Head of Brand & Product Marketing

We are looking for a Head of Brand & Product Marketing to join our team. This is building, not maintaining. You will own how Workstream is positioned, launched, and remembered, at the moment we expand from a vertical SaaS leader into an AI-native platform for the entire frontline workforce. You'll run product marketing, brand, content, and design as one team, report directly to our revenue leadership, and see your work show up in the pipeline within weeks, not quarters.

We are looking for leaders that thrive in a fast-paced environment. Ex-founders thrive here.

• This is a 4 to 5-days-per-week in-office role. We believe being together is important for building quickly, collaborating closely, and shaping the next chapter of Workstream
• We support relocation and visa sponsorship for the right candidate

• Positioning & Narrative: Own Workstream's positioning and messaging end to end, including the biggest open strategic question we have: leading with our restaurant dominance vs. the broader frontline-workforce story. You'll test it, not debate it.
• Product Launches: Run GTM launches for a portfolio that now ships AI products (like our AI assistant for frontline teams) alongside hiring, HR, and payroll. Messaging, pricing & packaging input, launch plans, and the enablement that makes Sales dangerous in the first week.
• Brand & Content: Lead our content and design team across the website, case studies, video, webinars, and social. Raise the bar on everything customer-facing, and use AI to produce at a pace a team twice our size couldn't match a year ago.
• Working with Sales: Arm AEs and partnerships with narratives, competitive teardowns, ROI stories, and customer proof. Sit in on deals. Talk to lost prospects. Change the message when the market tells you to.
• Team Leadership: Manage and grow a small, high-output team of product marketers, content marketers, and designers, and be the strongest IC on it when it matters.

• Slope over pedigree: 5+ years in B2B marketing with real product marketing depth, but we care more about what you've shipped and how fast you're improving than the logos on your resume.
• Management experience: You have built and led hungry and dynamic marketing teams in the past.
• Founder energy: you've started something (a company, a category, a function from zero) and you default to action; former founders welcome!
• A writer and an operator: you produce sharp positioning yourself, and you build systems so the team produces it without you.
• AI-native: you already use AI agents across your daily work and you'll push the team to do the same.
• Commercially ruthless: you measure marketing in pipeline and revenue, not impressions.
• Hungry: you outwork the market and you want the scope of a VP role earlier than a big company would ever give it to you.
• Experience with SMB buyers, hourly/frontline workforces, HR tech, or payroll is a strong plus.

• Based in (or relocating to) San Francisco; in-office at least 4 days per week
• Occasional travel for customer visits, conferences, and team events

• A mission-driven and value-based company dedicated to empowering deskless workers and local businesses
• An early employee opportunity at a Series B hyper-growth startup with over $120M in funding
• Work directly with the founding team and industry veterans to accelerate your career
• Competitive salary and equity
• Comprehensive health coverage: medical, dental, and vision. We pay 95% of your premiums for employees and 85% for dependents
• In-office amenities and stocked kitchen
• 401K plan
• Flexible PTO

The base salary range for this role is $160,000 and $190,000 annually, depending on experience and qualifications. In addition to base salary, this role includes participation in Workstream's stock option program, offering meaningful equity ownership in the company.