About the role

We are seeking a highly skilled and customer-focused Senior Support Specialist to join our Customer Operations team.

This role is critical to ensuring our customers receive quick, accurate, and thoughtful support. As a Senior Support Specialist, you will manage weekday support coverage, rotate on weekend support coverage, resolve escalations, and partner with our offshore team to ensure seamless support. You will report to the Head of Customer Operations.

Work environment

This role requires a motivated, detail-oriented professional who thrives in a fast-paced startup environment. Given the close working relationship with the founding team and Head of Customer Operations, our preference is for this candidate to live in the greater Chicago area. Commercial teams employ a hybrid work schedule (3 days in the office).

Responsibilities

• Serve as the primary point of contact for customer support, ensuring timely, high-quality responses to nuanced and time-sensitive inquiries.
• Own and resolve escalated issues, balancing empathy with efficiency to maintain strong customer relationships.
• Partner with the offshore support team to ensure handoffs, workflows, and extended coverage are seamless and effective.
• Collaborate with the Implementation and Customer Success teams to ensure knowledge sharing and smooth transitions between onboarding, support, and ongoing success.
• Identify recurring issues and collaborate with leadership to improve support processes, documentation, and self-service resources.
• Act as the voice of the customer by sharing insights with product and engineering teams to help drive continuous product improvement.
• Contribute to weekend support rotation, ensuring sustainable coverage for the team.

Requirements

• 3–5 years of experience in customer support, customer success, or a related client-facing role, ideally in SaaS.
• Exceptional communication skills — able to explain complex workflows simply and build trust with customers under pressure.
• Strong problem-solving skills, with the ability to quickly understand customer workflows and troubleshoot effectively.
• Experience balancing multiple priorities in a fast-paced environment.
• A proactive, ownership-driven mindset — you don’t just resolve issues, you look for ways to prevent them.
• Comfort working with support and project management tools (e.g., HubSpot, Intercom, Zendesk, Asana).

Bonus points

• Experience in the pet services, hospitality, or other service-based industries.
• Background in SaaS support within an early-stage startup environment.
• Familiarity with customer self-service and knowledge base management.

What we offer

• Competitive salary and performance-based bonuses.
• Health, Dental, and Vision Insurance: 85% coverage for employees, 60% coverage for dependents.
• Flexible Paid Time Off (PTO): Includes vacation, sick, personal days, and 5 company holidays.
• Opportunities for professional development and growth.
• Collaborative and inclusive work environment.