Enterprise Inside Sales Representative (Canada)

Getfilecloud; Calgary; Remote; CAD 70,000 - 110,000; Full time

Benefits offered by this job

Annual bonus

Fully remote

Flexible hours

Paid time off

Tech stipend

Job summary

FileCloud is seeking an Enterprise Inside Sales Representative to own the full sales cycle, from inbound leads to close, while working remotely from Canada. You will qualify, nurture, run discovery and tailored demos, and manage deals with input from Sales Engineers and partners.

This role focuses on fast response, multi‑stakeholder buying groups, and expansion within existing customers, with ongoing training, mentorship, and a competitive salary plus annual bonus.

Qualifications

• 5+ years in B2B SaaS sales with quota attainment.
• Handles high volumes of inbound leads with fast response.
• Experience closing multi-stakeholder deals including IT and security.
• Comfort with technical topics such as SSO/AD, encryption, cloud vs on-prem.
• Familiar with procurement and contract redlines.
• AI tools used to research accounts and analyze calls.
• Remote self-motivated with strong communication.
• Authorized to work in Canada without sponsorship.

Responsibilities

• Respond to inbound leads within one business hour.
• Nurture prospects until they're ready to buy.
• Run discovery and tailored demos.
• Manage deals end-to-end with cross-functional support.
• Own expansion opportunities within existing customers.
• Maintain CRM and deliver weekly forecast.
• Share market and competitive insights.

Skills

B2B SaaS sales

Quota-carrying

Inbound leads

Multi-stakeholder deals

Security knowledge

AI proficiency

Remote work

Canada work auth

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.