Director - Sales Enablement

Quark Expeditions is the leading polar expedition travel company headquartered in Toronto, Canada. We operate cruises to Antarctica and Arctic regions (Greenland, North Canada, Svalbard) on board of 3 modern polar expedition ships – Ultramarine, Ocean Explorer, and World Explorer. Since 1991, Quark has been establishing a tradition of firsts in polar travel: as the first to transit the Northeast Passage with adventure travellers; the first to take travellers to the far side of Antarctica; and the first to circumnavigate the Antarctic continent with guests. Quark Expeditions is part of Travelopia, the world’s leading experiential travel business, owned by KKR.

We are looking for a Director of Sales Enablement to join our team. Reporting to the Senior Director of Global Inside Sales, you will be equally comfortable setting strategy and diving into the details. This is a hands‑on leadership role: you will define and drive the enablement vision and roadmap while working alongside your team to bring it to life.

You will equip our Inside Sales, Outside Sales, and Client Experience teams with the tools, technology, learning programs, and processes they need to succeed. With a global scope and a fast‑paced environment, this role requires someone who thrives at the intersection of strategy and execution.

What we’ll offer:

• Competitive base salary of CAD $90,000–$140,000, plus a performance‑based bonus (5% on target, 10% max)
• Comprehensive health benefits
• Retirement savings plan with company contributions
• Generous paid time off, including a birthday day off
• Flexible hybrid work model (6 days per month in our Toronto office)
• Parental leave and family‑supportive policies
• Group‑wide travel discounts
• Familiarization (FAM) travel opportunities

What you’ll do:

Enablement Strategy

• Own the multi‑quarter enablement roadmap across Inside Sales, Outside Sales, and Client Experience
• Translate business priorities and sales performance data into a clear, sequenced set of initiatives
• Align stakeholders across Sales, Marketing, and Commercial leadership while maintaining a regular reporting cadence

Learning & Development

• Design and deliver onboarding programs that reduce ramp time and build consistent capability from day one across all three sales teams
• Build and own a continuous learning curriculum encompassing sales skills, product knowledge, methodology training, and coaching frameworks tailored to Inside Sales, Outside Sales, and Client Experience teams
• Partner with Sales leadership to identify capability gaps and translate them into targeted learning and development initiatives
• Establish assessment and certification frameworks to measure proficiency and program effectiveness

Sales Technology & Tools

• Own the full sales tech stack, including Salesforce CRM, sales engagement, content management, conversation intelligence, and AI‑driven analytics platforms
• Lead vendor evaluation and implementation hands‑on, including scoping, testing, and rollout — not just sign‑off
• Drive adoption across global teams through training, change management, and ongoing support programs
• Leverage performance and usage data to make evidence‑based decisions on technology investment and optimization

Process & Playbooks

• Design and optimize scalable sales processes from prospecting through close and client handoff
• Own and maintain the sales playbook library, including call frameworks, objection‑handling guides, competitive battlecards, and onboarding content
• Stay close to the sales floor to identify process breakdowns early and act quickly

Analytics & Performance

• Define the metrics framework for the function, including adoption rates, ramp time, win rates, and quota attainment
• Deliver regular performance updates to Sales leadership, highlighting results, insights, and areas for adjustment

What you’ll bring:

Required

• Extensive experience in sales enablement, revenue operations, or a related field
• Hands‑on experience owning and optimizing a B2B sales technology stack, with Salesforce as the primary CRM
• Demonstrated success designing and delivering learning and development programs that drive measurable improvements in sales performance
• Proven track record of executing enablement initiatives tied to clear commercial outcomes
• Experience supporting geographically distributed or global sales organizations
• Ability to operate effectively at both the strategic and execution levels

Preferred

• Background in sales or sales management
• Experience leveraging AI‑powered tools for sales insights and analytics
• Familiarity with sales methodologies such as MEDDIC, Challenger, or Command of the Message
• Exposure to business intelligence platforms such as Clari, Tableau, or Looker
• Experience implementing and managing sales content platforms such as Highspot, Seismic, or Showpad
• Experience scaling enablement through a period of organizational growth or transformation

We believe people perform best when they can be their true selves and diverse teams drive better results. We’re committed to fostering a diverse, equitable, and inclusive environment where everyone can succeed.

Travelopia ensures an inclusive workplace for all. If you need accessibility support during the recruitment process, please inform us here: View email address on ca.talent.com

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