Open to opportunities

Product Leader. AI-Native Builder.

Enterprise SaaS, Operational Systems & AI-Native Development

Former PM at Intapp (NASDAQ) and SS&C Technologies (NASDAQ)

I build products that scale — from enterprise SaaS to zero-to-one platforms. More technical than the average PM, I ship AI-assisted, design systems that drive operational efficiency, and partner effectively with engineering teams.

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Darrien Watson
🤖 AI Automation
⚙️ Internal Tooling
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01

The Quick Version

Ten years in product, spanning enterprise SaaS at Intapp and SS&C Technologies (both NASDAQ-listed), and founder-led startups where I built from zero.

My expertise runs deep in B2B platforms, payments infrastructure, and marketplace dynamics. At SquadTrip, I'm more technical than the average PM — shipping AI-assisted while collaborating with engineering.

Looking for product leadership roles at AI-native companies or B2B platforms where I can bring this blend of enterprise rigor and founder resourcefulness.

02

How I Think

Start with funnel math, not feature requests. Here's how I turned a 92% activation drop-off into a clear prioritization roadmap.

1

Map the Funnel, Find the Bottleneck

Sign Up
100%
Trip Created
64%
Trip Published
8%
92% drop-off
First Booking
5%
Revenue
3%
⚠️
Critical Insight: 8% Creation → Publication Rate

This single data point shifted the conversation from "whose request matters most" to "what moves the number that matters most."

2

Let the Math Decide, Not the Volume

🤖 Sales Automation — AI-powered prospect research & outreach HIGHEST LEVERAGE
💬 Support Automation — Claude trained on Intercom data HIGHEST LEVERAGE
EXPLICITLY DEPRIORITIZED (CUSTOMERS ACTIVELY REQUESTING)
📊 Aggregate Dashboard — cross-trip visibility DEPRIORITIZED
🏨 Rooming Assignments — group accommodation logic DEPRIORITIZED
📣 Referral Enhancements — nudges & email triggers DEPRIORITIZED
📈 Affiliate Analytics — partner performance tracking DEPRIORITIZED
Why: Automation compounds faster. Improving activation is the single highest-leverage intervention — every other feature only helps users who've already cleared the bottleneck.
3

Find Shared Dependencies Across Teams

SALES NEEDS

Better prospect visibility — who's active, where they dropped off, engagement signals

SUPPORT NEEDS

Faster access to customer payment history, trip status, and conversation context

↓
🔧 SHARED DATA PIPELINE

Build the unified layer once → unblock both teams simultaneously

The PM's job is to see these connections before either team does.
4

Sequence for Learning, Not Just Delivery

1
Phase 1 Performance 10× faster

Reduced load times from 29s → 2.8s

💡 Validated that speed was blocking engagement, not content
2
Phase 2 Information Architecture Self-serve reports

Restructured data so organizers stop exporting to spreadsheets

💡 Revealed which data views organizers actually need vs. assumed
3
Phase 3 Traveler Actions Task completion ↑

Redesigned how users take actions on travelers (JTBD framework)

💡 Built on Phase 1-2 learnings about real usage patterns
Each phase shipped independently and informed the next. Engineering had input on sequencing based on technical dependencies, which accelerated delivery.
03

AI Systems That Scale Teams

I build internal AI tools that multiply team capacity without adding headcount. The pattern: identify a constraint, design an AI solution, ship it, measure impact.

SYSTEM DESIGN SQUADTRIP · SALES ENABLEMENT

AI-Powered Interactive Demo Engine

Automation-first sales tool enabling personalized, self-guided product demos with AI-driven lead scoring, dynamic content assembly, and CRM integration.

Claude AI Core Automation Pipelines Data & Analytics
PROSPECT ENTRY
📧 Email Campaigns Drip sequences
🌐 Website CTA Embedded widget
🤝 Sales Outreach Personalized links
🔗 Partner Referrals Co-branded entry
↓
AI ORCHESTRATION LAYER
📊 Lead Scoring AI qualification
🧠 Claude AI Core Intent Analysis · Personalization Trained on Intercom + product data
🔄 CRM Sync HubSpot · Pipedrive
📁 Use Case DB
💰 Pricing Engine
⭐ Testimonials
📈 ROI Calculator
↓
DEMO EXPERIENCE ENGINE
🎯 Dynamic Demo Builder Persona-matched walkthrough
🧪 Interactive Sandbox Live trip creation flow
💬 AI Chat Assistant Real-time Q&A + objections
↓
OUTPUT & CONVERSION
📉 Engagement Analytics Heatmaps · drop-off
⚡ Auto Follow-Up Triggered sequences
🚀 Conversion Pipeline Demo → Trial → Paid
Segment-Aware Personalization Retreat leaders · Tour ops · Wedding planners
Behavioral Triggers Auto-escalate high-intent prospects
Multi-Touch Attribution Track demo → activation journey
A/B Demo Variants Test messaging & flow optimization
Sales Automation

AI SDR System

Problem: Manual outbound was consuming 15+ hours/week with inconsistent lead qualification and sub-2% response rates. Couldn't justify hiring a dedicated SDR at our stage.

Solution: Built an AI-powered outreach system that researches prospects, generates personalized sequences based on their company and role, scores leads by fit signals, and handles follow-ups. Human review kicks in only for engaged prospects.

