Director, Product Marketing

Senior Product Marketing Leader

As SQUIRE continues to scale, we're investing in building out our Product Marketing function. We're looking for a senior Product Marketing leader who will define the strategy, establish the operating model, and serve as the connective tissue between Product, Sales, Marketing, and Revenue. This leader is a data-driven, strategic builder who thrives at the intersection of insight, storytelling, and execution. They will shape how our products are positioned, how value is communicated across the customer journey, and how our go-to-market teams are enabled to win. This is a key opportunity for someone energized by improving conversion, sharpening sales effectiveness, and turning customer and marketing insights into real business impact. We're immensely proud of the product we've built and the impact it has on barbers and shop owners—helping them run better businesses and pursue their ambitions as local entrepreneurs. Now is the moment to tell that story more clearly, more consistently, and at greater scale.

In this role, you will:

• Stand up the Product Marketing function from the ground up
• Own SQUIRE's product narrative and category positioning
• Lead all major product launches
• Communicate our growing AI capabilities to the Barber community
• Build sales enablement, pricing & packaging strategy, and competitive intelligence
• Serve as a strategic partner to Product, Sales, and Executive Leadership

Reports to: Chief Marketing Officer

Job duties and responsibilities:

Product & Market Strategy

Own SQUIRE's core positioning, value propositions, and messaging framework

Define category narrative and how SQUIRE wins vs. competitors

Develop a deep understanding of barbershop, beauty, and SMB service verticals

Translate customer insights into product strategy and roadmap influence

Lead our messaging and positioning around how AI can help barbers thrive

Product Launch & Go-To-Market

Lead all major product launches end-to-end: positioning, messaging, packaging, launch plans, and adoption strategy

Build repeatable launch playbooks and operating cadence

Partner with Product, Growth, and Marketing on integrated GTM execution

Sales Enablement & Revenue Impact

Support the sales enablement team in making sure the front-line teams understand the benefits and value of our product offerings

Create messaging, pitch decks, one-pagers, battlecards, and demos that materially improve win rates

Be a key partner to Revenue leadership on pipeline, conversion, and expansion strategy

Pricing & Packaging

Lead pricing and packaging strategy in partnership with Product and Finance

Own packaging architecture, value metrics, and monetization strategy

Run pricing research, testing, and business case development

Build the Function

Establish Product Marketing operating model, processes, and KPIs

Hire and develop the Product Marketing team over time

Define how Product Marketing partners with Product, Sales, Growth, and Customer Success

Requirements and qualifications:

Experience

8+ years of Product Marketing experience in B2B SaaS, with experience in vertical SaaS strongly preferred (experience in the barber, beauty, wellness, or SMB services is a major plus)

Proven experience building or scaling Product Marketing functions

Experience working closely with Sales and Revenue teams in a high-growth environment

Skills & Strengths

You are:

Exceptional at messaging and positioning you can turn complex products into simple, compelling narratives

Strong in product launches you know how to drive adoption, not just ship announcements

Collaborative

Deeply experienced in sales enablement and revenue impact

Analytical and strategic about pricing & packaging

Comfortable operating at both strategic and hands-on levels

AI native