About this role.
Smartsheet is hiring a US-based, remote-eligible Regional Vice President to lead its SMB Commercial Sales organization and report to the VP of Commercial Sales. The leader will manage and develop more than 35 individual contributors and at least four sales managers, with accountability for bookings, revenue growth, quota attainment, and operating performance. Responsibilities include talent hiring and coaching, strategic customer engagement, sales-process improvement, forecasting, business reviews, and building a high-performance culture. Candidates need substantial sales-management experience, including management of managers, as well as B2B SaaS, Salesforce, consultative selling, and complex contract-negotiation experience. The position offers a $160,000 to $220,000 annual base salary plus incentive eligibility and comprehensive benefits.
Role DNA
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Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Core skills
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the Regional Vice President, Commercial Sales - SMB role at Smartsheet. I bring proven B2B SaaS sales leadership experience building high-performing teams, developing frontline managers, and driving predictable revenue growth across complex commercial customer segments.
- Leadership: I recruit, coach, and retain sales talent while creating accountable, high-energy cultures.
- Execution: I use Salesforce, operational reviews, pipeline discipline, and consultative methodologies to improve quota attainment and forecast quality.
- Strategic selling: I am experienced in executive customer engagement, solution packaging, negotiations, and navigating complex buying processes.
I would welcome the opportunity to help Smartsheet scale its SMB commercial organization and deliver exceptional customer and business outcomes.
Sample interview questions
I would assess the revenue plan, territory and segmentation model, pipeline coverage, conversion rates, forecast accuracy, rep and manager capability, and customer retention or expansion trends. I would then prioritize a small number of measurable initiatives, such as manager coaching cadence, pipeline-quality standards, or segment-specific plays, with clear owners and weekly inspection.
I set clear expectations for hiring profiles, onboarding milestones, activity and pipeline quality, forecast discipline, and coaching standards. I give managers autonomy to run their teams while holding regular business reviews that focus on leading indicators, talent development, and specific action plans rather than only end-of-quarter outcomes.
I use Salesforce as the system of record and establish consistent definitions for stages, qualification, next steps, close dates, and forecast categories. I inspect conversion, velocity, pipeline coverage, win-loss reasons, and rep-level trends, then translate those findings into targeted coaching and process improvements.
I begin with discovery of business outcomes, stakeholders, decision criteria, risks, and implementation requirements. I apply consultative selling and structured qualification such as MEDDICC to build a mutual action plan, align internal resources, address security and legal needs early, and ensure the proposed solution has a defensible value case.
I create an environment where expectations are transparent, achievement is recognized, and coaching is frequent and practical. I would use regular one-on-ones, team recognition, career-development plans, call and deal reviews, and data-driven performance conversations to reinforce both high standards and employee growth.
For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day.
Smartsheet is seeking an experienced sales leader to oversee a team of sales managers as a Regional Vice President (RVP) of Commercial Sales. The ideal candidate will scale, operate and continuously improve our commercial sales business through high performing teams, strategies and execution.
This leadership role is based in the US and reports directly to a VP of Commercial Sales.
You Will:
- Recruit, hire, coach, and develop sales talent across 35+ individual contributors and 4+ managers
- Ensure the team exceeds sales and operational targets on a monthly and quarterly basis
- Engage with our SMB customer base to directly work on strategic sales opportunities
- Provide day-to-day leadership of sales team and ensure proper application of sales methodology and departmental standards
- Develop, execute, evaluate and refine aspects of sales strategy, process, and workflow to deliver maximum customer engagement, bookings and revenue growth
- Monitor performance of sales representatives and teams for quota attainment, adherence to policies, and development of action plans, as needed. Develop and deliver business operational reviews summarizing key performance drivers and critical insight to increase future sales opportunities and required strategies and tactics.
- Create a high-performing, energized, and supportive culture, emphasizing reward and recognition
You Have:
- Minimum of 7+ years of sales management experience, preferably in a multi-contact, high volume inbound and outbound environment
- 2+ years of experience managing and developing a team of managers
- B2B and SaaS experience is required
- Strong leadership, organizational, communication and interpersonal skills
- Experience hiring, developing, and managing sales representatives and managers
- Highly proficient with SFDC and other sales- and customer-related systems
- Excellent presentation skills, both verbal and written Trained and practiced in the art of consultative, needs-benefits selling; proficiency with “Challenger Sale” and MEDDICC methodology preferred
- Skilled in solution packaging, proposal design, and contract negotiations
- Experience in navigating enterprise level contracts including security assessments and legal review
- Experience managing complex, enterprise customer sales cycles with implementation and change management requirements
- Ability to be creative, flexible, and objective in a highly dynamic, rapidly changing environment
- Working knowledge of SaaS based collaboration products and Salesforce.com
- BS/BA degree required; advanced degree preferred
Current US Perks & Benefits:
- Employer subsidized medical/vision and dental coverage for full-time employees
- 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 Sick Time Off
- US employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plans
- US employees receive 12 paid holidays per year
- Up to 24 weeks of Parental Leave
- Personal paid Volunteer Day to support our community
- Opportunities for professional growth and development including access to Udemy online courses
- Company Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet account
- Teleworking options from any registered location in the U.S. (role specific)
Smartsheet provides a competitive base salary range for roles that may be hired in different geographic areas we are licensed to operate our business from. Actual compensation is determined by several factors including, but not limited to, level of professional, educational experience, skills, and specific candidate location. In addition, this role will be eligible for a market competitive incentive opportunity.
Get to Know Us:
At Smartsheet, your ideas are heard, your potential is supported, and your contributions have real impact. You’ll have the freedom to explore, push boundaries, and grow beyond your role. We welcome diverse perspectives and nontraditional paths—because we know that impact comes from individuals who care deeply and challenge thoughtfully. When you’re doing work that stretches you, excites you, and connects you to something bigger, that’s magic at work. Let’s build what’s next, together.
Equal Opportunity Employer:
Smartsheet is an Equal Opportunity (EEO) employer committed to fostering an inclusive environment with the best employees. It is our policy to provide equal employment opportunities to all qualified applicants in accordance with applicable laws in the US, UK, Australia, Germany, Costa Rica, Japan, Bulgaria, India, and Singapore. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.
If there are preparations we can make to help ensure you have a comfortable and positive interview experience, please let us know.
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