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 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)

COMMITMENT TO DIVERSITY AND INCLUSION

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.

Apply for this Job

* Required
resume chosen  
(File types: pdf, doc, docx, txt, rtf)
cover_letter chosen  
(File types: pdf, doc, docx, txt, rtf)
When autocomplete results are available use up and down arrows to review
+ Add another education


Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Pathstream’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.


Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.


Please reach out to our support team via our help center.
Please complete the reCAPTCHA above.