Alessandra Colaci ⚡️

Legal + AI

Equipping lawyers, legal leaders, and legal ops pros with AI workflows, use cases, and tools to increase efficiency. First virtual Legal + AI Summit happening on October 14th-16th. Join us!

Founder & CEO

GC AI

Launched the GTM function at GC AI. Managed legal AI content, education, events, and product marketing efforts. Significantly increased enrollment, attendance, product education, and activation with legal AI classes and events.

Founding Marketer

Humans + AI

Providing specialized training and strategy on AI for business teams, covering areas such as prompt engineering, AI-driven workflows, content creation using AI, marketing strategies leveraging AI, data analytics through machine learning, policy development for AI integration, and creation of generative AI visuals.

• Collaborating with clients from diverse sectors to maximize AI utilization within their teams.
• Selecting and training on AI vendors/models to meet specific business requirements and streamline workflows.
• Crafting AI strategies for marketing, sales, and product teams to accelerate outcomes and enhance productivity.
• Regularly revising AI approaches to integrate the latest models, customizing solutions to achieve organizational goals.
• Conducting regular audits to refine AI workflows in response to technological updates and shifting strategic focuses.
• Development of specialized AI models for internal tools, fine-tuning for operational requirements.
• Leading training on generative AI for ideation, data analysis, and content creation including templates, presentations, and visuals.

Founder & AI Consultant

SparkPlug

Utilized AI workflows to manage product marketing efforts for multiple audience personas across website, messaging, sales enablement, competitive intelligence, and customer research.

• Trained marketing team to use AI and ChatGPT for content research, outlines, and generative AI images.
• Customer interview data analysis with AI across multiple segments and personas, as well as win-loss interviews.
• Grew enterprise leads by 85% with segmentation and messaging across personas using ChatGPT for personalization.
• Customer interview data analysis with AI across multiple segments and personas, as well as win-loss interviews
• Utilized AI to create 100+ pieces of content including guides, landing pages, templates, video training, and articles.
• Increased demo to close from 32% to 53% via collaboration with sales team and optimization of positioning.
• Started enterprise efforts from 0 and captured pipeline leads to include Best Buy, Home Depot, Lululemon, and Puma.
• Developed feedback loop with BD team, creating collateral and assets for them that led to 67% increase in pipeline.
• Launched 15 new product features and announcements, with segmented customer announcements and analytics.

Head of Product Marketing

Mailshake

Launched one of the first OpenAI micro-tools built on the API. Oversaw efforts to impact messaging, demand generation, acquisition, and retention. Developed strategies across full customer lifecycle including go-to-market, sales enablement, video, split-testing, content, SEO, and partnerships.

• Worked in-tandem with OpenAI developers to plan the first AI email writer.
• Developed AI model fine-tuning strategy and created data to train the model for optimal prompt output.
• Performed product positioning exercises through user interviews, case studies, audience research, and site tests.
• Increased Hubspot contacts by 158% after implementation and created workflows based on segmentation.
• Created research panels to inform messaging tests on headlines and page content, resulting in 29% lift.
• Ran multiple pricing tests, ranging from messaging to layout, that led to 20% increase in demos booked.
• Implemented customer lifecycle strategies that led to 39% increase in revenue per user and 176% increase in LTV.
• Launched new affiliate program and surpassed revenue goal by 242% by customizing page content and co-branding.
• Worked cross-functionally with Sales, Product, and Customer Support teams on enablement and content assets.
• Scaled traffic to 367k monthly site visitors, 34k backlinks, 55k organic keywords, and domain rating of 79.
• Executed go-to-market launches for new features and audiences, including email, site messaging, and notifications.

