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Sr. Director, Enterprise Sales



Sales & Business Development
New York, NY, USA · Remote
Posted on Thursday, September 28, 2023

Are you an extraordinary 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 Senior Director of Enterprise Sales to offer our world-class career pathing and upskilling solutions to new and existing clients. You will utilize your strategic business development expertise and refined negotiation skills to drive the sales of our SaaS solutions to enterprise accounts.

You may be the perfect fit if you are mission-driven, curious, a self-starter, a strategic thinker, and have a track record of success in enterprise SaaS sales.

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.
  • 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.
  • Sales Strategy: Develop and implement effective sales strategies and challenger insights to drive business growth and achieve sales goals.
  • Product Expertise: Maintain thorough knowledge of Pathstream offerings to present and discuss with prospective clients. Understand customer needs and propose the best solutions accordingly.
  • Cross-Functional Collaboration: Collaborate with internal teams such as Product, Engineering, Marketing, and Customer Success to help implement pilots, drive account growth, and increase customer satisfaction.
  • Sales Forecasting: Accurately forecast own individual sales activity and revenue achievement through proper use of sales tools and methodologies.

What we’re looking for:

  • You have 7+ years of experience successfully selling enterprise sales solutions, ideally in financial services such as retail banks and insurers (life/health/P&C).
  • You have proven credibility in consulting and authentically engaging with senior executive decision makers (e.g. heads of Retail Banking, Contact Centers, Claims, Talent, etc.)
  • You have experience navigating complex enterprise sales cycles and landing new business.
  • You have excellent negotiation, presentation, and communication skills to effectively persuade prospects of the value of our solutions.
  • You 100% believe in our mission to help frontline employees advance in their careers.
  • You are resilient and adaptable, and are comfortable creating new resources and processes needed to succeed, while adapting to changing market conditions, customer needs, and internal priorities.
  • You are able to travel as needed for client meetings and industry events.
  • You live within commuting distance from NYC, as this is a hybrid role.

Role/Department Overview:

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

What we do:

At Pathstream, our mission is to create the most accessible and effective career pathways to the jobs in this current economy. We accelerate growth for employers by increasing the skills of their most valuable asset, their employees. Additionally, we unlock growth potential for the individual through interactive learning programs that feature hands-on labs and contextualized coursework preparing them for the real tasks they'll need to advance, without needing to leave their employer of choice. Our curriculum is constantly updated as technologies change and the job market evolves.

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.