Account Executive

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.