Cleverbird Tech
Fractional PMO · Portfolio · AI
I’m Lindsay Haddock—an independent technology and operations advisor. I help senior leaders resolve competing portfolio priorities, unblock product and operating decisions, and turn AI opportunity into focused action and measurable value. Deep roots in tech, health and wellness companies.
Fractional leadership for owner-operators
and technology leaders.
LinkedIn recommendation
“She brings structure without rigidity, direction without pressure, and always keeps the team aligned on what truly matters.”
LindsayTechnology and transformation leadership
Global operating experience
Portfolio leadership
More recommendations
“Lindsay not only delivered, but the customer is willing to write a reference letter. It was a difficult customer and as a sales rep, I could not be happier.”
“Her ability to understand and professionally manage conflicting motivations is a rare skill.”
How I help
For owner-operators and technology leaders who need portfolio clarity, steadier delivery, or a practical start with technology or AI—without adding a full-time executive.
An experienced portfolio leader in your operating rhythm, part-time. I set up intake and prioritization, governance people actually use, and the reporting leaders need to make investment calls they can defend.
Best for: growing companies with too many priorities, or teams between PMO leaders.
Align technology strategy, investments, and decision rights with business outcomes. Then build the planning rhythms, metrics, and cross-functional practices that keep product and delivery teams moving.
Best for: leadership teams after rapid growth, a reorg, or a stalled transformation.
Find the use cases worth pursuing, test them with clear measures and stop points, and redesign workflows around what works—keeping people and judgment in the loop.
Best for: teams with AI interest and no clear first move.
Facilitated sessions where your team frames, designs, and decides on a real problem together—from AI experiment design with the AI Experiment Canvas to portfolio prioritization and premortems.
Best for: leadership offsites, kickoffs, and teams stuck in debate.
Client work · 3-day launch
A brand, portfolio site, commission inquiry flow, and Instagram and Venmo payments, live in three days and running on an automated deployment setup Cheryl never has to touch.
“Lindsay brought my artistic vision to life… The entire experience was thoughtful, professional, and tailored to my business.”
— Cheryl Flores, Art In Motion by Cheryl
Visit the live site (opens in a new tab)My approach
Connect strategy, governance, people, process, data, and technology before prescribing change.
Turn competing priorities and incomplete information into options leaders can act on.
Build lightweight operating mechanisms that improve accountability, flow, and visibility.
Leave teams with clearer ownership, better habits, and systems they can sustain.
Ideas tested in practice
Cleverbird Labs is the learning and experimentation division of Cleverbird Tech—a place to explore practical, human-centered applications of AI, emerging technology, and better ways of working.
Questions become experiments, tools, and useful guidance that help leaders prepare for what comes next.
Explore Cleverbird Labs (opens in a new tab)Can AI help a solo founder move from idea to a credible MVP? See what held up, where human judgment mattered, and what the experiment changed.
Read Experiment 01 (opens in a new tab)A fillable canvas and expanded workbook for shaping a focused, responsible AI experiment before your team commits time and resources.
Get the canvas (opens in a new tab)
Who you’ll work with
For nearly two decades, I’ve worked inside complex technology organizations—including a $5.5B enterprise operating in 95 markets—leading enterprise PMOs and $40M+ portfolios, product operations, and digital transformation.
Much of that work has been in regulated healthcare and wellness environments, where governance, evidence, and execution all matter. I built Cleverbird Tech to bring that experience to a small number of engagements at a time.
Credentials & recognition
Let’s discuss the decisions, operating challenges, or delivery priorities in front of your team.
Start a conversation hello@cleverbirdtech.com
