Commercial AE III- Lead at Cayosoft Inc – Westerville, Ohio

About Cayosoft

Cayosoft helps organizations secure, govern, monitor, and recover Microsoft identity infrastructure across Active Directory, Entra ID, and Microsoft 365. Our platform enables organizations to reduce risk, improve operational resilience, and accelerate identity governance and automation at scale.

Position Overview

As a Commercial Account Executive III, you will serve as a senior member of the Commercial Sales team, responsible for driving consistent revenue growth while handling more complex deals, larger accounts, and strategic opportunities within the SMB and mid-market segments.

In addition to owning and closing SMB and mid-market opportunities, you will partner closely with Enterprise Account Executives within your territory to identify, develop, and progress enterprise-level opportunities, contributing to broader pipeline growth across the region.

Responsibilities

• Own and drive the full sales cycle from prospecting through close across SMB and mid-market accounts
• Consistently exceed revenue targets through effective pipeline generation, deal management, and closing execution
• Partner closely with Enterprise Account Executives to identify and develop enterprise-level opportunities, contributing to pipeline growth and account expansion within the territory
• Act as a strategic extension of the Enterprise sales motion by uncovering larger, more complex opportunities within existing and new accounts
• Build and maintain strong relationships with key stakeholders across business and technical functions
• Lead negotiations, pricing discussions, and contract execution with minimal support
• Partner closely with Sales Engineering, Marketing, and Channel teams to drive both sourced and influenced pipeline
• Mentor and support junior account executives as the team grows, sharing best practices and contributing to onboarding and development
• Maintain highly accurate pipeline management and forecasting in CRM (e.g., Salesforce, HubSpot)
• Drive partner collaboration and joint account planning to expand reach and accelerate deal cycles
• Represent Cayosoft at industry events, webinars, and customer engagements
• Stay current on Microsoft technologies (Active Directory, Azure AD, Microsoft 365, etc.) and industry trends
• Travel up to 15% within assigned territory

Ideal Candidate Qualifications

• Bachelor’s degree or equivalent experience preferred
• 7–10+ years of B2B software sales experience, including SMB and mid-market segments
• Proven track record of consistently meeting or exceeding quota
• Demonstrated experience selling into Microsoft-centric environments, including Active Directory, Azure AD (Entra ID), and Microsoft 365, with the ability to align solutions to customer architectures, security considerations, and evolving industry trends
• Strong experience managing full sales cycles independently
• Experience handling more complex deals and multi-stakeholder sales processes
• Demonstrated ability to mentor or lead within a sales team
• Strong negotiation, communication, and relationship-building skills
• Experience working with channel partners and co-sell motions preferred
• Proficiency with CRM tools and sales technologies

We’re a mission-driven team passionate about helping organizations secure their most critical identity infrastructure. Our culture is built on:

We believe in building a diverse, respectful, and supportive environment where people can do their best work and grow their careers.

Equal Opportunity Employer

Cayosoft is proud to be an Equal Opportunity Employer. We are committed to creating a diverse and inclusive environment for all employees and applicants. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, genetic information, veteran status, or any other characteristic protected by applicable law.