VP of Marketing

Bucket.io

• Established go-to-market strategies to launch in multiple verticals and customer personas. Built funnels across channels using product marketing, competitive analysis, and conversion testing.
• Led a team consisting of 2 Account Managers, 2 Designers, and 2 Developers, working closely with sales & CEO.
• Strategized go-to-market launch that resulted in 4x over revenue goal and 10x over goal for new customers.
• Engaged leads via email, content, social chatbots, and site messaging, leading to a 52% increase in new users.
• Launched paid ads across Facebook, Instagram, YouTube, and retargeting, with a 45% lower cost per acquisition.
• Achieved a 14:1 (1,400%) ROAS and 64% attendance rate for webinars with demand generation campaigns.
•Developed entire funnel for customer acquisition including site messaging, A/B optimization, and CRM emails.

Head of Growth

Influence Buzz - eCommerce and SaaS Marketing

• Achieved significant improvements in client results that led to: 373% increase in social impressions, 177% increase in engagement, 91% increase in site visits, 900% increase in site traffic from Facebook, and 36% increase in email subscribers
• Managed client Facebook ad campaigns, including strategy, content development, and analytics
• Planned marketing content and analytics for diverse businesses in B2B Software as a Service and eCommerce
• Managed internal and external team and directed day-to-day operations for marketing content, PPC ads, and website
• Guest speaker on over 30 podcasts and co-host of multiple shows
• Created podcast about video marketing and grew listenership to the top 10 in iTunes New and Noteworthy

Director of Digital & Product Marketing

eCommission Financial Services, Inc.

• Oversaw all aspects of marketing, including communications, SEO, direct mail, events, content, email, PPC and PR
• Increased email click-through rate by 118%, and delivery from 50% to 95%
• Boosted visibility and awareness of the brand as a finance industry leader, leading to a 40% increase in new customer acquisition 
• Reduced ineffective spend by over $500,000 yearly, while still increasing customer base and revenue
• Managed marketing team and web/graphic designer with roadmap and asset creation for all communications channels
• Developed process and analytics improvements to increase customer acquisition and marketing effectiveness
• Directed all online and offline campaigns, with yearly budget of $1 million+, while consistently increasing results
• Managed complete brand update and site redesign, with a new mobile-responsive focus and A/B split testing of key pages
• Optimized Adwords campaigns and implemented additional new ad channels such as Facebook and LinkedIn
• Negotiated new content partnerships and developed fresh content in order to increase organic SEO
• Implemented multiple new analytics and business tools which enabled more effective insight into customer behavior

Director of Marketing

11 Main, Inc.

• Managed the following teams for this SaaS and ecommerce company: Communications, Data, Sales, Content, SEM, Email, Video, Social Media, and PR
• Built up marketing team from 1 to 20 direct reports in 6 months
• Managed a yearly marketing department budget of over $10 million
• Developed pricing A/B split testing that led to a 20% increase in signups
• Actively participated in the CEO’s Executive Strategy Team to determine future product development
• Initiated a marketing campaign that resulted in an additional $200,000 in revenue in only 2 months
• Increased affiliate program’s monthly revenue by over 300% in 1 month
• Head of Business Intelligence team that included Business Analyst and technical Data Analysts
• Created multiple ad hoc reports, as well as daily/weekly/monthly report creation with visuals for easy trend analysis
• Planned KPI’s and performance measurement via report creation and dashboards to increase campaign effectiveness and impact business development goals
• Improved Salesforce report development for the sales team, to effectively measure conversion and top leads
• Oversaw spec creation for internal tools and API integrations for external vendor tools
• Converted Sales Department into a Customer Success Team, in order to address all points in the customer lifecycle
• Budgeted and developed SMS engagement and push notifications for promos and mobile messaging
• Planned and designed screens and responsive layouts, as well as native apps, from design to testing and live release
• Greatly improved website’s SEO and trained staff to enhance search optimization
• Planned new email marketing campaigns, and redesigned and rewrote content, resulting in a 3x increase in click-through
• Maximized performance of customer-facing pages and product by coordinating with VP of Product Management
• Integrated sales reports in salesforce.com and improved sales team utilization of Salesforce

