for the team

Contribute to the AE playbook: what's working in discovery, demos, objection handling and negotiation, and feed it back to your manager

Mentor newer AEs through call reviews, deal strategy and territory planning as a senior peer on the team

Lead by example on activity and pipeline discipline,…