Senior Software Implementation Specialist

Trader Interactive•Toronto, ON

About The Position

At Trader Interactive, we make buying and selling a great experience. We're a group of go-getters who decided they didn't want to settle for the status quo. We come together as one team to build value and drive innovation across our industries - but we have fun while we do it and make sure our people are always our #1 priority. When it comes to your career, we want to provide big opportunities to help you make a big impact. But for this to be possible, we strive to feel small. Small enough to quickly change tack, small enough to learn from different teams and small enough to connect authentically with leadership.

Requirements

4+ years of experience in software implementation, customer onboarding, or technical account management within a B2B SaaS company, including direct experience with complex, multi-stakeholder implementations.
A proven track record managing large dealer group accounts, enterprise clients, or OEM/manufacturer program implementations.
Demonstrated ability to train non-technical end users across seniority levels, from dealership owners to frontline staff.
Experience coaching, mentoring, or QA-reviewing junior colleagues in an implementation or customer-facing role.
Confidence serving as an escalation point for complex issues — diagnosing root causes and communicating clearly with high-value or frustrated customers.
Strong cross-functional coordination skills, with the ability to hold timelines across Product, Sales, Technical, and Support without direct authority.
Exceptional organization and attention to detail, with the ability to manage a portfolio of concurrent complex implementations.
A customer-first mindset paired with commercial awareness of what a delayed or poor-quality go-live costs the business.

Nice To Haves

Experience implementing or supporting DP360 CRM, Salesforce, HubSpot, or a comparable dealer-facing CRM in multi-user, multi-rooftop environments.
Background with OEM programs or manufacturer-driven deployments involving compliance and brand-standard requirements.
Familiarity with dealership verticals — powersports, RV, marine, equipment, automotive, or commercial truck.
Experience owning or contributing to implementation playbooks, onboarding standards, or QA frameworks.
Exposure to L1/L2 support escalation structures.
Background managing distinct implementation processes across multiple product lines in a SaaS environment.

Responsibilities

Owning end-to-end implementation for our most complex accounts — large multi-rooftop dealer groups, multi-user CRM deployments, and OEM program rollouts requiring bespoke configuration.
Running structured kick-off calls and scoping sessions that accurately capture complexity and align stakeholders before configuration begins.
Configuring DP360 CRM and iMotor Dealer Websites to match each dealer's business structure, workflows, and integration needs.
Delivering hands-on training to dealership teams — from owners and GMs to sales and F&I staff — so everyone's confident and operational at go-live.
Coaching and mentoring junior Implementation Specialists, including QA-reviewing their work before go-live and supporting new hire ramp-up.
Serving as a named escalation point for L1 service tickets that exceed standard resolution capability, investigating root causes and feeding learnings back into playbooks.
Acting as a senior liaison between dealers and internal Sales, Product, and Technical teams on high-visibility, high-complexity engagements.
Owning and evolving implementation playbooks, onboarding standards, and QA frameworks used across the team.