About the Role

Five Nines is seeking a highly experienced Senior Account Executive to drive new business growth within key industries across the United States, including the banking sector. This is a strategic, high-impact role suited for a seasoned seller who excels at leading complex, multi-stakeholder deals in a managed services environment. You will be responsible for owning a territory, developing strategic plans, and executing full-cycle sales from initial prospecting through final close. The ideal candidate has at least ten years of demonstrated success in technical B2B sales, thrives in high-autonomy environments, and consistently exceeds revenue targets.

Why Join Five Nines

• Sell with Confidence: Join a nationally recognized MSP with consistent performance on the MSP 501 list for twelve years and multiple recognitions on the Inc. 5000 list.
• Senior-Level Earnings: Competitive base salary with an uncapped commission structure. On-target earnings for this role are approximately $250,000 with accelerators for overachievement.
• Autonomy and Leadership Support: You own your territory and sales cycle with strong executive backing and access to technical and operational resources.
• Career Growth: Opportunities to mentor junior sellers, influence go-to-market strategy and grow into leadership-focused paths.
• Exceptional Culture: We prioritize employee experience, client impact, and long-term retention.
• Work-Life Balance: Remote and hybrid flexibility, open PTO, and paid holidays.
• Benefits That Matter: High-quality medical, dental, and vision coverage, telemedicine, EAP, and a 401(k) with company match.
• High-Caliber Team: Collaborate with experienced technical experts and dedicated service teams who support you in winning and retaining clients.

What You Will Do

Territory and Revenue Ownership

• Own a national or multi-state territory and develop strategic plans to penetrate mid-market and regulated industries.
• Consistently meet or exceed annual revenue goals by managing a robust pipeline of qualified opportunities.

Full-Cycle Sales Leadership

• Lead complex, multi-phase sales cycles that include prospecting, technical scoping, solution design, proposal development, negotiation, and closing.
• Serve as the executive-facing point of contact during the sales process, presenting to boards, C-level leaders, and compliance stakeholders.

Strategic Engagement and Deal Strategy

• Develop and deliver compelling presentations tailored to executive audiences.
• Lead high-stakes RFP responses, pricing strategies, and competitive positioning with minimal oversight.
• Collaborate with internal technical teams, cybersecurity experts, and service leaders to ensure alignment and feasibility.

Market Influence and Industry Presence

• Represent Five Nines at regional and national associations.
• Participate as a subject matter contributor or speaker when appropriate.

Pipeline Accuracy and Forecasting

• Maintain rigorous pipeline discipline and forecasting accuracy using HubSpot CRM.
• Report insights and trends to leadership to help shape company sales strategy.

Collaboration and Internal Leadership

• Mentor account executives when needed.
• Provide market and client feedback to product, service, and marketing teams. 

Required Skills and Experience

• Ten or more years of business-to-business sales experience with a proven track record of exceeding quota in complex, multi-stakeholder environments.
• Strong preference for candidates with managed services or MSP sales experience.
• Demonstrated success engaging C-level executives and handling long, multifaceted sales cycles.
• Technical fluency with IT infrastructure and Microsoft technologies and the ability to translate technical concepts into business value.
• Experience owning a territory and executing a structured account plan with minimal supervision.
• Strong negotiation, presentation, and executive communication skills.
• Proficiency with HubSpot CRM or similar tools.
• Willingness to travel nationally up to 50 percent 

Preferred Skills and Experience

• Familiarity with banking procurement processes.
• Understanding of financial regulatory frameworks such as GLBA, FFIEC, FDIC, or OCC guidelines.
• Experience selling into community banks, credit unions, or other regulated financial institutions.
• Exposure to risk, audit, or compliance-driven sales environments.

What we bring to the table:

• Competitive base salary and commissions
• Full health care benefits options including health, dental, vision, and disability
• 401K plan with company match
• Unlimited PTO
• Flexible work schedule