Product @ LinkedIn | Author of “Reimagined: Building Products with Generative AI” | “PM Learning Series” Host | Sharing insights about building products and leading innovative teams

👋 Hello! I’m Shyvee—a forward-thinking product lead who combines creativity, human psychology, and AI to build thriving communities and drive impactful product growth.

Previously a Product Lead at LinkedIn and instructor with LinkedIn Learning, I now focus on driving product growth and adoption while activating professional communities on Microsoft Teams, empowering people to connect, collaborate, and future-proof their careers. With a unique passion for community-building and hands-on AI learning, I’ve created a global, multi-disciplinary community that supports individuals while fueling product adoption and growth along the way. Learn more: https://AICommunityLearningProgram.substack.com/about

Throughout my career, I’ve engaged over 100K followers, reaching 40M+ views. My PM Learning Series has featured esteemed guests, including cofounders and CPOs from leading Silicon Valley startups. As President of the Kellogg Alumni Club in San Francisco, I’m a frequent speaker and have influenced digital strategies at organizations like VMware, Disney, Cisco, YMCA, Toyota, HSBC, Telstra, and other Fortune 1000 companies.

My superpowers lie in strategic thinking, innovative problem-solving, and data-driven storytelling, all grounded in a deep understanding of user psychology and enhanced by AI. I leverage AI for rapid prototyping, automating go-to-market workflows, and building high-impact solutions that resonate with users and drive real business outcomes.

I’m also the coauthor of the Amazon bestseller Reimagined: Building Products with Generative AI, a practical guide for integrating AI into product strategy, featuring over 150 examples and 30 case studies. Learn more: https://a.co/d/btmnJfu

Shyvee Shi

If you own €10M+ DTC and migration, ROAS, stack, or AI decisions keep turning into debates, you’re carrying the execution risk.

Most ecommerce directors and CDOs aren’t short on ideas.
They’re short on a shared, evidence-backed picture of what’s actually happening across vendors, platforms, and dependencies.

In complex organisations, the problem isn’t effort.
It’s missing sequence, unclear ownership, and decisions that can’t be defended when things fail.

I’ve done this in fashion and lifestyle environments with brands like Vans, The North Face, Timberland, and Dickies.
Including situations where DTC went from ~€1M to €10–20M over a couple of years by tightening execution, not “rebranding the business”.

The same pattern shows up in €100M+ organisations, just at a larger scale.

How I work:

• Map reality vs perception (KPIs, dependencies, failure points)

• Clarify who does what (in-house, agency, SI) and where accountability breaks

• Prioritise execution — what’s ready now vs what needs foundations first

If you’re leading digital operations and trying to align stakeholders while stopping budget blowouts,
DM me “RISK”.

Marco Lanzi

Nobody tells you this when you take the Head of Digital role.

You don’t just own results.
You own everything that can go wrong.

Even when:
	•	you didn’t build it
	•	you warned people early
	•	you didn’t choose the vendor


𝗪𝗵𝗲𝗻 𝘁𝗵𝗶𝗻𝗴𝘀 𝗯𝗿𝗲𝗮𝗸, 𝘁𝗵𝗲 𝗾𝘂𝗲𝘀𝘁𝗶𝗼𝗻 𝗶𝘀𝗻’𝘁:
“What happened?”

𝗜𝘁’𝘀:
“Why didn’t you prevent this?”

That’s the invisible weight of the digital leaders role.

You sit between:
	•	vendors selling certainty
	•	teams delivering complexity
	•	executives demanding outcomes

𝗔𝗻𝗱 𝘆𝗼𝘂’𝗿𝗲 𝗲𝘅𝗽𝗲𝗰𝘁𝗲𝗱 𝘁𝗼 𝘁𝗿𝗮𝗻𝘀𝗹𝗮𝘁𝗲 𝗰𝗵𝗮𝗼𝘀 𝗶𝗻𝘁𝗼 𝗰𝗼𝗻𝗳𝗶𝗱𝗲𝗻𝗰𝗲.

Here’s what I’ve learned the hard way:

The job isn’t to be right.
The job is to be defensible.

The Digital leaders who survive long-term don’t rely on:
	•	trust
	•	intent
	•	or “best efforts”

They rely on:
	•	documented risks
	•	quantified trade-offs
	•	visible decision logic

Not to avoid failure.
But to avoid surprise.

𝗕𝗲𝗰𝗮𝘂𝘀𝗲 𝘀𝘂𝗿𝗽𝗿𝗶𝘀𝗲𝘀 𝗸𝗶𝗹𝗹 𝗰𝗿𝗲𝗱𝗶𝗯𝗶𝗹𝗶𝘁𝘆 𝗳𝗮𝘀𝘁𝗲𝗿 𝘁𝗵𝗮𝗻 𝗺𝗶𝘀𝘀𝗲𝗱 𝘁𝗮𝗿𝗴𝗲𝘁𝘀.

