Chief of Staff (CTO) at Cedar in San Diego, CA

Help reinvent how housing gets designed, permitted, and built in America.

Cedar is building the operating system for urban housing delivery. We combine architectural expertise with software, automation, and data systems to dramatically accelerate how projects move from land acquisition to approved designs and construction. The result: faster timelines, higher quality, lower risk, and more housing in the cities that need it most.

Our team blends architects, engineers, and product builders. We design beautiful, responsive housing—and we build the software systems that make great architecture scalable.

The Role

We're looking for a Chief of Staff to work directly with our CTO and keep our engineering org running.

Cedar's engineering team has outgrown what one person can hold in their head. Sprints need running, commitments need chasing, reviews and check-ins need to actually happen on schedule, and requests need somewhere to land other than a DM. Right now too much of that sits with our CTO, which means it competes with the strategic and technical work only he can do.

Your job is to own that structure and hold everyone to it. You'll manage the operating rhythm the team runs on, and make sure it doesn't quietly erode: planning happens, decisions get written down, follow-ups close, nothing slips unnoticed. A big part of the job is simply watching closely: you'll see problems before anyone else does, and your job is to say so early rather than wait for them to surface on their own.

You'll also be engineering's interface to the rest of Cedar, and handle the operational glue around the team—hiring coordination, onboarding, and office logistics—working alongside a founder every day while doing it. Part of that is direct executive support: his calendar, inbox, meeting prep, and the occasional personal item. If that part of the work isn't for you, this isn't the right role.

This is a high-ownership, early-career role with a lot of surface area. It is not a product management role, though it overlaps in part with some traditional PM responsibilities. If you're organized by instinct, cheerfully persistent, and want to see up close how an early-stage company actually gets built, there's a lot of room to do great work here.

What You'll Work On

• Running sprint planning, monthly planning, and retros. Setting agendas, capturing decisions, publishing them
• Making sure every week is properly planned and everyone has high-value work loaded—flagging when someone's idle or pointed at the wrong thing
• Keeping the board honest and chasing every open commitment until it's closed or explicitly dropped
• Interrogating what didn't get finished and why, so the same slip doesn't repeat
• Watching for early signs of trouble (a stalled project, an engineer who's gone quiet, a decision nobody made) and raising them to the CTO while they're still small
• Scheduling and prepping meetings, then making sure the follow-ups actually happen
• Managing the CTO's calendar, inbox, and meeting prep, plus occasional personal logistics (~15%)
• Keeping our management rhythm on the rails. 1:1s, check-ins, and performance reviews happen on schedule, with prep done and notes captured
• Coordinating feedback cycles: setting up the conversations, chasing the inputs, making sure nothing stalls halfway
• Serving as engineering's interface to the rest of Cedar. Fielding requests, coordinating updates outward, and carrying issues from the team back in
• Cataloging and organizing incoming requests so nothing lands in a DM and disappears
• Building the lightweight process that keeps work legible. Definitions of done, written decisions, clear owners
• Coordinating interview loops and keeping the hiring pipeline moving (~10%)
• Onboarding, HR logistics, vendors, supplies, space, and team events (~10%)

What We're Looking For

• Roughly 3–8 years in. You've supported a founder or executive directly before, as a chief of staff, founder's associate, ops lead, or senior EA whose scope grew well past the desk. Not a fit for new grads or a first job out of school
• Comfortable around engineers and product people: you can read a Linear board, follow a sprint retro, and know who to ask when something's off
• Fluent with AI tools and use them every day
• Cheerfully persistent: you'll ask a senior engineer the same question a third time without flinching
• Observant. You notice when something's off before it becomes a problem, and you say so rather than assuming someone else has it
• Organized by instinct, and you default to writing things down
• Comfortable holding senior people to commitments
• Someone who enjoys working in a fast-moving startup environment

Location

San Diego, CA (in our Encinitas office). Reports to the CTO.

Compensation & Benefits

• Competitive salary
• Meaningful equity ownership
• Healthcare, dental, and vision
• Early-stage ownership and impact