Customer Success Manager

Company: Hubstaff
Location: Remote | Canada or USA

About Hubstaff:
Hubstaff is a remote-first company that helps organizations optimize productivity and workforce operations through its platform for time tracking, team management, project insights, and payroll automation. We empower distributed teams to work smarter.

The Role:
We are seeking a Customer Success Manager to own the entire customer journey for approximately 150 mid-market customers across North and South America. Your focus will be on ensuring rapid activation, long-term adoption, retention, expansion, renewal, billing, and escalation management. You will act as a trusted advisor, collaborating cross-functionally to deliver world-class experiences and drive sustainable growth.

What You'll Do:

• Own client activation and onboarding: Guide new customers from deal close through successful adoption, leading live onboarding sessions and check-ins to ensure quick time-to-value.
• Manage ongoing customer relationships: Conduct value-driven business reviews, track progress toward goals, and proactively drive retention and growth.
• Drive Gross and Net Revenue Retention (GRR & NRR): Manage renewals, expansion opportunities, and at-risk accounts.
• Build and maintain strong, trust-based relationships with key decision-makers and users.
• Deliver key account insights: Report on customer health, renewal risk, and expansion opportunities to leadership.
• Develop scalable processes and playbooks to streamline lifecycle management.
• Use data to drive action: Monitor adoption metrics, health alerts, and engagement data to identify risk or opportunity and implement success plans.
• Educate and enable customers through webinars, product walkthroughs, and resources.
• Collaborate cross-functionally with Product, Support, and Engineering teams.
• Continuously experiment and iterate on engagement approaches and playbooks.

What You'll Bring:

• 4+ years of experience in Customer Success within a PLG SaaS company.
• Proven experience managing 100+ mid-market accounts.
• Strong ownership mentality and accountability for customer results.
• Exceptional relationship and communication skills, able to engage executive and operational stakeholders.
• Comfort working with data, dashboards, and customer metrics.
• Experience influencing renewal, retention, and expansion outcomes.
• Familiarity with tools such as Vitally, HubSpot, Slack, and Stripe is a plus.
• Self-motivated and comfortable working autonomously in a distributed team.

Compensation & Contract:

• This role can be structured as either an employee (PEO/EOR) or an independent contractor, depending on the country.
• US Employee Base Salary Reference: $100,000/year.
• 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 helping teams operate effectively.
• 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 and skill development programs.
• Global company retreats.