Senior Account Executive

Senior Account Executive

📍 Remote (Canada) │ Hybrid Available – Kitchener, ON

🧑‍💼 Reports to: Manager, New Sales

💰 Salary range: $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, hitting or exceeding published benchmarks

• Bring AI into your own workflow — account research, call prep, follow-up and forecasting — and share what works with the team

Collaborate across the business

• Partner with BDRs on outbound targeting, meeting quality and handoff feedback

• Partner with Marketing on lead quality, campaign feedback and product-led buying signals

• Feed win-loss insights, objection patterns and competitive intelligence back to Marketing and Product

• Partner with the Enterprise team on franchise-location opportunities that sit under a national or network relationship

Key Metrics You'll Own

• New ARR and quota attainment

• Pipeline coverage

• Stage conversion rates vs. benchmark

• ACV and product attach rate

• Sales cycle length

• Forecast accuracy

Immediate Priorities

In your first few months, you'll ramp to the formula and start proving it:

1. Complete onboarding and ramp to full quota productivity on the defined timeline

2. Build pipeline to target coverage against quota within your first 90 days

3. Run discovery, demo and proposal stages at or above published benchmarks

4. Close your first deals with a clean, documented handoff to Onboarding & Activation

✅ What You'll Bring

• 5+ years of full-cycle B2B SaaS (or similar) direct sales experience, with a stable, proven track record of quota attainment

• Experience running discovery, demo, proposal and negotiation for multi-stakeholder deals — not just working a queue of inbound leads

• Skilled at building account-based plans and self-sourcing pipeline, not just closing what's handed to you

• Comfortable navigating franchise, multi-location or network buying structures, including access to decision-makers up to the C-suite

• A track record of building and defending an accurate forecast

• Proficiency with Salesforce and familiarity with sales tools like Gong and DocuSign

• Fluency with AI tools in your own workflow — research, call prep, follow-up and forecasting

• A consultative, industry-fluent selling style: you close deals customers are glad they signed

• Exceptional verbal and written communication skills

• Experience selling to blue-collar or field-based industries, or in vertical SaaS, is a plus but not required

🤝 Why 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.