Derek

I'm Derek. I grew up outside Boston, live in Chicago now, and I'm not a software developer. I came into micro-SaaS through the sales door: the part where someone on a team already loves your product and procurement still says no.

From 2013 to 2019 I was an AE at small B2B SaaS companies — twenty to eighty people, $2k–$15k ACV, no enablement team, no SDR army. I learned what a deal looks like when your champion goes quiet after the demo, and what changes when you stop pitching features and start mapping who actually signs.

From 2019 to 2023 I helped indie founders move upmarket as a fractional sales advisor. Same pattern every time: solid product, happy SMB customers, founder terrified of a forty-five-minute call with a director. I got good at the unglamorous part — finding the economic buyer, surviving security questionnaires, writing proposals that don't sound like a template, and knowing when to walk away from a deal that will eat six months.

Since 2023 I've advised a handful of bootstrapped SaaS founders on their first enterprise pilots. None became unicorns. A few turned $3k MRR into $15k MRR because one annual contract replaced twenty small accounts. I talk about the ones that stalled in legal review too.

My one-line philosophy:

A signed pilot with one real stakeholder beats a hundred "we'll circle back next quarter."

I'm a bootstrapper. Small products, real contracts, independence. I don't believe in enterprise theater: fake pipeline, bloated decks, or advice written for companies with a VP of Sales. Upmarket sales is a skill solo founders can learn for their first five-figure deal — not a personality type.

If you have paying SMB customers and you're wondering whether to chase your first team plan, annual contract, or "enterprise" tier, you're who I'm writing for. No guru energy, no seven-figure promises. Just the work of turning a product someone already uses into a deal someone with a budget can actually sign.