The Deep End
For startup leaders navigating the human side of building a company
Responsibility arrives before experience.
The Deep End exists to close that gap.
You are building something fragile, fast, and deeply human.
You are making decisions that affect runway, trust, morale, and momentum, often at the same time.
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The Deep End is a six-week, scenario-driven leadership program built specifically for startup environments. It helps founders and first-time leaders develop the judgment required to lead through ambiguity, conflict, and growth without losing their people or themselves.
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This is not leadership theory.
This is leadership under pressure.
Who Is This For?
The Deep End is designed for leaders operating in early-stage or scaling startups where the stakes are real, and
the margin for error is small.
This program is a strong fit if you are:
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A founder or co-founder leading a growing team
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Part of a founding or early leadership team
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A first-time people manager or director in a startup environment
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A high-performing individual contributor promoted into leadership before you felt ready
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Responsible for decisions that impact people, culture, and business survival
This program assumes you are already
in the deep end.
We're here to teach you to swim.
Testimonials From Our Alumni
What We'll Work Through
Over six sessions, tackle the moments new leaders tend to face without support:
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Understanding the impact of your words, reactions, and silence
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Creating trust without losing authority or speed
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Communicating direction when the path is still forming
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Supporting people without absorbing their stress
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Addressing conflict directly before it erodes culture
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Making hard decisions without abandoning your values
Each session blends:​
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Lived startup experience
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Facilitated discussion
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Research on employee pain points
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Practical reflection you can immediately apply
Our program provides space to explore and develop your own judgement, values, and approach to leadership.
What The Deep End Includes:
A mix of guided learning, real-world practice, and ongoing support.
Training
on your schedule
6 podcast style sessions for convinient learning, and a digital resource library.
Practice
with your peers
6 live weekly discussions applying the material to real-world leadership scenarios.
Community
to grow beyond with
Private Slack Channel to stay connected with your cohort and quarterly alumni roundtables.
About Our Trainer
Megan Pawlak, Founder of Benandanti Consulting
Megan has built a career around the parts of leadership most people wish came with better instructions. She has spent years inside and alongside startups, helping founders and first-time leaders navigate growth without losing trust, momentum, or compassion.
She is particularly drawn to moments when things get complicated, when growth outpaces experience, conflict shows up unexpectedly, or the “right” answer isn’t obvious. Rather than avoiding those moments, Megan believes leaders can learn to move through them with clarity and care.
The Deep End was built for those who believe it is possible to build a successful, sustainable business without leaving their humanity behind.
