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Head of Brand & Product Marketing (AI-Native Frontline Workforce Platform)

Workstream • United State
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AI Summary

Lead Workstream’s brand positioning, product marketing, and content strategy as the company transitions from a vertical SaaS leader to an AI-native platform for the global frontline workforce. Own GTM launches, team leadership, and commercial outcomes while driving growth in a fast-paced, mission-driven startup environment. Requires 5+ years in B2B product marketing, founder energy, and a results-driven mindset with AI-native workflows.

Key Highlights
Own end-to-end brand positioning and messaging for Workstream’s expansion into AI-native frontline workforce platform
Lead product marketing, content, and design for AI-driven launches (e.g., AI assistant for frontline teams) alongside core HR/payroll products
Report directly to revenue leadership with direct impact on pipeline and revenue within weeks, not quarters
Key Responsibilities
Define and execute Workstream’s positioning and messaging, balancing restaurant dominance vs. broader frontline workforce narrative
Lead GTM launches for AI products (e.g., AI assistant) and core HR/payroll solutions, including messaging, pricing, packaging, and launch enablement
Oversee content and design teams for website, case studies, video, webinars, and social media, leveraging AI for rapid production
Collaborate closely with Sales to arm AEs with narratives, competitive insights, ROI stories, and customer proof for deal execution
Manage and grow a high-output team of product marketers, content marketers, and designers, ensuring individual contributions align with strategic goals
Measure marketing success by pipeline and revenue impact, not just impressions or engagement metrics
Technical Skills Required
B2B Product Marketing Brand Strategy & Messaging Content & Design Leadership
Benefits & Perks
Mission-driven company empowering deskless workers
Competitive salary range ($140,000–$200,000 annually) + meaningful equity
Comprehensive health coverage (95% premium for employees, 85% for dependents)
401K plan, in-office amenities, and stocked kitchen
Flexible PTO
Nice to Have
Experience with SMB buyers or hourly/frontline workforce industries
Background in HR tech or payroll solutions
Former founder or category creator

Job Description


Workstream is a mission-driven company building the all-in-one HR, payroll, and hiring platform for managing the hourly workforce. There are 2.7 billion hourly workers, making up 80% of the global workforce, but this market has been heavily underserved by technology and deserves better. Workstream has been purpose-built for the hourly workforce from day one so that these businesses and their employees can thrive.

Our customers include leading brands from multiple sectors, including Burger King, Carl's Jr./Hardee's, IHOP, KFC, and Culvers. We are a high growth series B company and quickly expanding our product portfolio to deliver on our vision. We are backed by legendary VCs and industry experts like Founders Fund, BOND, and Coatue.

Grow With Us

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.

Location & Relocation

  • This is a 4-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

Day In The Life

  • 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.

Who You Are

  • 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.

Travel & Location

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

What We Offer

  • 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

Salary Range

The base salary range for this role is $140,000 and $200,000 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.

Know More About Workstream

  • https://www.workstream.us/blog/funding-series-b
  • https://techcrunch.com/2021/08/26/workstreams-text-based-recruitment-tool-gets-a-48m-bet-from-bond-and-beyond/
  • https://techbuzz.news/buzzworthy-august-27-2021/

Additional Information

Workstream 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.

We are committed to the full inclusion of all qualified individuals.

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