["Full-Time"]
Remote
SaaS
jobicy
About this role
Degreed is the leading enterprise learning system for workforce transformation, bringing together everything people need to learn and advance: courses, videos, articles, projects, and real-world skill insights, matched to individual roles, skills, and goals.
For businesses, Degreed builds the infrastructure for a culture of learning that attracts, develops, and retains top talent, driving performance at scale. Named to Fast Company's World's Most Innovative Companies of 2026 — alongside Google, Nvidia, and Adidas — Degreed is recognized for its AI-driven approach to closing the human readiness gap and turning learning ambition into measurable impact.
We believe learning is the key to unlocking opportunity, and our mission is to discover, empower, and celebrate the next generation of global expertise. Join us in shaping the future of learning and workforce development!
About the Role
We’re hiring a Sales Director to lead net-new enterprise acquisition within a defined U.S. region.
This is a high-impact individual contributor role focused on hunting, influencing, and closing complex enterprise deals in a rapidly evolving market.You’ll work with C-suite leaders—CHROs, CLOs, CIOs—to shape workforce transformation through a skills-first strategy, helping companies close the gap between AI investment and employee readiness.This role is ideal for a self-starter who combines strategic sales execution with executive presence, excels at creating urgency in “nice-to-have” sales environments, and thrives in a fast-changing, mission-driven culture.
Key Skills
Enterprise Sales Mastery: Ability to own complex, multi-stakeholder sales cycles from discovery to close, including procurement and legal navigation Value-Based Selling & Storytelling: Skilled in building compelling business cases that resonate with CHROs, CIOs, and other executive buyers Hunter Mentality: Proven success creating pipeline from a cold start in new or underpenetrated territories Challenger Mindset: Abil
Selling Motion
Sales Cycle
Enterprise
6–18 month cycles, complex multi-stakeholder deals
Prospecting
Outbound-Heavy
Self-sourced pipeline via cold outreach
Buyer Persona
C-Suite
Selling to executive decision-makers
Territory
Greenfield
Build territory from scratch — net-new logos
Requirements at a Glance
Typical Day — Sales Rep
Estimates based on role type and selling motion — actual may vary by company.
SaaS — Interview Intel
Typical Sales Cycle
30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)
Common Buyer Objections
- "We're locked into a contract with [competitor]"
- "We built something in-house already"
- "We don't have budget until next quarter"
- "Our team won't adopt another tool"
Key Industry Metrics
Hot Topics to Reference
- • AI-native product disruption
- • PLG vs sales-led motion debate
- • Vertical SaaS consolidation
- • Usage-based pricing models
Use these insights to speak the buyer's language in interviews.
Tags
How do you coach underperforming reps?
Template questionDescribe your forecasting methodology.
Template questionHow do you structure onboarding for new hires?
Template questionSales leadership roles require balancing individual contributor revenue with team performance management.
Expect to work with recurring revenue models where customer retention is as important as acquisition.
This remote-friendly role provides geographic flexibility while maintaining access to a SaaS market.
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