Outside Sales Representative - (Connecticut)

S&S Activewear; United States; On-site; USD 70,000 - 110,000; Full time

Benefits offered by this job

Discounts on apparel

401(k) plan

Vacation time

Job summary

S&S Activewear, a leading North American apparel distributor, seeks an Outside Sales Representative to drive growth in a designated territory. You will build strong relationships with owners and decision-makers, manage accounts, and lead strategic sales initiatives.

The role requires 3–4 days of travel each week, heavy emphasis on data-driven opportunity discovery, and collaboration with Account Managers. Remote work options available within the field structure.

Qualifications

• Bachelor's degree preferred.
• Minimum 2 years of field sales experience; promotional products/apparel experience valued.
• Strong communication skills, both verbal and written.
• Excellent time management and multitasking abilities; aggressive follow-through.
• Ability to travel up to 50% and work in a field-based role.

Responsibilities

• Drive territory P&L through sales and profitability metrics.
• Engage in in-person account management and strategic calls.
• Build relationships with owners and decision-makers across departments.
• Collaborate with Account Managers to maximize opportunities.
• Lead product launches and strategic sales planning within the territory.
• Coordinate with internal teams to optimize customer service and upsell opportunities.
• Maintain accurate reporting, sales funnel tracking, and program administration.

Skills

Communication

Presentation

Time management

Organization

Self-motivation

Analytical thinking

SPIN selling

Customer engagement

Education

Bachelor's degree preferred

Tools

MS Office

CRM systems

Job description

S&S Activewear is a leading North American, tech enabled specialty distributor of imprintable apparel, including t shirts, fleece, athletic wear, headwear, workwear, scrubs and accessories. We pride ourselves on being the “critical link” that enables our 100+ brand partners such as Adidas, Columbia and Gildan to reach our hyper fragmented base of customers, comprised of apparel decorators, eRetailers and promotional products distributors that embellish apparel items for diverse end consumer use cases (e.g., everyday wear, concerts, fitness attire, life events, team sports, etc.). At S&S, we differentiate in the market through a customer service focus, strategic product portfolio, world class distribution infrastructure, a collaborative growth culture and a relentless focus on technology and innovation.

Our success has compounded since the Company’s humble beginnings in 1988 as a regional t shirt distributor to a leading, multibillion dollar value-added distribution platform that drives market penetration for our suppliers while enabling growth, operations and fulfillment for a diverse range of customers across channels and business sizes.

Today, we continue to strive to be the apparel distributor of choice by inspiring and fostering growth for customers, employees and suppliers, anchored in our commitment to Lead with Respect, Never Settle, Own the Outcome, Win Together, and the belief that Innovation Powers Our Hustle. These values guide how we serve, how we collaborate and how we continuously improve, ensuring we deliver on our promise of service, deep relationships, innovation, continuous improvement and accountability.

ABOUT THE ROLE

The Outside Sales Representative role combines strategic account development with new business acquisition, serving as the primary field representative for S&S Activewear within a designated geographic territory. This dynamic position requires a sales professional who excels at building and nurturing comprehensive customer relationships while consistently driving revenue growth. The role demands extensive field presence, with 3-4 days of weekly travel and quarterly overnight engagements, varying based on territory scope. The ideal candidate brings polished interpersonal skills, commanding presentation abilities, and a natural talent for engaging effectively with business owners and key decision-makers. Success in this role requires strong analytical capabilities to transform customer data into actionable business opportunities, coupled with expertise in sales methodology and meticulous follow-through. Working in close partnership with Account Managers, this position demands both independent initiative and collaborative excellence to maximize customer engagement and sales potential. The successful candidate will demonstrate an entrepreneurial spirit balanced with strong team orientation, ensuring optimal territory coverage and customer service. This position requires the use of a personal vehicle for work-related travel.

