Lead Sales Trainer

The Lead Sales Trainer will play a key role in supporting the design and delivery of onboarding and everboarding (ongoing education) programs for our Sales, Client Sales, Business Development, Pre-Sales, and Marketing teams. This role is essential to helping new hires ramp quickly and ensuring tenured reps continue to develop their skills, adopt best practices, and stay aligned with evolving go-to-market strategies.

We’re looking for someone who brings both structure and creativity to training—someone who can lead engaging sessions, develop clear learning paths, and support broader enablement initiatives that drive sales performance over time. This role works closely with Sales Leadership, Product Marketing, Revenue Operations, and other cross-functional partners to ensure consistent messaging, process adoption, and skill development.

• Support the development and execution of onboarding and everboarding programs across Sales, Marketing, and Pre-Sales teams
• Contribute to building structured learning paths and certification programs to reinforce product knowledge, skills, and methodology
• Facilitate live and virtual training sessions, including in-person onboarding weeks in Chicago
• Help maintain and update enablement content such as playbooks, talk tracks, objection handling guides, and product training resources
• Partner with Sales Managers to reinforce key behaviors through coaching frameworks, ongoing education, and reinforcement programs
• Support the rollout of product launches, go-to-market initiatives, and sales methodology adoption (e.g., MEDDPICC)
• Assist in the administration and optimization of enablement tools including Seismic, Lessonly, Gong, Outreach, Highspot, LinkedIn Sales Navigator, and ZoomInfo
• Gather feedback and track program impact, using ramp time, performance trends, and rep engagement to guide improvements
• Collaborate cross-functionally to align training efforts with broader revenue goals and initiatives

• Bachelor’s degree required
• 6+ years of experience in sales enablement, training, or a related field, ideally in a high-growth B2B SaaS environment
• Previous experience in sales or technical sales strongly preferred
• Experience working with or enabling teams that sell into the Office of the CFO (e.g., finance, AR/AP, treasury, or accounting) is a plus
• Familiarity with MEDDPICC or similar sales methodologies; experience enabling or reinforcing them is a bonus
• Proven ability to support onboarding and ongoing learning programs
• Experience supporting Sales Manager enablement, and ideally adjacent teams such as Pre-Sales or Customer Success
• Confident communicator and facilitator with strong project management skills
• Comfortable using Sales Tools such as Seismic, Lessonly, Gong, Outreach, Highspot, LinkedIn Sales Navigator, and ZoomInfo
• Instructional design experience or coursework is a plus, but not required

The expected base salary range for this position is $105,000 - $145,000 annually.

Compensation may vary depending on several factors, including a candidate’s qualifications, skills, experience, competencies, and geographic location. Some roles may qualify for extra incentives like equity, commissions, or other variable performance-related bonuses. Further details will be provided by our Talent Acquisition team during the interview process.