Associate Director/Director of Support
Customer Service
Chicago, IL, USA
USD 120k-150k / year + Equity
About the role
We're seeking an experienced Customer Operations leader to help scale and strengthen our support organization. This is a leadership role focused on team management, process ownership, and cross-functional influence — you'll set the strategy for support quality, build and coach a team of specialists, and own the systems that make great support repeatable at scale. You will report to the Head of Customer Operations.
Work environment
This role is best suited for someone energized by building teams and improving systems, not just solving individual tickets. 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, with a hybrid schedule (3 days in office).
What will I be doing?
- Own support quality end-to-end — setting SLA targets, monitoring queue health, and building the escalation framework the team operates within.
- Serve as an escalation point for the highest-stakes customer issues.
- Hire, coach, and develop Team Leads and Support Specialists, including performance management, career pathing, and skills development programs.
- Own the partnership with the offshore support team — coverage models, quality consistency, and handoff processes across time zones.
- Analyze support volume and customer friction patterns, and bring structured recommendations and business cases to leadership.
- Partner cross-functionally with Implementation, Customer Success, and Product leadership to close knowledge gaps, influence roadmap, and surface customer insights at a strategic level.
- Design and own team coverage models, including weekend and after-hours support rotations.
- Build and maintain the documentation, playbook, and training infrastructure that lets the team scale without you.
- Own key support metrics (CSAT, SLA adherence, resolution time, escalation rate) and report on them to leadership.
You'll be successful in this role if you have…
- 7–10 years of experience in customer support or customer success, including at least 3+ years managing people managers or leads.
- Exceptional communication skills — able to de-escalate difficult situations, coach leaders, and translate customer problems into structured product and process recommendations.
- Strong operational and strategic instincts — you spot systemic issues before they surface and bring a plan, not just a diagnosis.
- Proven experience managing distributed or offshore teams, including building coverage and quality models from scratch.
- Comfort holding others accountable with directness and empathy in equal measure, at both the individual contributor and manager level.
- Deep familiarity with support tooling and workflows (Intercom, HubSpot, Zendesk, or similar), including using them to drive process design, not just execute within them.
Bonus points
- Experience in pet services, hospitality, or another service-based industry.
- Background in SaaS support at an early-stage startup.
- Experience building or contributing to knowledge bases and support documentation programs.
What we offer
- Competitive salary and performance-based bonuses.
- Health, Dental, and Vision Insurance: 85% coverage for employees, 60% for dependents.
- Flexible PTO including vacation, sick, personal days, and 6 company holidays.
- Opportunities for professional development and growth.
- Collaborative and inclusive work environment.
This range reflects the base salary compensation Goose reasonably expects to pay for this role. Where an individual candidate lands within the range is based on job-related factors such as skills, experience, and qualifications. This role is also eligible equity along with full benefits, including health, dental, and vision insurance, PTO, etc