We're Jiffy! We launched over a decade ago with a simple mission: use technology to combine an unparalleled level of 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!

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 the AI-enabled sequence flows and lists that reach them, write the copy that gets replies, and personally carry the best opportunities through to a closed, profitable relationship. If your instinct when handed a blank territory is to start pulling data and building lists that same day, this is your role.

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

What You'll Own

You'll build and maintain your own outbound lead lists from the ground up sourcing prospects, enriching records, segmenting by fit, and keeping the data clean enough to act on. You'll lean on AI to source faster and smarter than a manual motion ever could, using agentic tooling to enrich and qualify net-new enterprise prospects at volume.

You'll design and run AI-enabled sequence flows building multi-step, branching outbound logic, personalizing at scale, and letting the data route each lead to the right next touch. You'll write and continuously sharpen the copy inside those flows, customizing to the individual lead rather than blasting a template, and you'll treat reply rates, meetings booked, and conversion as signals to tune against, not vanity metrics.

When a lead turns hot, you'll carry it yourself: building orders, mapping out the customer's growth plan, connecting them to Jiffy design services, and crafting the operational fulfillment solution that closes the deal. You'll negotiate complex partnership agreements with large enterprise customers and promotional product distributors and make sure both sides hold up their end. You'll 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 our top accounts. And you'll use AI to pull learnings out of your 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 the 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 the high-quality delivery standard they require
• Experience building or owning an outbound motion as it scaled from early proof-of-concept to repeatable engine

Benefits

What We Offer

Location: This role can be located in one of the following area:. Irvine CA, SF, Dallas or Miami.

Hybrid model: Our policy requires at minimum 3 days onsite

The base compensation for this role is expected to range from $85,000 per year. Actual compensation will be based on a variety of factors, including skills, experience, qualifications, and overall fit for the role.

Total compensation may include base salary, performance-based bonuses, equity, and benefits. Final offers are tailored to each candidate and take into consideration their background and years of experience.

• 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 to help you stay healthy and balanced.
• Tools for Success: Choice of MacBook or PC laptop, plus equipment for your home office setup.
• Perks & Extras: Annual credit of $200 to use on our website plus more team merch drops than you will know what to do with!
• Professional Development: Annual stipend to support your learning and career growth.

EEO

Jiffy is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristics. Jiffy considers qualified applicants with criminal histories, consistent with applicable federal, state and local law.