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Director, GTM Technology & Operation

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 barbers in 4,000+ shops in more than a thousand cities around the globe. 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 Director, GTM Technology & Operations will be responsible for the overall strategy and management of the Marketing, Sales, and Post-Sales’ org technology stack. These systems are imperative for SQUIRE to attract, acquire, and retain customers from the first point of contact with a prospect to an engaged customer and all of the touch points + interactions in-between.


This hands-on leader and their team will work to ensure SQUIRE’s technology solutions are serving the needs of our GTM functions in executing against the company’s growth strategy which deploys both sales and product-led growth methodologies. With a focus on data flow, quality, and integrity across the technology stack, the ultimate goal is to create an ecosystem of tools and systems that allow our revenue-generating teams to operate smoothly and efficiently. 


REPORTS TO

Chief Financial Officer


JOB DUTIES AND RESPONSIBILITIES
  • Own the technological strategy and management best practices that support growth and scale for SQUIRE’s go-to-market functions (Marketing, Sales, Post-Sales)
  • Design and manage the Tech Ops Team prioritization frameworks that outline and solution for points of friction identified by the Executive Leadership team
  • Conduct audits and analysis of tool utilization to improve adoption and efficiency while addressing and solving any tech debt
  • Implement a unified approach to data management and warehouse strategy across GTM funnel to enable growth optimization
  • Establish and maintain data governance best practices to ensure data accuracy, consistency, and compliance across the GTM technology stack
  • Advance SQUIRE’s adoption of AI and other new emerging technologies to elevate how we engage, acquire, and retain barber shop owners and independent barbers
  • Collaborate with the Strategy & Insights to enhance reporting and analytics
  • Drive adoption and training of GTM tools that ensure alignment with business needs

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
  • 10+ years of technical revenue operations experience
  • 5+ years of people management experience
  • Experience solutioning for tech debt, data integrity, and system consolidation
  • Experience driving company-wide system overhauls + implementations and process improvements 
  • Experience with both sales-assisted and product-led growth strategies
  • Ownership of Marketing, Sales and Post-Sales tech stack, specifically with Salesforce, Marketo, Customer.IO, Salesloft GA4, Hubspot, Looker, Snowflake, Tableau and Chili Piper
  • Familiarity with scaling vertical SaaS companies


WHAT WE OFFER
  • Base Salary ($180,000 - $205,000) + Bonus (15%)
  • 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 recruiting@getsquire.com 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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Average salary estimate

$192500 / YEARLY (est.)
min
max
$180000K
$205000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Director, GTM Technology & Operation, SQUIRE

Are you ready to make a significant impact as the Director of GTM Technology & Operations at SQUIRE? We’re a company dedicated to empowering barbers and shop owners by providing them with seamless business management tools tailored to their unique needs. As the driving force behind our technology strategy, you’ll not only oversee the vital tech stack but also ensure that our Marketing, Sales, and Post-Sales operations are optimized to attract and retain customers effectively. With more than 10 years of experience in technical revenue operations and a strong background in people management, you’ll be leading a dynamic team focused on streamlining processes and enhancing how technology supports our growth. Your hands-on approach will help improve data integrity and quality across all systems, creating a cohesive ecosystem for our revenue-generating teams. You’ll collaborate closely with executive leadership to identify friction points and implement innovative solutions, including embracing AI and emerging technologies, all while promoting a culture of excellence. If you’re excited about driving change and want to be at the forefront of our mission to unlock barbers’ potential as both artists and entrepreneurs, we want to hear from you! Join us at SQUIRE, where our passion for community and innovation sets us apart.

Frequently Asked Questions (FAQs) for Director, GTM Technology & Operation Role at SQUIRE
What are the primary responsibilities of the Director, GTM Technology & Operations at SQUIRE?

The Director, GTM Technology & Operations at SQUIRE is responsible for the overall strategy and management of the technology stack supporting Marketing, Sales, and Post-Sales operations. This includes optimizing technology solutions, ensuring data integrity, improving tool adoption, and collaborating with various teams to drive growth and efficiency.

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What qualifications are needed for the Director, GTM Technology & Operations position at SQUIRE?

