Enterprise Inside Sales Representative (Canada)

Getfilecloud; Canada; Remote; CAD 90,000 - 130,000; Full time

Benefits offered by this job

Fully remote

Annual bonus

Paid time off 20 days

Birthday/Volunteer day off

Internet reimbursement

Hardware reimbursement

Wellbeing stipend

Lunch stipend

Job summary

FileCloud is seeking an Enterprise Inside Sales Representative to own the full sales cycle for a fully remote Canada team. You will handle inbound leads, run discovery and demos, close deals, and pursue expansion within existing customers.

The ideal candidate has 5+ years in B2B SaaS sales, experience with high inbound volumes, and comfort with security and compliance topics. This role offers a fully remote setup with flexible hours and a performance bonus.

Qualifications

• 5+ years in B2B SaaS sales with quota-bearing responsibility.
• Experience handling high volumes of inbound leads with fast response.
• Track record closing deals with multi-stakeholder buying groups including IT and security.
• Comfort with topics such as SSO/Active Directory, encryption, cloud vs. on-prem deployment and file servers.
• Experience navigating security questionnaires, procurement and contract redlines.
• AI proficiency: using AI tools to research accounts and sharpen responses.

Responsibilities

• Respond to inbound leads within one business hour and qualify fit.
• Nurture not-yet-ready prospects with personalized follow-up.
• Run discovery and tailored demos; qualify on pricing and decision timelines.
• Manage deals end-to-end: trials, proposals, security reviews, procurement and negotiation.
• Own expansion opportunities within existing customers.
• Keep CRM up-to-date and provide weekly forecasts.
• Share market and competitive insights with Marketing and Product.

Skills

B2B SaaS sales

Quota carrying

Inbound leads

Multi-stakeholder closing

SSO/AD

Security questionnaires

AI proficiency

Remote work

Canadian work eligibility

Job description

FileCloud is looking for a passionate Enterprise Inside Sales Representative to own the full sales cycle, to join our remote team in Canada. Every opportunity is inbound. You’ll qualify and nurture new leads, run discovery and demos, manage deals through evaluation and close, and win expansion opportunities within existing customers. This role is remote and will require working remotely with other team members.

About the Product & Company:

FileCloud is a hyper-secure EFSS (enterprise file sync and share) platform that provides industry leading compliance, data governance, data leak protection, data retention and digital rights management capabilities. FileCloud is a leader in content governance and collaboration for unstructured data, trusted and used worldwide across Global 1000 enterprises, educational institutions, government organizations, and service providers. Customers can run FileCloud on-premises, in their own private or government cloud, or as SaaS, with built-in governance for frameworks such as CMMC, ITAR, HIPAA and NIST 800-171. In addition to its enterprise file sharing solution, FileCloud’s product portfolio also includes Signority (acquired in May 2024), a Canadian-based e-signature and document workflow platform. We are currently expanding our team as we grow and improve FileCloud.

Key Job Duties:

• Respond to inbound leads (trials, demo and pricing requests, contact-sales forms) within one business hour, validate fit and quickly rule each lead in or out.
• Nurture not-yet-ready prospects with personalised follow-up until they're ready to buy.
• Run discovery and tailored demos, qualifying on pricing, access to decision-makers, need and timing.
• Manage deals end to end: trials and proofs of concept, proposals, security reviews, procurement and negotiation, with support from Sales Engineers, Legal and partners.
• Own expansion opportunities within existing customers, whether surfaced by internal colleagues or arriving as inbound requests from customers.
• Keep the CRM accurate and deliver a reliable weekly forecast.
• Share market and competitive insight with Marketing and Product.

Key Skills & Experience:

• 5+ years in B2B SaaS sales, including 3+ years in a quota-carrying, full-cycle role with a record of meeting or exceeding quota.
• Experience handling high volumes of inbound leads with fast response and disciplined qualification.
• A track record closing deals with multi-stakeholder buying groups, including IT and security.
• Comfort with technical topics such as SSO/Active Directory, encryption, cloud vs. on-premises deployment and file servers.
• Experience navigating security questionnaires, procurement and contract redlines.
• AI proficiency: use AI tools to research accounts and sharpen your responses to prospects, and to analyse your own calls, pipeline and performance when reviewing progress.
• Self-motivated and productive working fully remotely, with strong phone, video and written communication.
• Legal authorisation to work in Canada and not require employer sponsorship now or in the future.

Nice to have

• Experience selling file sharing, content collaboration, content management or managed file transfer (MFT) solutions. (A big plus)
• Experience selling into defense, government, healthcare, legal or financial services.
• Familiarity with compliance frameworks such as CMMC, NIST 800-171, ITAR, HIPAA, PIPEDA or GDPR.
• Experience co-selling with resellers or MSPs.
• Experience selling to US customers from outside the US.

What We Offer

• Be part of a team of passionate, committed individuals dedicated to building a world-class product
• Dedicated time for training and education opportunities
• A mentorship model wherein your mentor and team support your development
• A competitive salary with an annual bonus
• Fully remote working whilst offering flexible hours that fall outside of the companywide core hours of 9am -12pm (US Eastern Standard Time)
• 20 days of paid time off which increases by a further 2 days after 3 years of service and 3 days after 5 years of service (in addition to 10 public holidays in your country)
• Paid day off on your birthday or on an alternative day if your birthday falls outside a normal working day
• Paid day off to volunteer with the charity of your choice
• Paid monthly internet cost, as well as lunch and wellbeing stipend provided
• Reimbursement of all hardware costs associated with the role

Please note that we conduct background security checks for everyone joining our team.

AI-assisted screening may be used during the application review process.