Senior Manager of Engagement and Retention Marketing

Lulus.com

•	Created campaigns to engage fans via contests, blog posts, polls, and discussions 
•	Increased Facebook fan count by over 930% in a year, and continually increased fan engagement percentage and activity level
•	Built PR networks and media contacts, which resulted in brand being featured in national media such as The Today Show, Good Morning America, and The Nate Berkus Show
•	Designed and programmed features that allowed customers to interact with brand and each other and to participate in contests
•	Collaborated with hundreds of influential bloggers and major brands to cross-promote business via social media and blogs
•	Received overwhelmingly positive fan and customer feedback via Twitter and Facebook pages regarding brand campaigns and customer service 
•	Hosted numerous Twitter parties that resulted in thousands of tweets being sent by participants with mentions of the brand, which led to many new customers and consequent increase in sales
•	Set up and strategized cross-promotional campaigns with other companies and created beneficial partnerships
•	Analyzed metrics and statistics about the online community to understand how to most effectively involve fans and customers 
•	Identified power users and influencers in the online community, greatly increased interaction with them, and fostered their passion for the product. 
•	Created and held many successful fashion events in several large cities to increase brand awareness

Social Media Manager

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.


This week felt like watching the training wheels come off. 🚴🏻‍♀️

For a long while now, legal AI has been about experimentation and pilot programs. What I’m seeing shift is that AI companies are truly building for how legal work actually gets done, not just what sounds impressive in a demo.

The tools aren't just getting better, they're getting easier to deploy. Funding is happening left and right. And agentic AI? It's about to be everywhere.

Five main things caught my attention:

💰 GC AI raised a $60M Series B round. I'm proud to have been involved in their early growth as the Founding Marketer. Looking forward to seeing them continue to scale!

🤑 Clio raised $500M (largest legal tech round ever!) following its $1B vLex acquisition. Institutional investors are betting that AI-powered legal operations are the future.

🔍 OmniLex raised $4.5M for improved legal research and NLPatent secured $3M for agentic patent workflows.

⚙️ Alexi launched 74+ pre-built AI automations for contract review, due diligence, discovery, and risk assessments. Ready day one.

🤖 Thomson Reuters unveiled agentic workflows in CoCounsel that independently execute multi-step tasks and handle bulk review of up to 10,000 documents (minimal human intervention required).

You can swipe through the carousel for the full breakdown, or catch the deep dive in yesterday's Legal AI Insider newsletter on my profile with more news items.

PS: 🗓️ I'm hosting a webinar next week on 𝟮𝟬 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗮𝗹 𝗟𝗲𝗴𝗮𝗹 𝗔𝗜 𝗨𝘀𝗲 𝗖𝗮𝘀𝗲𝘀 because I want to keep helping legal professionals figure out what actually works. Real examples you can use in your work. Send me a message and I'll save you a spot.

Alessandra Colaci 

Training legal teams to use AI safely and effectively | Founder, Legal + AI

Legal AI Week in Review - Nov. 13, 2025

Some eye-opening investment dollars flowing into legal AI tools this week. 👀

I just published this week's Legal AI Insider covering the developments that caught my attention:

Over $560M in funding (Clio, GC AI, and others), agentic workflows launching from Thomson Reuters and Alexi, White & Case building their own AI assistant, and a surprising stat about legal aid adoption rates.

Over $560 million flowed into legal AI companies this week! Infrastructure capital. Security platforms. Workflow automation that legal teams can actua

Open article: Week In Review (November 12, 2025) by Alessandra Colaci • 4 min read

Anthony Natoli

LinkedIn

I work and partner with LinkedIn’s fastest growing tech companies, Enterprises and global brands as part of the New Business Marketing Solutions team.

Accomplishments thus far:

Responsible for 8+ figures of revenue generated since being off ramp in January 2024:

FY25: 112% to goal (8 figure quota)
FY24: 103% to goal (multi 7 figure quota)

Won a 1 million dollar customer in Q2 2025

Senior Account Executive

QA Wolf

Recruited to QA Wolf, a Series A Startup, to rebuild their entire outbound GTM motion for the SDR team.