If you’re in this role, let me say this clearly:

Feeling the weight doesn’t mean you’re failing.
It means you’re the one actually accountable.

The real danger isn’t pressure.

𝗜𝘁’𝘀 𝗰𝗮𝗿𝗿𝘆𝗶𝗻𝗴 𝗶𝘁 𝗮𝗹𝗼𝗻𝗲.

So tell me:

What part of your role feels heavier than what your title suggests?

CDO / Head of Digital in €10M+ DTC → avoid execution mistakes and tech overlaps before they slow you down

𝗦𝘁𝗼𝗽 𝘀𝗮𝘆𝗶𝗻𝗴: “We need more time.”
𝗦𝘁𝗮𝗿𝘁 𝘀𝗮𝘆𝗶𝗻𝗴: “Here’s what breaks if we don’t.”

The difference isn’t semantic.
It's the difference between begging and negotiating.

When you say “we need more time”:
	•	leadership hears delay
	•	stakeholders hear excuse
	•	the CFO hears over budget

When you say “here’s what breaks if we don’t”:
	•	you make risk quantifiable
	•	you move from opinion to evidence
	•	you let leadership own the decision

Example:

❌ We need four more weeks for testing.

✅ Without four weeks of load testing, we launch with:
→ search 400ms slower (≈ €180k/month in lost conversion)
→ checkout failing at 2× normal traffic
→ three critical integrations untested under peak load

The delay costs €200k in OpEx.
Launching as-is carries €500k+ in revenue risk.

𝗬𝗼𝘂𝗿 𝗰𝗮𝗹𝗹.

See the difference?

One framing makes you the problem.
The other makes you the person who quantified the problem.

The Digital leaders who get time and budget don’t ask for them.

They make the cost of not waiting more expensive
than the cost of waiting.

So be honest:

What request are you still framing as opinion,
that should be framed as math?

5 Shadow Monsters I've Seen Kill €50M+ in Digital Transformations

You've probably met all five.
You just don't name them.

Most transformation failures look the same:

✅ Budget approved
✅ Technology deployed  
✅ Team trained
❌ Business impact

The problems aren't loud.
They're lurking in your structure.

After reviewing 40+ digital transformations, 𝘁𝗵𝗲𝘀𝗲 𝗮𝗿𝗲 𝘁𝗵𝗲 𝟱 𝗦𝗵𝗮𝗱𝗼𝘄 𝗠𝗼𝗻𝘀𝘁𝗲𝗿𝘀 𝘁𝗵𝗮𝘁 𝘀𝗵𝗼𝘄 𝘂𝗽 𝗮𝗴𝗮𝗶𝗻 𝗮𝗻𝗱 𝗮𝗴𝗮𝗶𝗻:

⸻

𝗦𝗵𝗮𝗱𝗼𝘄 𝗠𝗼𝗻𝘀𝘁𝗲𝗿 #𝟭: 𝗧𝗵𝗲 𝗟𝗲𝗴𝗮𝗰𝘆 𝗟𝗮𝗯𝘆𝗿𝗶𝗻𝘁𝗵
(The undocumented dependency no one owns)

Problem:
Your "new" system depends on legacy code from 2003.
One person maintains it.
They're not on the project plan.
They retire in 6 months.

What works:
→ 𝗠𝗮𝗽 𝗲𝘃𝗲𝗿𝘆 𝗹𝗲𝗴𝗮𝗰𝘆 𝗱𝗲𝗽𝗲𝗻𝗱𝗲𝗻𝗰𝘆 𝗶𝗻 𝗪𝗲𝗲𝗸 𝟭
→ Make the "invisible" people visible in your budget
→ Document institutional knowledge before it walks out the door

⸻

𝗦𝗵𝗮𝗱𝗼𝘄 𝗠𝗼𝗻𝘀𝘁𝗲𝗿 #𝟮: 𝗧𝗵𝗲 𝗣𝗼𝗹𝗶𝘁𝗶𝗰𝗮𝗹 𝗛𝘆𝗱𝗿𝗮
(The endless escalation loop)

Problem:
Marketing wants speed.
IT wants control.
Sales wants flexibility.

Every decision becomes a committee.
Every committee spawns three more meetings.
Nothing ships.

What works:
→ 𝗢𝗻𝗲 𝗮𝗰𝗰𝗼𝘂𝗻𝘁𝗮𝗯𝗹𝗲 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻-𝗺𝗮𝗸𝗲𝗿 (𝘄𝗶𝘁𝗵 𝗿𝗲𝗮𝗹 𝗮𝘂𝘁𝗵𝗼𝗿𝗶𝘁𝘆)
→ Document trade-offs once, then decide
→ No re-litigation after the decision

⸻

𝗦𝗵𝗮𝗱𝗼𝘄 𝗠𝗼𝗻𝘀𝘁𝗲𝗿 #𝟯: 𝗧𝗵𝗲 𝗔𝗰𝗰𝗼𝘂𝗻𝘁𝗮𝗯𝗶𝗹𝗶𝘁𝘆 𝗣𝗵𝗮𝗻𝘁𝗼𝗺
(When everyone's responsible, no one is)

Problem:
14 people "own" the transformation.
Success metrics change when pressure rises.
When it fails, careers are fine—except yours.

