Chief of Staff
Remote (Fully remote within the United States, with occasional travel ) | Compensation: $100,000–$120,000 per year, depending on experience, plus benefits | Pacific Time strongly preferred | Reports to: Bryan Karas, CEO
About Playbook Media
Playbook Media is a performance marketing agency that helps brands scale through the growth curve. Since 2017 we’ve run paid media, creative, analytics and growth strategy across Meta, Google, TikTok and LinkedIn for DTC, B2B, lead-gen and enterprise brands. Along the way our clients have raised more than $1.6B in funding and generated more than $1B in revenue. Our subsidiary, GrowTal, runs a marketplace of vetted fractional marketing experts, which lets companies add senior talent without a full-time hire. Our newest venture is VibeMA, an agentic marketing platform. It turns campaign data into intelligence and automated action, so clients get answers and next steps instead of dashboards. We’re at an unusual moment: a proven agency, a talent network and an AI product being built side by side. This role sits at the center of all three.
The Role
We’re hiring a Chief of Staff to work as the right hand to our CEO.
This isn’t an executive assistant role. You’ll own actual functions — our deal desk, our marketing presence, and the follow-through that turns fast decisions into finished work. You’ll sit close to every part of the business: in the sales conversations, in the strategy, and alongside VibeMA, the agentic marketing platform we’re building to make campaign data genuinely useful for our clients.
It’s a high-access, high-trust seat, and it’s designed to accelerate the path to leadership. We expect the right person to grow into a senior operations role in the organization within two years.
What you'll own
- The deal desk. Pipeline hygiene, keeping the CRM honest, and the reporting that comes off it. You won’t carry a quota — our CEO closes — but the machinery underneath is yours.
- Sales support. Sitting in on sales meetings, running the follow-ups, making sure nothing goes quiet that shouldn’t.
- Marketing presence. Social media posts, website updates, and managing our outside partners in content production and SEO/AEO.
- Priorities and commitments. One current, trustworthy view of everything the CEO has open.
- Meetings. Prepare him beforehand, capture what came out, and drive what happens next.
- Contracts. Making sure they go out when promised and chasing anything sitting unsigned. You won’t be drafting them.
- Writing and materials. Turning direction into documents, decks, and clear next steps.
- VibeMA. Coordinating between the CEO, the team, and outside development.
What we're looking for
- Around five or more years in operations, executive support, chief of staff work, or agency-side project management.
- Deeply organized — you work from a system designed by you, that you could describe to someone else, not from memory.
- Fluent with AI tools. You use them daily and you’re the kind of person who pokes at a new platform to see what it can do. We want someone who comes in asking where these tools could take work off our plates.
- Strong spreadsheet skills. Pivot tables, lookups, and turning a messy export into something clean are everyday work here, not occasional.
- A strong writer. You’ll draft on the CEO’s behalf.
- Discreet. You’ll sit close to compensation, client, and personnel conversations.
- Willing to push back. The value of this seat depends on you saying so when something’s wrong.
- Genuinely curious about marketing. You don’t need agency experience, but you should want to understand the work.
- Able to travel occasionally — client and network dinners, and occasional in-person working sessions with the team.
Nice to have
- Agency or professional-services background, so margin math and delivery constraints come naturally.
- Hands-on CRM ownership.
What this role isn't
- An executive assistant role. There’s overlap in the skill set, but this seat carries more authority and access.
- A quota-carrying sales job.
- A people-management role. No direct reports.
- A client delivery or account management role.
Tools we use
Google Workspace, Slack, Monday.com, Clockify, HubSpot, Google Meet, Gemini and Claude. Familiarity with most of these is expected; you’ll pick up the rest quickly.
Compensation & Benefits
- Salary: $100,000–$120,000 per year, depending on experience. This is the full pay range for the role.
- Benefits: 401(k) with 5% company match, medical, dental, and vision coverage, uncapped vacation and sick time, parental leave, and training and personal development support.
- Schedule: Full-time, fully remote within the US. Pacific Time strongly preferred given the team’s working hours.
- Travel: Occasional travel is part of the role — client and network dinners, and in-person working sessions with the team.
Hiring process
- Application review.
- Initial screen.
- Second conversation with our COO.
- Working conversation with the CEO, built around a short real-world exercise. Nothing to submit.
Equal opportunity
Playbook Media is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected characteristic. [Confirm this matches the language used in our other postings and offer materials.]