Hired & lead a team of 7 rockstar SDRs.

Accomplishments prior to leaving:

→ Hired new team members, re-wrote outbound playbook and re-built tech stack infrastructure 
→ Built out lead-routing, qualification and SFDC account mapping & ownership
→ Increased meeting booked to SAO conversion rate from 30% to 80%
→ The team drove $2m in SAO qualified pipeline over 2 quarters 
→ Personally sourced $250k in pipeline

This helped QA Wolf hit their 2023 annual ARR goal, leading to a Series B round in 2024.

In addition to leading a team of SDRs, I reported directly to the co-founder / head of growth and worked cross-functionality with RevOps, Marketing, and Sales Leadership to optimize SAO & Pipeline production and efficiency.

Head of Sales Development

Lattice

Accomplishments before leaving for my first ever pursuit & opportunity into leadership:

→ FY23 Ramp: 102% quota attainment

Enterprise Account Executive

Outreach

Accomplishments before leaving:

→ FY22: 105% attainment | Closed 6 net-new logos in 9-months of ramp 
→ FY22: AVC $90k | $540k closed/won ARR
→ Built $1.2m in AE sourced pipeline in 9-months of ramp

New Logo Account Executive focused on companies with 500-10,000 employees

Demandbase

Promoted from AE to Sr AE after 1 year to work with Demandbase’s most innovative and strategic mid-market prospects & customers including Sprinklr, Braze, Accolade, Docebo, Fullstory, Checkout.com, D2L, Movable Inc, Axway, and many more.

→ Q1 2021 323% quota attainment 
→ Top rep globally for Q1

→ FY20 144% quota attainment | $2.5m in ARR closed/won
→ Top Mid-Market Rep in attainment & revenue globally 
→ FY20 Presidents Club

Senior Account Executive | Mid-Market

-FY18 130% Pipeline Attainment  
-Sourced over $2,000,000 in Closed/Won Opportunities
-Mid-market record for most meetings turned to pipeline in 1 month (22)
-Top SDR for Mid-Market Segment & rookie of the year
-Supported two AEs in our most strategic Mid-Market segment, San Francisco, CA
-Promoted to AE after 9 months in the role

Senior Sales Development Representative

Ethos Lending LLC

Full Cycle AE

150% quota attainment FY17 
125% quota attainment FY16

Presidents club FY16 & FY17

Business Development Representative

Senior Account Executive @ LinkedIn | AntNat Coaching | I post about sales, growth mindset and personal development based on my real-life experience

Senior Account Executive at LinkedIn | 10+ years in SaaS | In my role at LinkedIn, I work with high-growth tech companies, enterprises, and global brands to help them grow revenue.--~6 years ago, I almost quit sales...During the last week of Q4 in December 2019, I lost 3 deals in a single day and put up a 0 in my first Q4 as a SaaS AE. This was only a few weeks after I had hit a personal rock bottom, too. Just at the age of 26.Instead of throwing in the towel, I doubled down on feedback, learning, self development and skill building. 3 months later, I closed my first 6 figure ACV deal and never looked back. That same year (2020), I made President's Club and closed over $2.5m in ARR.Since then, my journey has lead me to where I am now.. As a result of my experiences, I now also share content that helps SDRs and AEs build and close more pipeline without sacrificing their personal development and mindset; all based on lessons from my real life experience.TLDR:  I am a normal guy with big goals who has been through some hard stuff and adversity. My mission is to use my real-life experience to help others crush it in sales &amp; life.In my free time, you will find me with my family, hanging down by the Jersey Shore, running, lifting, working out, hanging w/ my dogs, enjoying New York Sports, golf, trying new coffee shops and restaurants, and traveling.All content, thoughts and opinions are my own.For brand sponsorship opps please email anthony@natolisnuggets.com

Strategic Account Executive

Building a personal brand on LinkedIn changed my life. And no I’m not being dramatic. 

