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Director, Sales Onboarding, Training and Coaching (Remote Eligible)

March 7, 2026

You will develop and implement company-wide New Hires Sales Onboarding programs that provide an exciting, positive and seamless employee experience for new-hires and managers. As leader, you will oversee a Training team to ensure maximum effectiveness of the Sales team. You will establish procedures and guidelines for assessing the quality of training and make high-level changes if standards are not met or skill or knowledge gaps are identified. You will apply a forward-thinking, employee-centric approach to make employee onboarding, training and coaching programs a competitive differentiator. 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 report to our Senior Director of Worldwide Field Enablement located in our Bellevue, WA office. You Will: • Directly align with Regional Business Partners and consult with Sellers and Sales managers to provide onboarding and training on job-related challenges • Lead the team responsible for Onboarding Programs for both sales new hires and managers • Lead a team of global Trainers and Coaches ensuring ongoing learning and development from onboarding to ongoing learnings are established and implemented in the field • Partner with other teams to accomplish employee onboarding and ongoing training projects • Use data to guide better decision making and develop key metrics to review effectiveness of onboarding investments and ongoing training programs • Create internal employee research surveys, focus groups, to better understand and assess pain points and gap areas • Align process and solutions with cross functional teams and ensure global consistency while maintaining local flexibility as needed • Make recommendations on program changes and conduct arenaflex/benefit analysis of potential operational improvements • Identify individual and team training needs working with sellers and sales managers - build plans to fill gaps identified • Hold both Trainer and Coaches and Onboarding managers accountable for delivering and measuring outcomes of onboarding and ongoing training programs • Use multiple modalities to lead onboarding and training & coaching programs, in all roles across the company, (in a 1:1 or 1:Many environments). These include Live Training, eLearning, Virtual Training, arenaflex+, Podcasts, Documentation, Best Practices, Case Studies, Success Stories, Role-Playing, Scenarios and Certifications. You Have: • 8+ years of Onboarding, Sales Coach, Sales Training or similar role experience • 3+ years of global people management experience • Time and program management, teamwork, execution skills • Experience presenting to leaders and teams • Experience working with senior leaders • Strategic thinker with global mindset • Experience designing and implementing new programs • Experience leading large teams • Bachelor's degree 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! Apply tot his job

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...