Account Executive - Healthcare IT Managed Services in at Five Nines Technology Group, LLC

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.

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.