Most Career Advice Is a Ladder. Yours Should Be a Chess Game.
The traditional career advice is simple: show up, work hard, wait your turn. Climb the ladder one rung at a time.
That’s not how careers actually work—at least not the careers worth having.
The people who get promoted, build real influence, and do meaningful work aren’t just climbing. They’re thinking strategically. They’re building relationships before they need them. They’re positioning themselves for roles that don’t exist yet. They’re playing a chess game while everyone else is waiting in line.
I help you play the chess game.
Who This Is For
Career coaching works best for:
- Mid-career professionals who’ve hit a plateau and aren’t sure what move to make next
- Technical leaders (developers, engineers, data professionals) stepping into management for the first time
- Ambitious individual contributors who want to understand the path to senior leadership
- Professionals in career transition—changing industries, returning after a break, or navigating a significant pivot
- Anyone who wants a thinking partner with real executive and business experience
How We Work Together
Two calls per month
Each session is focused. We work through the specific challenges and decisions you’re facing—not generic career advice. I bring frameworks and experience; you bring the real situation on the ground.
Async support between sessions
Real decisions don’t wait for the next scheduled call. Between sessions, you can reach me for quick feedback on emails, negotiations, presentations, conversations you’re preparing for, and anything else that comes up.
The Chess Game Framework
Over the course of our engagement, we build a strategic view of your career: where you are now, where you want to be in 2–5 years, and the specific moves—skills to build, relationships to cultivate, opportunities to pursue—that bridge the gap.
What Changes
After working together, clients typically report:
- Clarity on what they actually want from their career (which is often different from what they thought they wanted)
- Confidence in advocating for themselves—in negotiations, performance reviews, and leadership conversations
- Visibility with the right people, because we work on strategic relationship building, not just performance
- Promotions and pay increases, because we’re building the case and making the right moves
- Reduced anxiety around career decisions, because you have a map instead of just reacting to what happens
About Dave’s Background
I spent 23 years in software development and technical leadership—individual contributor to team lead to project management to running my own business. I’ve made career pivots. I’ve negotiated offers. I’ve managed teams and been managed. I’ve coached people through career transitions, promotions, and leadership development.
I’m not going to tell you what the textbook says. I’m going to tell you what I’ve seen actually work.
Investment
Starting at $1,000–$1,500/month — includes two 60-minute calls per month plus async support.
The first step is a free 30-minute conversation to understand where you are and where you want to go.