[Hiring] Senior Customer Success Representative @Penbrothers

Role Description

Our client is looking for a Customer Success Representative to join their Customer Experience team as a sole contributor supporting their growing user base. In this role, you will serve as the primary point of contact for inbound customer inquiries, billing, and account management, while working closely with developers and internal technical teams.

This is not a traditional call center or BPO-scripted support role. The ideal candidate is an independent critical thinker with an entrepreneurial mindset, strong decision-making skills, and a seeker mentality to continuously improve internal processes. You should be comfortable communicating with both technical users (engineers) and administrative contacts, identifying system gaps, and managing account health proactive measures (such as usage tracking, upgrades, and churn risk mitigation).

What you’ll do

• Customer Support & Issue Management
  • Serve as the primary point of contact for inbound customer inquiries managed via Intercom.
  • Understand, qualify, triage, and resolve customer concerns independently without requiring micromanagement.
  • Proactively search internal knowledge bases (Slack, Intercom) to solve issues independently before escalating.
  • Identify issues that require escalation to Technical Support, Engineering, Product, or the CEO, maintaining clean handoffs.
  • Maintain high standards of written communication, ensuring clear and thoughtful customer interactions.
• Billing, Usage & Account Support
  • Handle customer queries regarding billing, plans, tier changes, and usage overages or drops.
  • Review customer usage metrics to identify churn risks or potential plan upgrade/upsell opportunities.
  • Assist with subscription add-ons (e.g., HIPPA, BAA compliance add-ons) and coordinate document sign-offs via email/Slack.
  • Process and coordinate invoice and payment details using tools like Stripe and Moneybird.
• Process Optimization & Systems Improvement
  • Maintain an alert, problem-solving mindset to identify process bottlenecks and reduce manual workload.
  • Recommend system improvements while maintaining a personalized "human touch" for customers.
  • Document FAQs, update internal guides, and bridge knowledge gaps across support tools.
• Team Collaboration & Communication
  • Report directly to the Technical Support Manager with a dotted line to the CEO.
  • Collaborate closely with distributed team members across US and European time zones.
  • Participate actively in internal video/audio syncs on Zoom and daily communications via Slack and G Suite.

Qualifications

• 5+ years of experience in customer support, customer success, or account management—preferably within a SaaS, IT, or developer-focused startup/growth company (<100 employees).
• Comfort interacting with software engineers/developers and ability to quickly grasp technical SaaS products.
• Strong critical thinking skills, self-motivation, high autonomy, and an entrepreneurial approach to problem-solving.
• Exceptional written and verbal English communication skills with experience interacting via video and async channels.
• Hands-on experience with modern customer support and operations tools (e.g., Intercom, HubSpot, Zendesk, Stripe, Slack, G Suite, Zoom).
• Looking for a stable, long-term opportunity to grow with a close-knit global team.

Nice to Have

• Prior experience with application performance monitoring, observability, or developer-facing platforms.
• Background handling usage-based subscription plans and add-on sales workflows.

What You’ll Get

• Meaningful work & Growth: We take every opportunity to stretch ourselves and deliver an excellent client experience.
• Employee as our biggest asset: We are genuinely invested in our people’s career and welfare.
• Global reach & local impact: Get to work with high-growth startups and dynamic companies from the comfort of your own home.
• Powering global startups: We’ve created 1,400 Filipino jobs that empower global start-ups to focus on growth.