Jobs in Winnipeg, Canada

Sales Development Representative | REMOTE (TORONTO) at Gatekeeper

Gatekeeper is a SaaS-based, next-generation Vendor & Contract Lifecycle Management (VCLM) and Third Party Risk Management (TPRM) solution. We help our customers 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 year over year, with customers including Ford, The Telegraph, Autotrader, SumUp, Crocs and Funding Circle. Due to our strong global growth and a 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 training and support you need to be set up for success.

Note : This is currently a fully remote position, open to applicants based in and around Toronto. This position may become a hybrid role in the future, requiring you to work in-office a few days a week.

• 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.

• 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.

• 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.

• 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

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.

• Mid-Senior level

• Full-time

• Sales and Business Development

• Software Development

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