I Turn Complex Products
Into Stories That Close.
Senior PMM at the intersection of product, sales, and market strategy. I've spent 9 years translating what engineering builds into language that moves buyers, across DevOps, cloud infrastructure, and enterprise software.
Experience at
Brands worked with
The person behind
the positioning.
I'm a Senior PMM who specializes in B2B tech, the kind with long sales cycles, complex buyers, and products that are genuinely hard to explain. My job is to make that easier: cleaner positioning, sharper messaging, and narratives that give sales teams something they actually want to use.
Over the years I've worked across DevOps, CDN, infrastructure, and enterprise software and services, categories where the product advantage is real, but invisible until someone tells the right story. That's where I come in.
Outside work, most of my time goes to my wife and three young kids, with the occasional round of golf when I can sneak away. It's a humbling teacher of the same thing the job demands: you can't control every variable, so you focus on the next decision and play to your strengths.
Featured Work
Real problems, clear thinking, measurable results.
Positioning & Launch
Release Orchestration Narrative
CloudBees
Challenge
Fragmented product narrative left sales struggling to differentiate in a crowded DevOps market. Deals stalled at the value conversation.
Insight
Buyers didn't care about features. They cared about pipeline risk and deployment confidence. The product solved a real enterprise pain point, but the story wasn't connecting.
Action
Rebuilt positioning around release intelligence. Developed a new core messaging framework and led narrative alignment across product, sales, and exec teams.
Impact
Grew the product line to $45M in year one (26% ARR growth) by reframing the story from Jenkins connector to enterprise release control plane.
Analyst Relations
Gartner MQ / Forrester Wave Strategy
Enterprise B2B
Challenge
Company was under-positioned in key analyst reports despite having a strong product. Narrative gaps were costing deals at the enterprise validation stage.
Insight
Analysts evaluate narrative as much as product capability. Internal teams weren't telling a coherent, differentiated story; every function had its own version of the truth.
Action
Led analyst relations strategy, reframed differentiation narrative, and coordinated cross-functional input for submissions and briefings.
Impact
Secured inclusion in both reports. The unified narrative laid the foundation for what became CloudBees Unify, a single platform story replacing a patchwork of disconnected products.
Partner Marketing
Partner Solution Launch
IBM / Akamai
Challenge
Joint solution had real technical value but lacked a market-facing story that either partner's sales team could articulate on their own.
Insight
Enterprise buyers needed to see the integrated value proposition, not two separate product pitches stapled together.
Action
Developed joint positioning, co-branded messaging architecture, and a launch playbook. Aligned stakeholders across two large, complex organizations.
Impact
Closed $125M in new ARR in the final quarter, exceeding the prior year's total ARR. First-ever co-created solution for enterprise application access through the channel.
Channel Enablement
Partner Marketing Playbook
Lenovo
Challenge
A distributed partner ecosystem lacked consistent, scalable marketing resources. Partners wanted to go to market but didn't have the scaffolding to do it confidently.
Insight
The bottleneck wasn't partner motivation; it was the absence of a repeatable framework partners could adapt and deploy without heavy support.
Action
Built a repeatable partner marketing playbook: messaging templates, campaign briefs, and co-sell enablement assets designed for self-service use.
Impact
Created the first centralized asset library telling the full Lenovo SSG software portfolio story, giving partners a single, consistent foundation to go to market with.
AI Product Launch
AI Platform GTM: Unify AI
CloudBees
Challenge
Launching three AI products (AI Assistant, First Responder, Unify AI) into a DevOps market skeptical of AI hype. Buyers had seen vague AI claims before and tuned them out.
Insight
Buyers didn't need an AI story. They needed proof that the product solved a pain they already felt: incident chaos, slow triage, and alert fatigue. Lead with the problem, let the AI be the mechanism.
Action
Developed product-specific messaging for each AI capability grounded in operational outcomes. Built agentic AI demo environments using Claude Code to give field teams something to show, not just tell.
Impact
Enabled sales motion for Unify AI suite; positioned First Responder as an integrated alternative to standalone incident management tools, expanding platform value for enterprise buyers.
Revenue Growth
Cloud Services GTM: Microsoft CSP
Lenovo
Challenge
Customers could buy M365 directly from Microsoft — and many did. The opportunity was shifting that motion to Lenovo, where cloud licenses became the entry point for layering on Managed Services and creating low-friction expansion.
