Director, Enterprise Sales, North America

Introduction to the Team & RoleAs the Enterprise Sales Director for North America, you will lead new logo acquisition for organizations of 5,000+ employees, one of the most strategic and fastest growing segments of 360Learning's business. Reporting to the Chief Sales Officer, you will manage a current team of 4 high performing Account Executives and own a strategic pipeline built on 6 and 7 figure deals.360Learning has strong commercial traction in Enterprise North America. This is a critical, high visibility mission: we need a leader who can quickly reach full autonomy and bring the segment to the next level of ambition the company has set for this market. This is a hands‑on coach role. You will directly support and, when needed, elevate into complex commercial cycles alongside your Account Executives, while also stepping back to read business and market trends and translate them into a clear strategic direction.
What You Will DoWithin 1 month, you will:
Complete your onboarding and ramp up on 360Learning's product, market positioning, and Convexity operating model
Meet individually with each of your 4 Account Executives to assess their pipeline, deal status, and account coverage
Review the existing Enterprise pipeline, forecast, and territory structure
Build working relationships with your key cross‑functional partners, mostly in Pre‑sales, Product, Alliances (Partners) and Professional Services.
Within 3 months, you will:
Run weekly pipeline and forecast reviews with rigor and accuracy, providing clear, rational visibility to the Chief Sales Officer
Identify the strengths and areas of improvement of each Account Executive and put in place a proactive coaching plan (call preparation, live deal support, debriefs)
Play an active, hands‑on role in strategic deal cycles, through escalation support and direct involvement in complex 6-7 figure ARR deals
Work closely with BDRs to qualify opportunities and deepen strategic discovery around prospects' business pain points
Start leveraging 360Learning's partner and alliances ecosystem to accelerate new logo acquisition
Begin to achieve world class performance and hit quarterly targets
Within 6 months, you will:
Own a full strategic read of your market, translating business and market trends into clear deal prioritization decisions
Be fully autonomous in driving the Enterprise North America segment toward the company's ambition in this market
Be involved in hiring and onboarding new Account Executives as the team scales
Have a proven track record of closing complex, strategic deals directly or through hands‑on support of your team
Meet and exceed quarterly sales targets with a clean, reliable forecast.
The Skill Set
Proven 3+ year track record as a top performing sales leader in software or SaaS (experience in HR solutions is a real plus), with direct experience managing Enterprise Account Executives
Demonstrated ability to close and support complex, strategic deals in the 6 to 7 figure range
Strong coaching mindset: able to diagnose individual strengths and areas of improvement and act proactively rather than reactively
Rigorous, data‑driven approach to pipeline management and forecasting, with genuine attention to detail and hygiene
Comfortable playing a hands‑on role in commercial cycles, including escalation and direct deal support
Experience collaborating cross‑functionally with Pre‑sales, Product, and Professional Services teams
Familiarity with leveraging a partner or alliances ecosystem to support new logo acquisition
Ability to hire, onboard, and set up new Account Executives for success
A customer‑first mindset, obsessed with impact rather than activity
Comfortable with a written, asynchronous culture and a strong fit with our Convexity operating model
Willingness to travel to meet prospects and attend trade shows
Strong written and verbal communication skills in English
What We Offer
Compensation: Pay structure includes base salary, variable incentive pay, and company equity
Benefits/Perks : Comprehensive health insurance starting your first day of employment RRSP contribution matching Generous parental leave Professional development opportunities through our own platform
Balance:
We offer unlimited days of annual PTO 5 days for sick leave Holiday time in accordance with the Ontario Holiday Calendar We are a remote‑first organization and promote flexible work hours
Diversity, Equity, and Inclusion : We have 6 active ERGs including Mental Health, Environmental/Sustainability, Women, Parents, LGBTQIA2S+, and Ethnic Diversity. Each group has at least one executive team member serving as a member of the group, bringing greater awareness to each group’s activities and providing a quick path to impact
Corporate Social Responsibility : Review our CSR Charter: 360learning.Com/blog/corporate-social-responsibility-charter
Culture : A framework that will help you make an impact - envision our way of working and our Convexity Culture: find out more about the teams, product and processes
Interview Process
Call with the Talent Acquisition Manager
Interview with the Chief Sales Officer (hiring manager)
Case study interview with the Chief Sales Officer & Sales Operations & EMEA VP Enterprise Sales
Clarification Interview with a North American Sales Leader
Culture Interview with 360Learning CEO
References & Offer
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