Customer Success Manager

Remote from: USA, Canada
Salary, yearly, USD: 100,000 - 100,000
Department: Customer Success
Employment type: Full Time,
Job posted: 7 Jun 2026
Apply before: 7 Jul 2026
Experience level: Midweight
Views / Applies: 9 / 3

Built to help teams track time, boost productivity, and automate payroll with powerful insights.

Computer Software
2012

AI Summary

Hubstaff is seeking a Customer Success Manager to own the end-to-end customer journey for a portfolio of ~150 mid-market accounts in North and South America. The role focuses on onboarding, adoption, retention, expansion, and renewals, requiring strong relationship-building and data-driven action. You will collaborate cross-functionally with Sales, Product, Marketing, and Support to drive measurable outcomes. Ideal candidates have 4+ years of Customer Success experience in a PLG SaaS company and a proven ability to manage 100+ accounts. This is a remote-first, strategic position reporting to the Director of Customer Success.

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 requires 4+ years of experience with complex mid-market accounts, cross-functional collaboration, and strategic ownership of retention and expansion metrics, making it challenging but not entry-level.

Salary Analysis

AI Insight The offered salary of $100,000 is competitive and falls near the median for a Customer Success Manager in the US market, which typically ranges from $75,000 to $130,000. This position offers a solid base with potential for growth through expansion and retention achievements.

Key Skills

Customer Success SaaS PLG Retention Onboarding Data Analysis Account Management Cross-functional Collaboration Renewals HubSpot

Cover Letter Sample

Dear Hiring Team,

I am writing to express my strong interest in the Customer Success Manager position at Hubstaff. With over 5 years of experience in customer success within PLG SaaS environments, I have successfully managed portfolios of 150+ mid-market accounts, driving high activation rates, retention, and expansion. My background includes leveraging data to identify risk and opportunity, conducting strategic business reviews, and collaborating cross-functionally to enhance customer outcomes.

I am particularly drawn to Hubstaff's mission to optimize productivity for distributed teams, and I am eager to apply my skills in onboarding, adoption, and retention to help your customers achieve measurable value. My experience with tools such as Vitally, HubSpot, and Stripe, combined with my ability to build trust with executive stakeholders, makes me a strong fit for this role.

I look forward to the opportunity to contribute to Hubstaff's growth and customer success. Thank you for considering my application.

Sincerely, [Your Name]

Possible Interview Questions

Can you describe a time when you turned an at-risk customer into a loyal advocate? What steps did you take?

I once had a customer who was unhappy with the product's reporting features. I listened to their concerns, worked with the product team to provide a temporary workaround, and scheduled a business review to align on their goals. Over the next quarter, I ensured they saw value from other features, and they ended up renewing and expanding their contract.

How do you prioritize your time when managing a large portfolio of accounts?

I use a health scoring system based on product usage, engagement, and feedback. I segment accounts into tiers (high/medium/low risk) and allocate time accordingly. For example, I spend 60% of my time on high-value and at-risk accounts, 30% on proactive engagement for growth, and 10% on operational tasks.

Describe your experience with driving expansion revenue. Can you give a specific example?

In my previous role, I identified a customer that was underutilizing our premium features. I conducted a training session and demonstrated how they could increase efficiency, leading them to upgrade their plan by 30% within three months.

How do you handle a situation where a customer's expectations are not aligned with the product roadmap?

I first empathize and validate their need. Then I transparently explain the current roadmap and timeline. I work with their team to find alternative solutions or workarounds in the interim. I also escalate their feedback to product management and keep them updated on progress.

What metrics do you consider most important for measuring customer success, and how do you track them?

Key metrics include Net Revenue Retention (NRR), Gross Revenue Retention (GRR), Time-to-Value (TTV), product adoption rate, and Customer Health Score. I use tools like Vitally and HubSpot to monitor these and set up alerts for any negative changes.

Customer Success Manager

Remote | Canada or USA

About Hubstaff

Hubstaff helps organizations around the world optimize productivity and workforce operations. Trusted by 95,000+ businesses, our platform powers time tracking, team management, project insights, and payroll automation.

