Customer Success Manager

Remote | Canada or USA

At Hubstaff, our mission is to empower people to have their most productive workday. We do this by providing the industry-leading workforce analytics and time tracking platform for remote and distributed teams. We've been fully remote for over a decade — long before it became a trend — and we continue to believe that remote work represents the most significant shift in the modern workplace since the advent of the PC.

Our platform helps more than 140,000 global users track time, gain visibility into work, manage schedules, and automate payments with transparency and accountability at its core. We're a product-led company with a winning culture, strong momentum, and a long-term vision: to become an essential part of every remote company's tech stack. And we're just getting started.

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.