Insight
The win pattern was already in the data. Specific account profiles, deal stages, and triggers predicted CSP upsell. The problem wasn't motivation; it was prioritization and messaging fit.
Action
Built win intelligence and automated lead scoring to surface the right accounts. Created messaging that framed Microsoft cloud as margin expansion, not a product add-on. Unlocked MDF investment to fund the outreach motion.
Impact
+272% YoY revenue growth on Microsoft cloud services.
Career Highlights
The work that moved the needle.
- Led GTM strategy for 20+ major product launches across enterprise B2B markets: DevOps, CDN, cloud infrastructure, and edge computing
- Built messaging frameworks adopted by 500+ person sales orgs globally, improving deal velocity and rep confidence
- Drove C-suite alignment across 20+ engagements, delivering executive narratives used in board presentations and analyst evaluations
- Launched joint solutions with 10+ partner orgs including Akamai and Lenovo, generating $150M in attributed partner pipeline
- Simplified complex B2B technology (release orchestration, feature management, security software, and edge computing) into clear market narratives that closed deals
- Drove analyst relations strategy that improved positioning in Gartner Magic Quadrant and Forrester Wave evaluations
- Led cross-functional teams spanning product, sales, engineering, design, and executive stakeholders across distributed organizations
What Colleagues Say
Recommendations from LinkedIn.
Drew is equal parts strategic thinker and expert doer. We worked closely together at CloudBees, where I worked on the brand side and he worked on the product marketing side. Drew was a go-to subject matter expert for the broader marketing team, and I personally loved pressure-testing messaging ideas with him because of how deeply he understood the technology, the market, and our audience. He was very effective at translating that depth of knowledge into clear, accessible language.
As one of the longer-tenured employees at CloudBees, Drew had seen the company and its product portfolio through many changes and pivots. Through it all, he remained adaptable, positive, collaborative, and focused on what would create the greatest impact for customers.
Beyond his expertise, Drew is simply a kind, thoughtful colleague who is incredibly easy to work with. Any team would be lucky to have him.
Anna Tannas
Brand Strategist | Creative Operations Leader
Strategy, Systems, & Storytelling
Senior to Drew at CloudBees, didn't manage directly
Drew is what I call a proactive thinker, builder, and operator. He's incredibly easy to work with because he takes the initiative to address issues well before they become problems. Drew has a knack for connecting people across functions, building alignment, and delivering work that addresses the company's most pressing needs. Whether he's solving an immediate challenge or building a new capability from the ground up, he brings strong ownership and sound judgment. I highly recommend him!
Bryan Elanko
Technical PMM Leader | PMA Ambassador
ex-Shopify
Worked together on the same team
Drew has been key in driving some of our product go-to-market releases. His focus on market segments along with the right go-to-market tactics has helped increase pipeline and signings. Drew is also a great communicator and has lead sessions and webinars successfully by boiling down complex topics in a way that is easy to understand for everyone.
Joe Gallego
Director, Global SAP Practice
Go-To-Market | Agentic AI
Worked together on the same team
Anyone who works with Drew would vouch for his dedication and commitment towards his work. Excellent organization and execution are striking characteristics of Drew's working style. He is a great person to work with because he easily lightens up an intense situation with his sense of humor. He is very good at setting up goals and motivating the team towards achieving them with positive results. It has been a great experience of working with him on several projects during our MBA and I am confident that he would be a great asset for any team that he works with.
Abhijit Jain
Analytics & Data Pipeline Architect
Product & E-Commerce | AI Agents
MBA colleagues at NC State
"Ridiculously efficient" is what comes to mind when I think of Drew — his organization, inspiration and insight into all aspects of c-store marketing make him fantastic to work with. I've had the pleasure of working with Drew for the last two years on Kangaroo Express' digital marketing endeavors, and all of the effort he puts in to learning all the details, considering all the angles, and following up on required information immediately, has not gone unnoticed. Drew absolutely "gets" marketing and always comes up with the best strategies to reach the end goal. He would be a solid asset to any team!
Keely Tyler
Business Owner/Operator
Kangaroo Express
Drew was Keely's client
How I Actually Use AI
Knowing which bucket a task belongs to matters more than knowing which tool to use.
Runs without me
A Python CLI I wrote on the Claude API, with web search built in, that generates full competitive intel reports on demand. It loops on searches, synthesizes the findings, and hands back a structured report ready for sales or positioning.
