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.
As part of the IT PMO, we lead high-impact, cross-functional projects that align with Smartsheet’s strategic priorities. Smartsheet is looking for an experienced Sr IT Systems Project Manager to drive quality, consistency, and business value as a key member of our IT PMO team. The Sr IT Systems PM works closely with the IT Enterprise Systems team who manages the development, use, and support of Smartsheet’s enterprise business applications. The Sr IT Systems PM also partners across Finance, Legal, People & Culture, and Procurement to lead complex projects from discovery through post-launch. This role operates within a high-performing team that prioritizes proactive leadership, collaboration, and accountability. Candidates must demonstrate strong judgement, influence across stakeholders, and the ability to lead with structure in evolving and sometimes ambiguous environments.
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 Director, IT Program & Project Management in our Bellevue. You may work remotely from anywhere in Costa Rica where Smartsheet is a registered employer.
You Will:
- Lead concurrent cross-functional projects of varying complexity through all phases of the project management lifecycle, including discovery, planning, execution, and closure
- Facilitate the project discovery process, ensuring projects are aligned with strategic goals and deliver measurable benefits
- Leverage Smartsheet’s project framework, which combines waterfall-based discovery with agile execution.
- Define and manage project scope, schedule, resources, milestones and deliverables
- Create structure in ambiguous, evolving, or ad hoc settings
- Align stakeholders across business and technical domains with strong leadership
- Establish stakeholder alignment and actively manage stakeholder engagement
- Create and maintain project documentation including RAID logs, dashboards, delivery plans, and lessons learned
- Proactively escalate risks, drive decision-making, and model ownership of outcomes
- Collaborate with resource managers to manage project team allocations and forecast project needs
- Communicate trade-offs between customer expectations, team capacity, and technical feasibility to business partners and align on prioritization
- Build trust and credibility with technical and business partners through transparency, follow-through and clarity
- Provide technical and analytical guidance to project teams
- Act as a cultural contributor to the IT PMO by sharing best practices, mentoring peers, and supporting the maturity of how projects are delivered
- Welcome the opportunity to try something new
You Have:
- 8+ years of focused project management experience, including large cross-functional systems or integration projects
- 6+ years experience leading IT or enterprise systems-related initiatives
- Flexibility to align to multiple timezones
- Strong understanding of project management standards and best practices (PMI, PMBOK, SDLC)
- Experience managing projects in both waterfall and agile (“wagile”) environments
- Excellent written, verbal, and visual communication skills with experience presenting to senior leadership
- Ability to drive accountability without authority; strong facilitation and conflict resolution skills
- Familiarity with risk management, SOX compliance, and IT general controls
- Commitment to continuously improving team performance, tools, and practices
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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