Sr. Sales Enablement Program Manager, Global Onboarding & Ramp

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.

The Sr. Sales Enablement Program Manager will be a key contributor to our Global Sales Readiness team, focusing on the execution and evolution of our global ramp program. You will join a team of enablement professionals dedicated to ensuring every new hire reaches full productivity with speed and confidence.

In this role, you will leverage your prior sales experience to bridge the gap between initial training and real-world execution. You won't just facilitate; you will coach, diagnose productivity hurdles, and partner with your peers in Enablement to ensure our global onboarding engine is consistent, scalable, and highly effective. Serving as a vital link between new reps, their managers, and the broader sales org, you will help identify and close the gaps that stand in the way of new hire success.

This role is eligible for remote work within Costa Rica. You must reside in Costa Rica. You will report to our Senior Manager of Global Field Enablement based in Boston, MA.

You Will:

• Collaborate on Global Onboarding: Partner with the Sales Readiness team to co-deliver and refine the end-to-end ramp program, ensuring a consistent, high-impact experience for every new hire across all regions.

• Facilitate with Impact: Lead high-energy workshops, role-plays, and certification sessions, translating complex product features and sales methodologies into actionable skills.

• Provide Hands-on Coaching: Support new reps through their first 90+ days by conducting 1:1 and group coaching sessions to address real-time sales challenges, objection handling, and pipeline development.

• Identify Productivity Gaps: Maintain a pulse on new hire performance metrics; collaborate with your team to diagnose where reps are stalling and suggest program improvements to accelerate time-to-productivity.

• Ensure Global Consistency: Align regularly with peer Enablement Managers to ensure training delivery is standardized across different cohorts and geographies.

• Engage Stakeholders: Partner with sales leadership and frontline managers to ensure the ramp program stays aligned with the current needs of the field and evolving business goals.

• Iterate on Solutions: Assist in developing a blended-learning approach (classroom, self-paced, and on-demand) to scale enablement efforts as the company grows.

You Have:

• 2-3 years in a quota-carrying sales role: You have "carried a bag," understand the pressure of a target, and can speak the language of a salesperson with high credibility.

• 4+ years of Enablement or Training experience: Proven track record of facilitating global programs and coaching sales teams in a SaaS environment.

• Master Facilitator: You have a "command the room" presence and the ability to keep learners engaged in both virtual and in-person environments. B2 English Proficiency Level or higher.

• Analytical Mindset: You are comfortable looking at Salesforce or Tableau dashboards to identify trends and measure the success of the ramp program.

• Sales Methodology Fluency: Deep understanding of modern sales frameworks (e.g., MEDDICC, Value Selling, or Challenger) and how to apply them to the buyer’s journey.

• Strategic Empathy: The ability to understand the struggles of a new rep and the patience to coach them through technical and behavioral growth.

• Project Management Skills: Ability to manage a global program with multiple stakeholders while delivering high-quality assets on tight timelines.

• Willingness to Travel: Ability to travel up to 10% to support global kickoff events or onsite intensive training.

Perks & Benefits:

• Fully paid Health & Life insurance for full-time employees and family members

• Monthly stipend to support your work and productivity

• 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 LinkedIn Learning 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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