Candidates for the Director, GTM Technology & Operations role at SQUIRE should have over 10 years of technical revenue operations experience, at least 5 years in management, and a proven track record of improving system efficiency and data integrity. Familiarity with tools such as Salesforce, Marketo, and data warehousing solutions is essential.

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How does the Director, GTM Technology & Operations contribute to SQUIRE’s growth?

The Director, GTM Technology & Operations plays a critical role at SQUIRE by developing strategies that leverage technology to improve both sales and customer retention. This includes creating a cohesive tech ecosystem that streamlines operations and enhances the customer journey, ultimately supporting the company’s growth objectives.

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What is the work culture like at SQUIRE for the Director, GTM Technology & Operations?

At SQUIRE, the work culture for the Director, GTM Technology & Operations is collaborative and innovative. The company values creativity, embraces new technologies, and encourages a proactive approach to solving challenges, all while supporting the unique needs of barbers and shop owners.

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What benefits does SQUIRE offer for the Director, GTM Technology & Operations role?

SQUIRE offers a competitive base salary of $180,000 to $205,000, bonuses, stock options, comprehensive medical, dental, and vision insurance coverage, a robust 401K plan, and generous PTO policies, ensuring a supportive environment for employees.

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Common Interview Questions for Director, GTM Technology & Operation
What experience do you have in managing a technology stack for revenue operations?

In your response, highlight specific past roles where you managed technology solutions for Marketing, Sales, or Post-Sales teams, emphasizing any systems you implemented that contributed to significant growth or efficiency improvements.

Join Rise to see the full answer
Can you discuss your approach to ensuring data integrity in a GTM technology stack?

Discuss a systematic approach to data governance you've implemented in past roles, including how you aligned with teams to monitor data quality and compliance, and the tools or practices you found most effective.

Join Rise to see the full answer
How do you prioritize tool adoption across different teams?

Provide examples of how you’ve rolled out new tools while ensuring team buy-in, focused communication strategies, and the training methods you've employed to drive adoption and overcome resistance.

Join Rise to see the full answer
Describe a time when you solved a significant tech debt issue.

Share a concrete example of a significant tech debt challenge you faced, your thought process for analyzing the issue, the steps you took for resolution, and how it positively impacted the organization.

Join Rise to see the full answer
What strategies have you found effective for supporting sales-assisted and product-led growth?

Discuss how you’ve tailored technology strategies to support both sales-assisted and product-led initiatives, emphasizing collaboration with sales teams and metrics you tracked to measure success.

Join Rise to see the full answer
How would you leverage AI in GTM operations?

Talk about your vision for incorporating AI technologies into GTM operations, discussing specific areas where you believe AI can enhance customer acquisition, engagement, and retention.

Join Rise to see the full answer
How do you keep yourself updated with emerging technologies in the SaaS landscape?

Emphasize your commitment to continuous learning through industry conferences, webinars, and professional networks. Mention how you’ve applied your learnings to drive innovation in your previous roles.

Join Rise to see the full answer
What is your experience working with stakeholders across the company?

Describe your collaborative approach to interfacing with various teams, ensuring alignment between tech operations and overarching business goals, and how you handle differing priorities.

Join Rise to see the full answer
Can you give an example of how you improved system efficiency?

Share a case where you identified inefficiencies within a system, the steps you took to optimize processes, and the measurable outcomes that followed, such as time savings or increased productivity.

Join Rise to see the full answer
Why do you want to work at SQUIRE as the Director, GTM Technology & Operations?

Articulate your passion for the barbering industry and how SQUIRE’s mission aligns with your values and ambition to leverage technology to empower individuals and businesses. Reflect on what inspires you about SQUIRE’s commitment to community.

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Flex-Friendly
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Dental Insurance
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SQUIRE is the world’s leading and fastest-growing software technology company offering a booking and payment platform that connects people with great barbers nationwide.

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BENEFITS & PERKS
Dental Insurance
Disability Insurance
Flexible Spending Account (FSA)
Health Savings Account (HSA)
Vision Insurance
Performance Bonus
Paid Holidays
FUNDING
DEPARTMENTS
SENIORITY LEVEL REQUIREMENT
TEAM SIZE
EMPLOYMENT TYPE
Full-time, on-site
DATE POSTED
April 16, 2025

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