Most founders think closing a pilot is the hard part. Micah Steiger (Stern '18) will tell you the real work starts after the prospect says yes.

Steiger is an enterprise sales leader currently at Datadog, with 14 years of experience across financial services, healthcare, and CPG. Before Datadog, he worked at an e-commerce startup chasing logos like Walmart, P&G, and L'Oreal. He came to Summer Launchpad to share what actually separates a pilot that converts from one that quietly dies on the vine.

Not Every Pilot Deserves Your Time

Getting a prospect to say yes to a pilot feels like a win. Steiger's point was that the real work starts right after.

He broke pilots into three buckets. Free trials are easy to hand out, but if the customer has nothing on the line, you rarely get feedback worth acting on. Paid POCs are the opposite. Someone willing to pay upfront is someone who's serious. His advice was blunt: anchor high, ask for money first, negotiate down later if you have to.

The managed POC sits in the middle, and it's the one Steiger actually pushes founders toward. It runs on a set schedule, and both sides agree upfront on what success looks like.

He was also upfront that a pilot doesn't always need to pencil out financially on its own. Landing a name like Goldman Sachs or P&G can be worth taking a loss on, since the credibility opens doors revenue alone never will.

Build the Plan Before the Pilot Starts

The centerpiece of Steiger's talk was something he calls a mutual activity plan. Agree on three criteria each side needs to see, set a clear meeting cadence, and define exactly what triggers a purchase decision. All before the pilot kicks off, not once it's already moving.

"Pilots don't fail in week six. They fail in week zero, when nobody agrees on what winning looks like."

Three things kill pilots most often: no agreed KPIs going in, a customer who goes dark without warning, or a vendor who doesn't check in enough to catch problems early. His advice for founders running their own pilots was to run fewer of them and run them well. A handful of managed engagements will teach you more than a dozen self-led trials ever will.

Ask the Uncomfortable Questions Early

Before committing to a pilot, Steiger runs through a short list: Who actually needs to sign off on this purchase? Where does the budget come from, and does anyone above this contact know the project exists? Who's the real executive buyer?

If nobody internally knows the project is happening, take that seriously. He even described one tactic for testing real engagement: quietly cutting off a lukewarm prospect's access and watching whether they notice.

On the classic "we don't have budget" objection, his take was that it's rarely the final word. Help the prospect build their own internal case instead. Quantify the hours the team is already sinking into the problem, how many people it touches, how often it comes up. Something like "if we solve even 40 percent of this, the payback is six months" gives them something concrete to bring to their own boss.

Don't Chase Every Logo That Waves at You

One of the sharper warnings from the talk was about drifting away from your own product. Steiger described watching a previous startup slowly turn into an agency, building one-off customizations for Walmart, Dollar Shave Club, and P&G separately, chasing each big name's wish list instead of building one strong product.

His fix was simple. Catalog every feature request across every prospect. If ten different customers ask for the same thing, it belongs on the roadmap. If it's just one, let it go.

A Reality Check on Outreach

Steiger didn't sugarcoat the outreach grind either. Expect roughly a 1 percent response rate across 100 contacts, and about 13 touches before you get a real yes or no. Thursdays and Fridays tend to land better than the start of the week. No single channel wins on its own. Email, cold calls, LinkedIn, and in-person events all play a role, and events like AWS re:Invent remain some of the highest value pipeline moments founders can access.

On AI, He Was Refreshingly Balanced

Steiger doesn't think AI is a shortcut around doing the work. Used well, it's a real productivity boost for building account plans and personalizing outreach at scale. But he warned against reps leaning on AI output without ever internalizing the account knowledge themselves. He compared it to relying on Google Maps instead of actually learning a route: convenient in the moment, but it quietly erodes the deeper understanding that makes someone good at their job over time.

He closed by pointing founders toward Datadog's former CMO Alex Rosemblat's episode on building pipeline from day one, which digs into how product-led growth and traditional enterprise sales can work together instead of competing.

Lessons for Founders

• Agree before you start. Build the mutual activity plan before the pilot begins, not once it's already in motion.
• Money is a signal. A customer willing to pay for a pilot is far more likely to become a paying customer later.
• Some logos are worth the loss. Brand credibility can open doors revenue alone never will.
• Protect your roadmap. Chase patterns across customers, not the loudest single request.
• AI is a tool, not a replacement for knowing your account.