Enterprise Account Executive, Western US

Accelerate your career with this critical role!

About Cayosoft:

Cayosoft Inc., a global independent software vendor, delivers exciting and innovative products that help organizations manage their Microsoft infrastructures throughout their journey from on-premises, to hybrid, to public and private cloud. Applying deep expertise in IT operations and a focus on delivering practical new functionality, Cayosoft helps customers worldwide remove barriers to adopt a modern cloud infrastructure. Cayosoft’s solutions secure, simplify, automate and control Active Directory, Exchange On-premises, Office 365, Exchange Online and Azure Active Directory, OneDrive, SharePoint and Teams. Headquartered in Columbus, OH, we are a fast-growing start-up, with a competitive product advantage, and a great vision of the future.


We are seeking a highly motivated, articulate, energetic and positive individual (hunter) with a proven track record selling complex technology solutions to join our Sales Team as an Enterprise Account Executive. In this position you will be responsible for selling to enterprise companies; directly to end users and by leveraging support from potential channel partners. As a senior member of the sales team, you will sell our market leading software solutions by gaining a thorough understanding of the client’s business and the industry in which they operate in. You will uncover corresponding IT initiatives whereby Cayosoft can help resolve the customer’s needs, developing compelling business value proposals and ultimately closing business. You must have the ability and experience to find, manage, negotiate and close six and seven figure SaaS contracts while embracing a highly dynamic and rapidly growing environment.


  • Demonstrate the ability, and desire, to spend much of your time out-bounding / prospecting utilizing the telephone, direct mail, webinars, client visits and other marketing programs / tools in an effort to uncover new prospects while fielding inbound inquiries and managing existing accounts for cross-sell / up-sell opportunities.
  • Collaborate with marketing to develop and execute on a territory plan that will focus on new accounts but also include white space analysis (existing customers) and channel motions.
  • Work with the VP of Sales & Sales Team to develop business plans, which align to the assigned geographic (territory) and business needs.
  • Marshal and lead the appropriate technical resources to demonstrate Cayosoft’s Advantages to prospects & customers.
  • Coordinate and lead RFP process with internal teams to ensure the highest quality and complete submission while complying with indicated deadlines.
  • Document and share POC success criteria internally and with prospect to ensure proper alignment throughout the sales cycle.
  • Provide customers with detailed and accurate quotations and cost calculations.
  • Accurately track activities and manage opportunity pipeline daily in CRM to provide up to date and clear view of your business.
  • Develop and maintain a deep understanding of the territory including customers, prospects, partners, influencers, and competitors.
  • Maintain and nurture existing client relationships engaging with key client personnel to determine what additional Cayosoft solutions would be beneficial to add or expand our footprint and ARR.
  • Maintain the highest level of customer and partner satisfaction within the accounts in your territory.
  • Demonstrate the ability to create and manage conversations at all business and technical levels of client/potential client’s organization from the CEO – Systems Administrator.
  • Effectively understand where in the sales process you are and who holds the financial approval.
  • Build pipeline to 5x quota.


  • Bachelors (BA/BS) degree and/or proven equivalent experience
  • 7 + years of Business-to-Business software sales experience
  • 5 + years of experience territory planning and development
  • 5 + years of Enterprise or Strategic software sales experience
  • 3 + years of experience selling Windows Management Products
  • 2+ years aligning with partners and alliances
  • Proven results driven in a quota-oriented sales environment and an understanding of technology and technological innovation.
  • Proven success in rolling up a forecast to sales leadership, MEDDIC knowledge is a big plus.
  • Proven negotiation skills and the ability to know who the decision makers and executives are to persuade the need and ROI.
  • Strong experience presenting to C-Suite (or one level below) with a good understanding of technology.
  • Professionalism, personal integrity, a high internal commitment to achieve success, the ability to build and maintain vast network of professional relationships.
  • Salesforce.com experience
  • Proficient with Microsoft Office Suite, Word, Teams, Outlook, Excel, and PowerPoint
  • Exceptional Business Acumen
  • Excellent listening skills and ability to persuade, using communication that conveys concepts in a creative way.
  • Positive attitude, high energy, drive, and sense of urgency
  • Strong organizational and time management skills
  • Flexible and resilient problem solver
  • Zoominfo experience is desirable.


  • Customer Focus: Act in ways that demonstrate customer focus and satisfaction by building effective relationships with customers, identifying, meeting and exceeding customer expectations, and by treating customers with dignity and respect.
  • Territory Management: Manage territory, considering each and all accounts collectively; establish accurate plans, forecasts, prioritize efforts; generate short term results while holding a long-term perspective to maximize overall territory viability.
  • Effective Communication: Deliver oral and written communications that are impactful and persuasive with intended audience.
  • Industry knowledge In-depth knowledge of given industry and relevant marketplace; can speak with authority, e.g., on industry trends, best practices, competitive practices, regulatory issues, etc.
  • Effective Selling: Utilize solutions-oriented, systematic approach to selling, leverage mastery of sales best practices.
  • Business Acumen: Understand key aspects of business, e.g., business models and competitive positioning; also understand how business operates, include role of structure, systems, and processes; can speak in business language when applying professional expertise.
  • Financial Acumen: Use financial analysis to make decisions, evaluate opportunities and choices; know how financial decisions impact business success.

Additional Details:

  • Travel: 30%

Cayosoft, Inc. is dedicated to creating an inclusive work environment for everyone. We embrace and celebrate the unique experiences, perspectives, and cultural backgrounds that each employee brings to our workplace. Cayosoft, Inc. strives to foster an environment where our employees feel respected, valued, and empowered.

To apply for this position, email your resume directly to hr@cayosoft.com.

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