[Remote] Enterprise Sales Director at Benepass

Miramar, Florida, United States

Not SpecifiedCompensation

Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Fintech, HR Tech, Employee BenefitsIndustries

Requirements

3–6 years of B2B SaaS or benefits technology sales experience, ideally within health, wellness, or total rewards
Proven track record of consistently meeting or exceeding quota in a full-cycle AE role
Experience selling to HR, Benefits, or Finance executives
Strong discovery, presentation, and objection-handling skills
Familiarity with benefits administration, LSAs, FSAs, HSAs, or wellness platforms a plus
Consultative selling mindset—able to translate complex benefits concepts into simple, value-based conversations
Self-starter who thrives in a fast-paced, mission-driven environment
Comfortable operating in Salesforce and using sales engagement tools (e.g., Outreach, Gong, LinkedIn Sales Navigator)
Preferred Experience
Prior experience with companies like Garner Health, Health Equity, Sequoia, Gusto, or Betterment at Work
Understanding of HRIS/payroll integrations and data exchange processes
Exposure to selling through benefits brokers or consultants

Responsibilities

Own the full sales cycle from prospecting to close for large employers
Build and manage a robust pipeline through outbound efforts, referrals, and partner channels
Conduct discovery with benefit and total rewards leaders to identify pain points and align Benepass solutions to business goals
Deliver compelling product demos and ROI presentations that articulate Benepass’ differentiated value
Partner cross-functionally with Solutions Consulting, Marketing, and Partnerships to accelerate deal velocity and improve win rates
Navigate multiple stakeholders (benefits, finance, procurement, IT) within complex buying groups
Maintain accurate forecasting and pipeline hygiene in Salesforce
Meet and exceed quarterly and annual revenue targets
Represent Benepass at industry events, conferences, and webinars to build relationships and market presence

Skills

Key technologies and capabilities for this role

Enterprise SalesFull Sales CycleProspectingPipeline ManagementOutbound SalesConsultative SellingBenefits TechnologyStrategic SellingSolution SellingDeal Closing

Questions & Answers

Common questions about this position

What experience is required for the Enterprise Sales Director role?

Candidates need 3–6 years of B2B SaaS or benefits technology sales experience, ideally in health, wellness, or total rewards, with a proven track record of meeting or exceeding quota in a full-cycle AE role.

What key skills are needed to succeed in this position?

Strong discovery, presentation, and objection-handling skills are required, along with experience selling to HR, Benefits, or Finance executives.

Is this a remote position or does it require office work?

This information is not specified in the job description.

What is the salary or compensation for this role?

This information is not specified in the job description.

What makes a strong candidate for this Enterprise Sales Director position?

A strong candidate has 3–6 years of B2B SaaS or benefits sales experience, a track record of exceeding quota, and skills in discovery, presentations, and selling to HR/Benefits executives, with passion for improving employee experience.

Benepass

Platform for managing employee benefits efficiently

About Benepass

Benepass helps companies manage and distribute employee benefits efficiently and in a personalized manner. It operates in the employee benefits market, offering services such as health and wellness programs and professional development funds. The main product is a versatile benefits platform that includes virtual and physical cards, as well as mobile wallets, allowing employees to access and manage their benefits easily. Employers can customize the platform to set rules for contributions and eligibility. Benepass generates revenue through a B2B model, charging companies for access to its services, and partners with financial institutions for secure transactions. A key differentiator is its user-friendly mobile app and responsive customer service, which enhance the employee experience. The goal of Benepass is to improve how companies take care of their employees, boosting morale and productivity.

New York City, New YorkHeadquarters

2019Year Founded

$33.3MTotal Funding

EARLY_VCCompany Stage

Consumer Software, Enterprise Software, FintechIndustries

51-200Employees

Benefits

Healthcare: We pay $430 per month toward your health insurance and fully cover dental and vision. You also get membership to OneMedical, Teladoc and Talkspace

Flexible, autonomous work: We’re remote first so live where you’re most happy. We come together in-person as a team 3-4 times per year.

Benepass perks: $500 to set up your home office, $100 per month for wellness, however you define it, $150 per month for home internet and cell phone, $150 per month for co-working

Risks

Benebot's AI tool may face data privacy and compliance challenges.

$20 million funding round increases pressure to scale and meet investor expectations.

Competitive landscape intensification could impact Benepass's market share.

Differentiation

Benepass offers a versatile platform with virtual and physical cards and mobile wallets.

The company integrates AI with 'Benebot' for enhanced benefits education and administration.

Benepass provides a user-friendly mobile app and responsive customer service for employees.

Upsides

Increased demand for personalized benefits solutions positions Benepass for growth.

AI integration in benefits platforms is a significant trend Benepass is capitalizing on.

Remote work models boost demand for flexible benefits, aligning with Benepass's offerings.

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