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Director, Enterprise Sales



Sales & Business Development
New York, NY, USA
Posted on Friday, June 7, 2024

Director, Enterprise Sales

Pathstream | Revenue | New York, NY (Hybrid)

Role/Department Overview:

This is a full-time exempt position in our New York, NY HQ and reports to the Chief Revenue Officer.

What we do:

Pathstream was founded on the premise that substantial unrealized economic & human potential exists within each organization’s frontline workforce. We are reshaping the way employees and managers on the frontlines excel in their careers. In this age of rapid tech evolution, our enterprise partnerships transform frontline teams from transactional to relational, from back office to middle office, and from task-oriented to strategic. We impact companies’ bottom lines with improved productivity, increased retention, and differentiated quality of customer experience; employees experience the benefits of greater success in their current roles while unlocking future professional growth.

Job Description:

Are you an extraordinary enterprise sales professional who loves winning business while making a real-world impact on the lives of others? If so, let’s get to know one another. Pathstream is looking for a highly motivated and experienced Director of Enterprise Sales to offer our world-class upskilling, coaching, and career pathing solutions to Fortune 500 enterprises in a range of industries, such as financial services, insurance, and retail, that are in the midst of digital transformations. You will utilize your strategic business development expertise and refined negotiation skills to drive the sales of our human-in-the-loop web-based solutions to business unit leaders at Fortune 500 enterprise accounts.

You may be the perfect fit if you like fast-paced environments and are mission-driven, curious, a self-starter, a strategic thinker, highly adaptable to changing market conditions, and have a track record of success in enterprise SaaS sales with frontline division leaders.

What you’ll be doing at Pathstream:

  • New Business Development: Identify, engage, and secure new enterprise accounts, ensuring a robust pipeline of opportunities. Identify and qualify leads, build relationships with prospects, and help the CEO and CRO close new business. This end-to-end pipeline work will constitute ~80% of your selling focus in 2024.
  • Account Management: Cultivate and expand relationships within existing accounts to increase revenue and ensure customer satisfaction by providing strategic guidance, identifying opportunities for expansion, and supporting their talent transformation agenda. This existing account work will constitute ~20% of your selling focus in 2024.
  • Sales Strategy: Help develop and implement effective sales strategies and challenger insights to drive business growth and achieve sales goals.
  • Sales Team Management: Collaborate with the CRO to develop and execute on a hiring plan for a small team of account executives whom you will manage heading into 2025.
  • Product Expertise: Maintain a thorough knowledge of Pathstream offerings to present to prospective clients. Understand customer needs and propose the best solutions accordingly. Attend conferences to meet new and existing prospects and to build industry knowledge and gather competitive intelligence.
  • Cross-Functional Collaboration: Collaborate with internal teams such as Marketing, Customer Success, Product, Engineering, and Learning & Design, to help implement pilots successfully and to help convert pilots to post-pilot contracts.
  • Sales Forecasting: Accurately forecast own individual sales activity and revenue achievement through proper use of sales tools and methodologies.

What we’re looking for:

  • 8+ years of professional experience and at least 5+ years of experience successfully selling enterprise SaaS solutions in industries undergoing digital transformation, such as financial services, insurance, retail, telecom, travel & hospitality, and healthcare
  • Strong ability to navigate complex enterprise sales cycles and secure new business selling into heads of frontline business divisions such as contact centers and retail branches
  • Existing relationships with Fortune 500 decision-makers (VP or higher) of frontline divisions in the industries above
  • Experience with early stage startups with early product market fit and the ability to excel in a fast paced environment
  • Excellent negotiation, presentation, and communication skills to effectively demonstrate the value of our solutions
  • Experience with building and managing productive enterprise sales teams, with a track record of achieving results
  • Willingness to travel as needed and reside within commuting distance from NYC for a hybrid role with office attendance expected several days a week
  • You believe in our mission to help frontline employees advance in their careers

What we offer:

  • Competitive salary and commission structure
  • Transparent and social culture, challenging work, fast learning cycles, practical training, and meaningful feedback
  • Strong sense of ownership and strategic work that impacts our product, users, colleagues, business, and world
  • Comprehensive benefits package
    • 100% employer-paid medical, dental, and vision insurance coverage for you and 50% for your partner/spouse and dependents
    • Health, commuter, and parking flexible spending accounts
    • Employee Assistance Program (mental health, financial health, legal support, and more)
    • Free access to wellbeing apps like Ginger and Headspace
    • Flexible paid time off and paid holidays
    • Generous paid parental leave
    • Short and long-term disability insurance
    • Annual professional development budget
    • Company-provided laptop
    • Remote-first culture
    • Life insurance (100% company paid)
    • 401(k)


Our company values diversity and believes diverse teams make innovation possible. We work on complex, difficult problems with no linear or clear solutions. We need a diverse team that can bring different perspectives and approaches, and whose experiences reflect the full set of stakeholders we seek to serve. As such, Pathstream is an equal opportunity employer. We encourage all qualified applicants from any race, color, religion, sex, gender identity, sexual orientation, national origin, disability status, protected veteran status, or other characteristics to apply.