Jonathan Awad enforces an internal SLA to reply on Slack and email in under 20 minutes (or even two minutes). Responding instantly delivers delight, shows extreme reliability, and allows founders to simply acknowledge an issue and buy time. Waiting a full day eliminates that grace, forcing you to have a complete solution immediately.
Enterprise buyers take major personal risk evaluating early-stage software and rarely get upside for doing so. Instead of pitching product first, Awad asks prospective champions if they harbor founder ambitions and introduces them to venture capital investors. This gives them immense career value upfront, creating a self-reinforcing dynamic where buyers champion the startup's product in return.
Rather than running a slow or continuous fundraising effort, planning dozens of investor meetings weeks in advance and packing them closely together creates the urgency required to close a round. While macroeconomic shocks can disrupt this pipeline, compressing dozens of meetings into tight weekly blocks forces decisions and uncovers high-conviction lead investors.
Prospective enterprise customers often refuse to be the first to share proprietary data into a shared consortium. Baselayer bypassed this barrier by coordinating interest so 15 to 20 institutions joined at once, while also bundling five auxiliary products and analytics scores into their suite so clients received standalone value immediately without waiting for consortium density.
Enterprise champions face internal political risk and cannot easily pitch a vendor with zero customer proof. While founders must never misrepresent commitments to investors, early customer conversations allow for soft implication of broader market interest. This provides internal advocates with the necessary cover to answer risk-averse internal inquiries and move procurement forward.
Founders frequently limit outreach to people who appear capable of buying immediately. In contrast, reaching out broadly to hundreds of adjacent contacts—such as old college peers or acquaintances connected to target companies—and providing useful industry artifacts creates latent reciprocity. Over time, these contacts change jobs, get promoted, and generate deal flow.
Jonathan Awad advocates 'SWAG' selling—'sell without acting greedy.' Instead of pitching with neediness or begging for pilots, founders project that their company is busy, the product works, and industry peers are already on board. Letting prospects know it is completely fine if they pass relieves buying pressure and counterintuitively increases the founder's closing power.