Sales Development Representative | REMOTE (TORONTO)

Gatekeeper; Toronto; Remote; CAD 50,000 - 70,000; Full time

Job summary

A leading SaaS solution provider is seeking a Sales Development Representative based in Toronto. In this fully remote role, you will be responsible for high-volume outbound calling, engaging with C-suite leaders and contributing to team growth. Successful candidates should have experience in B2B sales, be proactive communicators, and thrive in a competitive environment. This position offers a comprehensive benefits package and opportunities for professional development.

Benefits

Generous paid vacation allowance

Comprehensive benefits package

Learning & Development opportunities

Technology provided for remote work

Gatekeeper for Good matching support

Team retreats

Qualifications

• 6+ months in Sales Development or B2B sales with a track record of quota attainment.
• Comfortable engaging senior legal and finance executives.
• Set high personal standards and celebrate wins.

Responsibilities

• Own high-volume outbound calling to create net-new relationships.
• Continuously test and refine messaging to stay ahead.
• Contribute to special projects that grow the outbound program.

Skills

Outbound phone prospecting experience

Fearless communicator

Competitive & hungry

Grit & accountability

Positive team player

Job description

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Description

Gatekeeper is a SaaS-based, next-generation Vendor & Contract Lifecycle Management (VCLM) & Third Party Risk Management (TPRM) Solution. We help our customers to restore visibility of their vendor contracts, take control of their vendor and contract processes, and safeguard compliance of their third parties.

Gatekeeper has consistently achieved significant, profitable growth YoY, with our customer base including Ford, The Telegraph, Autotrader, SumUp, Crocs, and Funding Circle.

Due to our strong global growth and private equity partnership from Vista Equity Partners, we are expanding our high-impact SDR team. This is a rare chance to join a true technology innovator, where you will receive all of the training and support you need to be set up for success.

Note: This is a fully remote position, open to applicants based in and around Toronto.

In this role, you will:

• Own high-volume outbound calling. Create net-new relationships by phone with General Counsel, CFOs, Procurement, and other C-suite leaders.
• Continuously test, learn, and refine messaging to keep us ahead of the market.
• Contribute to special projects that help grow the outbound program.

What success looks like:

• Daily call activity that consistently meets or beats target.
• Booking qualified meetings with senior legal, finance, and procurement stakeholders.
• Taking personal responsibility for continuous and never-ending improvement in your role.
• A visible, positive impact on team morale and performance.

Requirements

• Outbound phone prospecting experience: 6+ months in Sales Development or B2B sales with a track record of quota attainment—preferably achieved through cold calling.
• Fearless communicator: Comfortable engaging senior legal and finance executives; able to ask hard questions and handle objections with poise.
• Competitive & hungry: You love the scoreboard, set high personal standards, and celebrate wins—then ask how to raise the bar again.
• Grit & accountability: You take ownership of your number, seek feedback, self-coach, and keep pushing when others would stop.
• Positive team player: Bring energy, share best practices, step in to help peers, and elevate the whole squad.

What We Offer

• 100% remote working: no offices and no commute.
• Generous paid vacation allowance.
• Comprehensive benefits package including:
• Private Medical & Dental cover.
• GRSP Matching.
• Employee Assistance Program.
• Learning & Development opportunities for lifelong learners.
• Technology: we provide everything you need to do your best work.
• Gatekeeper for Good: Match funding to support non-profit organizations in your local community.
• Gatekeeper retreats.

We live by our company vision and values. If these resonate with you, if you thrive on cold-calling senior executives, and love to win, then we’d like to talk to you.

About Us

A market-leading product, a skilled and supportive team, and distinctive values make Gatekeeper a uniquely rewarding place to work.

We’re proud of the company we’re building, and we’d love for you to be part of it.

Seniority level: Mid-Senior level

Employment type: Full-time

Job function: Sales and Business Development

Industries: Software Development

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