Director of Operations (Chief of Staff)

Job Description

Job Description

We're looking for someone to build the operational backbone of a company in the middle of a strategic rebuild. No corporate playbooks or "we've always done it this way." We need a sharp operator who can take a messy, high-context environment and turn it into something that runs cleanly, while acting as a strategic right hand to the CEO.

Planoly is an established, profitable platform trusted by 30,000+ creators, solopreneurs, and small content-first businesses. We have strong brand equity, deep creator-economy expertise, and a loyal customer base. We're entering our next chapter with new ownership, a new product vision, and are looking for a key hire to accelerate our time to market with our new vision.

The head of operations will own the business infrastructure and partner with the CEO to keep the company running with intention and working smarter.

What You’ll Do

You'll own operations end to end and serve as chief of staff to the CEO. The split is roughly 60/40 operational execution vs. strategic coordination, but it flexes depending on what the business needs that week.

• Rethink how the company operates from the ground up. Challenge legacy processes, eliminate unnecessary complexity, and default to AI-native solutions wherever they outperform traditional approaches

• Run the company's operating rhythm: weekly syncs, monthly business reviews, internal comms, and quarterly/annual planning.

• Act as a strategic partner to the CEO: prioritize leadership time, prepare board materials, ensure decisions get made and followed through across the org. Represent leadership in meetings when needed.

• Own people operations: payroll, benefits, onboarding/offboarding, comp cycles, and the employee experience from offer letter to exit

• Manage the vendor landscape - contracts, renewals, negotiations, and the occasional scope evaluation

• Build and maintain SOPs that are lean by design ensuring they are documented, owned, and automated or AI-assisted where possible. If a process currently lives in someone’s head, your job is to get it out and make it better than it was.

• Lead cross-functional initiatives end to end when big projects with no clear owner arise. Own the plan, the contributors, the timelines, and how steps are managed in concert with each other.

• Hire and manage resources (VAs, AI tools and agents) to amplify the overall teams efficiency and quality of work.

• Over time, expand operational oversight into customer-facing functions to ensure the full customer experience reflects the same rigor and intention as internal operations.

Who You Are

A systems thinker who can translate chaos into simplicity and a cross-functional leader who can rally a team through influence and clarity.

• You reach for AI tools instinctively because you’ve experienced first hand how much faster and better work can get when you build AI into your workflows from the start.

• You follow up before anyone asks. You don't drop things and you don't let other people drop things either.

• You context-switch between an HR issue, a vendor negotiation, and a board prep without losing the thread on any of them.

• You manage up well and show sound shared judgement. You know when to bring the CEO a decision and when to just handle it and send a summary after.

• You're direct when something isn't working and you come with a recommendation.

• You've built SOPs that people actually followed, not just documents that lived in a folder.

• You thrive in ambiguity and don't need a fully scoped job to start making things better.

• You have a high level of ownership and a nothing is above me, nothing is below me mentality.

• Bonus: experience in SaaS, creator-led businesses or social media.

Why Planoly

We are an established creator tool, founded in 2016 as the original visual planner for Instagram. We exist to enable over 1M people to create distinctive, independent businesses that support a flourishing life. With over 30k customers, no VCs, and strong brand equity, you’ll have a rare clean slate to build something truly new alongside a team steeped in marketing, the creator economy, and human-first advantage.

• Strategic Rebuild: New ownership, new product vision, and the operational foundation being built from scratch. You're designing the system versus maintaining bureaucracy.

• Human-First AI: We believe AI augments human creativity—it doesn’t replace it. Taste still matters.

• No VC Strings: Profitable, bootstrapped. We answer to our customers, not a cap table.

• Creator DNA: Deep roots in the creator economy and marketing. We are a beloved brand and know this audience inside and out.

What We Offer

• Competitive salary commensurate with experience

• Founding team equity participation

• Comprehensive health, dental, and vision benefits

• Flexible PTO and a remote-first culture that trusts you to manage your time

• Annual team offsites and the occasional IRL jam session when it matters