Board-level counsel and executive coaching grounded in 15+ years of actually acquiring, running, and scaling software businesses.
Schiller Strategies was founded on a simple premise: the best counsel comes from people who've held the role, made the call, and lived with the result.
We bring 15+ years of operating experience across software businesses of every size — from early-stage startups to Constellation Software portfolio companies with global reach. We've led business units, full P&Ls, led engineering, support, implementation, and sales organizations, and navigated every stage of the software company lifecycle: build, acquire, integrate, and scale.
Our background spans clinical documentation software, chronic disease management platforms, healthcare IT, and enterprise SaaS — giving pattern recognition across sectors and business models. Computer science foundations and business immersion means we can go deep on product, people, or numbers — wherever the conversation needs to go.
That experience is what Schiller Strategies brings to every engagement. Not a framework. Not a benchmarking report. Operator judgment, applied to your specific situation.
Every engagement is different. What doesn't change is the approach: direct, practical, and focused on what actually moves the business forward.
Independent counsel for boards and investors navigating inflection points — capital decisions, leadership transitions, strategic pivots, or governance challenges.
Direct work with leadership teams to sharpen decision-making, close execution gaps, and build the operating culture that actually scales — not the one that looks good in an all-hands.
For the work that doesn't fit neatly into the org chart — new market entry, acquisition integration, product pivots, organizational restructuring, or high-stakes projects that need senior attention.
You need someone who's sat in the chair, made the call, and lived with what came next.
The perspective here comes from running businesses, not advising on them. That means a different set of questions, a higher tolerance for complexity, and counsel that accounts for how organizations actually behave under pressure.
From VP of Product to President to portfolio operator at Constellation Software — Dan has owned P&Ls, managed boards, and led teams across engineering, support, implementation, and sales. Across healthcare IT, enterprise SaaS, and beyond.
Whether you're the founder who built it or the firm that acquired it, we've been in both positions. That makes us more effective when those interests need to be aligned — and more direct when they don't.
The highest-value work happens over time. We prefer ongoing relationships where we can build context, speak candidly, and be useful at the moments that actually matter — not just for a quarterly review.
"The best strategic advice accounts for what's happening on the ground. Most advisors never get close enough to know."— Dan Schiller, Founder
If you're building, acquiring, or backing a software company — and you need a straight answer from someone who's been in the seat — reach out.