I build
GTM nervous systems
that scale revenue with AI

Efficiently & sustainably scaling revenue from $10M to $100M ARR.

Henry Finkelstein

I'm looking for full-time roles in Transformative AI and RevOps

↓ Scroll to explore

What Leaders Are Saying

Perspectives from executives and operators I've partnered with

"

Henry is an incredibly gifted problem solver. He is a results oriented professional who is an absolute delight to work with!

Matt Metcalf
Matt Metcalf
Chief Executive Officer
LinkedIn Profile
"

Henry is, without a doubt, one of the most impressive people I've ever known. He is analytical, intuitive and creative with frequent flashes of brilliant insight. Henry ... impressed me with his energy, enthusiasm and incredible work ethic and drive.

Melissa McCool
Melissa McCool
Chief Operating Officer
LinkedIn Profile
"

Henry has this incredible drive and work ethic - he sets goals and works relentlessly to achieve them. He is talented and adaptable - he can quickly jump in on almost anything ... I admire how thoughtful and methodical he is when making decisions and crafting highly effective processes and structures.

Jeff Yang
Jeff Yang
Chief Technology Officer
LinkedIn Profile

Transformational Objectives & Key Results

Millions in incremental revenue & cost savings.

First-principles AI strategy aligning people > process > tech with team maturity.

🤖

Deploy AI Agents
Across GTM & Ops

CloudTrucks

~$2.2M
Annualized Incremental Revenue + Savings
20x faster speed to lead
34% increase in SQL conversion rate
60% reduction in human sales reps
30k monthly call volume to Voice AI
Managing hybrid team of 86 (6 humans + ~80 AI agents)
📈

Accelerate GTM Data
Insights & Actions with AI

CloudTrucks

18x
Growth in Team Efficiency
14% improvement in AI on-call resolution
11 AI workflows in prod (incl. team training)
37 report automated rev architecture suite
28 point AI agent eval framework
2 power Gemini Gems shared and trained cross-functionally
🚀

Build GTM Operations
from Founder-Led Motion

Rising Team

328%
ARR Growth in 18 Months
10x increase in qualified leads
Implemented 1st integrated GTM tech stack
Created 1st GTM playbooks, scripts, enablement
Led structured interviews to hire 1st AE + CSM
Cross-functional alignment across marketing, sales & customer success
🔥

AI-first GTM transformations for efficient, sustainable $$$ impact.

What Teammates Are Saying

Perspectives from peers and direct reports I've worked alongside

"

Henry is a true transformational AI leader. He doesn't just understand the technology; he has a talent for designing and implementing AI-driven workflows that accelerate team performance and achieve tangible business outcomes. Henry is an exceptional leader who knows how to build, innovate, and inspire.

Eva Myrback
Eva Myrback
Sr. Business Operations Manager
LinkedIn Profile
"

Henry is that rare leader who strikes the balance between reason and compassion. Henry addresses business problems by synthesizing theory, best practices, and his own experience to formulate a logical, experimental approach, which he then applies systematically. ... In a compassionate way, Henry takes a similar approach to his team. He creates an environment of psychological safety where he challenges and encourages all team members to improve the team and its processes, even if that means overturning his own ideas. He sets goals clearly, but doesn't tell the team how to achieve them.

Glen Dils
Glen Dils
Customer Success Manager
LinkedIn Profile
"

Henry is an inspiring leader who truly cares about his team. He challenged me to push my limits and always made me feel connected to the mission and purpose of our work. He consistently looked out for my interests and ensured that I felt supported. ... Henry is a dedicated and talented professional who brings out the best in his team and everyone he works with.

Serena Haddad
Serena Haddad
Account Executive
LinkedIn Profile

My Career Path

Three chapters that shaped how I think about building sustainable, AI-powered revenue operations

Total: ~5 minutes of narrative
Pre-GSB: Building Foundation
~2 min
Early Career

Pre-GSB: Building Foundation

How I discovered the intersection of operations, data, and revenue growth that would define my career.

Key Themes:
  • First exposure to revenue operations
  • Learning GTM fundamentals
  • Early wins and pattern recognition
At GSB: Strategic Transformation
~2 min
Stanford Graduate School of Business

At GSB: Strategic Transformation

Combining academic rigor with hands-on projects to develop frameworks for scaling revenues and teams.

Key Themes:
  • Business training meets real-world experience
  • Frameworks for innovation and growth
  • Network building and thought leadership
Post-GSB: Scaling Impact
~2 min
Recent Years

Post-GSB: Scaling Impact

Applying everything I learned to drive measurable revenue growth and operational efficiency at high-growth startups.

Key Themes:
  • Building GTM infrastructure from zero
  • Implementing Enterprise AI at scale
  • Managing hybrid human-AI agent teams
💡

Structured Interview Question #1 + Why This Narrative Matters

Every structured interview starts with a "Tell me a little bit about yourself and your background."

