Michael Grinich - founder & CEO of WorkOS
WorkOS founder Michael Grinich explains how to sell outcomes to engineering leaders, test conferences before committing, build a company around a durable “why” and handle the conversations founders most want to avoid.
Michael Grinich is the founder and CEO of WorkOS, a platform that helps software companies add the capabilities they need to sell to enterprise customers.
Recorded at the Engineering Leadership Conference, this conversation moves from enterprise marketing and event strategy into product empathy, solo founding, evolving leadership roles, difficult feedback and the principles that keep a growing company pointed forward.
The Q&A below is experimental — extracted from the episode transcript with AI. If you spot a mistake, let us know at jack@scalingdevtools.com.
How is selling to engineering leaders different from reaching individual developers?
Engineering leaders may have begun as hands-on developers, but now allocate scarce people against business goals. They care less about a language or framework choice than staffing, security, priorities and the effect on revenue. WorkOS therefore leads with the deals a company can unlock and the teams it does not need to build, then provides code and architecture detail when the buyer needs it.
What should happen after a promising conference conversation?
The booth is usually only step one. Capture enough context to follow up, then schedule the deeper discussion the buyer actually needs: product capability, solution architecture, security, pricing or procurement. Some of WorkOS’s customer relationships began with a brief event exchange and converted months later, so success comes from continuing the relationship rather than forcing a full sale in a noisy hall.
How should an early startup decide whether to sponsor a conference?
Scout it personally first. Buy one ticket, attend without a booth and ask whether the audience, tone and topics match potential customers. Only bring the team and spend sponsorship money after the event proves relevant. The largest cost is focus: salespeople, engineers and founders are removed from their normal work, so a selective test is more valuable than filling the calendar with plausible conferences.
Why are frameworks a poor starting point for new product ideas?
Frameworks make an existing market legible, but their categories constrain what you imagine next. Talk to many users instead, build empathy for the work and repeatedly ask why the pain exists. That messier route reaches the bedrock of an unmet need. A product concept shaped around a real frustration is stronger than choosing an empty box in an analyst diagram.
Why does articulating the company’s “why” matter?
A precise description of the customer’s frustration can create trust before a seller explains the implementation. It also becomes an asset in hiring and fundraising because people understand why the work deserves years of effort. The useful answer is not merely making money or shipping a technology; it is the durable change in a customer’s life or business that the company exists to produce.
What is more durable than falling in love with one solution?
Fall in love with the problem and the customers living with it. Features will fail, but empathy for ambitious technology teams moving upmarket can sustain the next attempt. WorkOS has kept a consistent direction because “help companies become enterprise-ready” sits above SAML, SCIM or any individual product. Developer joy and the customer group remain invariants while the implementation expands.
Was the full WorkOS vision obvious at the beginning?
No. I saw a gnarly in-house problem, knew early people who might buy a solution and liked the people dealing with it. The larger market and mission sharpened only as the company learned. A startup idea can resemble a progressive image loading: the rough shape appears first and detail arrives over time. The founder needs enough conviction to begin, not a clairvoyant view of the finished company.
What should someone consider before starting alone or with co-founders?
The central questions are whether people collaborate well, trust one another and can genuinely share responsibility. Roles are unclear at formation and diverge as a company grows; one co-founder may build an organization while another wants to remain an individual contributor. Keep discussing how responsibilities evolve, where skills are missing and whether equity and leadership still reflect the work the company requires.
How should founders approach a conversation they are afraid to have?
Fear and procrastination are strong evidence that the conversation is necessary. Start by saying plainly that it will be difficult, then address the issue directly. Early feedback may correct performance before a larger decision is needed; delay only prolongs uncertainty for everyone. If the founder will not confront a failing hire, product or direction, nobody else has the authority to do it for them.
What is the CEO’s distinctive job as the company matures?
Strong leaders should run today’s operations without everything depending on the founder. The CEO’s deeper job is to shape the organization six to twelve months ahead: recruit missing strengths, establish values, improve how feedback works and evolve the company toward its next form. Competitors deserve awareness, but driving from the rear-view mirror sacrifices the forward attention required to create the next market.
Links & references
- WorkOS ↗
- Michael Grinich on X ↗
- Engineering Leadership Community ↗
- Crossing the Enterprise Chasm podcast ↗
- Start With Why ↗
- AWS re:Invent ↗
This episode is brought to you by WorkOS.