Account Executive

We launched over a decade ago with a simple mission: use technology to combine unparalleled customer service with the fastest delivery in the blank apparel, direct-to-film transfer, and custom apparel industry. We're more than a T-Shirt company; we're a support system for the creator economy, the home hobbyist, the small business owner, and more. Today, we help millions of small businesses and customers build their vision from scratch.

About the role

As an Enterprise Account Executive, you'll own the outbound engine end-to-end—from building the list to landing the account to growing it. This is a hands-on, build-it-yourself role for an experienced, full-cycle seller who would rather construct a sharp, AI-driven campaign than inherit one. You'll source net-new enterprise businesses and promotional product distributors, build AI-enabled sequence flows and lists, write copy that gets replies, and personally carry the best opportunities through to a closed, profitable relationship.

You'll report directly to Jiffy's Head of Partnerships. We move fast and pivot strategy week over week to match market demand, so we need someone who can set their own direction, run experiments, and tell us what's working without being told what to test.

Responsibilities

• Build and maintain your own outbound lead lists from the ground up—sourcing prospects, enriching records, segmenting by fit, and keeping data clean.
• Use AI to source, enrich, and qualify net-new enterprise prospects at volume with agentic tooling.
• Design and run AI-enabled sequence flows—building multi-step, branching outbound logic, personalizing at scale, and letting data route each lead to the right next touch.
• Write and continuously sharpen copy inside those flows, customizing to individual leads rather than blasting templates, and treat reply rates, meetings booked, and conversion as signals to tune against.
• Personally carry hot leads through to close—building orders, mapping growth plans, connecting customers to Jiffy design services, and crafting operational fulfillment solutions.
• Negotiate complex partnership agreements with large enterprise customers and promotional product distributors, ensuring both sides uphold their commitments.
• Serve as the point of contact for your book on logistics and claims issues, working cross-functionally with operations and customer service to resolve them for top accounts.
• Use AI to extract learnings from customer conversations—surfacing product opportunities, unmet needs, and offers that should shape our roadmap.

Requirements

Basic Qualifications

• Bachelor's degree
• 5-10 years in outbound sales or business development, with direct, hands-on, full-cycle experience building pipeline into enterprise accounts
• Demonstrated history of personally sourcing and building lead lists—not just working lists given to you
• Hands-on experience building AI-enabled or automated sequence flows and AI-assisted lead sourcing—you've used agentic tools to do more than send mail merges
• Strong copywriting instincts: you've written outbound sequences from scratch and can show how iterating on messaging moved your numbers
• Proven track record of scaling pipeline and beating targets as an individual contributor
• Power user of agentic outbound sales tooling (Apollo, HubSpot, Claude, Instantly, Apify, and similar) to source, enrich, personalize, and scale at high volume
• Confident living in the data—you can work through large datasets, segment customer types, and find signals that lift campaign performance
• Exceptional communication and negotiation skills (experience engaging C-level executives a plus)
• A self-starter who can take a vague brief, set firm strategy, and deliver results with minimal direction

Preferred Qualifications

• Experience selling into enterprise accounts at a rapid-scale startup
• Experience in the promotional product distributor category, with an understanding of scaled enterprise relationships and high-quality delivery standards
• Experience building or owning an outbound motion as it scaled from early proof-of-concept to repeatable engine

Benefits

• Location: Irvine, CA; San Francisco, CA; Dallas, TX; or Miami, FL (hybrid model requiring at least 3 days onsite)
• Compensation: Base salary ranging from $85,000 per year, with total compensation including performance-based bonuses, equity, and benefits. Final offers tailored to experience and qualifications.
• Comprehensive Benefits: Full medical, dental, and vision coverage (with a portion of premiums paid by Jiffy)
• Retirement Planning: 401(k)
• Wellness Support: Annual wellness benefits
• Tools for Success: Choice of MacBook or PC laptop, plus home office equipment setup
• Perks & Extras: Annual $200 credit to use on our website, plus team merch drops
• Professional Development: Annual stipend to support learning and career growth