Senior Account Executive - Strategic & Expansion

At Jiffy.com, we are America’s destination for print-ready artwork and unmatched speed, empowering crafters, small business owners, and hobbyists to turn their creative visions into reality. With high-quality apparel, diverse transfer types, and seamless customization, we make the process fast, efficient, and fun. As we continue our rapid growth, we are looking for a VP of Operations to drive cross-functional process excellence, cost efficiencies, and scalable operational infrastructure to support our ambitious goal of reaching $1B+ in revenue.

As Jiffy moves deeper into the custom and organizational apparel space, we’re looking for a Strategic Account Executive who can manage and expand our highest-value B2B relationships. This role is all about unlocking long-term value—by delivering great service, growing wallet share, and acting as a trusted partner to customers who need fast, reliable apparel fulfillment at scale.

You’ll inherit and grow a portfolio of accounts with recurring or expanding needs—whether that’s employee swag, field team uniforms, large-scale events, or campus partnerships. You’ll work closely with internal teams to ensure smooth operations, while always staying one step ahead of customer needs.

Key Responsibilities

• Own a portfolio of strategic customers and develop deep, long-term relationships across stakeholders
• Identify upsell and expansion opportunities across departments or programs
• Ensure operational excellence across fulfillment, reorder flow, and delivery—solving problems before they arise
• Serve as voice of the customer internally—bringing back insights to influence product and service enhancements
• Build structured QBRs, forecasting, and account health reviews to track revenue growth
• Collaborate with sales leadership and marketing to refine our approach to strategic B2B customers

Requirements

Qualifications & Skills

• 5+ years of experience in account management, customer success, or enterprise sales
• Experience working with high-volume apparel buyers, marketing departments, campus programs, or operations teams
• Someone who is equal parts relationship-builder and operator
• A track record of growing existing accounts through upsell, trust, and reliability
• Ability to navigate procurement, finance, and stakeholder complexity with ease
• High attention to detail—you pride yourself on follow-through and proactive service
• Strong communicator who can drive alignment both externally and cross-functionally

Benefits

Why Join Jiffy?

• Opportunities to grow within the company
• Generous compensation and employer paid benefits
• Annual wellness and professional development Stipend
• Perks of getting lots of clothing!