Sr. Regional Director, Key Accounts -East

Smartsheet; Boston (MA); Remote; USD 175,000 - 235,000; Full time

Job summary

Smartsheet seeks a seasoned 'Sr. Regional Director, Large Enterprise' to lead a sales team focused on exceeding quotas and driving growth in Fortune 500 accounts. The role involves strategic sales management, collaboration with cross-functional teams, and requires substantial experience in SaaS and enterprise sales.

Benefits

HSA, 100% employer-paid premiums

401k Match

Monthly stipend for productivity

Flexible Time Away Program

12 paid holidays per year

Up to 24 weeks of Parental Leave

Opportunities for professional growth

Teleworking options

Qualifications

• 10+ years of experience in the software industry.
• 5-10 years of sales management experience.
• Proven ability to execute sales methodologies (e.g. MEDDIC).

Responsibilities

• Build and lead a Sales team to exceed sales quotas.
• Develop new business opportunities in Large Enterprise accounts.
• Partner with various departments to close software solutions.

Skills

Communication

Leadership

Sales Management

Multitasking

Education

Bachelor’s (BA/BS) degree or MBA preferred

Job description

For over 20 years, Smartsheet has helped people and teams achieve–well, anything. From seamless work management to smart, scalable solutions, we’ve always worked with flow. We’re building tools that empower teams to automate the manual, uncover insights, and scale smarter. But more than that, we’re creating space– space to think big, take action, and unlock the kind of work that truly matters. Because when challenge meets purpose, and passion turns into progress, that’s magic at work, and it’s what we show up for everyday.

Smartsheet is seeking an experienced sales leader to lead a team of Account Executives as a Sr. Regional Director,Large Enterprise. The ideal candidate will have a history of building and leading teams to over perform in quota attainment, close transformational transactions, and align strategically with large customers.

This role is part of the Large Enterprise Sales organization and is based in your own remote home office.

You Will:

• Build and lead a Sales team to exceed quarterly and annual sales quotas
• Effectively predict and deliver sales results through accurate monthly, quarterly, and annual sales forecasting
• Serve as player/coach in the execution of a complex, solution-based sales process encompassing multiple groups within Large Enterprise accounts
• Play a leadership role in developing new business opportunities by coaching Account Executives to build and execute account-focused strategies
• Drive Smartsheet senior executive engagement in target accounts
• Successfully execute across all disciplines of sales management, including Account/Opportunity/Relationship planning and sales methodology execution
• Partner with Sales Engineering, Consulting, Customer Success and Marketing management to identify and close software and professional services solutions in Large Enterprise accounts
• Proactively identify and address issues that will increase growth velocity in the assigned sales region
• Other duties as assigned
• Travel as needed (30-50%)

You Have:

• 10+ years of experience in the software industry with current SaaS experience preferably on the business applications side (selling to sales, marketing, HR, finance, manufacturing, IT)
• 5- 10 years experience in sales management providing the tools, training and support to ensure team success
• Demonstrated track record in leading Enterprise sales teams to exceed quotas by winning new business and driving substantial growth in Fortune 500 accounts
• Proven ability to drive Strategic sales teams in executing “land-and-expand” sales strategies in Large Enterprise accounts
• Relevant sales/sales leadership experience in vertical markets such as financial services, healthcare, insurance and/or public sector
• Excellent communication and interpersonal skills and the ability to multitask, work cross-functionally within the organization, and thrive in a collaborative environment
• Motivate and lead; embody Smartsheet’s core values; operate with integrity and a sense of urgency
• Demonstrated ability to execute sales methodologies (e.g. MEDDIC)
• Experience working in a fast-paced, evolving, high growth software company
• Bachelor’s (BA/BS) degree or MBA preferred

Current US Perks & Benefits:

• HSA, 100% employer-paid premiums, or Buy-up medical/vision and dental coverage options 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.

US Base Salary Pay Range $175,000 — $235,000 USD

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, and India. 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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