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Director, Enterprise Sales

Location: Remote - Midwest
Secondary Location(s): Remote
Employment Type: Regular
ID: 5302
# of Openings: 1


Director of Enterprise Sales


This position is responsible for targeting F500/F1000 companies within the assigned sales territory, generating a high quality pipeline through personal outreach efforts, developing relationships with benefits consultants and responding to RFP’s and formulating a sales strategy and plan to close large, enterprise-level (250K+) sales transactions.

With directives from the SVP of Enterprise Sales, this position’s primary responsibility includes selling WageWorks products to existing and new enterprise-level accounts while meeting or exceeding sales targets.  This is an outsides sales role responsible for identifying, prospecting and developing executive level relationships with new clients and key consultants and brokers to increase revenue. This position is responsible to understand customers’ needs and sell value by leveraging WageWorks’ unique capabilities.


This position may reside in a Company location or remotely and reports to the Senior Vice President of Enterprise Sales.  The nature of the work entails that candidates demonstrate an ability to collaborate internal WageWorks’ departments to best position WageWorks’ solutions in response to formal or informal requests for proposals (RFP’s) or information.


With goals and objectives set by senior sales leadership, this position is responsible for targeting F500/F1000 companies within the assigned sales territory, generating a high quality pipeline through personal outreach efforts, developing relationships with benefits consultants and responding to RFP’s and formulating a sales strategy and plan to close large, enterprise-level (250K+) sales transactions. Meets with prospects, current clients, benefit consultants and strategic partners and uses consultative selling to determine customer needs.  Creates excitement about WageWorks’ products and services and sells value by leveraging WageWorks’ unique capabilities.

Possesses excellent presentation skills highlighting how WageWorks products and services can best meet a client’s requirements.  This entails the ability to clearly articulate the benefits of WageWorks’ solutions and vision to all levels; including business managers and “C” level executives.

Develops a robust pipeline (3 to 4 times quota) through continual outreach campaigns to prospects, clients, benefit consultants and WageWorks partners to generate new business. Follows sales team’s policies and processes, and utilizes prescribed templates and tools.  Tracks critical account, sales and pipeline data utilizing

Demonstrates a broad understanding of HR and benefits outsourcing including industry trends, benefit plan designs and other related topics.

Possesses a competitive drive, is self-motivated and can think strategically.

Collaborates with internal departments on all aspects of client facing activities i.e. implementation, relationship management, client escalations etc. in order to create satisfied clients.


Generates new sales opportunities by leveraging existing client relationships, responding to Request for Proposals (RFP’s), outbound prospecting, and participating in vendor/trade shows and symposiums to promote WageWorks products and services.

May assist with or perform other sales activities as requested by WageWorks’ sales leadership.

Performs other duties as assigned or apparent.


The ability to effectively plan, manage and achieve sales goals in an outside sales environment as described.  This position requires at least 7-9 years of outside sales experience meeting/exceeding sales targets with extremely strong closing skills.  The ability and skill to effectively present to “C” level decision makers are required.  Knowledge of business organizational structures and buying influences is critical for success.

Requires working knowledge of sales planning and goal setting, successful strategic and consultative selling techniques, and related information.  Requires strong prospecting, qualifying, closing and time management skills.

Requires experience introducing/selling new technology-based, high value services to small, medium, or large domestic companies.  Incumbents must aggressively pursue sales targets and have a track record of achieving sales goals.

Requires strong analytical and strategic skills with proven ability to develop processes and procedures to track and maximize sales revenues.

Experience selling complex solutions to large F500/F1000 clients in the healthcare industry is strongly preferred.

Incumbents must have proficient skills and abilities with a personal computer and have a solid knowledge, understanding and experience with Microsoft Office Suite, specifically with Excel and Word.  Additionally, a strong understanding of contact management tools is required.


Frequent travel, including overnight, may be required as dictated by business needs.


A thorough knowledge and understanding of business, sales, marketing or similar vocations generally obtained through the completion of a four-year bachelor’s degree program or equivalent combination of experience and education.



Build Your Career at WageWorks!

WageWorks enables millions of people to save money on critical expenses like healthcare, dependent care, and commuting, through Consumer-Directed Benefits, such as Health Savings Accounts (HSAs), Flexible Spending Accounts (FSAs), Health Reimbursement Arrangements (HRAs) and Commuter Benefits. WageWorks is a leader in the industry serving more than 6.5 million people for over 100,000 employers, including 63% of the Fortune 500 and numerous public sector clients.

WageWorks believes that our success is achieved by its People. Values describe how we work together to achieve our success. It is our employees that drive results through living our Company Values. Every employee at WageWorks is expected to uphold and demonstrate the six Company Values listed below as an additional component of the job description and as a standard of individual performance.

Customer-Centric: Our Customer comes first. We aim to serve our Clients and their employees, our brokers and partners, as well as our internal customers.

Caring: People are at the heart of our company. We care about people: our Clients, our Clients’ employees and their families, our partners, and local communities, and our fellow employees at WageWorks.

Passionate: We love what we do and are passionate about delivering Consumer-Directed Benefits that save people money and enrich their lives.

Accountable: We are dedicated to making our team and the company succeed, and we are open, honest, ethical and conscientious, as we deliver on our commitments.

Leading: Our actions inspire new ideas and drive change each and every day.

Respectful: We value the diversity of our people, treat them with dignity and respect, encourage their development and reward their performance.

Why Work for WageWorks?

If you're looking for a career that provides plenty of growth opportunities, responsibility, and interesting challenges to tackle, you will find it here.

If you want to join a fast-moving, high-growth, exciting company that's a market leader, you’re looking in the right place.

But mostly, if you want to help people live happier, healthier, and more productive lives, then you’ll want to work for WageWorks.

WageWorks provides equal employment opportunity without regard to pregnancy, childbirth or related medical conditions, race, religious creed, color, national origin or ancestry, citizenship, mental or physical disability (including HIV and AIDS), medical condition, veteran or military status, marital or registered domestic partnership status, age, sex, sexual orientation, genetic information, gender identity or any other basis protected by federal, state or local law, ordinance or regulation.

Employment will require successful completion of a background check.

Equal Opportunity for Disabled Veterans, Recently Separated Veterans, Other Armed Forces Service Medal Veterans.

Drug free workplace.

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