Customer Success Manager

Customer Success Manager

Location: Remote (Canada or USA) Company: Hubstaff Contract: Permanent Seniority: Senior Industry: Tech

About Hubstaff

Hubstaff empowers over 95,000 businesses worldwide to optimize productivity and workforce operations. Our platform provides solutions for time tracking, team management, project insights, and payroll automation. As a remote-first company for over a decade, we are dedicated to helping distributed teams work smarter.

About the Role

We are seeking a Senior Customer Success Manager to oversee the entire customer journey for approximately 150 mid-market clients across North and South America. Your primary focus will be on ensuring rapid activation, long-term adoption, retention, and expansion of Hubstaff. This role is crucial for ensuring customers achieve measurable outcomes and lasting value from our platform.

You will act as a trusted advisor, managing onboarding, adoption, retention, expansion, renewals, billing, and escalations. This strategic, hands-on position requires close collaboration with Sales, Product, Marketing, and Support teams to deliver exceptional customer experiences and drive sustainable growth. The ideal candidate thrives on building strong relationships, solving complex problems with empathy, and leveraging data to drive impact. You will report to the Director of Customer Success (UK-based) and work within a collaborative, remote-first environment.

Key Responsibilities

• Own client activation and onboarding: Become a Hubstaff subject matter expert, guiding new customers from deal closure to successful adoption. Lead onboarding sessions, follow-ups, and check-ins to ensure rapid time-to-value.
• Manage ongoing customer relationships: Conduct value-driven business reviews, track customer goal progress, and proactively drive retention and growth within your portfolio.
• Drive Gross and Net Revenue Retention (GRR & NRR): Manage renewals, identify expansion opportunities, and proactively address at-risk accounts to ensure customer retention and growth.
• Build strong, trust-based relationships: Engage with key decision-makers and daily users, acting as their advocate and advisor.
• Deliver key account insights: Report on customer health, renewal risks, and expansion opportunities to Hubstaff leadership.
• Develop scalable processes: Contribute to improving Customer Success practices by creating and refining playbooks for onboarding and lifecycle management.
• Utilize data to drive action: Monitor product adoption metrics, customer health scores, feature usage, and engagement data to identify risks or opportunities and implement targeted success plans.
• Educate and enable customers: Conduct webinars, product walkthroughs, and share resources to enhance customer confidence, adoption, and satisfaction.
• Collaborate cross-functionally: Work with Product, Support, and Engineering teams to resolve issues, advocate for customer feedback, and influence product roadmap decisions.
• Experiment and iterate: Test engagement strategies, refine playbooks, and share learnings to improve customer outcomes and internal efficiency.

Requirements

• 4+ years of experience in Customer Success within a Product-Led Growth (PLG) SaaS company.
• Proven experience managing 100+ mid-market accounts, balancing proactive engagement with operational efficiency.
• Strong ownership mentality and accountability for customer results.
• Exceptional relationship-building and communication skills, capable of engaging effectively with both executive and operational stakeholders.
• Comfortable working with data, dashboards, and customer metrics to inform decisions and drive performance.
• Experience influencing renewal, retention, and expansion outcomes, preferably 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 environment.

What We Offer

• Fully remote role with flexible working hours.
• Meaningful work that helps thousands of teams operate more effectively.
• A supportive culture built on trust, autonomy, and work-life balance.
• For employees: Private health insurance, paid time off, and local benefits.
• Annual stipends for home office, wellness, or professional development.
• Clear career progression pathways, mentorship, and skill development programs.
• Global company retreats to connect with our remote team in person.

Compensation & Contract: Hubstaff hires either employees (via PEO/EOR) or independent contractors, depending on the country. Compensation is benchmarked to local market rates. For a full-time employee in the US, the expected base salary is $100,000/year, plus bonus. This role includes a quarterly bonus plan tied to retention and expansion targets.