3.2× response rate improvement
12hrs saved per week
AI handles pattern-based qualification; humans focus on relationship-building and closing.
Support Automation

AI Support Agent

Problem: Support volume was growing 40% quarter-over-quarter. Average first response time had slipped to 4+ hours. Hiring wasn't in budget.

Solution: Trained Claude on 18 months of Intercom conversation history — 2,400+ resolved tickets. System handles common queries instantly, drafts responses for edge cases, and escalates complex issues with full context to the human team.

68% queries resolved by AI
<2min median first response
Team now focuses on complex escalations and relationship-building instead of routine answers.

These systems freed our team to focus on high-value work — the kind that actually moves the needle. The methodology transfers to any company: find the bottleneck, build the AI solution, measure the impact.

04

What I Do Best

Product Leadership

  • End-to-end ownership: discovery → specs → shipping → measuring
  • Complex B2B workflows (legal tech, financial services, travel)
  • Jobs-to-Be-Done, outcome-driven roadmaps, experimentation

AI-Native Development

  • More technical than the average PM — prototype, debug, ship
  • Built governance frameworks for Claude Code
  • AI across product lifecycle: design, prototyping, PRDs, code review
  • Deeper empathy for engineering workflows
Core Strength

B2B Platform & Payments

  • Payments infrastructure design and optimization
  • Marketplace dynamics and multi-sided platforms
  • Enterprise SaaS for AmLaw 100 and institutional finance
05

Selected Work

Product thinking in action — not just outcomes, but the approach behind them.

Product Strategy

Unified Agent Workspace

Context

Support agents at a mid-market HR platform toggled between 5-6 disconnected systems on every customer call — a workflow that cost minutes per interaction and degraded service quality.

Approach

Decomposed 6 compounding problems, designed an 11-feature MVP with phased architecture, and built a working prototype — all grounded in a "read before write" principle.

Deliverables

Full case study →

Product strategy, interactive prototype, data architecture, delivery plan, and success framework.
Performance

Dashboard Performance Optimization

Context

SquadTrip's trip dashboard was loading in 29 seconds, causing significant user drop-off at the most critical moment — when organizers were trying to manage their trips.

Approach

Diagnosed bottlenecks through performance profiling, prioritized fixes by impact/effort ratio, and shipped iteratively rather than attempting a big-bang rewrite.

Outcome

10× faster load time

29s → 2.8s, directly impacting user retention

Activation

Conversion Funnel Analysis

Context

Only 8% of users converted from "Trip Created" to "Trip Published" — the critical activation metric for a marketplace business.

Approach

Mapped the complete user journey, identified friction points through session analysis, and designed targeted intervention experiments at each drop-off point.

Learning

Activation > Acquisition for marketplaces

Getting users to their "aha moment" faster compounds across the entire funnel.

AI Implementation

AI-Powered Support System

Context

Needed to scale customer support without adding headcount — a common early-stage constraint.

Approach

Trained Claude on Intercom conversation history to handle common queries, with clear escalation paths to human support for complex issues.

Learning

AI as augmentation, not replacement

The goal is freeing humans for high-touch interactions, not eliminating them.

06

Career Timeline

01

Enterprise Foundation

SS&C Technologies NASDAQ
Intapp NASDAQ

Built products for demanding, regulated industries — from hedge funds and private equity at SS&C to AmLaw 100 law firms at Intapp. Learned to navigate enterprise sales cycles, compliance requirements, and complex B2B workflows.

02

Founder

SquadTrip, Co-Founder · 2022 – Present
Techstars '22 Phocuswright Hot 25 $1.5M+ Raised

Scaled a B2B travel platform from zero to $20M in gross transaction volume. Built payments infrastructure from scratch, established operational processes and systems, and grew the team while wearing every hat — product, engineering, ops. Raised from Forum Ventures, Atento Capital, and others.

  • Infrastructure: Designed and built payments systems, booking engines, and real-time collaboration tools
  • Operations: Created processes for support, QA, and customer success that scale without headcount
  • Team: Hired, onboarded, and developed team members across product, engineering, and operations
03

What's Next

Seeking a product leadership role at an AI-native company or B2B platform. Particularly interested in payments, marketplaces, and developer tools — domains where I've built deep expertise.

I've also been consulting in this space — helping early-stage startups with product strategy, AI implementation, and go-to-market. References available upon request.

07

What I'm Looking For

I'm seeking a product leadership role at a company building AI-native products or B2B platforms. I'm drawn to teams tackling payments, marketplaces, or developer tools — domains where I've built deep expertise.

I'm particularly excited about companies where AI isn't just a feature but a core part of how the team operates. I've spent the last two years building workflows where Claude is my primary development partner, and I want to bring that experience to a team pushing the frontier.

Also Available

Selective consulting with early-stage startups (Seed to Series A) who need product leadership without the full-time commitment.

Let's Talk

Whether you're hiring or need consulting help, I'd love to connect.

💼

Hiring?

Let's discuss how I can contribute to your product team.

dcharltonwatson@gmail.com LinkedIn Profile
🚀

Need Consulting?

Product strategy, AI implementation, and growth systems for early-stage startups.

dcharltonwatson@gmail.com