Manual research can't keep pace with AI launches — the landscape shifts mid-cycle. The CLI handles velocity; I vet every report against analyst calls and win/loss data before it ships.
Scales my judgment across the team
A custom GPT I built and maintained for our sales team, loaded with current messaging, competitive battlecards, and objection-handling, refreshed on a bi-weekly cadence. Reps asked competitive questions in plain language and got answers grounded in live positioning.
Team leverage was the design principle, and it landed: reps self-served about 80% of their positioning and competitive questions, instead of routing every answer through PMM.
Shipped what the process wouldn't
Our demo environment was weak and I couldn't fix it through official channels. So I used Claude Code to build my own: four industry-specific demo apps on our feature management product, each tailored to the pipeline patterns I found analyzing deals by vertical. The SE team adopted it for their own cycles.
In the early going we skipped two POVs entirely. Deal cycle time was one of my core PMM metrics, and this moved it directly.
The calls I keep human
Positioning decisions, what we're choosing to claim versus competitors, what an analyst told us off the record. AI doesn't touch those. That boundary isn't caution, it's quality control.
Tools in rotation
Perplexity
ChatGPT
Claude Code
Otter.AI
Whispr Flow
Gamma
Talks & Thought Leadership
On stage and on camera, translating complex topics for technical and business audiences.
Platform Engineering: Market Dynamics, DevOps Integration & Build vs. Buy
Walked through the market forces shaping platform engineering, its strategic role in modern DevOps, and a framework for navigating the build vs. buy decision in enterprise organizations.
Watch Recording
Release Orchestration: Bridging the DevOps SDLC
An Ignite-format talk: 5 minutes, 20 slides, auto-advance every 15 seconds. Covered Release Orchestration as a capability: what it enables for engineering organizations and how it bridges the gaps in the software delivery lifecycle.
Watch RecordingClaude Code: Live Platform Demo
Shared a live walkthrough of Claude Code (Anthropic's AI coding platform), demonstrating real-world workflows. The post reached the developer tools and AI community on LinkedIn.
View Post
Agentic AI in DevOps: Exploring Use Cases for the CloudBees MCP
Explored how agentic AI and the Model Context Protocol (MCP) are reshaping DevOps workflows, from automated pipeline management to intelligent release decisions. Written to position CloudBees at the frontier of AI-native DevOps.
Read Post
The Release Gap: Why CI/CD Isn't Enough
Original research and narrative establishing the "release gap" concept: the critical distance between continuous delivery and production confidence. A flagship asset for CloudBees pipeline intelligence positioning.
Download eBook
Putting Cloud Native in Perspective
A strategic guide for enterprise teams navigating the shift to cloud native, covering containers, microservices, and the organizational realities that determine whether the transition succeeds.
Download eBookWhat I Do
Four core disciplines. Every engagement draws on all of them.
Positioning & Messaging
I build the narrative infrastructure that makes a product impossible to ignore, from category framing to competitive differentiation that actually lands.
- Buyer persona and jobs-to-be-done research
- Competitive positioning and battlecard development
- Core messaging frameworks and value proposition architecture
Launch Strategy
Launches that move metrics. I coordinate across product, sales, and marketing to make sure the story lands, and the pipeline follows.
- Cross-functional GTM planning and launch playbooks
- Tiered launch frameworks scaled by market impact
- Post-launch measurement and iteration cadence
Sales Enablement
I give sales teams the story, tools, and confidence to have better conversations. Assets they actually use, not ones that collect dust in a shared drive.
- Pitch decks, battlecards, and objection-handling guides
- Buyer-stage content mapped to the sales funnel
- Sales training and messaging adoption programs
Executive Narrative
Board decks, analyst briefings, investor narratives. I translate market strategy into the language that shapes decisions at the highest level.
- Gartner MQ and Forrester Wave preparation
- Board and C-suite presentation strategy
- Market category and thought leadership narrative
What You Get With Me
Beyond the resume. This is how I actually show up.
First-Principles Thinker
I don't inherit assumptions. I start with what's actually true about the market, the buyer, and the problem, and build from there.
Cross-Functional Translator
I speak product, sales, and exec. I'm the person who gets every function aligned on the same story in the same language.
Builder/Operator Mindset
I ship. I don't just strategize. I build the assets, run the plays, and iterate on what's working. Strategy and execution, not either/or.
Let's Build Something
Worth Talking About.
I'm open to Senior Level Product Marketing and Alliance Marketing Manager positions. Let's see if there's a fit.