Senior 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 our Senior Account Executive, you'll be the player-coach who scales Jiffy's outbound engine. You'll personally carry a book of the highest-value enterprise and promotional product distributor opportunities while leading and developing a team of two Account Executives. This is a hands-on leadership role for a tenured, full-cycle seller who has also built the systems behind the selling the lists, the sequences, the routing, the reporting and who knows how to turn an individual motion into a repeatable, measurable engine that a team can run.

You’ll report directly to Jiffy's Director of B2B Partnerships and serve as the senior operator on the outbound team. We move fast and pivot our strategy week over week to match where market demand actually lives, so we need someone who can set direction for themselves and their reps, run their own experiments, and tell us what's working before we ask.

You’ll lead from the front. You’ll personally source, build, and close a book of net-new enterprise accounts and promotional product distributors building your own lead lists, enriching and segmenting records, writing the copy that gets replies, and carrying the best opportunities through to a closed, profitable relationship. Your reps should be able to watch how you sell and how you build, and learn from both.

You’ll manage and develop two Account Executives setting targets, running pipeline reviews, coaching on outbound strategy and messaging, and holding the team accountable to reply rates, meetings booked, and conversion. You’ll be responsible for ramping new sellers quickly and lifting the performance of the ones already in seat.

You’ll own the Rev Ops backbone of the outbound team. You’ll design and maintain the sequence flows, lead-routing logic, data hygiene standards, and reporting that the team runs on, leaning on AI and agentic tooling to source, enrich, and personalize ’ll build the dashboards and definitions that tell us and leadership what's actually moving, and you’ll keep the tech stack (Apollo, Hub Spot, Instantly, Apify, Claude, and similar) tuned and connected.

You’ll negotiate complex partnership agreements with large enterprise customers and distributors, serve as the senior point of contact for your book on logistics and claims issues, and work 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 team's customer conversations surfacing product opportunities, unmet needs, and offers that should shape our roadmap.

• Bachelor's degree
• 5-7 years in outbound sales or business development, with direct, hands-on, full-cycle experience building pipeline into enterprise accounts
• A Rev Ops background — you've owned or built the systems behind a sales motion: sequencing, lead routing, data hygiene, tech stack administration, and pipeline reporting
• People management experience — you've directly managed, coached, and ramped sellers (AEs and/or SDRs) and can show how you lifted their numbers
• 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, both as an individual contributor and through a team
• Power user of agentic outbound sales tooling — Apollo, Hub Spot, Claude, Instantly, Apify, and similar — to source, enrich, personalize, and…