Lead strategy and execution for end-to-end client booking across web and mobile, owning discovery, booking flows, checkout, confirmations, cancellations, and rebooking. Drive conversion, rebooking, and retention via data, experimentation, and AI; partner with Engineering, Design, Marketing, and Data to deliver scalable, high-quality B2C experiences and measurable business outcomes.
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.
POSITION TITLE
Staff Product Manager
SUMMARY
We’re looking for a Staff Product Manager to own and evolve the end-to-end client booking experience across web and mobile. The booking experience is the front door to SQUIRE. It drives first impressions, repeat usage, and directly impacts business performance across our platform. As we expand into new verticals and AI-powered workflows, this role ensures booking remains intuitive, trustworthy, and high-converting. This is a senior individual contributor role with broad ownership. You will lead strategy and execution across discovery, booking flows, and rebooking - balancing client experience, business outcomes, and platform scalability.
REPORTS TO
Director of Product Management
JOB DUTIES AND RESPONSIBILITIES
- Product Strategy & Roadmap
- Define and drive the multi-quarter vision for client booking
- Own discovery, booking flows, checkout, confirmations, cancellations, and rebooking
- Ensure experiences scale across geographies, shop types, and future verticals
- Make clear tradeoffs across UX quality, performance, and business goals
- Client Experience & Conversion
- Deeply understand client behavior and friction across the booking funnel
- Improve conversion, rebooking, and retention through data and experimentation
- Elevate trust, clarity, and reliability across critical booking moments
- Execution & Cross-Functional Leadership
- Partner closely with Engineering and Design to ship performant, high-quality consumer experiences
- Translate strategy into clear requirements and measurable outcomes
- Collaborate with Lifecycle, Marketing, and Data to ensure launches drive impact
- Growth & Learning
- Own key metrics including conversion, rebooking rate, funnel drop-off, and client retention
- Establish clear learning goals and remain accountable to outcomes
- Thoughtfully leverage AI and automation to improve discovery and confidence in booking
REQUIREMENTS
- 7+ years of product management experience
- Direct experience building booking, reservation, or scheduling products at scale
- Proven track record improving conversion or retention in B2C environments
- Strong product judgment across UX, systems, and business impact
- Experience in B2C or B2B2C platforms
- Ability to influence cross-functional teams without direct authority
NICE TO HAVE
- PLG or lifecycle optimization experience
- Exposure to AI-driven consumer workflows
- Experience supporting multiple verticals or international markets
WHAT WE OFFER
- Base Salary ($170,000 - $190,000)
- 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.
Similar Jobs
Aerospace • Information Technology • Software • Cybersecurity • Design • Defense • Manufacturing
Develop and maintain embedded software for avionics systems, ensuring compliance with standards, and integrating software with hardware components.
Top Skills:
BashCContinuous DeploymentContinuous IntegrationDistributed Version Control SystemsHardware DebuggersLinuxPythonReal-Time Operating Systems
Aerospace • Information Technology • Software • Cybersecurity • Design • Defense • Manufacturing
Lead design, implementation, maintenance, and troubleshooting of LAN/WAN networks for the Virtual Warfare Center. Document requirements, estimate costs, research components, integrate new technologies, and ensure reliable, secure connectivity across multi-site modeling and simulation environments.
Top Skills:
Cisco Routers,Cisco Switches,Cisco Ios,Tcp/Ip,Lan,Wan
.png)
Cloud • Insurance • Payments • Software • Business Intelligence • App development • Big Data Analytics
Provide cloud operations and Windows-domain technical support: liaise with development/support teams, document procedures, perform SQL backups/restores and scripts, troubleshoot servers, networks, and configurations, and assist with testing and deployments during the assigned shift.
Top Skills:
Sql,Sql Server Management Studio,Microsoft Windows Server,Windows Desktop,Powershell,Vbscript,Command Line Batch Files,Tcp/Ip
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
