Enterprise Inside Sales Representative (Canada)

FileCloud

• $80K — $95K *
US-AnywhereRemote in Calgary, AB
Enterprise Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years in B2B SaaS sales, with 3+ years in a full-cycle, quota-carrying role.
  • Proven ability to manage high volumes of inbound leads with quick qualification.
  • Experience closing deals with multi-stakeholder buying groups, including IT and security.
  • Technical knowledge of SSO/Active Directory, encryption, and cloud vs. on-premises deployment.
  • Familiarity with navigating security questionnaires and procurement processes.
  • Proficient in using AI tools for account research and performance analysis.
  • Self-motivated and effective in a fully remote work environment.

Responsibilities

  • Respond to inbound leads within one business hour and validate fit.
  • Nurture prospects with personalized follow-ups until they are ready to buy.
  • Conduct discovery calls and tailored demos to qualify leads.
  • Manage the entire deal process from trials to negotiations with support teams.
  • Identify and pursue expansion opportunities within existing customer accounts.
  • Maintain accurate CRM records and provide reliable weekly forecasts.
  • Share market insights with Marketing and Product teams.

Benefits

  • Join a passionate team dedicated to building a world-class product.
  • Access to dedicated training and education opportunities.
  • Mentorship model for professional development.
  • Flexible remote work hours outside core hours of 9am-12pm EST.
  • 20 days of paid time off, increasing with tenure, plus 10 public holidays.
  • Paid day off for your birthday or an alternative day.
  • Paid day off to volunteer for a charity of your choice.
  • Monthly reimbursement for internet costs and a lunch/wellbeing stipend.
  • Reimbursement for all necessary hardware costs.
Full 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.

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

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