Lead technical vision and execution for SQUIRE, managing global engineering teams to deliver scalable, secure consumer-facing products, modernize legacy systems, and integrate generative AI to improve velocity and quality.
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 Vice President of Engineering will play a pivotal role in shaping the future of our technology and product development. This individual will be responsible for shaping the technical vision, strategy, and execution of our engineering department while driving innovation and ensuring scalability, performance, and customer satisfaction. The VP of Engineering will collaborate closely with executive leadership and cross-functional teams to deliver high-quality software solutions while fostering a culture of continuous improvement and operational excellence.
REPORTS TO
Chief Product & Technology Officer
JOB DUTIES AND RESPONSIBILITIES
- Strategic Leadership
- Develop, articulate, and drive the execution of a comprehensive technical roadmap that supports SQUIRE’s strategic goals, incorporating feedback from cross-functional stakeholders to ensure engineering efforts remain laser-focused on delivering customer value and driving market differentiation.
- Provide regular status updates and strategic recommendations to the executive leadership team, anticipating challenges and identifying opportunities for innovation or competitive advantage.
- Technology Vision & Execution
- Lead and manage a diverse engineering team, including offshore and nearshore teams of developers working with React, React Native, Node.js and other modern technologies.
- Lead the engineering team in delivering scalable, reliable, and secure software solutions that meet current and future business needs.
- Direct initiatives for the modernization of legacy systems and accelerate the delivery of new product capabilities, prioritizing the strategic integration of AI/ML tools to drive efficiency.
- Champion the application of Generative AI across the entire development lifecycle—from code generation and testing to operational excellence—to maximize engineering velocity and quality.
- Establish and enforce best practices in software development, architecture, and operational excellence.
- Implement generative AI to accelerate the development of code.
- Ensure that the technical and payments architecture supports scalability, performance, and reliability as SQUIRE grows.
- Customer & Partner Alignment
- Work closely with the Director, Product Management and Director, Product Design to ensure seamless integration of technical capabilities with product vision and user experience.
- Cultivate an environment of experimentation and learning around emerging AI technologies to maintain a competitive advantage in our technical practices.
- Collaborate with Product Leaders to define clear acceptance criteria, delivery timelines, and post-launch success metrics.
- Collaborate with leaders across Sales, Marketing, and Customer Success to understand evolving customer requirements and market shifts; offer technical insights that help refine go-to-market strategies, product positioning, and customer onboarding.
- Culture & Growth
- Establish a high-performance, AI-driven engineering culture rooted in curiosity, continuous improvement, and open communication, driving the adoption of new AI-powered tools and methodologies.
- Mentor and guide engineering managers and technical leaders, enhancing team productivity, engagement, and performance.
- Develop formal career pathways, rotation programs, and succession plans to nurture future leaders.
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
- Proven success as a senior engineering leader, with 15+ years of progressive experience, including 8 years or more leading large engineering teams.
- Experience working with Claude and Cursor for writing code, test plans, bug fixes and code reviews
- Demonstrated ability to lead large-scale initiatives with a focus on speed and agility without compromising quality.
- A track record of building and scaling consumer-facing products that deliver exceptional user experiences, especially on mobile devices.
- Deep expertise in modern engineering practices, including cloud infrastructure, microservices, and scalable system design.
- Strong technical foundation, with deep knowledge of modern full-stack development practices, architectures, and tools, including JavaScript frameworks (e.g. Node.js, React.js) and mobile development frameworks (React Native).
- Exceptional leadership and communication skills, with demonstrated ability to lead through periods of change and a track record of building and nurturing high-performing, inclusive teams.
- E-Commerce, FinTech or Payments experience preferred
- B2C or B2B2C experience preferred
WHAT WE OFFER
- Base Salary ($250,000 - $300,000) + Bonus (25%)
- New hire stock grant
- 100% employer paid medical, dental, and vision insurance for you and your dependents
- 401K plan with company contribution
- Generous PTO and Parental Leave policies
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.
Top Skills
React,React Native,Node.Js,Javascript,Claude,Cursor,Generative Ai,Ai/Ml,Cloud Infrastructure,Microservices,Payments
SQUIRE New York, New York, USA Office
Our HQ is located in the Nolita neighborhood of lower Manhattan and is surrounded by bars, restaurants, shopping and some of NYC's most iconic landmarks.
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