Back to jobs
New

Director of Sales

New York, New York, United States

Flex is a growth-stage, NYC headquartered FinTech company that is creating the best rent payment experience. It’s hard to believe that it’s 2025 and paying rent on time is expensive, inflexible, and difficult. We’re here to change that! Flex enables our users to pay rent throughout the month on a schedule that better fits their finances and budget. Our mission is to empower as many renters as possible with flexibility over their most significant recurring expense. After deliberately keeping a stealth profile as we built up unprecedented investor support and an enthusiastic user base, we are looking for motivated individuals to help us keep our mission growing. Will you be a part of the team?

About the role

The Director of Sales will be responsible for leading and developing a high-performing sales team to achieve ambitious revenue targets and drive market share growth with a focus on enterprise-level clients and key accounts. This role requires a strategic leader with a proven track record in sales management, account planning, and team development. The Director of Sales will be instrumental in crafting and executing strategic account plans for our top key accounts, fostering a culture of continuous improvement through regular coaching, ensuring a robust sales pipeline, and ultimately delivering strong unit performance results. 

This is a hybrid position with on-site expectations of 3 days per week in our New York Headquarters. For candidates outside of the NY/NJ area, you may be eligible for our relocation assistance program.

What you’ll do

Sales Strategy & Planning

  • Develop and execute a comprehensive sales strategy to drive revenue growth, expand market reach, and create strategic plans for key enterprise accounts.
  • Analyze market trends, competitor activity, and customer needs to continuously refine sales tactics and strategy.
  • Collaborate with Revenue Operations, Marketing, and Product teams to ensure alignment with overall business objectives.
  • Represent Flex at industry events and conferences to enhance brand visibility and generate new opportunities.

Team Leadership & Development

  • Recruit, build, and lead a high-performing enterprise sales team, providing ongoing coaching, mentorship, and performance management to foster a culture of excellence.
  • Establish a results-driven team environment that encourages collaboration, accountability, and continuous learning.

Pipeline & Performance Management

  • Oversee all aspects of the sales pipeline, from lead generation to deal closure, ensuring accurate forecasting and process efficiency.
  • Monitor key sales metrics and performance indicators, driving the team to consistently meet and exceed revenue targets and quotas.
  • Prepare and present regular sales performance reports, utilizing CRM data to deliver insights on progress, challenges, and market opportunities to senior leadership.

Key Qualifications

  • 8+ years of experience in sales, with at least 4 years in a senior leadership role managing enterprise sales teams.
  • A demonstrable track record of exceeding revenue targets in a competitive B2B environment, ideally within FinTech, PropTech, or SaaS industries.
  • Proven success in developing and executing strategic account plans for large, complex, and key enterprise accounts.
  • Extensive experience in recruiting, coaching, and developing a high-performing sales team focused on enterprise-level clients.
  • Deep understanding of complex sales cycles and methodologies for navigating large organizations.
  • Exceptional negotiation and communication skills, with experience presenting to and building relationships with C-level executives.
  • Proficiency in using CRM software (e.g., Salesforce) for pipeline management, forecasting, and reporting.
  • Strong analytical skills with the ability to use data to drive strategy and performance.
  • Willingness and ability to travel frequently to meet with key clients and strategic partners.

The compensation range for this role will be commensurate with the candidate's experience and Flex's internal leveling guidelines and benchmarks. For working locations in NY/NJ/CA, the OTE pay range will be $344,000-366,000. 

 

Life at Flex:

We understand that it takes a diverse team of highly intelligent, curious, determined, empathetic, and self aware people to grow a successful company. Our HQ is located in New York City, but we have employees located throughout the US, Australia, Canada and South America. We are growing quickly, but deliberately, with a focus on building an inclusive culture. Our dynamic team has incredible perspectives to share, just as we know you do, and we take great pride in being an equal opportunity workplace.

We offer many employee benefits. For full time, U.S. based employees we offer:

  • Competitive pay
  • 100% company-paid medical, dental, and vision
  • 401(k) + company equity
  • Unlimited paid time off + 13 company paid holidays
  • Parental leave 
  • Flex Cares Program: Non-profit company match + pet adoption coverage
  • Free Flex subscription

 For full time non-US employees, we offer

  • Competitive Pay
  • Company Equity
  • Unlimited PTO

Create a Job Alert

Interested in building your career at Flex? Get future opportunities sent straight to your email.

Apply for this job

*

indicates a required field

Resume/CV*

Accepted file types: pdf, doc, docx, txt, rtf

Cover Letter

Accepted file types: pdf, doc, docx, txt, rtf

Select...
Select...
Select...
Select...

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 Flex’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Select...
Select...
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.

Select...

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
Select...

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.