About this role.
Degreed is seeking a Sales Director as an individual contributor focused on net-new enterprise acquisition in a defined U.S. territory. The role owns complex, multi-stakeholder sales cycles from outbound prospecting and executive discovery through procurement, legal, and signed contracts. Success requires value-based selling to senior HR and IT leaders, strong territory planning, accurate forecasting, and disciplined Salesforce use. The Sales Director will collaborate with SDRs, presales, marketing, legal, and value engineering while operating independently in a fast-moving workforce-transformation market.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would start by segmenting accounts by strategic fit, workforce-transformation triggers, buying-center access, and likely deal potential. I would create focused account plays combining executive outreach, relevant business hypotheses, partner or marketing signals, and multithreaded engagement. I would inspect conversion and velocity weekly, reallocating effort toward segments and messages producing qualified opportunities.
For the CHRO, I would focus on workforce capability, internal mobility, retention, skills visibility, and measurable learning impact. For the CIO, I would address AI readiness, integration, data governance, security, scalability, and adoption across the technology ecosystem. I would then connect both perspectives to a shared business case around organizational readiness and performance.
I use discovery to quantify the cost of inaction, such as delayed AI adoption, critical skill gaps, productivity losses, or retention risk. I align those risks to executive priorities and establish a compelling future-state outcome with success measures and a decision timeline. Rather than relying on pressure, I help stakeholders recognize the strategic consequences of maintaining the status quo.
I introduce the full buying process early, map every approval stakeholder, and build a mutual action plan with owners, dates, and dependencies. I engage internal legal, security, presales, and value resources before they become blockers, while maintaining executive sponsorship and clear commercial alignment. I update risks and next steps in the CRM so the forecast reflects verified customer commitments.
I qualify opportunities against clear exit criteria, including business pain, champion strength, decision process, commercial path, and confirmed next steps. I separate hopeful activity from evidence-based deal progression and regularly inspect pipeline by stage, aging, close-date integrity, and stakeholder engagement. When risk emerges, I document it early, revise the forecast promptly, and create a concrete recovery plan.
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: Ability to shift customer thinking, challenge the status quo, and build consensus across stakeholder groups
- Territory Strategy & Execution: Proficiency in account segmentation, pipeline management, and quarterly planning
- Executive Communication: Confident leading high-stakes conversations and tailoring messages by audience
- Resilience & Agility: Comfortable operating in a fast-paced, constantly evolving environment with minimal hand-holding
- Sales Enablement & CRM Discipline: Familiarity with using AI tools, CRM systems (e.g., Salesforce), and forecasting methodologies to drive visibility and performance
Key Responsibilities
- New Logo Acquisition
- Generate and convert a consistent flow of qualified pipeline across your assigned US territory
- Own the entire sales process from outreach to signed contract for net-new enterprise clients
- Break into cold accounts through outbound efforts, strategic account plays, and executive influence
- Executive Engagement & Strategic Selling
- Lead tailored discovery and ROI-driven solution design for senior HR and IT decision-makers
- Present Degreed’s platform in ways that resonate with executive pain points and strategic objectives
- Reframe customer thinking, build urgency, and drive consensus across siloed buying teams
- Sales Process Execution
- Navigate complex deal cycles including procurement, compliance, security, and legal
- Maintain high standards of CRM hygiene, forecasting accuracy, and sales documentation
- Collaborate cross-functionally with SDRs, presales, marketing, legal, and value engineering to close deals
- Territory & Performance Management
- Develop and execute a quarterly territory plan with measurable KPIs and revenue goals
- Track deal velocity, pipeline health, and quota attainment with a focus on continuous improvement
- Leverage AI-powered tools and sales enablement best practices to improve efficiency and outcomes
Compensation
We are committed to fair and equitable compensation practices.
The total pay range for this role is $250,000 – $300,000.
Actual compensation packages are based on several factors that are unique to each candidate, including but not limited to: skill set, depth of experience, certifications, specific work location, and internal equity.
Benefits
We take care of our people with a comprehensive benefits package designed to support your well-being, growth, and success.
At Degreed, We Value
🔷 Diversity & Inclusion – We celebrate diverse perspectives and backgrounds, fostering an inclusive environment where everyone can thrive and contribute.
🔷 Growth Mindset – Learning is at the heart of what we do. We empower our employees to continuously develop their skills and grow their careers in alignment with their unique strengths and aspirations.
🔷 Collaboration – The best ideas come from working together. We cultivate a culture of open communication, teamwork, and shared success.
By joining Degreed, you’ll be part of a community that values learning, collaboration, and meaningful impact. If you’re passionate about driving change through upskilling and workforce transformation, we encourage you to apply and contribute to our mission.
Work Environment & Physical Demands
Degreed offers flexible work arrangements tailored to each role. Some positions are fully remote, while others follow a hybrid model for employees near an office. Please check the job details for role-specific requirements.
For remote and hybrid roles, you’ll collaborate virtually using tools like Zoom and Slack. This role may require prolonged computer use and stationary work, with the ability to interpret written and verbal communication effectively.
We are committed to creating an inclusive and adaptable work environment that enables every team member to thrive and do their best work.
Additional Information
Degreed is an equal opportunity employer committed to fostering a workplace free from discrimination and harassment. We do not discriminate based on race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws. This policy applies to all aspects of employment, including recruitment, hiring, career development, compensation, and training.
🔷 Accessibility & Accommodations – We are dedicated to full inclusion and will provide reasonable accommodations for applicants with disabilities throughout the hiring process. If you need assistance, please let us know.
🔷 Fair Hiring Practices – In compliance with the San Francisco Fair Chance Ordinance, we consider qualified applicants with arrest and conviction records.
🔷 E-Verify Participation – Degreed participates in the E-Verify employment verification program.
Global Data Privacy Notice for Job Candidates & Applicants
If you’re applying from specific regions, your personal data may be processed in line with applicable privacy laws, including the General Data Protection Regulation (GDPR) and the California Consumer Privacy Act (CCPA). To understand how we handle applicant data, please review our Global Data Privacy Notice and related policies:
• Global Privacy Notice
• DPR Compliance Details
By submitting your application, you acknowledge and agree to our use and processing of your data in compliance with applicable laws.
Fraudulent Recruitment Warning
Beware of fraudulent recruitment scams using the Degreed name. Scammers may impersonate our company, website, or hiring team. Degreed will never:
🚫 Conduct recruitment via WhatsApp, Telegram, or direct-messaging platforms.
🚫 Request sensitive personal or financial information in unsolicited communications.
🚫 Offer jobs requiring upfront payments or promising unrealistic returns.
🔵 Official Degreed communications will always come from a @degreed.com email address or phone number during the hiring process.
If you encounter suspicious activity, please report it immediately. Stay vigilant and protect yourself from fraud.
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