Senior Account ExecutiveRemote (Canada) │ Hybrid Available – Kitchener, ONReports to: Manager, New SalesSalary range: $90,000–$100,000 CAD baseAbout EncircleEncircle 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 RoleRestoration 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 DoingOwn the full sales cycleProspect and build pipeline in your territory: self-sourced outbound plus inbound and BDR-sourced meetings, managed as one connected funnelRun discovery, demo, proposal and negotiation using SPICED and the documented playbook, converting at or above benchmark at every stageBuild and defend a monthly forecast — pipeline coverage, stage conversion and deal velocity you can stand behindOwn deal strategy for complex, multi-stakeholder accounts: franchise and network structures,



multi-location operators and independent restoration relationshipsBe the trusted advisor restoration contractors rememberDiagnose 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 itRun demos and presentations tailored to the room, from field crews to owners and executive leadershipBuild account-based plans for named target accounts, including multi-location and franchise prospectsUse real ROI data and customer proof points to build a business case that holds up to scrutinyClose clean and hand off cleanerClose deals with signed contracts and accurate CRM data that sets up a smooth transitionPartner with Onboarding & Activation on a mutual onboarding plan at the point of close, so every recent customer starts strongPartner with Account Management on account context and handoff for multi-location and franchise-influenced accountsMaintain Salesforce hygiene so your pipeline and deal data are accurate and usable by the wider businessRaise the bar for the teamContribute to the AE playbook: what's working in discovery, demos, objection handling and negotiation, and feed it back to your managerMentor newer AEs through call reviews, deal strategy and territory planning as a senior peer on the teamLead by example on activity and pipeline discipline, hitting or exceeding published benchmarksBring AI into your own workflow — account research, call prep, follow-up and forecasting — and share what works with the teamCollaborate across the businessPartner with BDRs on outbound targeting, meeting quality and handoff feedbackPartner with Marketing on lead quality, campaign feedback and product-led buying signalsFeed win-loss insights, objection patterns and competitive intelligence back to Marketing and ProductPartner with the Enterprise team on franchise-location opportunities that sit under a national or network relationshipKey Metrics You'll OwnNew ARR and quota attainmentPipeline coverageStage conversion rates vs.



benchmarkACV and product attach rateSales cycle lengthForecast accuracyImmediate PrioritiesIn your first few months, you'll ramp to the formula and start proving it:Complete onboarding and ramp to full quota productivity on the defined timelineBuild pipeline to target coverage against quota within your first 90 daysRun discovery, demo and proposal stages at or above published benchmarksClose your first deals with a clean, documented handoff to Onboarding & ActivationWhat You'll Bring5+ years of full-cycle B2B SaaS (or similar) direct sales experience, with a stable, proven track record of quota attainmentExperience running discovery, demo, proposal and negotiation for multi-stakeholder deals — not just working a queue of inbound leadsSkilled at building account-based plans and self-sourcing pipeline, not just closing what's handed to youComfortable navigating franchise, multi-location or network buying structures, including access to decision-makers up to the C-suiteA track record of building and defending an accurate forecastProficiency with Salesforce and familiarity with sales tools like Gong and DocuSignFluency with AI tools in your own workflow — research, call prep, follow-up and forecastingA consultative, industry-fluent selling style: you close deals customers are glad they signedExceptional verbal and written communication skillsExperience selling to blue-collar or field-based industries, or in vertical SaaS, is a plus but not requiredWhy Encircle?We VALUE our people:Balance: Flexible hours, self-managed vacation and trust to manage your time.Remote-first: Work where you're most productive — with access to our collaboration hub in Kitchener.Growth-oriented: We support your learning and career development.Well-being: We care about the full human — inside and outside of work.Encircle is an equal opportunity employer committed to building a diverse and inclusive team. We encourage all qualified candidates to apply and will work with applicants to accommodate accessibility needs throughout the hiring process.A Note on Authenticity:We value genuine interest and authentic interaction. Please be aware that we reserve the right to disqualify candidates if it is determined that application materials or interview responses are excessively generated by AI tools or misrepresent your personal skills and experience.

📌 Senior Account Executive (Kitchener)
🏢 Encircle
📍 Kitchener