Director of Sales

Director of Sales

📍 Remote (Canada) | Hybrid Available – Kitchener, ON 🧑💼 Reports to: VP of Sales

Encircle is leading the $1.6 trillion property insurance industry out of the dark ages of pen and paper, into the digital age of transparency and empowerment. Our easy-to-use software platform enables thousands of restoration contractors and insurance professionals across North America to process claims faster and with greater accuracy.

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

About the Role

The Director of Sales will take responsibility for developing the sales team, refining our sales approach, and building a predictable revenue engine. You’ll work closely with Marketing, Product, and Customer Success to ensure that our sales efforts line up with customer needs and company goals.

Key Responsibilities

- Lead and manage our AE and BDR teams (currently 8 and growing), providing coaching, support, and clear expectations.

- Recruit and develop sales talent, focusing on consistency, accountability, and strong communication across the group.

- Own new ARR business targets, forecasting, pipeline coverage, and share updates with leadership on performance, challenges, and opportunities. Key metrics include win rate, sales cycle length, activity expectations for the team, pipeline creation goals and more.

- Own our sales process from first contact to close, ensuring it’s effective, repeatable, and easy for the team to follow as we scale. Our current sales methodology aligns to SPICED.

- Responsible for GTM strategy including territory design and segmentation, pricing input, outbound and pipeline development strategy, enterprise accounts, and more.

- Review pipeline health, understand key deal blockers, and work with the team to move opportunities forward.

- Work with Marketing to align campaigns, improve lead quality, and strengthen the handoff between teams.

- Partner with Product to bring back customer insights that support roadmap decisions.

- Partner with Customer Success to drive fast time to value, referrals, and strengthen the handoff between teams.

- Partner with GTM operations and business systems to create efficiencies and scale.

- Support the team in building relationships with key accounts and identifying opportunities for larger or multi-location customers.

- Assist with operations and enablement initiatives that lead to positive outcomes for the sales team.

- Travel for customer visits, prospect meetings, sales events and industry trade shows is required (approx. once a month).

What You Bring

- 5+ years of progressive experience in SaaS sales, including 3+ years in a leadership role managing sales teams.

- Experience working with field service, construction, restoration, or similar blue-collar industries is helpful, but not required.

- A proven ability to build a sales process, coach a team, and hit revenue targets.

- Comfort using CRM and sales tools such as Salesforce and Gong.

- Strong communication skills and the ability to work well with cross-functional partners.

- A steady, practical approach to leadership—focused on clear expectations, accountability, and performance.

- The ability to succeed in a growing environment where you’ll be a player and a coach as we scale.

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

Equal Opportunity

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.

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