Senior Director of Training

Company Overview

iboss is a cloud security company that enables the modern workforce to connect securely and directly to all applications from wherever they work. Built on a containerized cloud architecture, iboss delivers security capabilities such as SWG, malware defense, RBI, CASB and data loss prevention to all connections via the cloud, instantaneously and at scale. This eliminates the need for traditional network security appliances, such as VPNs, firewalls and web gateway proxies, which are ineffective at protecting a cloud-first and mobile world. Leveraging a purpose-built cloud architecture backed by 230+ issued and pending patents and more than 100 points of presence globally, iboss processes over 150 billion transactions daily, blocking 4 billion threats per day. More than 4,000 global enterprises trust the iboss Cloud Platform to support their modern workforces, including a large number of Fortune 500 companies. To learn more, visit

Job Description

iboss is seeking a Director of Training to design, build, and lead a comprehensive training function that supports employee growth, customer success, and partner enablement across the organization. This role will develop scalable training programs for Sales, Sales Engineering, Customer Success, and Support teams, ensuring employees have deep product knowledge and the skills needed to succeed in a fast-paced, high-growth cybersecurity company. The ideal candidate combines strong instructional design expertise with a solid understanding of cloud security, SASE, or enterprise SaaS environments.

Key Responsibilities

• Design, build, and lead a company-wide training strategy covering onboarding, product knowledge, sales enablement, and technical certification programs
• Develop and maintain training curricula for Sales, Sales Engineering, Customer Success, and Support teams, ensuring content stays current with product releases and roadmap changes
• Partner with Product Management and Product Marketing to translate technical product updates into clear, digestible training materials
• Build and manage a Learning Management System (LMS) to track training completion, certifications, and skill development across the organization
• Create and lead onboarding programs for new hires to accelerate ramp time and time-to-productivity
• Develop technical and sales certification programs to validate employee and partner proficiency on the iboss platform
• Design and deliver train-the-trainer programs to scale enablement across regional and global teams
• Partner with Sales and Sales Engineering leadership to identify skill gaps and build targeted training interventions
• Support partner and channel enablement programs, ensuring reseller and MSP/MSSP partners are equipped to sell and support the iboss platform
• Measure training effectiveness through assessments, feedback, and performance metrics, and continuously refine programs based on results
• Manage a team of trainers/instructional designers (if applicable) and/or work cross-functionally with subject matter experts to develop content
• Stay current on adult learning best practices, e-learning tools, and training technology to keep programs modern and engaging

Qualifications

• 7+ years of experience in training, learning and development, or enablement, ideally within a B2B SaaS, cybersecurity, or technology company
• Experience building training programs for technical audiences (Sales Engineering, Support, or similar) as well as sales-focused audiences
• Familiarity with cloud security, networking, or SASE/Zero Trust concepts strongly preferred
• Experience with LMS platforms and e-learning authoring tools (e.g., Articulate, Camtasia, or similar)
• Strong instructional design skills, with the ability to translate complex technical concepts into clear, engaging training content
• Excellent presentation, facilitation, and communication skills
• Experience managing or mentoring a team, or working cross-functionally with subject matter experts, preferred
• Bachelor's degree required; certification in instructional design a plus

Benefits

• Competitive compensation
• Unlimited Paid Time Off (PTO)
• Health, Vision, Dental, open to domestic partners
• 401K with company match

The duties and responsibilities described above are essential functions of the job.

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, status as a veteran or as an individual with a disability.