Digital Sales Representative

SailPoint is the leading AI-driven security platform, providing autonomous governance built for the modern enterprise. By leveraging AI and machine learning, SailPoint simplifies and automates identity security—delivering the right access to the right resources at the right time, at the scale our enterprise customer’s demand. We take pride in our award-winning culture, recognized by our employees as a "Best Place to Work" for 15 consecutive years.
We are seeking a driven and proactive Digital Sales Representative to accelerate pipeline and revenue growth. In this role, you will leverage your SaaS sales experience to engage prospective customers, build strong relationships, and drive new opportunities using the SailPoint sales model. You will collaborate closely with field teams—including Outside Account Executives, Sales Engineers, and Channel Partners—to acquire new logos and expand existing accounts.
The ideal candidate is an organized, dynamic communicator with strong persuasive skills and a deep understanding of modern digital sales methodologies. You bring proven experience closing transactional deals or managing upsells, specifically within the software/SaaS industry.
Qualifications:
Current experience in Enterprise Software Sales in an ISR type of role.
Proven ability to close deals successfully is preferred.
1-5 years experience in SaaS Sales in an ISR/SDR/BDR role.
Bachelor's degree preferred
Must live in Canada
OTE: $120,000 CAD ($84,000 Base / $36,000 Uncapped Commission)
The Path to Success
Our most successful DSR’s achieve these milestones to achieve early productivity & success. Within the first month your goals will include:
Complete Getting started Checklist, including Pre/Post Revenue Onboarding Coursework, attending HR onboarding Sessions, Access Identity University, and complete role specific suggested courses.
Familiarize yourself with the High-level Function Org Chart; a high-level understanding of our main 5 business functions and the teams that compose them.
Make use of all video collateral to augment onboarding training.
Learn the SailPoint pitch.
Meet the team – Digital Sales, your AE’s, Marketing, Channel, Sales Leadership. (Schedule intro meetings with key stakeholders as identified by your manager)
Meet your buddy and set up Bi-weekly meetings & 1 to 1’s with your manager.
Listen in and shadow your first discovery call.
Ensure access to and familiarity with all tools in your digital tech stack.
Walk your manager through prospecting efforts with LinkedIn, 6Sense, Outreach, ZoomInfo. Demonstrate knowledge in how to uncover corporate insights and persona-based imperatives.
Demonstrate how to sequence prospects, both outbound and inbound, effectively action all leads within time bound SLAs, and convert to opportunities within Salesforce.
By the time you have been with SailPoint for 3 months you will have:
Completed Revenue Onboarding.
Completed mock discovery call and refined SailPoint Pitch.
Created a development plan for yourself and reviewed with your manager for alignment.
Continued to have periodic meetings with your buddy.
Shadowed 4 Discovery Calls.
Aligned and mapped your top 4 accounts.
Made your first 10 calls in Outreach.
Booked your first discovery call.
Created a minimum of one opportunity in Salesforce.
Delivered against Core KPI’s as documented in KPI Dashboard.
By the end of your first 6 months, along with the previous milestones you will have:
Achieved funnel & pipeline targets and all critical activities managed through the KPI dashboard.
Closed a deal, as marked by DSR Closer, with support from AE (Account Executive).
By the end of your first 12 months at SailPoint, along with the content in the previous milestones you will have:
Delivered against yearly target for funnel and pipeline.
Maintained KPI results on track with targets.
Closed deals independently without support of AE.

Work arrangement
No