People & Culture · AI Transformation · New York

anna.
levitt.

a year spent building what the role is hiring for.

First HR hire at 8 employees. Head of People at 750 and $1B in revenue. Now helping leaders bring AI into their organizations without losing their people.

See what I built ↓
Built01

things i made, not roles i held.

One body of work, two outlets: How to Boss AI for thinking and advisory, Bubble Boss Co. for coaching.

How to Boss AI01

AI Compass

An AI readiness diagnostic with tracks for C-suite, leaders, and individual contributors.

why
Leaders kept asking where to start, and the answer is different for each audience.
what happened
Live, with completions across two distinct tracks.
Take the Compass →
How to Boss AI02

How to Boss AI

A weekly newsletter on leading through AI without losing people.

why
Most AI writing is about tools. Very little is about the people who have to use them.
what happened
0 to 600 subscribers in six months.
Read the newsletter →
How to Boss AI03

AI skills library

A reusable library of AI skills and context files for voice, brand, and client work.

why
To run a practice on an AI-native operating model instead of just advising on one.
what happened
Runs day-to-day client and content work across several AI platforms.
Bubble Boss Co.04

Wheel of Life

An interactive coaching tool for mapping balance across the areas of a life.

why
To give coaching clients a clear starting point before the first session.
what happened
Live and used in coaching intake.
Try the Wheel →
How to Boss AI05

AI Amplified

A 16-question self-check on whether AI is amplifying you or automating you away.

why
People need a way to see where their clarity, judgment, creativity, and ownership stand next to AI.
what happened
One line on what happened.
Take the self-check →
Bubble Boss Co.06

Breathe Easy

A guided 4-4-4-4 box breathing exercise for calm and focus.

why
One line on why you built it.
what happened
One line on what happened.
Try box breathing →
Choose a lens02

Step 2 of 4 · the builder

most useful when the system does not exist yet.

First HR hire at a construction management firm at 8 employees, then led People through growth to 750 employees and $1B in revenue, a national expansion, and an acquisition surge. Owned the full employee lifecycle with a very small team.

8 → 750
employees, from first HR hire to Head of People
$1B
in revenue supported by a lean People team
18 yrs
building one People function from scratch
  • Partnered with the CEO and executive team on org design, workforce planning, and change strategy
  • Designed and ran the performance cycle every year, from manager prep through calibration
  • Built recruiting, benefits, compliance, and employee relations from nothing during the 2008 crisis
Bio03

the 18-year arc.

I joined a construction management firm as its first HR hire at 8 employees and stayed 18 years, building the People function as the company grew to 750 employees and $1B in revenue.

Today I run Bubble Boss Co.: AI advisory and fractional People leadership through How to Boss AI, and one-on-one coaching through Bubble Boss Co.

  1. 2025 – now

    Founder & Fractional Head of People

    Bubble Boss Co.

    AI advisory, executive coaching, and fractional People leadership. Built AI Compass, launched How to Boss AI, completed MIT's Applied Agentic AI program.

  2. 2019 – 2025

    Head of People & Culture

    JRM Construction Management

    Led People through national expansion to 750 employees and $1B in revenue. Moved to UKG, built the first people analytics platform.

  3. 2011 – 2019

    Director of HR

    JRM Construction Management

    Scaled as a two-person department through an acquisition surge. Wrote the SOPs, built multi-state compliance, ran the move to Namely.

  4. 2007 – 2011

    People Operations Manager

    JRM Construction Management

    Joined as the sole HR function at 8 employees. Built everything from scratch through the 2008 financial crisis, growing to 80.

  5. 2005 – 2007

    EA to Chief Executive Officer

    Stamack

    Supported the CEO through a company wind-down and joined the founding group that became JRM.

Principles04

Map the work, document it, systematize it, then train people to run it.