What works:
→ 𝗢𝗻𝗲 𝗲𝗻𝗱-𝘁𝗼-𝗲𝗻𝗱 𝗼𝘄𝗻𝗲𝗿 𝘄𝗶𝘁𝗵 𝗿𝗲𝗮𝗹 𝗰𝗼𝗻𝘀𝗲𝗾𝘂𝗲𝗻𝗰𝗲𝘀
→ Lock metrics on Day 1 (no moving targets)
→ Their promotion depends on the outcome

⸻

𝗦𝗵𝗮𝗱𝗼𝘄 𝗠𝗼𝗻𝘀𝘁𝗲𝗿 #𝟰: 𝗧𝗵𝗲 𝗔𝗱𝗼𝗽𝘁𝗶𝗼𝗻 𝗜𝗹𝗹𝘂𝘀𝗶𝗼𝗻
(Deployed doesn't mean used)

Problem:
You rolled out to 5,000 users.
4,200 logged in once.
100 use it daily.

Leadership celebrates "95% deployment success."
Customers still call the old support line.

What works:
→ 𝗠𝗲𝗮𝘀𝘂𝗿𝗲 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝗼𝘂𝘁𝗰𝗼𝗺𝗲𝘀, 𝗻𝗼𝘁 𝗳𝗲𝗮𝘁𝘂𝗿𝗲 𝗮𝗱𝗼𝗽𝘁𝗶𝗼𝗻
→ Track daily active users, not logins
→ Celebrate impact, not go-live

⸻

𝗦𝗵𝗮𝗱𝗼𝘄 𝗠𝗼𝗻𝘀𝘁𝗲𝗿 #𝟱: 𝗧𝗵𝗲 𝗗𝗮𝘁𝗮 𝗗𝗲𝘀𝗲𝗿𝘁
(When the CFO asks "Is this working?" and you have no answer)

Problem:
You have dashboards full of activity metrics.
The CFO wants ROI.

You show "85% of training completed."
They ask "What's the revenue impact?"

Silence.

What works:
→ 𝗦𝗵𝗼𝘄 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 𝘃𝗮𝗹𝘂𝗲 𝗶𝗻 𝗖𝗙𝗢'𝘀 𝗹𝗮𝗻𝗴𝘂𝗮𝗴𝗲
→ Build your political shield with outcome data
→ Track revenue impact, cost reduction, risk mitigation

⸻

The reality:

Digital transformation isn't about implementing technology.

It's about making accountability unavoidable.

So real talk:

Which Shadow Monster is eating your project alive right now?

𝗠𝘆𝘁𝗵: “We’ll optimize it post-launch.”

𝗥𝗲𝗮𝗹𝗶𝘁𝘆: That’s when your credibility dies.

Here’s why this phrase is career poison.

When leadership hears “post-launch optimization”, they think:
“We’ll ship it working, then make it better.”

What actually happens after launch:
	•	the team moves on
	•	new priorities flood in
	•	“optimize” becomes “maintain”
	•	users form opinions in week one, and keep them

Here’s the brutal math:

Week 1 performance = your reputation for 12+ months.

𝗙𝗶𝗿𝘀𝘁 𝗶𝗺𝗽𝗿𝗲𝘀𝘀𝗶𝗼𝗻𝘀 𝗮𝗿𝗲𝗻'𝘁 𝗷𝘂𝘀𝘁 𝘀𝘁𝗶𝗰𝗸𝘆.
𝗧𝗵𝗲𝘆'𝗿𝗲 𝗽𝗲𝗿𝗺𝗮𝗻𝗲𝗻𝘁.

If checkout is slow on launch day, customers remember.
If search underperforms initially, they stop using it.
If mobile is clunky at go-live, they don’t come back.

“Post-launch optimization” assumes:
→ you’ll have time (you won’t)
→ you’ll have budget (you won’t)
→ users will give you a second chance (they won’t)

The Digital leaders who launch successfully, don’t plan to fix it later.

They ask:
“What can’t we afford to get wrong on day one?”

Then they prioritize ruthlessly around that.

Because you only get one first impression.

And “we’ll optimize it post-launch”
is usually followed by:

“Why is adoption so low?”

So be honest:

So before you say 'we'll optimize it post-launch' in your next planning meeting:

What are you planning to 'optimize post-launch', 
that should be non-negotiable at launch?

𝗕𝗲𝗰𝗮𝘂𝘀𝗲 𝗜 𝗽𝗿𝗼𝗺𝗶𝘀𝗲:
The team that has to fix it won't be available.
The budget to improve it won't be approved.
And the users who left won't come back to check.

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