Chief of Staff

Spiffy is looking for a Chief of Staff.

You’ll work directly with the CEO on the highest-leverage initiatives — and in the process, you’ll get a front-row seat to scaling a high-growth startup from the inside. This is a good fit if you want to 10x your career trajectory, work on category-defining tech, and earn S tier comp and equity while you do it. This is ideal for someone with a background in consulting, venture, strategy, or early-stage startups — especially if you’ve been a founder or are ready to be one soon.

About Spiffy 🌟

Spiffy is using AI to reimagine commerce. We envision a future where retailers and brands can easily deploy hyper-personalized shopping experiences — so customers convert faster, with zero friction. Our core engine combines cutting-edge research and real-time reinforcement learning to deliver a self-improving AI sales team on any product page.
We’re already seeing commercial success with top brands, and are scaling fast. Come build the future of shopping with us.

What You’ll Actually Do

• CEO Amplifier 🎯:
You’re the force multiplier. You’ll make sure the CEO’s time is spent on the hardest, highest-impact problems. Whether it’s prepping an investor pitch, shaping a GTM motion, or tackling ops chaos, you’re the fixer, planner, and thought partner.
• Company Swiss Army Knife 🧠:
You’ll own cross-functional initiatives across product, legal, ops, and GTM. Expect everything from launching playbooks to joining exec calls to being the emergency brake when a decision needs a gut check.
• Fast-Track Operator 📈:
This job will stretch you. You’ll walk away knowing how to run a company — because you’ll have helped run this one. Your job is to learn fast, ship faster, and clear roadblocks before anyone else notices they exist.

Who This Is Perfect For

• You’re a self starter who is clear in their communication and extremely proactive with exceptional prioritization skills.
• You have a low ego and are willing to help no matter how big or small the task is.
• You’re obsessed with impact and allergic to mediocrity.
• You thrive under pressure and in ambiguity — because it means you get to figure it out first.
• You aspire to start your own company or rise to the C-suite, and you’re hungry for the kind of experience that accelerates that path.
• You love being in the room where it happens — and you’re not afraid to speak up once you’re there.
• You’re organized enough to manage chaos, curious enough to dive deep on anything, and humble enough to take out the trash if that’s what moves the ball forward.

The Good Stuff

• 💰 Top Compensation + Equity — We pay like your time matters. Because it does.
• 🏙️ Seattle HQ — We’re hybrid, but this role is in-person 2-3x per week. Think startup war room energy.
• 🧠 Mentorship and a Front Row Seat— You’ll see every part of how a startup grows.
• 🩺 Full Health Coverage — Medical, dental, vision.
• ✨ A Rare Seat at a Rocket Ship — We’re well-funded and moving fast.