We’ve been a remote-first company for over a decade — and we’re on a mission to help distributed teams work smarter, not harder.

The Role

We’re hiring a Customer Success Manager to own the customer journey end to end — ensuring rapid activation, long-term adoption, retention, and expansion of Hubstaff across a portfolio of ~150 mid-market customers across North and South America.

Your focus will span Onboarding, Adoption, Retention, Expansion, Renewal, Billing, and Escalations, ensuring every customer achieves measurable outcomes and lasting value from Hubstaff.

This is a strategic and hands-on role: you’ll act as the trusted advisor to your customers, collaborating cross-functionally with Sales, Product, Marketing, and Support to deliver world-class experiences and sustainable growth.

This role is ideal for someone who thrives on building strong relationships, solving complex problems with empathy, and driving impact through data and insight. You’ll report to the Director of Customer Success (UK-based), working with peers across the Americas and Europe in a highly collaborative, remote-first environment.

What You’ll Do

Own client activation and onboarding — become a Hubstaff subject matter expert and guide new customers from deal close through successful adoption. Lead live onboarding sessions, follow-ups, and check-ins to ensure customers realize time-to-value quickly.
Manage ongoing customer relationships — conduct value-driven business reviews, track progress toward customer goals, and proactively drive retention and growth across your book of business.
Be directly responsible for Gross and Net Revenue Retention (GRR & NRR) across your book of business. Manage renewals and the associated process, expansion opportunities, and at-risk accounts, ensuring Hubstaff’s customers are retained and setup to grow with us.
Build and maintain strong, trust-based relationships with key decision-makers and daily users, becoming their advocate and advisor.
Deliver key account insights: report on customer health, renewal risk, and expansion opportunities to the wider Hubstaff leadership team.
Develop scalable processes and playbooks that streamline onboarding and lifecycle management, contributing to a continuously improving Customer Success practice.
Use data to drive action: monitor product adoption metrics, health and associated alerts, feature usage, and engagement data to identify risk or opportunity, and implement targeted success plans.
Educate and enable customers through webinars, product walkthroughs, and resources that increase confidence, adoption, and satisfaction.
Collaborate cross-functionally with Product, Support, and Engineering teams to resolve issues quickly, advocate for customer feedback, and influence roadmap decisions.
Continuously experiment and iterate: test engagement approaches, refine playbooks, and share learnings to enhance customer outcomes and internal efficiency.

What You’ll Bring

4+ years of experience in Customer Success within a PLG SaaS company.
Proven experience managing 100+ mid-market accounts, balancing proactive engagement with operational efficiency.
Strong ownership mentality — you’re accountable for your customers’ results and take initiative to solve problems before they escalate.
Exceptional relationship and communication skills, able to engage both executive and operational stakeholders with credibility and empathy.
Comfortable working with data, dashboards, and customer metrics to inform decisions and drive performance.
Experience influencing renewal, retention, and expansion outcomes, ideally in a PLG or subscription-based SaaS model.
Familiarity with tools such as Vitally, HubSpot, Slack, and Stripe is a plus.
Self-motivated, comfortable working autonomously in a distributed team, and energized by a high-growth, evolving environment.

Compensation & Contract

We hire either employees (PEO/EOR) or independent contractors, depending on the country.

Compensation is aligned to local market benchmarks to ensure fairness across regions.
As a reference, a full-time employee in the US can expect a base salary of $100,000/year, plus bonus. This role includes a quarterly bonus plan based on retention and expansion targets.

Why You’ll Love Working at Hubstaff

Fully remote role with flexible working hours
Meaningful work — you’ll help thousands of teams operate more effectively and sustainably every day
Supportive culture built on trust, autonomy, and balance
Private health insurance, paid time off, and local benefits (for employees)
Annual stipends for home office, wellness, or professional development
Clear career progression pathways, mentorship opportunities, and skill development programs
Global company retreats in unique destinations, connecting our remote team in person

Inclusion at Hubstaff

We welcome and celebrate diverse backgrounds, perspectives, and experiences. Everyone deserves to feel valued and supported — and we’re committed to creating an inclusive environment for all.

Apply now >