Director, Enterprise Sales, North America

Introduction to the Team & Role

As 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, escalate 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 Do

Within 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

Who We Are

360Learning enables companies to upskill from within by turning their experts into champions for employee, customer, and partner growth. With our LMS for collaborative learning, Learning & Development teams can accelerate upskilling with the help of internal experts instead of slow top-down training. 360Learning is the easiest way to onboard and upskill employees, train customer-facing teams, and enable customers and partners–all from one place.

360Learning powers the future of work at 1,700 organizations. Founded in 2013, 360Learning has raised $240 million with 400+ team members across North America and EMEA.

Learning Includes Everyone.

In concert with our culture, 360Learning believes learning includes everyone and that means embracing the strengths of diversity, connectedness, and inclusion. Through conscientious efforts, our global footprint celebrates cultures, perspectives, and experiences from all over the world to support our platform that is built for all regardless of race, ethnicity, gender identity or expression, sexual orientation, religion, age, neurodiversity, disability status, citizenship, veteran status or any other aspect which makes an individual unique or protected by laws and regulations in the locations where we operate. Thus, 360Learning is proud to be an equal opportunity workplace, and we commit to continue this throughout our processes for recruitment, compensation, benefits, performance, promotion, and all other conditions and terms of employment. We want to learn from and with you!