Customer Experience Specialist, Squire
$65k
+ Bonus (10%) and new hire stock grant
Barbershop operations management software
Be an early applicant
Barbershop operations management software
101-200 employees
Be an early applicant
$65k
+ Bonus (10%) and new hire stock grant
101-200 employees
Company mission
Squire's mission is to give your barber shop the technology they need to succeed in today’s fast-paced environment.
Role
Who you are
- 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
What the job involves
- 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
- 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
- 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
- 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
Our take
Squire takes point-of-sale management tools and focuses them entirely on the needs of barbershops. Before launching, co-founder Dave Salvant spent time talking to 600 different barbershop owners to understand the boxes Squire had to tick to be a worthwhile product. This included taking cashless payments and providing key insight into employee productivity, hours worked, and commission calculations.
This time spent in barbershops paid off, as Squire now has more than 2,000 customers in North America and the UK. There is considerable opportunity in the United States alone, as they have a potential customer base of more than 135,000 barbershops.
In March 2020, Squire’s revenue fell to zero when the COVID-19 pandemic forced barbershops to close. Luckily, the company had raised $34 million just days before this in a Series B funding round, which enabled it to help barbershops adapt and survive during their lockdowns. Now things have returned to normal, Squire is in high demand and in 2025, is valued at $750 million.
Steph
Company Specialist at Welcome to the Jungle
Insights
-19% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Jul 2021
$60m
SERIES D
Dec 2020
$44m
SERIES C
Total funding: $146.8m
Company benefits
- Work from home opportunities
Company HQ
Nolita, New York, NY
Leadership
Songe LaRon
(Co-Founder & CEO)Majored in Philosophy at UCLA, and then studied Law at Yale. Started out as a Legal Secondee at Credit Suisse, before joining Skadden Arps as an M&A Associate. Co-founded Squire in 2015, with support from Y Combinator.
Dave A. Salvant
(Co-Founder & President)Studied Political Science at the University of Albany, and then joined Infogroup as an Account Manager in 2008. Moved to JP Morgan as 2010 to work as a Private Client Banker. Joined AXA US as a Senior Regional Sales Executive, and then enrolled at the University of Wisconsin-Madison to study for an MBA. Co-founded Squire in 2015.
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