The Lead Sales Trainer designs and delivers onboarding and ongoing education programs for Sales and Marketing teams, leading training sessions and developing learning paths to improve sales performance.
What You'll Do:
The Sales Enablement Lead 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
What You'll Bring to the Team:
- 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.
Don't meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they meet every single qualification. At Billtrust, we celebrate and support diversity and are committed to creating an inclusive environment for all employees. So, if your experience aligns but doesn't exactly match each and every qualification, apply anyway. You may be exactly what we are looking for! What You'll Get:
- Work from Anywhere: Your home, a coffee shop, a company paid WeWork.... you decide!
- A Culture that Lives its Values: Our values are not just words or window dressing, they guide our decisions - big and small - each and every day.
- Flexible Working Hours: We support your lifestyle- the results are what count.
- Open PTO: Work-life balance is important. We believe in giving our employees time to truly relax and recharge.
- Sabbatical: A paid leave to reward longevity and commitment to Billtrust.
- Paid Parental Leave: To promote parent-child bonding and increase gender equity at home and in the workplace.
- Opportunities for Growth: Professional development can take many shapes. Join one of our seven ERGs or participate in our Mentor-Mentee, and Leadership development programs- we foster an environment where all employees can grow.
- Recognition: From Billtrust Bucks and CEO Shoutouts to Culture Champion and CEO Excellence Awards, our employees are recognized for hard work and outcomes achieved.
- Benefits: Medical, dental, vision, 401(k) with company match, short-term and long-term disability, flexible spending accounts, HSA, and life, cancer, and AD&D insurance.
- Minimal Bureaucracy: An entrepreneurial environment of ownership and accountability allows you to get work done.
Finance leaders turn to Billtrust to control costs, accelerate cash flow and improve customer satisfaction. As a B2B order-to-cash software and digital payments market leader, we help the world's leading brands get paid faster while transitioning from expensive paper invoicing and check acceptance to efficient electronic billing and payments. With over 2,600 global customers and more than $1 trillion invoice dollars processed, Billtrust delivers business value through deep industry expertise and a culture relentlessly focused on delivering meaningful customer outcomes. #LI-Remote
Top Skills
Gong
Highspot
Lessonly
Linkedin Sales Navigator
Outreach
Sales Tools
Seismic
Zoominfo
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