Here’s why you should consider it.. 4.5 years later and from 2k connections to nearly 60k:

-It helped me build thousands of connections, brand deal opps, network opportunities, & referrals
-It’s helped me tell my personal story and impact thousands
-It helped me land my current role! 

Most importantly, some of my content has helped others land new roles, hit their quota, earn more money and change their habits/behaviors, etc to live a better life. How damn cool?

& so much more.

All of this helped change the trajectory of my career & life.

The most common objections people tell themselves:

1. I don’t have the time
2. People will judge me

For “I don’t have the time” - I call BS. Show me your screen time and I bet we can find 30 minutes a day to post or comment. More tactical examples to help with this below.

For “people will judge me” - welcome to the club. Anything worth doing in life will A.) Put you out of your comfort zone and B.) Draw attention from people who are just sitting on the sidelines. That’s ok. Life is too short to take criticism from those not on the same path

Tactical:
-You don’t need to post every single day to start
-Stop scrolling TikTok/IG for 30 minutes and post instead
-Find content inspiration from others in your network. Reframe into your own story
-Tell YOUR story. Everyone has a journey to share
-Start with sharing lessons from your real life experience
-Share customer wins and how you are helping them
-Post content you genuinely enjoy
-Use DMs to actually connect with people you see posting on LinkedIn
-Comment your POV on posts! Another way to get into the mix! One of my comments had 50k impressions last week.

There’s a lot more here to share but I wanted to keep it simple.

At the very least, you build yourself career insurance, meet some great people and get your work out into the world. Who knows, you might end up landing some new clients, build that business or land that next dream role you’ve been wanting.

Happy Friday!

Senior Account Executive @ LinkedIn | Sharing lessons from my real-life experience to help sales reps win in sales & life | Sales Professional, Creator & Speaker

Soft skills in sales are what separate top performers. Here are 19 soft skills that you rarely will learn in a traditional sales training that can make all the difference:

→ Knowing how to get to friction fast
→ Balancing confidence with humility
→ Project Managing & Uncovering risk
→ Knowing what questions to ask & when
→ Listening for what’s not being said directly
→ Reading power dynamics inside an account
→ Knowing when to push vs when to pull back
→ Knowing how to influence & test champions
→ Navigating internal politics to get deal support
→ Remaining patient while still driving momentum
→ Turning complex problems into simple language
→ Conflict management when stakeholders disagree
→ Building trust without over-explaining or overselling
→ Framing conversations so customers feel ownership
→ Managing your own emotions and ego when you lose
→ Emotional regulation when deals slip or urgency drops
→ Executive presence on calls without being performative
→ Having good energy & not needy so prospects open up
→ Asking uncomfortable questions without sounding combative

Here's how you learn soft skills:
-Sometimes they come naturally to people (intangibles)
-9 out of 10 times you need to put in the reps and learn from losses
-Overcoming hard things in your personal life or past helps you build EQ
-Having a fun, interesting and joyful life out of work helps you remain centered

For me personally, I learned these things from getting burned in deals (learning the hard way) and overcoming hard things in life.

I try to learn from losses the best I can and constantly seek feedback.

I no longer put 'deals' on a pedestal or let them impact my self-worth. This works for me because it drives the energy in which I operate. This is how you 'detach'.

What did I miss?

Sunday: 

-Football
-Lots of coffee 
-Little bit of work
-Diner for breakfast 
-Recovery / rest day 
-HomeGoods, TJMaxx, PetCo

Feeling like Frank The Tank in this scene of Old School. 

Ready for a short week and Thanksgiving with the family. 

New puppy comes home next week. 

Excited for week 2 of my new running journey. 

Lots of good momentum at work with clients. 

Feeling grateful for everything. 

Let’s go.

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The Battle

Alessandra Colaci ⚡️

Anthony Natoli

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The Battle

Alessandra Colaci ⚡️

Anthony Natoli

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Alessandra Colaci ⚡️'s LinkedIn Performance

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Performance ScoreAlessandra Colaci ⚡️'s LinkedIn Performance