Your GTM teams are working hard and still missing their targets.It's time to turn on your machine.

Fractional GTM operations leadership for Series A–C startups tackling hard problems and ready to scale demand, systems, and teams together.

What I work on

GTM strategy & planning

Before you fix the system, you need to know what's actually broken. I analyze the data and work through the problem in a structured way, then build a plan the business can execute.

  • GTM diagnostic
  • Growth readiness audit
  • Business case development

Revenue data & reporting

Most teams have dashboards. Few can explain the actual drivers and how to fix them. I define the metrics, establish a single source of truth, and build reporting that drives action.

  • AI-native forecasting and pipeline reporting
  • Funnel and cohort analysis
  • Experiment design and A/B testing

GTM systems & CRM

A solid stack needs to be lean, integrated, and properly configured. I audit what you have, define the architecture, and drive the rebuild.

  • HubSpot and Salesforce architecture
  • Lifecycle stages and routing logic
  • Tech stack design and vendor selection

Pipeline & demand efficiency

Demand problems show up two ways: not enough of it or a leaky funnel. I'll help you fix pipeline and conversion, so you stop throwing good money after bad.

  • Channel optimization and growth loops
  • Lead nurture and lifecycle workflows
  • CAC and payback modeling

Post-sales operations

Sales gets the attention, but expansion, retention, and support often determine whether you hit your targets, and they shouldn't be an afterthought.

  • Activation and onboarding
  • AI-native knowledge and self-serve
  • Renewal and expansion motions

Operating rhythm

A great strategy is meaningless without execution. I install the milestones and mechanisms that drive visibility, accountability, and alignment across the team.

  • OKRs and quarterly planning
  • Capacity modeling and headcount planning
  • Pipeline and business reviews

How I operate

Regardless of the domain, my approach is the same.

01

Analyze

I dive into the data to understand the what and why, building the models and analyses that surface the drivers, then turning insight into hypotheses that drive action.

02

Design and build

I build end-to-end. Strategy, XFN planning, and implementation, building intentional systems that solve your pain points and move your metrics.

03

Drive adoption

I don't throw over the wall and pray. I bring experienced leadership that knows how to influence and manage change so that the work is actually adopted.

04

Hand off

Automations, documentation, training and enablement so the team owns it after I leave. Everything is built to outlast the engagement.

How we partner

Fixed scope

You have a specific question or a known gap.

A defined deliverable at a fixed fee. I'll scope it, execute without hand-holding, and hand you something concrete (a diagnosis, a readiness plan, a system rebuild). A good way to start before committing to something bigger.

Ongoing

There are many challenges and you lack capacity to own them all.

I embed and do the work across whatever surfaces the problem touches. You get one senior operator across the full problem, not a specialist who stops at the edge of their lane.

Advisory

You have a team who could benefit from a senior perspective.

Regular access to someone who has seen your problem at high-growth startups. A sounding board for the leader and a guide for the team, so you're confident in the calls you're making and the things you're building.

What to expect

Growth

1.8×

YoY growth while cutting CAC 30%

Series B defining a new category with no clear playbook.

Built a full-funnel engine, optimized with high-velocity experimentation, turning demand and conversion gains into revenue.

Quality & Velocity

20%

Forecast accuracy gain, shipped in 5 days

Early-stage startup flying blind with no pipeline visibility.

Built a Claude Code solution that surfaced recommendations and gave clear line of sight to EOY targets.

Efficiency

25%

Efficiency gain with zero headcount increase

Series B post-sales team drowning in repetitive inquiries.

Owned the build-vs-buy decision and implemented an AI-native knowledge system that drove self-serve for customers.

Why me

Jonathan Diamond
Jonathan Diamond Fractional GTM operations leader partnering with Series A–C startups tackling hard problems and ready to scale demand, systems, and teams together.

I've worked on this problem before.

And if I haven't, I'll figure it out. I've led GTM Ops, BizOps, and Customer Ops, and been consistently tapped in my career to solve problems because of how I approach them, not because I already knew the answer.

I do the work and stay until it lands.

I own the full arc. Strategy and execution across whatever the problem touches, plus the change management to make sure it actually lands. The work isn't done when it's built. It's done when the team adopts and owns it.

Senior judgment with fast execution.

I bring the experience to know what's worth building and the latest tools to build it faster than was possible before. Analysis, systems, and automations that used to take weeks, now done in days.

And I'll be honest about what I'm not.

I'm not a certified platform admin and I'm not a consultant who leaves a deck. I'll be upfront with how far I'll get on my own and tap my network when you need something out of my lane.

Built at AirbnbForwardOysterSubstack