Jonathan Blessing
Founder & Managing Partner
Jonathan Blessing founded Launch Day Advisors after more than two decades in the technology services market—leading firms, structuring complex engagements, and overseeing high-stakes technology initiatives. He has seen visions, teams, and software come together—and understands that the right partnership often determines whether a project ultimately succeeds. Launch Day works exclusively on the buyer side of technical partner selection.
He previously founded and led Series Digital for ten years prior to its acquisition and served as CEO of DOOR3, an independent technology consultancy building and modernizing business applications. His work includes direct engagement with organizations such as the U.S. Department of Defense, the U.S. Department of Justice, The New York Times, Sony Classical, Goldman Sachs, and Stanford University.
Launch Day Is for the Buyers.
I founded Launch Day Advisors because of a persistent asymmetry in the market that harms project outcomes. Vendors run competitive sales processes every day. Their teams refine messaging, package case studies, and negotiate terms as a matter of routine. Buyers, by contrast, undertake major technology projects infrequently, often under time pressure. From the outset, buyers are at a disadvantage: sellers are better at selling than you are at buying. That asymmetry favors them.
Buyer and seller incentives are structurally misaligned. Vendors are built to win work. Buyers are accountable for results. Those priorities intersect, but they are not the same—and the difference shows up in scope, pricing, and risk allocation.
AI has increased the pressure. Sales cycles are shorter. Claims are grander. Subsidized pilots and accelerated timelines create urgency where patience is required. Signing a contract commits time, capital, and credibility—and concentrates risk in a single decision. Buyers should not walk into that moment alone. Launch Day exists to correct the imbalance: to bring structure to selection, clarity to incentives, and discipline to negotiation. We restore balance.