Open to opportunities

Product Leader. I build teams and platforms that scale.

Multi-surface platforms across the full customer lifecycle — and the product orgs that ship them

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

I build and lead product organizations from the ground up — hiring and coaching PMs with clear ownership of outcomes — along with the web, mobile, and CRM-backed platforms that serve operators and end-customers at once. More technical than the average PM, I partner deeply with engineering and use AI across the product lifecycle to move faster.

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Darrien Watson
👥 Team Building
🔄 Lifecycle Platforms
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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.

I've built and led product organizations from the ground up — hiring, managing, and coaching PMs with clear accountability for outcomes — and owned multi-surface platforms (web, mobile, CRM-backed) that serve two groups at once: the operators running day-to-day operations and the end-customers moving through discovery, transaction, and everything after.

Looking for product leadership roles at mission-driven organizations and platforms where I can bring this blend of enterprise rigor and founder resourcefulness.

02

How I Think

Start with the funnel math, not the feature requests. Here's the repeatable method I use to turn a problem — like a 92% activation drop-off — into a clear, defensible 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

Leadership in Practice

I build self-sufficient product teams, restructure orgs around clear ownership, and develop the people in them — from the PMs I manage directly to the founders I coach.

Team Building

Built a Product Org from Zero

The build: Hired and developed a cross-functional product team from scratch at SquadTrip — 2 PMs, 5 engineers, 2 QA, and 1 designer — structured around clear domain ownership.

The result: A self-sufficient team that ships without the founder in the room, with each PM accountable for outcomes in their domain.

10 person team built from scratch
2 PMs hired, managed & developed
I build teams that own outcomes, not task lists.
Org Design

Restructured a Group for Ownership

Problem: At Intapp, product ran on a shared-resources model — capacity was borrowed across initiatives and accountability for outcomes was diffuse.

Solution: Reorganized into a dedicated pod of 5 with end-to-end ownership of its domain — replacing borrowed capacity with a team accountable for results.

5 person dedicated pod formed
3× active usage growth across the base
Clear ownership beats shared resources every time.
Coaching & Mentorship

Developed Product Leaders at Scale

The work: Coached and mentored PMs and founders through 1:1s and structured workshops — as an Expert Speaker for Product That Counts (500K+ member PM community), Product Coach at Build in Tulsa, and Mentor at Black Travel Summit Launchpad.

The throughline: Developing other people's judgment — how to size opportunities, defend tradeoffs, and own outcomes.

100+ PMs & founders coached
3 accelerator programs
Leverage is developing leaders, not just shipping features.

One outcome I'm especially proud of: I helped a healthcare startup assemble an AI-enabled product team — restructuring how they build so a lean team could do the work of a far larger one, saving them hundreds of thousands in resource costs. Leadership leverage isn't just hiring — it's designing the team and the system around it.

04

What I Do Best

Building & Leading Product Teams

  • Built product orgs from the ground up — hiring, managing, coaching PMs
  • Org design around core domains with clear ownership of outcomes
  • OKR alignment; operating at both strategic and execution levels
Core Strength

Multi-Surface Platforms & Lifecycle

  • End-to-end ownership: discovery → specs → shipping → measuring
  • Web, mobile, and CRM-backed platforms serving operators + end-customers
  • Jobs-to-Be-Done, outcome-driven roadmaps, experimentation

AI-Native & Technical Depth

  • More technical than the average PM — prototype, debug, ship
  • AI across the product lifecycle: design, prototyping, PRDs, code review
  • Deeper empathy for engineering workflows
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 $30M+ 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 where I can build and lead a product organization and own multi-surface platforms that serve real people across a full lifecycle. Especially drawn to mission-driven organizations solving problems that matter.

I've also been consulting — helping teams with product strategy, org design, and AI implementation. References available upon request.

07

What I'm Looking For

I'm seeking a product leadership role where I can build and develop a high-performing product team and own the strategy for multi-surface platforms that serve operators and end-customers across a full lifecycle. I'm especially drawn to mission-driven organizations solving meaningful problems at scale.

I bring enterprise rigor from regulated industries, founder resourcefulness from building zero-to-one, and a data-driven approach to every decision. I also use AI across the product lifecycle — not as a buzzword, but as a practical way to ship faster and partner more deeply with engineering.

Also Available

Selective product strategy consulting for teams that need senior product leadership on a fractional basis.

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