Mastering the Complex Enterprise Sale: Build the Enterprise Muscle

In this newsletter, I break down the 3 critical muscles every tech company needs to scale upmarket. Plus, I share 15 tactical tips to help you navigate enterprise sales with more speed, clarity, and confidence. The Solution: Build the Enterprise Muscle Enterprise success starts with a strong foundation. Here’s a high-level three-part framework: 1. P&L-Focused … Read more

Mastering the Complex Enterprise Sale: A Playbook for Tech Leaders

  In this newsletter, I’ll break down why enterprise tech sales are uniquely complex, the common mistakes companies make, and the opportunities in this space. I’ll also provide a mini-playbook to help you navigate these deals and build a sustainable enterprise business. What is Enterprise Tech? For this discussion, Enterprise Tech refers to tech companies—primarily … Read more

The AI Shift: 3-Step AI Opportunity Assessment

Here’s an assessment you can use to determine where you stand, and where to start.  AI Opportunity Scorecard: Executive Assessment Worksheet Instructions Rate each factor on a scale from 1 (Low) to 5 (High) based on your business’s readiness and potential impact. Use the final score to prioritize AI initiatives. Step 1: Assess Business Impact … Read more

The AI Shift: Adapt, Reinvent, or Be Left Behind

The AI Shift: The Next Great Business Transformation First, there was the internet—it redefined commerce. Then came SaaS—it reshaped business models. Now, AI is fundamentally shifting how businesses operate. A Lesson from History: Why Some Companies Win While Others Fade Consider how technology evolved: On-Premise Era: Businesses bolted cloud capabilities onto outdated systems, accumulating tech … Read more

Accelerating Time to Revenue in 2025 (Part 3): A 5-Step Strategy Execution Framework

Here’s the framework I use with CEOs and Boards to accelerate time to revenue: 1. Face Your Reality Take an objective snapshot of your business: Review your P/L, growth trends, churn, and R&D investments. Drill into unit economics: gross margin, COGS, and year-over-year changes. Understand the underlying factors driving your current state (e.g., flawed models … Read more

Accelerating Time to Revenue in 2025 (Part 2): Execution as a Discipline

In my experience, many executives don’t stop and ask “Are we solving the right problem? Is our strategy even the right strategy?” We fail to ask the tough questions upfront and spend the bulk of our time grinding away without ever zooming out. Eventually falling short of our plans, and personally burned out. In this … Read more

Accelerating Time to Revenue in 2025 (Part 1): Why Most Fail

With Q1 well underway, businesses are now deep into executing their 2025 plans. For many CEOs and Boards, the priority this year is clear: reducing time to market and accelerating revenue generation. What Does Accelerating Time to Revenue Mean? From conversations with executives, there are various ways to define this: Closing more deals. Increasing deal … Read more

Why Digital Strategies Fail: The Legacy – Innovation Chasm

DIGITAL ROADMAP SUCCESS MODEL: BALANCING LEGACY TECH WITH INNOVATION I often see leadership teams focus on two extremes when it comes to their digital strategy and roadmap. 1- They go all in on new apps and step-change bets; things that are sexy and customer facing, but forget about the foundational elements. Or 2 – Technology … Read more

4 Stages Of Marketing – Tech – Ops For Digital Growth: From Disjointed To Customer Driven

I was advising a CEO of a mid-market consumer based company. She told me that as part of their digital efforts, they had a lofty goal of shifting half of their sales to digital channels. The focus was on building out a direct to consumer channel,  but progress had been slow. I asked her how … Read more