Sales Development Representative | REMOTE (TORONTO)

Gatekeeper | part of Cinergy Group; Toronto; Hybrid; CAD 60,000 - 80,000; Full time

Job summary

A leading SaaS company is looking for a Sales Development Representative to join their remote team. In this role, you will focus on creating relationships with senior executives through high-volume outbound calling. The ideal candidate will have experience in B2B sales or sales development, along with strong communication skills and a passion for achieving quotas. This position offers a supportive development environment and generous benefits.

Benefits

100% remote working

Generous paid vacation allowance

Comprehensive benefits package

Learning & Development opportunities

Match funding for local non-profits

Company retreats

Qualifications

• 6+ months in Sales Development or B2B sales experience with strong quota attainment.
• Experience in cold calling and prospecting.
• Ability to engage with senior executives confidently.

Responsibilities

• Own high-volume outbound calling to create new relationships with executives.
• Continuously refine messaging to stay ahead in the market.
• Contribute to projects that enhance the outbound program.

Skills

Outbound phone prospecting

Communication skills

Competitive nature

Accountability

Team player

Job description

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 neverending 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

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 organisations in your local community

• Gatekeeper retreats

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