Alessandra Colaci ⚡️

Head of Marketing at SparkPlug⚡️AI Marketing Advocate

I help legal professionals adopt AI in a practical and secure way.

With over 15 years in tech and a focus on AI workflows, I work with law firms, in-house counsel, and legal operations teams to build custom AI solutions that improve efficiency. From automating routine tasks to enhancing document review, I translate complex AI capabilities into clear, usable workflows that legal teams can actually implement.

My journey into AI began when I helped launch one of the first micro-tools built with the OpenAI API, an AI email writer created before ChatGPT existed. Since then, I have led AI strategy at SaaS companies, trained teams on AI adoption, and implemented AI-driven systems.

I hold a certification from MIT in Artificial Intelligence for Business. My specialties include:
	•	AI workflow development for legal teams
	•	Prompt engineering for legal use cases
	•	AI training and enablement for internal teams
	•	AI tool audits and evaluations
	•	Aligning AI adoption with privacy, security, and compliance standards

Whether you’re exploring legal AI tools, automating intake, or building a knowledge assistant, I help legal teams implement AI in a way that is strategic, ethical, and aligned with business outcomes.

If you’re exploring AI for your firm or legal department, I’d be happy to connect and share ideas.


Head of Product Marketing

Live view of my inbox today….

…I’m also pictured here in other people’s inboxes. 😅

Alessandra Colaci 

Legal + AI GC Summit 2/25, online | Founder & CEO, Legal + AI

Peep Laja

CEO @ Wynter. 3x Founder. Insights over assumptions. Host of How to Win podcast.

Most of your future revenues are gonna come from future customers. 

If you knew *exactly* what your target customers

think about your category (and your company in particular),
what their top priorities and very big problems are,
what unsaturated channels they use to learn about solutions, 

this is what'd happen to your business:

- you'd nail your messaging, speaking exactly to their pain points
- your conversion rates would go up because your pitch resonates better,
- your CAC would go down as you'd use the right channels with the right message,
- you'd create more meaningful content that moves the dial,
- you'd be more deliberate and accurate in providing more value at every touch point,
- you'd know how to price your products to maximize willingness to pay,
- you'd know how to differentiate,
- you'd know where your go-to-market strategy is off, and could fix it. 
 
The beautiful thing?

You can know all of this with Wynter in under 48 hours.

Agencies are getting fired.

We surveyed B2B SaaS mid-market marketing leaders about where they're cutting budgets.

The #1 answer wasn't paid ads. Wasn't tools. Wasn't events.

It was agencies.

Here's what they told us:

"Agencies have no concept of what it is to actually run a business."
"They assume we have endless time to implement new ideas."
"I need execution, not strategy. I have plenty of strategy."

58% of these leaders are under extreme or high pressure to show short-term pipeline.

They don't have 90 days for a "discovery phase." They don't want another brand positioning deck. They don't need a 50-slide audit.

They need someone to do the work.

Yet most agencies still sell like it's 2015:

❌ Weeks 1-4: Discovery 
❌ Weeks 5-8: Strategy development
❌ Weeks 9-12: The "Playbook" presentation 
❌ Week 13+: "Now you execute it"

Meanwhile, the CMO needed results in Week 2.

Here's the truth agencies refuse to hear:

Mid-market companies don't hire you because you're smart. They hire you because they're underwater.

When you show up with strategy theater instead of execution, you're solving a problem they don't have.

The agencies that survive won't be the ones with the best decks.

They'll be the ones who show up Day 1 and ask: "What can I take off your plate today?"

If you want to have access to the same set of data, you can subscribe to Wynter's ICP Pulse: https://lnkd.in/ggh7yHPf

(Data from Wynter's Dec 2025 survey of mid-market B2B SaaS marketing leaders)

Everyone is doubling down on AI. And most everyone hates the results.

We used Wynter to survey 50 B2B mid-market marketing leaders. 56% are increasing their AI budget in Q1.

But when you read the fine print, the mood isn't excitement. It’s frustration.

Actual quotes from the survey:

"Often AI turns out slop."
"My team is just bumbling through it."
"It's all garbage."

The disconnect is massive.

We have AI SDRs sending robot emails. AI content that sophisticated buyers smell instantly. AI ad variations that are uninspiring.

The problem isn't the technology. The problem is that we are trying to automate the thinking instead of the grunt work.

B2B buyers have excellent BS detectors. Your AI-generated email might save you 20 minutes. But if it costs you the deal, you optimized for the wrong thing.

Efficiency at the cost of effectiveness is just a faster way to fail.

