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 looking for a proven enterprise SaaS sales leader to develop and lead the Costa Rica SMB Sales team. You will develop and refine the Commercial sales strategy to accelerate growth across North America. Leading efforts to create account strategies, refine sales plays, expand executive relationships, incorporate the customer journey, and sell high-value solutions are essential success factors for this role. These elements need to be synthesized into a cohesive strategy that supports accelerating growth in software and services bookings.
You have a proven track record of consistently exceeding sales goals with solid leadership acumen, great attitude, accountability, high energy, integrity, discipline, and experience in making data-driven decisions. As a leader on this team, you will play a crucial role in making Smartsheet the Collaborative Work Management market leader.
You will report to the VP of Sales and be based in Costa Rica
You Will:
- Recruit, hire, and develop a high-performing SaaS sales team, including Directors, Managers, and Account Executives.
- Execute on the company plan, which includes significantly increasing sales output while developing relationships with senior leaders and C-level executives.
- Develop trust-based relationships with leaders across the business, including Product & Engineering, Marketing, Finance, Operations, Sales Engineering, and Customer Excellence.
- Develop pricing/packaging and product competencies to play a leadership role in structuring, pursuing, and winning large, complex deals.
- Successfully develop and execute across all disciplines of sales management, including Account/Territory/Opportunity planning, sales methodology execution, forecasting, and professional development.
- Actively use our core applications to manage business, including Smartsheet, Salesforce.com, Tableau, LinkedIn, DiscoverOrg, Clari, Google Workspace, and others.
You Have:
- Demonstrated track record of exceeding sales objectives, leading enterprise SaaS sales teams, and driving substantial growth with experience in making data-driven decisions
- Proven ability to drive sales teams in executing land and expand sales strategies to predictably expand accounts, culminating in being chosen as a standard
- Product-led Sales and Value-led Sales experience
- Multi-persona, Multi-use case platform selling experience
- Demonstrated competence in effectively engaging and developing value-based relationships with C-level executives
- Minimum of 7 years experience, including second line management, leading strategic software, preferably in Commercial Sales SaaS teams. Third line management preferred.
- 10+ years of experience in the software industry with recent enterprise SaaS experience, preferably on the business applications side (selling to sales, marketing, HR, finance, manufacturing, and the PMO)
- Excellent interpersonal skills and the ability to multitask, work cross-functionally within the organization, and thrive in a collaborative environment
- Demonstrated sales methodologies (e.g., MEDDIC)
- Experience working in a fast-paced, high-growth software company where change is a constant
- Smartsheet, Salesforce.com, Google Apps, and Tableau skills
- Bachelor’s (BA/BS) degree required, MBA preferred
Perks & Benefits:
- Fully paid Health & Life insurance for full-time employees and family members
- Monthly stipend to support your work and productivity
- Asociacion Solidarista with employee and employer contributions, as well as potential alliances with entities such as universities, gyms, etc.
- 12 days paid Vacation + Flexible Time Away Program
- 20 weeks fully paid Maternity Leave
- 12 weeks fully paid Paternity/Adoption 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 and your own personal Smartsheet account
- Teleworking options from any registered location in Costa Rica (role-specific)
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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