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Kaseya is a leading provider of AI-powered IT management and cybersecurity software serving Managed Service Providers (MSPs) and internal IT organizations globally. The company, backed by Insight Partners, manages over 15 million endpoints worldwide and supports customers in more than 20 countries.
The Sales Enablement Instructor is a core member of Kaseya's GTM Onboarding team, reporting to the Senior Manager of GTM Onboarding. This role is responsible for delivering high-impact New Hire Training (BaseCamp) that prepares sales representatives to sell effectively from day one.
Key responsibilities include:
- Facilitating live New Hire Training sessions (Day 0-15) covering core curriculum, product knowledge, sales process, systems, and role-play practice for each cohort
- Delivering everboarding sessions for reps in the ramp tail (Day 16-180), including reinforcement, targeted coaching, and specialized sessions
- Providing 1:1 coaching and role-play feedback to connect classroom learning to real customer conversations
- Reviewing assessments and certifications, tracking rep progress, and flagging at-risk reps to managers
- Partnering with the Instructional Design team to build and refine content, including competency-based tracks and e-learning modules
- Contributing to onboarding improvement projects, such as piloting new session formats or assessments
- Coordinating with subject matter experts and guest speakers to prepare sessions
- Sharing field feedback to drive continuous program improvement
- Supporting delivery across regions and time zones as assigned
- Maintaining accurate records of coaching notes, assessment results, and session delivery
- Modeling sales behaviors and methodology to reinforce consistent standards
The ideal candidate combines strong facilitation presence with real sales credibility, sound coaching instincts, and a genuine commitment to helping every seller succeed.
Qualifications:
- 3-5 years of experience in sales training, sales enablement, or B2B sales, ideally in SaaS or technology
- Proven ability to facilitate engaging live and virtual training for groups of sellers
- Strong coaching skills with comfort giving direct, constructive feedback in role-plays and 1:1 settings
- Solid understanding of B2B sales cycles, discovery, objection handling, and deal progression
- Ability to simplify complex products and concepts into clear, practical guidance
- Highly organized, adaptable, and comfortable in fast-paced environments with frequent iteration
- Experience with LMS platforms and sales tools such as Salesforce and Showpad
- Excellent written and verbal communication skills
- Bachelor's degree or equivalent experience
- Willingness to flex hours occasionally to support sessions in other regions
Preferred Experience:
- Prior quota-carrying sales experience (Account Manager or Account Executive)
- Familiarity with sales methodologies such as MEDDPICC, Command of the Message, or Challenger
- Experience with AI roleplay or conversation intelligence tools
- Exposure to instructional design or adult learning principles
- Experience supporting global teams across multiple time zones
- Train-the-Trainer or similar facilitation certification
