$250K - $1M/yr
Full-time
Medical, Retirement
Posted 6 days ago
Job description
Enterprise Sales Director – Fortune 500 – Remote (US) – SaaS – Up to $200,000 Base + Double OTE We're hiring an Enterprise Sales Director to lead new business growth with Fortune 500 and other large, complex enterprises across the US. This role is ideal for a senior seller who can both carry a number and act as a strategic leader across large, multi-threaded SaaS deals. Role Overview Role: Enterprise Sales Director – New Business & Account Expansion Location: Remote – USA Base Salary: Up to $200,000 (DOE) On-Target Earnings: Up to Double OTE (uncapped commission) Team / Personal Quota: Typically $2,000,000–$4,000,000+ ARR per year Typical Deal Size: $250,000–$1,000,000+ ARR, often multi‐year What You'll Do Own and drive new business with Fortune 500 and large enterprise accounts, from C‐level engagement through to close.
Build and execute strategic account plans for named enterprise accounts, identifying key initiatives, stakeholders, and expansion paths. Lead complex, multi-threaded sales cycles involving multiple business units, senior executives, procurement, legal, and security. Coach, support, and align with AEs / account teams on strategy, deal execution, and stakeholder mapping to progress high-value opportunities.
Run executive-level discovery, value workshops, and ROI-based conversations to position the platform as a strategic, long-term partner. Negotiate large, multi-year SaaS agreements with a focus on maximizing ARR, retention, and expansion potential. Maintain high forecast accuracy and clear visibility into pipeline, risks, and upside across a defined book of business.
Partner closely with Product, Marketing, Sales Engineering, and Customer Success to shape solutions and win complex, competitive deals. Act as a senior face of the business at industry events, executive briefings, and customer meetings, building long-term strategic relationships. What We're Looking For Proven track record selling SaaS into large enterprise / Fortune 500 accounts in a new-business or strategic role.
Experience closing complex, multi-stakeholder deals with six- and seven-figure ARR contract values. Consistent history of achieving or exceeding multi-million-dollar ARR targets (individual or team). Strong executive presence with the ability to engage, challenge, and influence C‐suite and VP-level stakeholders.
Deep experience in value-based and consultative selling, with comfort building business cases and multi-year roadmaps. Ability to operate strategically while staying close enough to the deal to unblock, coach, and close. Comfortable working remotely in a high-autonomy, high-accountability environment.
If you meet most of these requirements and have sold complex SaaS into large enterprises, we strongly encourage you to apply. Benefits Competitive base salary plus uncapped commission (realistic double OTE). 100% remote with flexible working hours.
Comprehensive health benefits, including access to virtual care and mental health support (where applicable). Monthly home office / technology stipend to support your remote setup. Annual learning & development budget (courses, conferences, executive programs).
Retirement plan options with company contributions (e.g., 401(k) or local equivalent). Additional performance-based bonuses, incentives, and President's Club / recognition programs. Wellness allowance for gym, wellness apps, or other wellbeing initiatives.
If you're a senior enterprise seller who enjoys leading strategy, winning complex deals, and driving significant new ARR at the Fortune 500 level, we'd love to hear from you—apply now. #J-18808-Ljbffr
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Frequently asked questions
Q: What skills or qualities help someone succeed as a Director Enterprise Sales?
A: To succeed as a Director of Enterprise Sales, key technical skills include proficiency in sales strategy development, data analysis, and CRM software management, as well as a deep understanding of the company's products or services and industry trends. Essential soft skills include strong leadership and communication abilities, emotional intelligence, and the capacity to build and maintain relationships with key stakeholders, including clients and cross-functional teams. By combining these technical and soft skills, a Director of Enterprise Sales can effectively drive revenue growth, lead high-performing sales teams, and navigate complex business environments.
Q: What is the career path for a Director Enterprise Sales?
A: A Director of Enterprise Sales typically follows a career progression that starts with entry-level roles such as Sales Representative or Account Manager, advancing to mid-level positions like Senior Account Manager or Regional Sales Manager, and eventually leading to senior roles like Director of Enterprise Sales or Vice President of Sales. Key opportunities for skill development in this role include building leadership and management skills, expanding sales strategy and planning expertise, and cultivating strong communication and negotiation abilities. Long-term career prospects for a Director of Enterprise Sales may include transitioning into executive leadership roles, such as Chief Revenue Officer or CEO, or pursuing opportunities in related fields like business development or strategy consulting.
