Sr. User Enablement Specialist

Senior User Enablement Specialist

About Lendesk

We’re a financial technology company on a mission to help people feel confident in their mortgage decision and deliver a seamless experience. Our flagship product is an advanced digital mortgage origination platform that connects borrowers, brokers, and lenders. We’re a fast-growing team of 70+ employees, composed of innovative and engaged individuals working collaboratively to deliver a unique digital home buying experience. We’re also a remote-first company with team members across Canada.

At Lendesk, diversity is our strength. What makes us different, makes us stronger. We believe that a variety of backgrounds, cultures, beliefs, experiences, identities, and voices make for a better and inclusive workplace

Job Description

We are hiring a Senior User Enablement Specialist (Sr. UES) to support our Canadian operation, reporting to our Director of User Development and Enablement under Sales. The Sr. UES will play a key part in helping brokers and partners successfully use our SaaS Solution.

The Sr. UES will collaborate with Sales and Customer Success to ensure prospects transition smoothly into onboarding to full platform adoption. This is a hands-on role in a fast-moving SaaS environment, ideal for someone who loves problem-solving, client communication, and turning new users into confident advocates.  This includes primary users of the system as well as secondary (company management and ops stakeholders).

It is expected from Sr. UES to assist in building out and enhancing our processes to drive additional impact as well as assisting in mentoring other UES as the team grows.

What You'll Be Doing:

• Act as the primary point of contact for clients immediately after the sales handoff.
• Guide brokers and brokerages through onboarding, training, and integrations to ensure successful adoption.
• Drive client engagement, addressing early friction points and reinforcing platform value.
• Conduct training sessions, follow-ups, and product walkthroughs to support activation.
• Monitor usage and adoption metrics; flag and escalate accounts at risk of churn.
• Work directly with Sales Agents and Customer Success to ensure seamless client transitions.
• Gather insights from client experiences to help refine workflows, automations, and product strategy.
• Proactively solve client issues by collaborating with technical and support teams.
• Provide regular reporting on adoption rates, account health, and success metrics.

What You Bring:

• 3+ years of progressive sales experience in a technology role
• Must have knowledge in the Canadian mortgage industry
• Experience in technology and system integration
• Track record of building and nurturing long term business relationships with business decision makers
• Proven track record of high activities (high volume of calls and meetings)
• Entrepreneurial mindset- ability to be proactive, innovative, and take ownership of your relationships
• Proven track record of conversion, objection handling, and closing experience in a remote first environment
• Experience in managing processes, forecasting and building data driven strategies
• Having a high level of autonomy and accountability 
• Is bilingual (English and French) to support our Québec based clients.
• Prefferred:  
  • Experience in mortgage technology, fintech, or SaaS platforms.
  • Experience with Zapier
  • Background in training or enablement (virtual or live sessions).

What We Offer In addition to the exciting work, great people and a fun and supporting culture, we offer extensive benefits and perks package:

• Competitive salaries: base + commission structure
• Comprehensive benefit plan including dental, medical, as well as health and wellness and vacation stipends
• Lendesk is remote first - your office is where you choose it to be across Canada!
• The latest in hardware and software tools
• Budget for continuous development and training

You must be a current Canadian resident to be considered for this role. A candidate selected for this position must pass a criminal background check.

Lendesk is committed to offering competitive salaries to all our team members. This role has a salary range of $68,500-$103,000. For experienced candidates, we typically hire near the midpoint of the salary band to ensure that there is room for growth and development. Compensation is determined based on the skills, experience, and qualifications you bring to the team, as well as the impact you will have on the business and the growth you'll achieve in the role. Throughout your time at Lendesk, we'll continue to have conversations about your career and development and you'll have the opportunity to build an amazing career with us.