Independent Operator • 2026
Revenue Growth Expertise for

Founder-Led & Bootstrapped
Software Companies

Serving organizations outside traditional VC/PE ecosystems. Equitable operational expertise for self-funded companies in the $5M-$30M ARR range—including AI-first startups.

Your Growth Challenges Are Different

VC-backed companies have armies of operators. You deserve the same level of expertise— without the equity dilution or board complexity.

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Founder-Led Focus

Built for companies where founders still drive the vision and own their decisions. No committee consensus required.

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Bootstrapped Mindset

Efficient capital deployment. Every dollar counts. Growth strategies designed for profitability, not just top-line vanity metrics.

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Equitable Partnership

No hidden agendas. No portfolio priorities. Just focused expertise to help you scale your way, on your timeline.

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AI-First Ready

Deep understanding of AI-native business models, product-led growth, and the unique GTM challenges of 2026's landscape.

Go-to-Market Operational Expertise for Predictable Growth

Head of Sales Assist

Hands-on expertise to unblock your sales team and deliver consistent revenue—without waiting for a full-time hire.

  • Accelerate new VP/CRO performance and reduce ramp time
  • Establish operating cadence and decision frameworks
  • Remove tactical blockers and provide project completion air cover
  • Build repeatable processes that scale with your team

Interim/Fractional CRO

Strategic and tactical revenue leadership to scale operations and optimize your unit economics for sustainable growth.

  • Design scalable revenue systems and team interfaces
  • Harmonize metrics and instrumentation through RevOps
  • Serve as connective tissue across marketing, sales, and CS
  • Execute with founder-level urgency and care

Advisory & Guidance

Expert counsel on GTM strategy, revenue models, and critical hires to maximize your company's value and optionality.

  • Strategic planning and measurement frameworks
  • Validate revenue model and pricing strategy
  • Guide critical GTM and leadership decisions
  • Prepare for due diligence and value conversations

2026: The Year of AI-First Revenue Models

AI-native companies face unique GTM challenges that traditional SaaS playbooks don't address. Usage-based pricing, product-led growth, and rapidly evolving buyer expectations require different operational expertise.

I've spent the past year working with AI-first startups to understand what actually works— and what's just hype. Let's build your revenue engine for the reality of 2026, not 2019.

AI-First Revenue Capabilities

  • Hybrid pricing models (subscription + usage + outcome-based)
  • Product-led growth motion design and optimization
  • AI-powered sales enablement and automation
  • Customer success for consumption-based models
  • Rapid iteration on GTM as product evolves

Revenue Operations Excellence

Foundational Systems & AI-Augmented Processes
That 10x Your Revenue Outcomes

Not through more headcount—through better processes, clearer metrics, tighter alignment, and strategically deployed AI agents that handle the operational load so your team can focus on what humans do best.

Growth Architecture That Scales

Built on Winning by Design principles, I establish foundational systems that don't just work today—they scale as you grow from 20 to 200+ people, and adapt as AI agents take on increasing operational responsibility within your revenue motion.

Design operating cadence and decision-making frameworks
Codify repeatable processes for planning and execution
Create accountability structures that actually stick
Build systems that survive leadership transitions
Identify where AI agents can own operational steps end-to-end
The Five Operational Pillars — AI-Augmented

My approach to revenue operations centers on five interconnected capabilities. In 2026, each pillar has a human layer and an emerging AI-agent layer— knowing where to deploy which is the new operational discipline.

Interact

Enable teams to work better together across the revenue cycle.

Agent Candidates
  • Meeting prep briefs auto-generated from CRM + product usage data before every customer call
  • Cross-functional Slack digests surfacing blockers across sales, CS, and product without manual standup overhead
  • Automated deal room creation and stakeholder mapping on new enterprise opportunities

Interface

Strengthen connections across functions—marketing, sales, CS, and product.

