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 360

Learning'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.
360

Learning 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 Do
Within 1 month, you will:

Complete your onboarding and ramp up on 360

Learning'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 360

Learning'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

Willin…