SE Leadership
The Dark Org Chart
Every company has two org charts. The formal one requires an invitation. The other runs on influence, and it usually decides who gets promoted.
Read →Director, Named & AI Labs SEs @ Datadog
The SE role is changing fast.
Here's what that looks like from the inside.
I work with a talented group of SE leaders and individual contributors covering Datadog's largest enterprise accounts. Right now we're navigating AI adoption together: building new workflows, rethinking what we hire for, and figuring out what high-performance SE teams actually look like when AI is part of the equation. I write about what we're learning, including what isn't working.
The SE Edge
A weekly newsletter for SE leaders navigating the AI transformation in technical sales. Practical. Honest. From someone running a real SE org.
- AI integration in SE teams
- Hiring, comp & career frameworks
- POV strategy & deal execution
- What the hype gets wrong
25+Years in enterprise tech
100+
SEs hired & developed
$1B+
Enterprise deals supported
Field Ready
Free tools for the people running real deals.
Practical, shareable, occasionally fun. Built by a Sales Engineer for the SEs, AEs, and managers who run enterprise deals. Tools to sharpen your instincts, assess where you stand, and unstick the deal in front of you.
- SE Leadership ToolsCoverage planning, first 90 days, team trivia.
- Assessment & PlanningDeal Pulse MEDDPICC scoring, EBR builder, POV MAP, AI Readiness.
- Games & SimulationsThe SE Trail, Objection Blaster, Deal Tetris, SE Escape Room.
- Always freeNo signup walls. No paywalls. Built and maintained as a give-back.
Writing
Essays on Sales Engineering, AI transformation, and enterprise GTM
SE Leadership
The Super Buyer Problem
AI is giving SE teams an enormous edge over buyers right now. That asymmetry won't last. The leaders who see it coming are already building for the world after it.
Read →SE + AE Partnership
Our Plan, Our Quota
The framing shift that changes the AE-SE pipeline conversation from a fight into a partnership. One tweak, and both sides make the number more often.
Read →AI + Leadership
From Answers to Action
AI makes any analysis instant. The new challenge is knowing which questions are worth asking and being ready to act on the answers. A four-part framework for turning AI insights into real decisions.
Read →AI & The SE Role
What AI actually does to a Sales Engineering team, and what we're figuring out together
The real question isn't whether AI replaces SEs. It's which parts of the job change, which parts don't, and how teams navigate that transition together. Here's what we're learning in real time.
Read →SE Leadership
The Nine-Month Problem
Every SE team has a version of the same deal in their pipeline. It started well and somehow stalled. Here is why ramp takes so long, and what the fastest-ramping SEs do differently.
Read →Deal Execution
Discovery That Actually Works
Most SEs treat discovery as a box to check before the demo. The ones with the highest win rates treat it completely differently.
Read →SE Skills
How to Run a Demo That Actually Moves a Deal
The best demos aren't the most thorough ones. They're the ones where the customer feels genuinely understood.
Read →Deal Execution
Building Technical Champions
Every enterprise deal has someone who will fight for you when you're not in the room. Or someone who won't. Here's how to build the real thing.
Read →Deal Execution
Handling Technical Objections
The objection is rarely about the technology. Here's how the best SEs figure out what's really being asked, and what to do about it.
Read →Deal Execution
When You're Not the Only One in the Room
Competitive deals aren't won by attacking the competition. They're won by being the SE the customer trusts most.
Read →SE Leadership
The AE-SE Partnership
The quality of this relationship often determines the ceiling on what's possible in a deal. And when it's great, it's one of the best things about this job.
Read →Career
SE Comp and Career
SE stands for Sales Engineer. Big S, big E. The companies that get comp right understand that, and build their programs accordingly.
Read →SE Leadership
The SE Manager's First 90 Days
The transition from top SE to SE manager is harder than most people expect. Here's what actually matters in the first three months.
Read →AI and SE
AI Tools for SEs Right Now
The tools that are actually changing how SEs work today, not the ones that might matter someday. Practical, specific, and field-tested.
Read →SE Leadership
What executives actually want from a QBR
The SE is the only person in a QBR with the credibility and context to make it genuinely valuable for the customer. Here is what the best ones do with that.
Read →POV Strategy
5 signs a POV is already dead, and how to avoid them
Most POVs fail before they start. After working through hundreds of enterprise evaluations alongside sales teams, here are the patterns that show up every time.
Read →Hiring
SE hiring is harder than it looks, and most interview processes make it worse
Most SE interview processes select for the wrong things. After rethinking how our team evaluates candidates, hire quality improved significantly. Here's what we changed and why.
Read →AI Prompts for SE Teams
Practical prompts tested with real SE teams. New prompts go to newsletter subscribers first, then appear here the following week.
5-Minute Account Brief
Generate a structured pre-call brief from your CRM data and a quick web search. Replace the full 30-60 minute manual research process.
I have a customer call in [X minutes] with [COMPANY NAME]. Using my Salesforce/CRM connection, pull: - Current opportunity stage, amount, and close date - Last 3 activities logged on this account - Any active POV records and their status - Products currently in scope Also search the web for any news about [COMPANY NAME] in the last 14 days. Return a brief with: deal status, 3 discovery questions tailored to their situation, top talking points, and one suggested next step to propose at end of call.
Works best with Salesforce or Snowflake connected via MCP. Adjust field names to match your CRM setup.
Success Criteria Workshop Prep
Draft a starting point for POV success criteria in the customer’s language, not yours. Use as a conversation starter in the kickoff meeting, not as a finished document.
I'm starting a POV with [COMPANY] for [PRODUCTS]. Their stated goals are: [PASTE WHAT CUSTOMER SAID] Their environment: [KNOWN TECH STACK/CONTEXT] Key stakeholders: [NAMES AND TITLES] Draft POV success criteria structured as: 1. Business outcomes (in their language, not ours) 2. Technical milestones (specific, measurable) 3. Timeline with key dates 4. Definition of done Avoid vague language like "improved visibility." Frame everything from the customer's perspective.
Bring this draft to the kickoff and edit it together with the customer. Criteria they help write are criteria they own.
About Jason
I'm the Director of Sales Engineering for Named Accounts & AI Labs at Datadog. My teams cover the company's largest enterprise accounts across North America and the AI model providers running their infrastructure on Datadog.
I've spent 25+ years at the intersection of engineering and enterprise sales, starting as a Software Engineer at Microsoft and working through product management, individual SE work, and team leadership at companies including Fluke Networks, Mandiant, Rapid7, Malwarebytes, Splunk, and Datadog. Every role has been a team sport.
Right now, the work I find most interesting is figuring out how AI changes the SE function in practice: building new approaches with my team, rethinking what we hire for, and trying to separate what actually matters from the noise. I write about what we learn along the way, including the things that don't go as planned.
Background
- Datadog Director, Named & AI Labs SEs
- TrustInSoft Director, SE
- Splunk Senior SE
- Rapid7 Senior SE Manager
- Malwarebytes Principal SE
- Mandiant Senior SE
- Fluke Networks Software Engineer, SE & PM
- Microsoft Software Test Engineer