Agent Candidates
  • Bi-directional CRM ↔ product analytics sync with enrichment agents that flag expansion signals and churn risk in real time
  • Handoff agents that write and route transition summaries when accounts move between sales and CS
  • ICP scoring agents that continuously re-rank your pipeline against evolving ideal customer profiles

Plan

Drive strategic planning and execution with clarity on priorities and resources.

Agent Candidates
  • Territory and quota modeling agents that run scenario analysis across rep capacity, TAM, and historical attainment
  • QBR package generation—agents that pull metrics, write variance narratives, and draft board-ready slides from structured data
  • Capacity planning agents that model hiring curves against pipeline coverage ratios

Measure

Harmonize metrics through RevOps instrumentation—one source of truth across the revenue org.

Agent Candidates
  • Anomaly detection agents that monitor pipeline velocity, win rates, and NRR—alerting on deviations before they become misses
  • Attribution agents that reconcile multi-touch marketing data with closed revenue across channels
  • Consumption metric agents for usage-based models that translate product signals into ARR forecasts

Communicate

Align messaging across the organization—internally and externally.

Agent Candidates
  • Win/loss interview synthesis agents that extract recurring themes and feed them back into sales playbooks automatically
  • Competitive intelligence agents that monitor market signals and update battlecards on a defined cadence
  • Personalized outreach agents operating within brand guardrails—scaling top-of-funnel without sacrificing signal quality
Agentic Revenue Operations

The next frontier isn't AI-assisted workflows—it's AI agents that own discrete revenue processes end-to-end, escalating to humans only on exceptions. I help you identify, design, and deploy these automations within your existing stack—without over-engineering or over-spending.

Ready Now

Pipeline Hygiene Agent

Monitors CRM for stale deals, missing fields, and stage progression anomalies. Flags reps on exceptions and updates forecast categories automatically. Eliminates the weekly RevOps data cleanup cycle.

HubSpot / Salesforce + n8n / Zapier
Ready Now

Onboarding Milestone Agent

Tracks new customer product adoption against defined milestones. Triggers CS plays when engagement drops below threshold—before the customer raises a risk flag. Reduces time-to-value and early churn.

Product analytics + CS platform
Ready Now

Revenue Reporting Agent

Compiles weekly and monthly revenue metrics from CRM, billing, and product data. Writes structured narrative summaries and distributes to stakeholders. Reclaims 4–8 hours/week of RevOps bandwidth.

Data warehouse + LLM + Slack/email
Emerging

Expansion Signal Agent

Continuously monitors usage patterns, support tickets, and engagement signals across your customer base. Surfaces expansion-ready accounts to CS with context and suggested plays—before the QBR conversation.

Multi-source enrichment + CRM write-back
Emerging

Forecast Reconciliation Agent

Runs scenario models against pipeline data, historical conversion rates, and rep-submitted forecasts. Surfaces discrepancies and generates confidence-adjusted projections for leadership review.

CRM + forecasting tool + LLM reasoning
Emerging

Competitive Response Agent

Monitors public signals—competitor pricing pages, G2 reviews, job postings, press releases—and updates internal battlecards. Sales reps always have current intelligence without RevOps manually curating it.

Web monitoring + structured knowledge base

The right time to deploy agents is after the underlying process is well-defined and instrumented—not before. That's the work we do together first.

I'm not here to double your outcomes—I'm here to 10x them through better systems, clearer processes, tighter execution, and AI agents that scale what your team already does well.

Operational AI-driven excellence in 2026. Get there from Here. Ask for Help early.

Extended Network

Independent doesn't mean isolated. Access to world-class operators when you need them.

John Williams

John Williams

Chief Principal

+1 (202) 465-7129

Advisewell

Advisewell

Blackbelt Executives

Extended operator network

Pavilion

Pavilion Community

Global Executives

Cross-functional expertise

John Williams in a meeting room
Let's Talk About Your Growth

Free 15-minute strategy session to explore if we're a fit. No pitch, no pressure—just honest conversation about your revenue challenges.

Book Your Strategy Session