Sales Enablement Instructor

Kaseya is the leading provider of AI-powered IT management and cybersecurity software, serving Managed Service Providers (MSPs) and internal IT organizations worldwide. Our comprehensive platform helps organizations efficiently manage, secure, and automate their IT environments, driving operational efficiency and long-term business success.

Backed by Insight Partners, a leading global software investor, Kaseya has experienced sustained double-digit growth and continues to expand its global footprint. Today, Kaseya supports customers in more than 20 countries and manages over 15 million endpoints worldwide.

Founded in 2000, Kaseya was built by builders - and we're still building. We look for people who create rather than wait, who see a hard problem and lean in, and who treat challenges as raw material. At Kaseya, everyone plays a role in shaping the future of IT: whether you're in engineering, product, sales, marketing, customer support, or operations, your work helps protect, defend, and optimize IT environments across the globe.

We're building teams that grow, perform, and make an impact. If you're driven by the itch to make things better - a product, a process, a career - you'll fit right in.

At Kaseya, we don't just raise the bar. We build it.

The Sales Enablement Instructor is a core member of Kaseya's GTM Onboarding team, responsible for delivering New Hire Training that gets reps ready to sell. Reporting to the Senior Manager, GTM Onboarding, the Trainer facilitates live BaseCamp sessions, coaches reps through the first six months of ramp, and helps build the content that powers the program. The ideal candidate combines strong facilitation presence with real sales credibility, sound coaching instincts, and a commitment to helping every seller succeed from day one.

Key Responsibilities
- Lead and facilitate live New Hire Training (BaseCamp, Day 0 to 15) for each cohort, covering core curriculum, product knowledge, sales process, systems, and role-play practice.
- Deliver everboarding sessions for reps in the ramp tail (Day 16 to 180), including reinforcement sessions, targeted coaching, and plug-and-play sessions for tenured or struggling reps.
- Provide 1:1 coaching and role-play feedback, helping reps connect classroom learning to real customer conversations.
- Review assessments and certifications, track rep progress, and flag at-risk reps to their managers and the Senior Manager.
- Answer new-hire questions, prepare upcoming sessions, and cover delivery for teammates as needed.
- Partner with the Senior Manager and the Instructional Design team to build and refine content, including competency-based tracks and e-learning for the tiered New Hire Training model.
- Contribute to assigned onboarding improvement projects, such as piloting new session formats or assessments.
- Coordinate with SMEs and guest speakers to prepare sessions, and join prep calls and post-session debriefs.
- Share field feedback on what is and is not working so the program improves cohort over cohort.
- Partner with managers to reinforce training on the floor and support reps who need extra help ramping.
- Support delivery for other regions and time zones when assigned.
- Help run afternoon activity blocks, including role-play practice, e-learning check-ins, and certification prep.
- Maintain accurate records of coaching notes, assessment results, and session delivery in the team's tracking tools.
- Model the sales behaviors and methodology the program teaches, reinforcing a consistent standard across every cohort.

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 a fast-paced environment 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, such as 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.