Account Executive - Healthcare IT Managed Services

Description

Do you love the thrill of a cold call that turns into a real conversation with a CEO? Five Nines is looking for a disciplined, high-activity Account Executive to build new business with hospitals, health systems, and clinics across the United States. You'll spend a big part of every week on the phone opening doors with executives who have never heard of us, then own those opportunities all the way to a signed agreement. If you handle rejection well, run your own pipeline, and want uncapped upside backed by a nationally recognized brand, this is your territory. Are you in?

A few things that make Five Nines special:

Sell a brand that opens doors. Five Nines has made the MSP 501 list 12 consecutive years, including a Top 100 ranking in 2025, and has been honored 9 times on the Inc. 5000.

Culture is our #1 competitive advantage. We hire for values first and prioritize employee experience, client impact, and long-term retention.

Built by IT people, for IT people. You'll work alongside some of the most talented technology professionals in the industry, and you'll learn, grow, and have fun doing it.

Real flexibility. Hybrid and remote options, open PTO, and paid holidays, because we trust our people to own their results.

Leadership that has your back. You run your territory your way, with executive support and resources behind you to win.

Requirements

In this role, you'll have the opportunity to:

Own your territory. Build and work your own plan targeting hospitals, health systems, and clinics of roughly 50 to 250 employees across the U.S.

Hit the phones with a head start. You'll start with a curated, vetted prospect list and a proven call script, then make 300 cold calls a week, backed by email outreach, to open conversations with executives who don't know us yet.

Fill your calendar. Turn that outreach into at least two first meetings a week with qualified decision makers.

Run the whole deal. Take every opportunity from first call through discovery, proposal, negotiation, and signed agreement.

Sit across from the C-suite. Build relationships with CEOs, CFOs, COOs, administrators, and practice administrators, and position Five Nines as their partner in security, compliance, and operational continuity.

Get sharper every week. Receive specific coaching on your own calls through our proprietary revenue intelligence and call coaching systems.

Win in the room. Deliver tailored presentations and proposals to executive audiences and contribute to RFP responses.

Be the face of Five Nines. Represent us at regional and national healthcare association events and keep your pipeline and forecast sharp in HubSpot.

Requirements

3+ years of B2B sales experience with a proven record of meeting or exceeding quota.

Demonstrated success building pipeline through high-volume cold calling and proactive outbound outreach.

Comfort engaging C-level executives and leading business-level conversations.

Ability to explain technology concepts in plain, non-technical terms.

Self-motivated and able to execute a territory plan without heavy oversight.

Experience with a CRM (HubSpot preferred).

Willingness to travel up to 20%, primarily for industry events and select client meetings.

Nice to have:

IT managed services or technology sales experience.

Knowledge of the healthcare industry, including how hospitals and clinics operate and buy.

Familiarity with HIPAA or other healthcare compliance requirements.

What you will get out of the role:

Big earning potential: Competitive base salary plus uncapped commission, with clear OTE goals of $100K to $150K+.

A clear path up: Defined routes into sales leadership, supported by mentorship and job shadowing.

Benefits that matter: High-quality medical, dental, and vision coverage, telemedicine, EAP, and a 401(k) with company match.

Time to recharge: Open PTO and paid holidays.

Flexibility: Work remotely or hybrid, with the independence to manage your own week.