US REMOTE

WHO WE ARE

SQUIRE is the leading business management system designed for the needs of barbers, shop owners, and their communities. We believe the pursuit of artistry and autonomy should not be restricted by the complexities of running a business. With SQUIRE, we provide custom-branded tools, resources, and guidance to help barbers of all stages and experience levels attract and retain more customers, efficiently manage their shop operations, and increase their revenue.

Founded in 2015, SQUIRE is trusted by more than 30,000 barbers across 5,000+ shops in more than a thousand cities worldwide. From streamlined booking and opening new shops to real-time earning dashboards and building lasting customer relationships, SQUIRE supports shop owners in seamlessly bridging the gap between their personal craft and business goals. SQUIRE enables barbers everywhere to unlock their full potential both as artists and as entrepreneurs.

For more information, please visit getsquire.com or download the SQUIRE app from the App or Play Store.

SUMMARY

The Customer Experience Specialist (CES) is a retention-focused, pooled customer support role. The primary objective of the role is to reduce churn and downgrades by engaging customers at critical moments, such as cancellation requests, downgrade inquiries, escalations, and identified product adoption gaps.

CES partners closely with Tier 1 Support, Customer Success, and Support Leadership to deliver high-impact, high-judgement customer interactions that retain revenue, drive adoption, and reinforce the value of the SQUIRE platform. This role combines strong product knowledge, objection handling, and consultative guidance, leveraging automation and usage-based signals.

REPORTS TO

Manager, Technical Customer Support

JOB DUTIES AND RESPONSIBILITIES

Retention & Churn Mitigation
Handle inbound cancellation and downgrade requests, identifying root causes and executing save strategies aligned with policy and commercial guardrails.
Engage escalated customers who are at risk of churn due to product confusion, perceived value gaps, or operational friction.
Upsell Support & Post-Onboarding Adoption
Support inbound upgrade requests, ensuring customers understand plan value and feature differences
Conduct follow-up outreach after upgrades to drive early adoption and reduce post-purchase churn.
Product Expertise & Consultative Guidance
As a SQUIRE platform expert, provide practical, outcome-oriented guidance: not just how features work, but how customers know features are working for them.
Act as a trusted product translator during retention, upgrade, and adoption conversations.
Customer Training & Enablement
Deliver video-based training sessions ad hoc as needed to achieve product adoption (new shop employees, customers upgrading plans or adding features, etc)
Reinforce self-service resources and best practices to reduce future friction and support dependency.
Cross-Functional Collaboration & Program Evolution
Partner with Support, Customer Success, Product, and Ops to refine save motions, upgrade experiences, and adoption workflows.
Contribute feedback on where automation can replace or augment manual outreach as volume and maturity increase.
The duties and responsibilities outlined above are not a comprehensive list and additional tasks may be assigned from time to time based on business needs.

REQUIREMENTS AND QUALIFICATIONS

2+ years in Support, Customer Success, or Customer Experience (preferably in SaaS or SMB environments).
Experience managing a high-volume book of business in a pool or scaled environment with a strong retention and objection-handling focus.
Strong product aptitude: able to explain workflows, features, and outcomes clearly without relying on T2 for standard questions.
Confident in delivering customer training via Google Meets or similar.
Problem-solving and analytical skills to identify trends and recommend solutions.
Ability to meet and exceed performance targets while managing multiple priorities.
Excellent communication and relationship-building skills with a customer-first mindset.
Familiarity with CRM systems and digital customer experience tools.
**If hired, candidates must first complete a minimum 3-month period as a Tier I Support agent before transitioning into the Customer Experience Specialist (CES) role. During this time, they will be required to demonstrate proficiency in Tier I Support, including troubleshooting, issue resolution, escalation management, and customer interactions at the highest level. Only after successfully meeting performance expectations at this level will they be eligible to assume full CES responsibilities.

WHAT WE OFFER

Base salary ($65,000) + Bonus (10%)
New hire stock grant
100% employer-paid medical/dental/vision insurance for you and your dependents
401K plan with company contribution
Generous PTO and Parental Leave policies

SQUIRE jobs

Customer Experience Specialist