What's Actually Keeping You Stuck?
You've proven product-market fit. Now your board, investors, and team expect you to scale like a real company. But you're still operating like a startup.
Your board is asking questions you can't answer
"What's your hiring plan?" "How are you scaling sales?" "Where are the bottlenecks?" You know you need better systems and metrics, but you're too busy running the business to build them.
You're losing deals because your GTM is inconsistent
Your sales team is giving different pitches. Your materials are outdated. Prospects are confused. You're losing deals you should be winning because you don't have a repeatable sales motion.
Critical projects keep stalling because no one owns them
You know you need to launch that product, fix onboarding, prepare for your next fundraise—but everyone's underwater. There's no one to actually own and drive these projects to completion.
You're hiring but losing top candidates to competitors
Your hiring process takes too long. Candidates drop out. Your team is too busy to interview. By the time you make offers, the best people have accepted elsewhere.
You're personally doing work that should be delegated
You're writing job descriptions. Fixing broken processes. Coordinating between departments. You know a VP of Ops should be doing this, but you can't afford a full-time hire yet.
Your next fundraise depends on proving you can scale efficiently
Investors want to see you can grow without burning cash. You need operational rigor, hiring plans, and systems that prove you're not just scrappy anymore—you're scalable.
I've Been the Person CEOs Call When They're Stuck
At Bravado, the CEO was drowning in operations with no Chief of Staff, no systems, and a board expecting growth. I built the role from scratch, created the operational infrastructure, hired 30 people across 10 countries, and got the company through their $26M Series B.
That CEO got out of the weeds. The board saw operational maturity. The company scaled without breaking.
HOW I HELP
Don't Just Advise. I Own and Execute
Most consultants give you a strategy deck. I build the systems, run the hiring, and execute the projects. Then I onboard your team with the playbook and process.
Make You Board-Ready
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Build the operational systems and metrics your board expects
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Prepare board materials that show you're scaling efficiently
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Create hiring and growth plans that prove you can execute
Fix Hiring Before You Lose More Candidates
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Run your hiring sprint end-to-end (sourcing through onboarding)
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Design onboarding that ramps people in 30 days, not 90
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Build comp frameworks so you can close candidates
Own Your Critical Projects
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Own the 2-3 projects you can't let fail
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Coordinate cross-functionally (product, sales, marketing aligned)
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Drive to completion without you having to follow up
Build Systems That Scale
(So You're Not the Bottleneck)
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Build cross-functional systems so teams can move without you
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Create operating rhythms (weekly syncs, quarterly planning, board prep)
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Document processes so they scale beyond you
I'VE BUILT THIS BEFORE
Hi! I'm Olivia Leavengood.
I know what it takes to scale.
I bootstrapped a 6-figure company in Year 1. I've been in the founder seat.
I've also scaled a startup from 12 to 75 employees as Chief of Staff. Built the role from scratch. Supported the CEO through their $26M Series B. Led hiring, operations, and strategic projects.
I began my career in GTM at IBM. I understand enterprise systems and how to build processes that scale.
In Good Company