SCHEDULE

Monday-Friday, Full-Time, Non-Exempt (Remote Available)

COMPENSATION

Salaried: (based on experience)

* This position is bonus eligible

BENEFITS

We offer a comprehensive benefits package designed to support your life, health, and future. Benefits begin 0-90 days after hire and include Vacation, Personal, and Sick time; Medical, Dental, Vision, Life Insurance, and Disability coverage; Flexible Spending Accounts; and a 401(k) plan. You’ll also enjoy discounts on brand-name apparel, fun employee events, and meaningful opportunities for growth and advancement. Join a company that invests in you from day one.

WHAT YOU WILL DO

• Drives territory P&L performance through strategic management of customer volume, sales, and profitability metrics
• Executes systematic in-person account engagement, demonstrating excellence in call planning, analysis, presentation delivery, and follow-through.
• Cultivates comprehensive relationships across customer organizations, from ownership through sales, service, and merchandising teams, while conducting strategic one-on-one meetings to uncover growth opportunities.
• Establishes strong partnerships with key stakeholders across customer departments including finance, marketing, operations, and production.
• Collaborates seamlessly with assigned S&S Account Manager to optimize customer service, sales opportunities, and engagement frequency.
• Master’s customers go-to-market strategies, including program management, merchandising schedules, and renewal processes.
• Leads new product launches, internal initiatives, and strategic sales planning with authority and
• vision.
• Leverages advanced merchandising expertise to highlight S&S Activewear's competitive advantages and drive strategic upsell opportunities.
• Orchestrates cross-functional collaboration, utilizing internal resources including trade marketing, decoration services, EDI, pricing, and custom solutions to maximize sales potential.
• Maintains impeccable administrative management through precise reporting, calendar organization, sales funnel tracking, and program administration.
• Ensures premium S&S Activewear brand presence through professional showroom and collateral management.
• Represents S&S Activewear at industry trade shows, events, and customer functions to strengthen market position and relationships.

WHAT WE’RE LOOKING FOR

• Bachelor's degree preferred with proven track record of professional achievement
• Minimum 2 years of field sales experience, with promotional products and apparel industry experience highly valued
• Superior communication abilities demonstrated excellence in both verbal and written interactions
• Exceptional multitasking capabilities with strong prioritization skills and time management expertise
• Self-motivated professional with proven ability to execute complex initiatives independently
• Demonstrates meticulous attention to detail and superior organizational abilities
• Results-driven performer with strong sense of urgency and commitment to excellence
• Brings a dynamic, high-energy approach with authentic enthusiasm for the role
• Advanced problem-solving capabilities with innovative solution development
• Expert in consultative sales methodologies, including SPIN selling techniques
• Strong merchandising acumen with proven ability to optimize product presentations
• Polished presentation skills with ability to engage diverse audiences effectively
• Technical proficiency in demonstrating digital tools and web-based solutions
• Sharp analytical mindset with strong financial acumen for strategic decision-making
• Demonstrated excellence in strategic planning and documentation
• Proficiency in Microsoft Office Suite and related business applications
• Travel Position requires up to 50% travel throughout assigned territory

PHYSICAL DEMANDS

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. While performing the duties of this job, the employee is regularly required to talk or hear.

WORKING ENVIRONMENT

This job operates in a professional office environment. This role routinely uses standard office equipment such as computers, phones, photocopiers, filing cabinets and fax machines. Reasonable accommodations may be made to enable people with disabilities to perform the essential functions.

EQUAL OPPORTUNITY EMPLOYER

S&S Activewear welcomes people of all backgrounds and experiences and are committed to creating a diverse culture and supporting human growth. We are proud to be an equal opportunity employer and committed to providing equal opportunity for all employees and applicants. We conduct business without regard to sex, race, creed, color, religion, marital status, national origin, citizenship status, age, pregnancy, sexual orientation, gender identity or expression, genetic information, disability, military status, status as a veteran, or any other protected characteristic. Our policy is to recruit, hire, train, promote, assign, transfer, and terminate employees based on their own ability, achievement, experience and conduct and other legitimate business reasons. S&S participates in E-Verify and will provide the federal government with your Form I-9 information to confirm you are authorized to workin the U.S.

This job offer is contingent upon the completion of a satisfactory back ground check.