These videos answer that question and share the why behind the what I've accomplished in my career. I share the evolution of thinking, the lessons learned, and the throughline between experiences that led to my current approach to AI-native Revenue Operations.

What Leaders Are Saying

Perspectives from executives and operators I've partnered with

"

Henry is an inspiring leader with exceptional strategic thinking and operational expertise. He possesses a distinct ability to build managerial and documentation systems that drive revenue growth and help companies scale. Henry is not only caring and genuine, but also an awesome person to work with.

Ryan Starks
Ryan Starks
VP Growth & Marketing
LinkedIn Profile
"

Henry is a strategic thinker whose methodical and detailed approach toward project planning and work results in successful outcomes every time. He has a keen ability to manage projects both efficiently and effectively. He would be an asset to any organization.

Noelle Simmons
Noelle Simmons
Senior Vice President, HR
LinkedIn Profile
"

Henry is a thoughtful and personable addition to any company. He has the ability to rally, lead, and influence any team to a common goal. Henry is valuable in any strategic capacity to include ground breaking projects as a project manager.

Jason Cooper
Jason Cooper
Director, IT Ops & Services
LinkedIn Profile

What Teammates Are Saying

Perspectives from peers and direct reports I've worked alongside

"

Henry is an incredible colleague and outstanding technology professional. He has a natural talent for understanding and communicating complex problems and recommending simple, effective solutions.

Clinton Rupp
Clinton Rupp
Technology Professional
LinkedIn Profile
"

In my time working alongside Henry I can easily place him in the handful of the best talent I have ever come across! Going the extra mile, every task was detailed and solutions were thoughtfully executed.

Levi Martin
Levi Martin
Operations Specialist
LinkedIn Profile
"

Henry is an awesome steward. He feeds me delicious treats, takes me on cool adventures, and gives me plenty of rubs. Five stars.

Meke Dom
Meke Dom
Head of Fuzzy Operations
🐕PawedIn Profile

When I'm Not Working

When I'm not scaling revenue or vibe coding, I study human Thriving from first principles. I spend time with my family and friends, ideally in nature. I practice a Zen tradition of ritual tea called Cha Dao ("The Way of Tea"). I produce and attend immersive events and festivals. I nerd out while I bulk out.

Trail running half at 8k elevation
 

Trail running half at 8k elevation

Serving tea at Stanford
 

Serving tea at Stanford

Backpacking and berries in Oregon
 

Backpacking and berries in Oregon

Naga Dragon in Golden Gate Park
 

Naga Dragon in Golden Gate Park

Running the miner's ditch ridge
 

Running the miner's ditch ridge

Blizzard storm
 

Blizzard storm

Tea chaxis
 

Tea chaxis

Picking apples
 

Picking apples

Underground big wheels racing
 

Underground big wheels racing

Troubadour music festival
 

Troubadour music festival

Crater lake
 

Crater lake

Meke signature move
 

Meke signature move

Audio-book-o-phile
 

Audio-book-o-phile

MOMA sound exhibit
 

MOMA sound exhibit

Sailing Translated9
 

Sailing Translated9

Event production
 

Event production

Repairing teaware
 

Repairing teaware

Full moon hike
 

Full moon hike

Hiking old growth
 

Hiking old growth

Red tea white bowls
 

Red tea white bowls

Yup, that beard
 

Yup, that beard

Annual review
 

Annual review

"In 2015, I produced a feature-length circus with 100 performers and creators. If you think your last Zoom call was a joke, try running a meeting with a bunch of clowns."

How We Know We're a Great Fit

The right fit drives mutual success

🏢

Company Stage & Culture

  • Series B/C stage with proven product-market fit
  • AI native approach to GTM
  • High-growth trajectory with ambitious revenue targets
  • Culture of experimentation and data-driven decision-making
  • Competitive compensation for top 1% performer
🎯

Role Characteristics

  • RevOps or Transformational AI leadership position
  • Direct impact on GTM strategy and execution
  • Ownership of AI/automation roadmap for revenue functions
  • Cross-functional collaboration with sales, marketing, customer success, product, and operations
👥

Team & Resources

  • Ability to build and lead a revenue operations team
  • Budget and authority to implement modern GTM stack
  • Executive partnership with CRO/VP Sales
  • Support for continuous learning and professional development
⚠️

What Won't Work

Being direct saves everyone time. These are environments where I won't be successful:

  • ×Early-stage (pre-Series B) without rapid MoM growth
  • ×Traditional sales approach without interest in AI/automation
  • ×C-suite not convinced on value and purpose of Revenue Operations
  • ×Role limited to tactical execution without strategic influence

If this resonates with your company's needs and culture, let's talk.

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📬

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