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.

Requirements

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 RevOps 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 at volume. You'll build the dashboards and definitions that tell us and leadership what's actually moving, and you'll keep the tech stack (Apollo, HubSpot, 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.

Basic Qualifications

• 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 RevOps 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, 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, build reporting, 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 for themselves and a team, and deliver results with minimal direction
  

Preferred Qualifications

• Experience leading a small outbound or SDR/AE team 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, including the RevOps infrastructure underneath it

Benefits

What We Offer

The base compensation for this role is expected to range from $125-150k 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.