Enterprise Account Director

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.

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.

• 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

• 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

• 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.