Group Creative Director, Gusto
$204-280k
Salary dependent on location
2+ days a week in office
Automated payroll, benefits & HR platform
Be an early applicant
Automated payroll, benefits & HR platform
1001+ employees
Be an early applicant
$204-280k
Salary dependent on location
2+ days a week in office
1001+ employees
Company mission
To grow the small business economy.
Role
Who you are
- 12+ years of experience in copywriting, creative direction, or brand storytelling within agencies, in-house creative teams, or a combination— including experience leading creative work in an environment where AI tools are part of the daily workflow
- Proven track record concepting and leading integrated brand campaigns across TV, digital, social, OOH, and experiential
- Deep expertise in brand voice development, messaging architecture, and multi-channel narrative strategy, including building systems — prompt libraries, review frameworks, guidelines — that make brand voice scalable across human and AI-assisted output
- A portfolio that demonstrates big-idea thinking, range across formats, and the ability to connect brand strategy to cultural relevance — including examples of work where you've directed, elevated, or made the call to override AI-assisted drafts
- Experience directing freelance writers, agencies, and production partners while maintaining creative consistency, including setting clear expectations about where and how AI fits into their workflows
- Sharp instincts for tone, pacing, structure, and emotional resonance across long-form and short-form copy — and a demonstrated ability to apply that editorial judgment to AI-generated work, not just work written from scratch
- Comfort operating in fast-moving environments where priorities evolve and collaboration is constant
- Ability to translate complex or technical subject matter into simple, human, compelling narratives
- Strong collaboration skills across strategy, creative, marketing, and cross-functional partners
- Experience using AI tools (e.g., ChatGPT, Claude, Jasper) to scale creative quality—building brand voice systems, AI-assisted review workflows, and messaging frameworks that empower others to produce on-brand work. A strategic point of view on how AI changes creative leadership and where human editorial judgment remains non-negotiable
- A maker mindset—you love the work itself, not just directing it
- When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees
What the job involves
- We're looking for a Group Creative Director, Copy who is a hands-on maker and conceptual leader: someone who loves developing big ideas, crafting compelling narratives, and shaping how a brand talks across every touchpoint
- And AI is important, so the person in this role needs to be confident shaping how AI-assisted creative work gets reviewed, directed, and held to a high standard
- This is a senior individual contributor role focused on campaign conceptualizing, brand voice, and multi-channel storytelling—working in close partnership with a fellow Creative Director to lead all campaign work
- In this role, you'll own the narrative direction for brand campaigns from brief through execution
- You'll make judgment calls about concept, tone, structure, and emotional resonance across TV, digital, social, OOH, and experiential
- You'll collaborate closely with brand strategy, marketing, design, and cross-functional partners to define what great looks like — and hold that bar even when AI is doing the drafting
- And you'll help raise the standard on creative quality not just through feedback, but through the systems that make quality repeatable: voice guidelines, prompt libraries, AI review workflows, and messaging frameworks that let the whole team — writers, freelancers, and agency partners — produce on-brand work without a director in the room every time
- If you're energized by big ideas, care deeply about language, and want to define how a brand shows up in the world, this role will be an excellent fit
- Concept and lead the creative direction for brand campaigns, integrated marketing, and awareness efforts across TV, digital, social, OOH, and experiential — setting the standard for what great looks like whether the draft starts with a human or an AI
- Develop and evolve brand voice guidelines, messaging frameworks, and tone-of-voice standards, including the prompt libraries and AI review workflows that make those standards usable at scale
- Write and direct campaign copy—from manifestos and scripts to headlines, social, and long-form narratives—and evaluate AI-assisted drafts with the same editorial rigor as anything written from scratch
- Partner with a fellow Creative Director to ensure conceptual cohesion across copy and visual for all campaign work
- Collaborate with brand strategy, marketing, product marketing, and cross-functional teams from brief through launch
- Provide incisive creative feedback to junior writers, freelance partners, and agency collaborators—including clear direction on when and how to use AI in their workflows, and where human judgment is non-negotiable
- Translate complex or technical subject matter into simple, human, compelling narratives, including in contexts where AI has produced a first draft that needs significant editorial lift
- Adapt brand voice and campaign narratives across channels and audiences without losing the thread, using AI to accelerate that adaptation while maintaining the consistency that only a senior creative director can enforce
Our take
For many small businesses, vital administrative tasks such as payroll, taxes, and benefits are manual tasks that take time and energy which many SMB owners don’t have. The three co-founders of Gusto – all coming from small business backgrounds – collaborated on a Fintech company that would handle employee payments, benefits administration, and compliance support specifically for small businesses.
The company may have started slowly, as the founders focused on nailing each individual aspect of Gusto’s operations, but has now skyrocketed to unicorn status with more than 400,000 customers and a multi-billion dollar valuation. And in 2021, Gusto began acquiring other companies to strengthen its offering and its position in a competitive market, including two other fintech startups, Ardius and Symmetry.
Through its continued acquisitions and fundraising efforts, the company has carved out a strong position for itself in the space. Although Gusto has found itself impacted by the macroeconomic situation, through the significant effect it has had on its clientele, the company still appears positive for the future after raising funds in 2023 that has seen it reach key profitability benchmarks. It continues to expand its platform, most recently partnering with Parafin to launch a payroll line of credit for small businesses. With a growing suite of services and a clear focus on supporting small businesses through changing economic conditions, Gusto looks set to sustain its momentum and further strengthen its position in the HR and payroll technology market.
Steph
Company Specialist at Welcome to the Jungle
Insights
45% employee growth in 12 months
Company
Funding (last 2 of 9 rounds)
May 2022
$55m
SERIES E
Aug 2021
$175m
SERIES E
Total funding: $706.3m
Company benefits
- Health and Wellbeing: Medical, dental, and vision insurance for employees and dependents. Family care and support, including family planning and fertility benefits. Gender-affirming care and support. A variety of mental health resources.
- Time Away: It's important to take time away for yourself or to take care of your family. Gusto offers paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more!
- Free meals and refreshments: If you work at one of our offices, enjoy food, drinks, and snacks— on us. Conversation and community is an added bonus!
- Perks:
Company HQ
Central Waterfront, San Francisco, CA
Leadership
Joshua Reeves
(Co-Founder & CEO)Studied Electrical Engineering at Stanford and went onto co-found Gusto in 2011.
Tomer London
(Co-Founder & CPO)Has a PhD in Electrical Engineering from Stanford. Was a Researcher at Intel, and then interned at Bump Technologies. Co-founded Vizmo, a mobile self-service technologies company, in 2008. Co-founded Gusto in 2011.
Edward Kim
(Co-Founder & Head of Engineering)Studied Electrical Engineering at Stanford. Was Senior Project Engineer at Volkswagen of America Electronics Research Lab and then co-founded Picwing, a printed photos company, in 2008. Co-founded Gusto in 2011.
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