Darrien Watson
Growth, Product & AI Systems Leader
Founder of SquadTrip | Building AI-powered systems to scale teams | Product, Growth, Strategy, Operations & EIR
$20M
Gross Transactions
Scaled with AI-driven growth engines
$1.5M
VC Raised
Capable CEO who can raise capital
7M
Impressions
Growth Minded Strategist
Product & Growth Execution
End-to-end delivery from discovery to go-to-market launch
AI & Automation Systems
Internal tooling, orchestration, and operational scaling solutions
Strategy & Scaling
Market vision, growth loops, and systematic alignment
Contact Me
About
I build companies and products that scale. From zero to millions in revenue, from idea to MVP, from manual ops to AI-powered systems - I've done it as a founder, product leader and operator.
My edge is combining AI with execution across three pillars:
Growth Architect
SEO, AI driven distribution, outbound sales, and inbound funnels.
Product Builder
Discovery, design, MVP, technical project management + embedding AI into products.
AI Systems Operator
Building AI + automation in operations, customer success, and support from the ground up.

I can go deep in one area
Or connect the dots across all three. That's how I turn ideas into AI-powered growth machines.
My Story
Strategic execution across product, growth, and operations with measurable results. Each initiative follows Challenge → Strategy → Execution → Results.
1
Act I:
Builder at SS&C Tech, Intapp
At Intapp and early roles, I learned to build SaaS products in complex industries.
2
Act II:
Founder at SquadTrip
At SquadTrip, I took a travel fintech platform from idea to $20,000,000+ in transactions, raised $1,500,000 in venture caputal, and built growth, product and customer systems from zero. I automated onboarding, QA, and support - embedding AI into every layer of the business.
3
Act III:
Next Move
Now, I'm looking for my next challenge: applying my blend of growth, product, and AI-powered systems to help companies scale faster, smarter and leaner.
Writing & Ideas
Sharing insights on product strategy, travel tech, and startup operations through thought leadership and industry publications.
AIOps / Automation / Leadership
I share how integrating AI and automation into org workflows can shift team capacity, streamline decision-making, and free up bandwidth for high-impact tasks.
ContentOps + Automation Insights
In this post, I explore how ContentOps, automation, and AI intersect — and how product organizations can leverage them to improve operations and scale output.
"Mastering the Art of Selling" - Techstars Feature
Featured interview discussing sales strategies, founder mindset, and building sustainable growth in competitive markets. Insights from scaling SquadTrip and lessons learned.
Speaking, Media & Recognition
Industry recognition and thought leadership through speaking engagements, awards, and media features.
Awards & Recognition
  • Techstars Featured Founder - Highlighted for sales and growth expertise
  • CEO Weekly Feature - “Darrien Watson: Pioneering a New Era in Group Travel With SquadTrip”
Media & Speaking
  • Techstars Blog Feature: In-depth interview on mastering sales strategies
  • Product Discovery Workshops: Leading sessions on product-market fit
  • Industry Panels: Speaking on AI automation and growth scaling
  • Podcast Appearances: Discussing startup operations and travel tech
Let's Connect
If you need someone who can:
  • Drive Growth and scale with AI
  • Build product from Discovery → MVP → Early Sales
  • Engineer systems that leverage AI + automation to compound scale
Let's talk.
Schedule
Ready to discuss opportunities and strategic partnerships? Click here
"I thrive at the intersection of product, growth, and AI automation — turning complex challenges into scalable solutions that drive measurable business impact."