The Customer Experience Specialist focuses on retaining customers by managing cancellations, upselling, and providing product expertise and training. They collaborate with support teams to enhance customer experience and reduce churn.
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 Retention Specialist (Customer Experience Specialist) is a retention-focused, pooled customer success 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.
Retention Specialists work 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.
JOB DUTIES AND RESPONSIBILITIES
- 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.
- 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.
- 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.
- 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.
- 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.
Retention & Churn Mitigation
Upsell Support & Post-Onboarding Adoption
Product Expertise & Consultative Guidance
Customer Training & Enablement
Cross-Functional Collaboration & Program Evolution
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 Customer Success, or Retention (preferably in SaaS or SMB environments).
- Fluency in verbal and written communication in Spanish.
- 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.
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
WHY JOIN SQUIRE?
- Impact: Play a key role in shaping the customer experience at a fast-growing, industry-leading tech company
- Growth: Opportunity to develop in a hybrid role that blends Customer Success and Support
- Culture: Join a team that values innovation, collaboration, and empowering small business owners
Interview Accommodations
SQUIRE is committed to working with and providing reasonable assistance to individuals with physical and mental disabilities. If you are an individual with a disability requiring an accommodation to apply for an open position, please email your request to [email protected] and someone on our team will respond to your request.
EEO Provision
SQUIRE provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.
This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.
Pay Transparency Nondiscrimination Provision
SQUIRE will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the contractor’s legal duty to furnish information.
E-Verify Participation
SQUIRE participates in E-Verify. Learn more about E-verify here.
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