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

We’re looking for a strategic leader to chart Squire’s next frontiers of growth. The Senior Director of New Markets will be responsible for identifying, validating, and scaling opportunities in new markets and verticals. You’ll guide market evaluation, build the business case for expansion, and serve as the connective tissue across Product, Marketing, and Sales to ensure successful execution.

This is a highly visible role that blends strategy, market intelligence, and cross-functional leadership. The ideal candidate thrives in ambiguity, knows how to bring structure to uncharted markets, and can balance analytical rigor with strategic storytelling.

Reports To

Chief Product & Technology Office
Chief Marketing Officer (dotted line)

JOB DUTIES & RESPONSIBILITIES

Vertical Expansion Strategy & Market Evaluation
Lead market sizing, opportunity analysis, and competitive research to identify high-potential geographies, industries, and customer segments.
Build business cases for expansion that balance customer needs, product capabilities, and long-term commercial strategy.
Partner with Product, Sales, and Executive leadership to prioritize and recommend where to play next.
Cross-Functional Coordination of New Market & Vertical Launches
Partner with Marketing to co-define entry strategies, success metrics, and investment requirements.
Coordinate across Product, Sales, and Marketing to align priorities, resource appropriately, and sequence execution.
Serve as the connective tissue between functions — driving accountability, clearing blockers, and keeping launches on track.
Product & Sales Enablement for Vertical Fit
Collaborate with Product Management to ensure vertical-specific needs are incorporated into roadmap planning and solution design.
Partner with Sales and Enablement to shape vertical account strategies and equip teams with insights, tools, and messaging tailored to target markets.
Ensure Customer Success and Support teams capture vertical-specific learnings, case studies, and proof points to fuel future growth.
Customer & Market Insight Integration
Champion vertical-specific customer insights across the organization, feeding learnings into Product, Marketing, and Sales strategies.
Identify adoption trends, unmet needs, and early proof points to inform scale-up strategies and de-risk market entry.

WHAT SUCCESS LOOKS LIKE

Clear prioritization of new verticals and geographies based on data-driven opportunity sizing and business cases.
Smooth cross-functional coordination that ensures Product, Sales, Marketing, and Customer Success are aligned on vertical strategies and execution.
Tangible progress in launching and scaling new verticals, measured by early adoption, customer wins, and revenue contribution.
Vertical-specific customer insights consistently integrated into product roadmap, sales motions, and marketing campaigns.
Well-defined success metrics and investment decisions made in partnership with Marketing, Sales, and Executive leadership.
Demonstrated impact on long-term growth trajectory through successful vertical expansion beyond the core market.

REQUIREMENTS & QUALIFICATIONS

10+ years of product marketing, strategy, or related experience, with 5+ years in a leadership role.
Proven track record of launching products into new markets or verticals at a B2B SaaS or tech company.
Strong grasp of market analysis, segmentation, and competitive positioning.
Skilled at partnering with Product and Sales leadership to drive measurable growth.
Exceptional storytelling and communication skills — able to influence executives and inspire cross-functional teams.
Data-driven mindset with proficiency in market research and analytics tools.

WHAT WE OFFER

Base Salary between $200,000 - $250,000
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