Staff Content Strategist

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

Content is the front door of gusto.com — and the words on that door shape whether someone walks in.

Gusto.com is one of our key acquisition channels. The content across our site isn't a marketing afterthought but a growth lever. Every page, headline, and CTA is an opportunity to build trust, convey clarity, and guide prospective customers from discovery to conversion.

We're looking for a Senior Content Strategist, Web to own the messaging, content strategy, and copy across the gusto.com experience. This role sits at the intersection of content design, editorial strategy, and growth, and reports into the Brand Studio team within our Design organization.

You'll set the strategic direction and execution for how Gusto talks to prospective customers: developing messaging frameworks, writing high-converting page copy, designing intent-led content structures and information architectures, and optimizing experiences through A/B testing and experimentation. You'll partner closely with designers, product managers, engineers, and web marketing teams.

You'll also be at the forefront of how AI transforms web content — both in how you work (using AI tools to accelerate ideation, drafting, and optimization) and in the experiences you help shape.. That means deciding how AI-produced content gets reviewed, how it's held to the same trust standards as anything else on the site, and where human judgment is non-negotiable.

If you're a strategic, data-informed writer who thrives at the intersection of content, design, and growth — and you want to own the content experience for a brand trusted by hundreds of thousands of small businesses — this is your role.

• →Own the content strategy across gusto.com — what gets said, to whom, in what order, and why — with clear accountability for how content performs against acquisition and conversion goals
• →Design intent-led content structures, page frameworks, and navigation flows that streamline user journeys from discovery to conversion
• →Build high-performance messaging frameworks that turn complex product value propositions into compelling, human-centric copy that drives measurable business impact
• →Write end-to-end web copy — from value propositions and headlines to CTAs, microcopy, and landing pages
• →Proactively identify moments of friction across the web experience, propose content solutions, and validate through A/B testing and experimentation
• →Partner closely with the interaction design lead, product managers, growth designers, engineers, and web marketing to ship cohesive web experiences
• →Contribute to and evolve content standards, voice guides, and style documentation that others use and build from
• →Use AI tools to accelerate your own workflow — and build systems that scale messaging consistency, voice implementation, and content QA across the site
• →Translate complex product and technical information into simple, human, accessible language

• 5–8 years of experience in content strategy, content design, UX writing, or web copywriting  with demonstrated ownership of complex, cross-functional digital experiences
• Demonstrated fluency with AI writing and ideation tools, and a track record of using them to do better work, not just faster work. Experience designing content experiences that are themselves AI-driven is required, not a bonus
• Experience governing AI-generated content at scale — including defining review criteria, quality standards, and the boundaries of where AI output is and isn't appropriate
• Experience setting or contributing to content standards, voice guides, style documentation, or content systems that others use and build from
• Remarkable writing and editing skills — clear, concise, accessible, and inclusive.
• Robust systems thinking — you can hold the big picture (how does this page connect to the broader journey?) while nailing the details (is this microcopy precision and on-brand?)
• Comfort working autonomously in ambiguous spaces — you can take a complex, poorly defined problem, define a content strategy, and drive it to completion without heavy oversight
• Experience designing for web with proficiency in Figma
• Track record of collaborating proficiently with product managers, engineers, brand and product designers
• Experience with high-volume experimentation and A/B testing on web experiences
• Experience shaping and socializing content strategy rationale with senior stakeholders, including executives
• You ship. Strategy that never becomes a live page isn't interesting to you.