Use AI to execute. Do not use it to think for you.

The math isn't mathing.

1 in 3 mid-market marketing leaders are under extreme pressure to show pipeline results immediately. Not "high" pressure. Extreme.

(58% report extreme or high pressure combined).

The problem? They are being asked to do it with less. Budgets are flat or decreasing across the board.

This is the Impossible Equation of 2026: 

→ Budgets: 📉 Down 
→ Goals: 📈 Up 
→ Attribution: 🤷‍♂️ Broken

One marketing leader told us: "We experience limited faith in performance and slower execution."

Another said: "We don't have a big enough pipeline... but I have to show results now."

When leadership confuses urgency with strategy, you get a disaster. You cut brand. You pump everything into short-term lead gen.

You aren't building a go-to-market engine. You are building a bonfire.

It burns bright for 90 days. You hit your Q1 number. But in 18 months, when the pipeline dries up because nobody knows who you are, the Board will ask: "Why didn't anyone think long-term?"

Because you didn't give them permission to.

The fix isn't more "hacks." 

It's understanding what your ICP is going through, then building brand around those insights.

When you know exactly which problems your ICP cares about, you don't need to burn cash on awareness. You invest in resonance.

But if your Board is demanding 40% growth on a flat budget with zero insight?

They aren't asking for execution. They are asking for magic.

And magic isn't a strategy.

Stop letting the board treat brand as a discretionary expense. Prove your mental availability with hard data. Run a brand tracking study to see if your ICP actually knows you exist: https://lnkd.in/gmKPZB8P

(Data from Wynter's survey of 50 mid-market B2B SaaS marketing leaders)

The "Attribution Death Spiral" is claiming victims.

We used Wynter to survey 50 B2B mid-market marketing leaders. 58% are under extreme or high pressure to show pipeline results. Most can't prove what's working.

Actual quotes:

"Bad attribution data makes it difficult to tie efforts back to ROI." 
"So many visits are categorized as 'Direct'." 
"Not enough confidence to defend marketing spend."

Here's the Death Spiral:

1→ You can't perfectly track Brand or Dark Social 
2→ So you cut those budgets and move to "trackable" channels
3→ Those channels only capture existing demand, not create it 
4→ CAC spikes, pipeline dries up, you blame "lead quality"

The truth: B2B deals involve 5-12 people over months. The LinkedIn post from July. The conference conversation in September. The analyst report in November.

You can't pinpoint which one "caused" the deal. That's fantasy.

But leadership demands certainty. So you build dashboards that give them lies dressed up as data.

First-touch. Last-touch. Multi-touch. All just educated guesses with impressive visualizations.

If you only fund what your CFO can understand, you'll starve what builds your business.

The most profitable marketing often shows up as "Direct" in your analytics.

Stop letting attribution models design your strategy.

You can start measuring what truly drives deals; top-of-mind awareness. Use Wynter to tun a brand tracking study with your ICP: https://lnkd.in/gmKPZB8P

Everyone hates AI SDRs.

We mock the robot emails. We laugh at the hallucinations. We call it spam at scale.

But here is the irony revealed in our latest data: Marketing leaders are buying them anyway.

We used Wynter to survey 50 mid-market SaaS marketing leaders. They know AI isn't perfect and often churns out slop.

So why are they doubling down? Why did one CMO explicitly say they want to "stop relying on human SDRs"?

Because the math is broken.

Why pay a human $65K plus benefits to send a template 36 hours late?

We looked at the complaints in the data:

Speed: Humans are taking 1.5 days to respond to high-intent leads.
Effort: They send generic messages that are just as bad as AI.
Reliability: Leaders have "lack of faith" in the ROI.

If you are just copy-pasting templates from a playbook, let's be honest: you're not an SDR, you're an expensive API call.

The bar for human performance has dropped so low that a $200/month chatbot is stepping over it.

The entry-level SDR isn't being replaced by superintelligence. They are being replaced because they stopped doing anything a script couldn't do.

If you want to survive 2026, you have to be better than a database query. Right now, the data says most aren't.

(Data from Wynter's survey of 50 mid-market B2B SaaS marketing leaders)

I've attended 89 marketing conferences over the years. 

Almost all of them had the same problem.

The best conversations happened in the hallway. At the bar. Never during the actual sessions.

So I built Spryng differently.

We hand-match attendees before the event. Similar company stage, similar challenges, similar goals.

Then we give you space to actually talk. Hallway conversations are the main event.

No panels. Minimal presentations. Just structured conversations with people who get your exact problems.

