HL Operations: A fractional Chief-of-Staff for founders who need change

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Founders, Get Out

of your own way

Work With a Fractional Chief-of-Staff to

Get Unstuck in 90 days.

Most Founders & CEOs are Overwhelmed

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Important decisions live everywhere.

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The days get consumed by reacting.

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Everything feels harder than it should.

HL Operations holds up a mirror and says:

"Here's what you say you want. Here's how you're actually operating. Those two things don't match."

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Founders

are the single point of failure

for 40–80 decisions per week.

Many CEOs are stuck in the weeds instead of focusing on strategic thinking, business development, fundraising, hiring, product development …

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And the bottom line suffers.

(and so do YOU and your people)

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I’m Holly Leonard, and for more than 20 years I’ve helped Founders get out of their own way.

I see the patterns CEO’s can't see because they're standing in the middle of them.

I tell the truth their business has been trying to tell them. Then I help them do something about it.

I am the connective tissue between

ideas, people, and execution.

(and I love it!)

  • “Holly is simultaneously personable and constructively direct, with enough structure to guide without feeling clinical, and enough warmth to say the hard thing.”

    —JP, CEO

HL Operations Gets You Unstuck

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So You & Your Team Can Thrive

People + Process = Outcomes.

“PPO” is the lens I use to diagnose and solve organizational problems.

Instead of treating symptoms, I look at whether the business has the right people in the right roles, clear ownership, repeatable processes, and operating rhythms that support execution and allow THEM to THRIVE. 

Organizations often chase outcomes directly (more revenue, faster growth, happier employees), but PPO argues that revenue, growth, customer experience, and culture are outcomes that emerge from getting the people and operating system right first.

How We Work Together

Every project starts the same way: I dig in and listen for the pattern(s) underneath the symptoms, stresses, and pain points. Then I work on a custom phased plan to get you on a path to your goals.

Founder Vision Workshop

First, I force clarity through a workshop where we start with the end in mind. This is essentially discovery work done differently.

Most of my clients begin to see their business and themselves differently just halfway through this first step.

Free for women, $2,500 for men.

Listening Tour

I want to understand where their time actually goes before I suggest anything, so next I go department by department on a listening tour: sitting in meetings, reading the Slack threads, interviewing teams.

What I find first are the recurring decisions that rarely require the founder but always reach them anyway: approving marketing copy, running the month-end close, signing off on entry and mid-level hires. (I also find a lot more!)

$3,000+ (depends on size & complexity)

Your Custom Plan

Every plan is based on what we discover together, but some of my go-to practices include:

  • DISC assessments to amplify strengths

  • Zone of genius mapping + activation

  • You / Me / We / They ownership mapping (RACI style)

  • Communication preference docs

  • "Pit and the peach" check-ins

  • Public team wins

  • Modeling transparency and vulnerability

  • Sourcing temporary talent from my network of partners

Custom proposals

  • “Holly is insightful, keen, and direct; the perfect match for founders with a growth mindset.”

    —AE, VP of Product Series B

If you can answer “Yes” to these 3 questions…

Are you a Founder-led CEO at $3–25M revenue?

Do you need help with an acute pain point ?

Do you have at least a $10,000 budget for this work?

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Book a Call

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Now Booking

Speaking Engagements

I love presenting on stages, conducting workshops, and speaking to groups about my work.

My “People + Process = Outcomes” framework allows me to create impactful content for many different audiences.

Need a speaker who will make change happen in that one session?

Contact Me