Account Executive - IT Managed Services

Account Executive – IT Managed Services

About the Role

Five Nines is seeking an Account Executive to lead new business development in several key industries, including the healthcare vertical, across the United States. This is a strategic, high-impact role focused on driving growth within mid-market organizations. You will own, develop plans, and execute full-cycle sales from prospecting to close. Our ideal candidate is a seasoned seller, capable of leading complex deals involving multiple stakeholders. You will work independently, manage your pipeline, and deliver results with autonomous execution.

Why Join Five Nines

• Sell with Confidence: Join a nationally recognized MSP (MSP 501 list for 12 consecutive years, including a Top 100 ranking in 2025, and honored 9 times on the Inc. 5000 list) with a proven track record of growth and innovation.


• Big Impact, Big Rewards: Competitive base salary plus uncapped commission with clear OTE goals ($100K–$150K+).


• Autonomy + Executive Support: We trust you to own your territory and sales cycle while giving you the backing of leadership and resources to win.


• Career Growth: Clear paths into leadership roles, supported by mentorship, and job shadowing.


• Exceptional Culture: We prioritize employee experience, client impact, and long-term retention.


• Work-Life Balance: Hybrid and remote flexibility, open PTO, and paid holidays.


• Benefits That Matter: High-quality medical, dental, and vision coverage, telemedicine, EAP, and 401(k) with company match.


• Be Part of Something Bigger: Work alongside some of the most talented technology professionals in the industry, learn, grow, and have fun while doing it.

What You’ll Do

• Own a Territory: Develop and implement a comprehensive territory plan to enter mid-market and regulated industries.


• Full-Cycle Sales Leadership: Manage the entire sales process—prospecting, discovery, solution design, proposal, negotiation, and closing.


• Partnership: Maintain accurate forecasting and CRM hygiene (HubSpot) to ensure visibility and accountability.


• Strategic Engagement: Build relationships with C-suite executives, boards, and compliance leaders to position Five Nines managed services as critical enablers of compliance, security, and digital transformation.


• Presentation Development: Create and deliver compelling presentations tailored to executive audiences to communicate value and solution alignment.


• Proposal and RFP Management: Participate in the generation of formal quotes and written responses to RFPs, ensuring accuracy and competitive positioning.


• Complex Deal Management: Coordinate internal teams and external stakeholders to ensure seamless delivery and client success.


• Market Presence: Represent Five Nines at national and regional association events.

Required Skills & Experience

• 5+ years of business-to-business sales experience with a proven record of exceeding quota, including pipeline you sourced yourself through outbound effort.


• Demonstrated ability to build and execute outbound prospecting campaigns independently, including cold calling, multi-touch email sequencing, and LinkedIn / Sales Navigator engagement, with the discipline to run full multi-channel cadences (7 to 12 touches) rather than stopping after two or three attempts.


• Proven success engaging non-technical executive buyers, including hospital CEOs, CFOs, and administrators, as well as physician-owners and practice managers at specialty clinics, and translating technology into operational and financial terms.


• Skilled at navigating gatekeepers and multi-threading outreach across an organization (for example, connecting with both the administrator and the physician champion), with the judgment to time outreach around clinic and hospital schedules.


• Relationship-first selling instincts suited to rural and community healthcare markets, where trust and referrals outweigh high-velocity tactics, including in-person presence at state hospital association, rural health, and practice-management events.


• Ability to work independently and execute a territory plan without heavy oversight.


• Experience with CRM systems and sales engagement tooling (HubSpot preferred), with strong sequence and pipeline hygiene.


• Willingness to travel up to 50%, including rural markets.

Preferred Skills and Experience

• IT managed services experience.


• Experience selling into healthcare, including hospitals, critical access hospitals, or physician practices, with working fluency in HIPAA, business associate agreements, and cyber insurance requirements.


• Familiarity with IT terminology (in particular, Microsoft technologies) and the ability to translate it into non-technical terms.


• Understanding of rural healthcare economics and funding mechanisms (Medicare/Medicaid dependence, CMS Rural Health Transformation Program, USDA/HRSA grants) that help partners fund technology investments.


• Exposure to the ambulatory EHR ecosystem (Epic Community Connect, athenahealth, eClinicalWorks, Greenway, Veradigm).


• Existing network within state hospital associations, NRHA, or MGMA communities.