Principal Customer Success Manager – Enterprise (West/Central)

Remote from: USA
Salary, yearly, USD: 135,000 - 172,500
Department: Customer Success
Employment type: Full Time,
Job posted: 7 Jun 2026
Apply before: 7 Jul 2026
Experience level: Senior
Views / Applies: 22 / 2

About company

About Smartsheet

Smartsheet is a platform for work management and automation solutions.

Computer Software
2005

Actively Hiring

AI Summary

This Principal Customer Success Manager role at Smartsheet focuses on building strategic relationships with large global enterprise customers, driving adoption, and mitigating churn. The position requires 10+ years of experience, strong business acumen, and the ability to operate with near full autonomy. Responsibilities include managing a diverse book of business, leading QBRs/EBRs, mentoring peers, and collaborating cross-functionally. This is a career-defining opportunity to influence the future of Customer Success in a fast-paced, collaborative environment.

Role DNA

Job Complexity

Easy Hard

Pace & Pressure

Relaxed Fast-paced

Autonomy Level

Guided Full Ownership

Communication Load

Independent Highly Collaborative

AI Insight The role demands extensive experience (10+ years), deep subject matter expertise, and the ability to manage high-stakes strategic relationships with C-level contacts, making it highly challenging.

Salary Analysis

AI Insight The offered salary range of $135,000 - $172,500 aligns well with market rates for a Principal Customer Success Manager in the US. The median of $153,750 is competitive, especially considering the remote flexibility and benefits.

Key Skills

Customer Success Enterprise SaaS Strategic Relationships Account Management Thought Leadership Cross-functional Collaboration Project Management Data Analysis Board of Advisors

Cover Letter Sample

I am excited to apply for the Principal Customer Success Manager position at Smartsheet. With over 10 years of experience in SaaS Customer Success, I have a proven track record of building strategic relationships with enterprise customers and driving adoption of collaborative platforms.

My expertise includes leading cross-functional initiatives, mentoring peers, and delivering value through data-driven insights and executive business reviews. I am adept at mitigating churn and identifying expansion opportunities, which aligns perfectly with the responsibilities outlined.

I am particularly drawn to Smartsheet's commitment to innovation and empowering teams. I am confident that my ability to operate autonomously and collaborate effectively will contribute to your team's success.

Thank you for considering my application. I look forward to the possibility of discussing how I can help Smartsheet achieve its goals.

Possible Interview Questions

Describe a time you managed a high-risk renewal with a large enterprise customer. What steps did you take to mitigate churn?

I once managed a customer who was considering not renewing due to dissatisfaction with product usage. I set up a series of executive touchpoints, conducted a deep dive into their business goals, and created a tailored adoption plan. By demonstrating clear ROI through quarterly business reviews, we not only renewed but also expanded the account by 20%.

How do you prioritize your book of business when managing diverse accounts?

I use a tiered approach based on revenue at risk, growth potential, and strategic importance. I segment accounts into high-touch, moderate-touch, and scaled engagement models. I leverage data from usage analytics and health scores to proactively address risks and allocate time where it has the most impact.

Can you provide an example of how you've mentored junior team members?

At my previous role, I implemented a mentorship program for new CSMs. I held weekly one-on-ones, conducted joint customer calls, and provided feedback on their engagement strategies. Over six months, three of my mentees improved their retention rates by 15% and were promoted.

Explain how you have used data to drive customer outcomes in a previous role.

I regularly analyzed product usage data to identify trends and gaps. For one customer, I noticed low adoption of a critical feature. I created a training series and shared benchmark data showing how similar companies benefited. This led to a 40% increase in feature usage and a high CSAT score.

How do you stay current with industry best practices and incorporate them into your customer engagements?

I actively participate in customer success communities, attend webinars, and read thought leadership blogs. I then curate relevant insights and share them with customers during EBRs. For example, I recently applied a new framework for value realization that helped a customer justify a larger investment.

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 a Principal Customer Success Manager who will focus on building high-value, strategic relationships with large, global customers. The role requires extensive experience in SaaS Customer Success, strong business acumen and exceptional communication skills.

The Principal Customer Success Manager is expected to provide thought leadership and mentorship, as well as lead and/or contribute to special programs and projects (minimum of 10% per working week). For the right candidate, this is a career-defining opportunity to join the market leader in Collaborative Work Management (CWM) and help influence the future of Customer Success as a vocation.

This role reports to a Sr. Manager of Sr. Customer Success and has flexibility to work remotely from the West or Central region.

You Will:

Manage a diverse book of business at scale, with a focus and engagement, enablement and adoption.
Understand your customer’s business model, go to market strategy and organizational structure.
Create and execute internal territory engagement plans and/or external joint customer enablement plans that focus on tailored, customer-specific strategy, proactive risk mitigation, value realization and expansion.
Use data to gain insights, provide guidance, increase customer adoption and identify opportunities for expansion.
Lead or influence renewals, partnering with internal teams to form a cohesive approach to mitigate churn and support expansion.
Positively impact revenue via early risk identification and mitigation strategies while also coaching customers to develop or enhance solutions that translate into expansion opportunities.
Support and/or lead high-impact Quarterly Business Reviews (QBRs) and/or Executive Business Reviews (EBRs) to showcase value, review progress against goals, and align on future strategy.
Serve as a Core Platform and Premium Application Subject Matter Expert (SME), mastering best practice and enablement strategies to drive customer product adoption.
Serve as a thought leader, advising customers on industry best practices and how to solve complex business problems with the platform.
Effectively partner with cross-functional teams (e.g. Sales, Training, Product, Professional Services, etc.) by developing strong relationships and coordinating efforts to present a unified, cohesive and elite customer experience.
Provide customer insight to internal teams like Product Management, Marketing, and Sales to inform innovation and improvement.
Meet or exceed all performance targets.
Perform other duties as assigned.

You Have:

10+ years of Customer Success or Account Management experience, preferably with SaaS model.
A Bachelor’s degree in a relevant field or equivalent experience is preferred.
The ability to operate with nearly full autonomy and very limited oversight.
A proven track record of leading cross-departmental initiatives and delivering outcomes.
A history of building successful relationships with VP and C-Level contacts.
Experience maintaining outcome-based relationships with a diverse customer account base.
Deep Customer Success and Smartsheet subject matter expertise.
A proven track record of mentoring peers.
Up-to-date Smartsheet Certifications (Core Product, System Administrator, Project Management, Control Center Lead, Control Center Blueprint Builder) or the ability to obtain within 6 months.
Willingness to travel periodically based on customer and business need.

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.

US Base Salary Pay Range

$135,000—$172,500 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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