Field Enablement Sales Trainer (Remote Eligible)

July 16, 2026

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The Field Enablement Sales Trainer will coordinate learning opportunities to help maximize our sales team's performance. You will mentor our Large Enterprise sales managers, designing and delivering individual and team training courses, and preparing educational material. You have experience working with sales techniques and the ability to motivate managers and employees of varying seniority. You will help our managers develop skills to achieve their quotas.

You will report to our Manager, Trainer and Coach located in our Boston office. This role is remote.

In 2005, Smartsheet was founded on the idea that teams and millions of people worldwide deserve a better way to deliver their very best work. Today, we deliver a leading cloud-based platform for work execution, empowering organizations to plan, capture, track, automate, and report on work at scale, resulting in more efficient processes and better business outcomes.

You Will:

Align with Regional Business Partners and consult Sales Managers to provide coaching and advice on coping with job-related challenges. Build plans to fill training gaps.
Train new hires by preparing them to meet and exceed sales proficiency, sales productivity, and training requirements beyond the initial onboarding window through a focus on sales process, sales messaging, sales tools, and other necessary sales success skills.
Use multiple modalities to train/guide/coach sales managers, in all roles across the company, (in a 1:1 or 1:Many environments). These include Live Training, eLearning, Virtual Training, Google+, Podcasts, Documentation, Best Practices, Case Studies, Success Stories, Role-Playing, Scenarios and Certifications.
Equip managers with strategies for pipeline management, account planning, sales process coaching, 1:1 and in manager-led forecast meetings, and provide necessary reinforcement in these areas.
Observe sales teams to ensure that training content for new hires and existing sellers aligns with current sales process and techniques
Develop educational material, including presentations, sales scripts and case studies working with the Field Enablement Knowledge Managers
Gather feedback on all training programs from trainees, managers and instructors to report back to the business its successes and areas of improvement
Maintain updated records of educational curriculum and material
Evaluate performance after each training engagement and report back to management observations - using insights, develop coaching opportunities
Research and implement technology and best practices to improve our trainee's experience

You Have:

Work experience as a Sales Coach, Sales Trainer or similar role
Large Enterprise sales experience in a SaaS company
5+ years delivering sales results in a quota carrying role preferred
Familiarity with role-playing activities and e-learning platforms
Experience creating presentations (e.g. videos or slides)
Experience motivating teams
Experience managing a full training cycle, including in-person activities and web-based learning
Managed teams/projects in multiple locations

Perks & Benefits:

HSA, 100% employer-paid premiums, or Buy-up medical/vision and dental coverage options for full-time employees
Equity - Restricted Stock Units (RSUs) with all offers
Lucrative Employee Stock Purchase Program (15% discount)
401k Match to help you save for your future (50% of your contribution up to the first 6% of your eligible pay)
Monthly stipend to support your work and productivity
Flexible Time Away Program, plus Incidental Sick Leave
Up to 24 weeks of Parental Leave
Personal paid Volunteer Day to support our community
Opportunities for professional growth and development including access to LinkedIn Learning online courses
Company Funded Perks, including a counseling membership, primary care membership, local retail discounts, and your own personal Smartsheet account

Equal Opportunity Employer:

Smartsheet is an Equal Opportunity Employer committed to fostering an inclusive environment with the best employees. We provide employment opportunities without regard to any legally protected status in accordance with applicable laws in the US, UK, and Australia. If there are preparations we can make to help ensure you have a comfortable and positive interview experience, please let us know.

At Smartsheet, we strive to build an inclusive environment that encourages, supports, and celebrates the diverse voices of our team members who also represent the diverse needs of our customers. We're looking for people who are driven, authentic, supportive, effective, and honest. You're encouraged to apply even if your experience doesn't precisely match our job description—if your career path has been nontraditional, that will set you apart. At Smartsheet, we welcome diverse perspectives and people who aren't afraid to be innovative—join us!

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