Next one is coming up March 24-25 in Austin. Built specifically for B2B SaaS marketers who are tired of generic conference advice.

But here's the thing.

If you grab a ticket before January 31st, you get access to something special: 

A VIP boat experience the day before the conference.

30 people total. Two boats. Split by company size so the conversations actually matter. The boat capacity is fixed. Once it's full, this offer disappears.

You'll spend an afternoon on Lady Bird Lake with people who understand 
your world. Facilitated discussions. Real problems. Real solutions.

Then we head straight to the pre-party.

The conference doesn't start until the next day, but the connections start on the water.

Go check out the Spryng website and grab your spot.

Most B2B vendors treat mid-market like "Enterprise Lite."

That's why you're losing deals.

We surveyed 50 mid-market marketing leaders. Here's what they told us:

"Tool vendors think they can solve our problems. But we still need someone on staff to set up, use, and learn from the tool. Sometimes tools create more work, not less."

This is the Mid-Market Reality Gap:

What vendors pitch: 
❌ "Infinite flexibility" 
❌ "Robust dashboards"
❌ "Dedicated onboarding manager" 
❌ "Enterprise-grade maturity models"

What buyers actually have: 

✅ Flat or decreasing budgets 
✅ Extreme pressure for short-term pipeline 
✅ Teams so lean they're bumbling through execution

When you sell "robust capabilities" to a team with zero bandwidth, you're not selling a solution.

You're selling homework.

Mid-market CMOs don't want to "unlock value." They want the value already unlocked.

They don't want to configure a dashboard. They want a decision handed to them.

If your product requires a dedicated Ops hire, a 6-week implementation, or a certification to use it properly, you're not mid-market friendly.

Here's what mid-market actually needs:

Can start using right away, no setup period. Delivers value in Week 1. Requires zero ongoing maintenance.

If using your tool feels like work, you've already lost.

"We can't afford to be right"

A startup founder told me over the holiday break: "My competitors spend $50k a year on market research. I can't afford a single study."

He's pitching the same buyers. Fighting for the same budget.

But his go-to-market strategy is based on limited customer conversations and gut feel sense of the market. 

His well-funded competitor is citing fresh data: "Our research from last month shows 67% of buyers rank [X] as their top concern." 

He's guessing the message. They're citing the pain.

Not because they're smarter. Because "being right" costs somewhere between ~$20,000 and $150,000 per study when you go to a market research firm.

If you're bootstrapped or early-stage, that's not a line item. That's runway. That's a hire.

So you're flying blind on positioning. Guessing at messaging. Making up what buyers will pay for.

Here's what kills you: Startups need precision more than the rich incumbents.

Big players can survive a bad campaign. Wasting $2M is cost of doing business.

You? One bad positioning decision costs you 6 months. 

Meanwhile, what buyers care about changes every month. Their concerns shift. Budget priorities flip. New competitors change the conversation.

The answers you needed in March are wrong by August. But you can't drop $20k every quarter to stay current.

We got tired of seeing startups priced out. So we built ICP Pulse at Wynter, essentially research-as-a-subscription.

Monthly surveys of 50 target buyers. Fresh answers every month. Summary and slide deck with what it all means. 

The incumbent pays $15,000 per study. You pay a ridiculously low price of $208/month. The playing field has been leveled. 

Now piloting with mid-market B2B SaaS marketing leadership. Google 'ICP pulse Wynter' or look for the link in the comments.

We tested Goldcast's homepage with their ICP.

In this episode of "Do you even resonate?" we learn what B2B demand gen and ABM directors actually think of them. (Volunteered by Anand "AP" Patel)

Clarity score: 3.9/5
Interest to learn more: 3.9/5

Both solid scores.

So what did people think?

The good:
• 86% understood what Goldcast does. That's excellent for B2B.
• "Create video content at scale" really resonates. People want to believe this promise.
• Big logos work as social proof. (They drew attention, but people still wanted quantified impact).

What they can improve:

• Positioning confusion. Is it a webinar platform? Virtual event platform? Video editing tool? 
• The word "agentic" is killing triggering people in a negative way. Direct quote: "the agentic promises make me skeptical of whether this is overhyped AI or it actually gets the job done." AI buzzwords trigger skepticism.
• "AI at scale" makes people think: this is slop. Need to address that objection immediately after making this statement.
• The page feels text‑heavy, busy, and repetitive 
• The “why us” and differentiated benefits are underplayed 

Want to featured next and get a message test on your homepage? Drop your URL and ICP below.

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