Who we are:

At Mediafly, we help the world’s top revenue teams work smarter and achieve measurable impact. Our platform brings together sales enablement, content, and performance insights so sellers have the coaching, tools, and intelligence they need to succeed. By weaving value selling into every workflow, we empower teams to accelerate deal cycles, boost win rates, and prove ROI.

For you, that means joining a company where innovation meets purpose—where your work helps businesses deliver more meaningful buyer experiences and drives results that truly matter. You’ll be part of a collaborative, growth-focused team that values expertise, creativity, and human connection.

You’ll own the full sales cycle for net-new enterprise accounts, focusing on landing high-value, multi-stakeholder deals and building a strong pipeline through proactive prospecting and strategic outreach.

We’re looking for a high-performing Enterprise Account Executive who thrives in a hunter role, someone who can identify, pursue, and close large, strategic opportunities within complex enterprise organizations. This role is ideal for a seller who excels at opening doors, navigating long sales cycles, and efficiently driving deals from first conversation to close.

You’ll own the full sales cycle for net-new enterprise accounts, focusing on landing high-value, multi-stakeholder deals and building a strong pipeline through proactive prospecting and strategic outreach.

This role is compensated on a 50/50 split between base and on-target variable compensation. The salary listed here is base only.

At Mediafly, we are committed to fostering pay equity and transparency, which are essential to creating a fair and inclusive workplace. We believe that clear and open compensation practices help build trust and ensure that all employees are compensated fairly for their contributions. The specific salary offered for a role will be determined by a variety of factors, including your individual skills, experience, geographic location, and other relevant considerations.

The salary range listed is a typical starting point for this role, but at Mediafly, your potential doesn’t stop there! We believe in rewarding talent, curiosity, and impact, which means there’s plenty of room to grow your career, and your compensation, over time. Join us, and you’ll have the chance to take on new challenges, expand your skills, and advance in ways that reflect your contributions and ambition.

Responsibilities of an Enterprise Account Director:

Hunt & close net-new enterprise business with a focus on large, complex, multi-year deals

Build and execute a targeted outbound strategy to engage senior decision-makers

Drive the full sales cycle, from prospecting and discovery through negotiation and close

Qualify opportunities rigorously to ensure deal efficiency and forecast accuracy

Lead value-based sales conversations tied to customer business outcomes and ROI

Navigate complex buying committees and procurement processes with confidence

Partner closely with SDR, Marketing, Professional & Creative Services, & Customer Success

Maintain a strong, predictable pipeline that consistently supports quota attainment

Accurately forecast and manage deals in Salesforce

What Success Looks like:

Consistently meeting or exceeding enterprise quota

Landing high-quality logos with strong expansion potential

Moving deals forward efficiently without unnecessary friction or delays

Establishing yourself as a trusted advisor to senior buyers

Bringing a disciplined, repeatable approach to enterprise hunting

We would love to meet with you if you have the following:

6–10+ years of B2B SaaS sales experience, with significant enterprise hunting experience

Proven track record of closing large, complex deals ($100k+ ARR, ideally higher)

Strong outbound and prospecting skills, you know how to create your own pipeline

Experience selling to enterprise buyers across multiple stakeholders

Confident in value-based selling and executive-level conversations

Highly organized with strong deal qualification and time management skills

Comfortable operating in a fast-growing, performance-driven environment

Experience with revenue enablement, sales enablement, or adjacent MarTech/SalesTech is a plus

Why Mediafly?

Remote based in US

Flexible working hours

Generous PTO

Competitive Salary

401K Retirement Plan with match

Transparent Career Growth Paths

Medical, Dental, Vision

Generous Paid Parental Leave

Remote Stipend

Learning & Development Stipend

Work in a creative environment with high energy

Mediafly is an equal opportunity employer, which means we do not discriminate on the basis of race, color, religion, marital status, age, national origin, ancestry, physical or mental disability, medical condition, pregnancy, genetic information, gender, sexual orientation, gender identity or expression. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome people of different backgrounds, experiences, abilities and perspectives and encourage all interested individuals to apply.

Thanks to our commitment to employee experience, Mediafly has been recognized as a Best Place to Work from Crain's, Inc. and BuiltIn.

Mediafly is a fully distributed company with an HQ in Chicago, IL.