Cold Outbound to $10M ARR: Shensi Ding's Merge Playbook

Shensi Ding didn't wait for customers to find her. She outbounded her way from zero to $10M ARR, cold-messaging tens of thousands of engineers and running demos from 9am to 9pm. Her company, Merge, has since raised $74.5M and become the integration backbone for hundreds of B2B companies.

Key Facts

• Seed Round: $4.5M raised in 3 weeks (August 2020) (Shensi Ding)
• Total Raised: $74.5M (Shensi Ding)
• Engineers Outbounded: ~50,000 during early hiring phase (Shensi Ding)
• Zero to $1M ARR: 7 months after turning on revenue (Shensi Ding)
• Customer Discovery: 100 conversations before building (Shensi Ding)

From 100 Conversations to a Validated Idea

Before building, Shensi and co-founder Gil conducted 100 customer discovery conversations. They weren't looking for enthusiasm — they were looking for extreme frustration with the status quo and doubt that anyone could actually solve it.

Shensi didn't quit her job on a hunch. While still chief of staff at Expanse (later acquired by Palo Alto Networks for ~$1B), she watched the company bleed deals to competitors — not because the product was worse, but because it lacked integrations. It took six months and a team of dedicated engineers to build a single integration. That pain, seen from the executive level, became the seed of Merge.

She and Gil cold-messaged product managers, founders, and customer success leads — anyone with an integrations page. They asked hard questions: Would you pay for this? Would you switch? How much better is this than what you have now? The signal they got wasn't 'this is amazing.' It was something more valuable: deep skepticism that the technical challenge could actually be solved, combined with desperate frustration at the existing options.

That doubt was the green light. As Shensi explains, if the main objection is 'I don't think you can build this' rather than 'I don't need this,' the market is real. The difficulty of execution becomes the moat.

"The feedback was that there was doubt that we can make it work, versus that this would be much better. And if that was really what the doubt was, then that means that it could be much better." — Shensi Ding

"If there's totally unengaged, that means it's not a good fit. If they're not engaged, it's actually more helpful for you than if they're just like, oh yeah, I'm super excited, I'm going to use this." — Shensi Ding

Raising $4.5M in 3 Weeks: The Seed Round Playbook

Merge raised a $4.5M seed round in three weeks by treating fundraising like a sales process: prep your pitch, leverage warm intros, create urgency, and go all-in for a short, compressed timeline. Shensi read extensively beforehand and ran the process like a debutante ball.

Shensi spent the six months between giving notice and going full-time preparing for the raise. She read everything available on seed fundraising, lined up introductions in advance, and planned the outreach sequence deliberately — starting with more comfortable meetings to sharpen the pitch before hitting top targets.

The process itself took three weeks of total focus. No building, no recruiting — just pitching. After each meeting, Shensi and Gil debriefed: what worked, what didn't, what to sharpen. They iterated the pitch in real time.

Her key insight: fundraising is a proxy for sales ability. The gamesmanship — how fast you respond, how you create FOMO, how you position momentum — mirrors what you'll need to close enterprise deals later. If you can't navigate the social dynamics of a seed round, revenue will be harder.

"I really view this seed as the debutante ball and you meet with everyone that you can. So you're introducing yourself to the industry as a new founder, as a new company." — Shensi Ding

"If you can't execute on your fundraise, if you need to fundraise, then it's going to be really hard to generate revenue too. Because you have to be able to navigate those personal relationships." — Shensi Ding

Outbounding 50,000 Engineers to Build the Team

With $4.5M in the bank and a massive technical product to build, Merge's first priority was hiring — not marketing. Shensi personally outbounded roughly 50,000 engineers on LinkedIn because she knew no one would randomly apply to an unknown startup.

Hiring through networks didn't work for Merge. Non-competes, the awkwardness of poaching friends, and a commitment to being in-person during COVID meant they had to source cold. So Shensi did what she always does: outbound at scale.

The result was a small but tight team — five people in the first phase, twelve by the Series A. Quality over quantity, but found through volume. The same muscle that worked for sales worked for recruiting.

The in-person mandate was non-negotiable from day one. When Shensi and Gil worked side-by-side in Gil's San Francisco apartment, they moved fast. When they worked remotely for a few days, progress slowed visibly. That experiment ended the remote debate permanently.

"I wouldn't give a fuck. No, because you wouldn't be successful at Merge. It doesn't matter if you're a rockstar engineer, because you wouldn't be a rockstar engineer at Merge." — Shensi Ding

"You care, you actually give a shit. If you're working remote, I don't care if Joe from Alaska is not working." — Shensi Ding

• Outbounded ~50,000 engineers on LinkedIn to source early hires
• Hired only 5 people in the first phase — quality required volume to find
• In-person from day one, even during peak COVID
• Turned down remote rockstar engineers without exception
• In-person accountability: 'If I'm sitting next to Joe, he has to respond to me sooner'

The Delayed Revenue Strategy: Don't Charge Until You See $1M

Merge deliberately avoided collecting revenue until Shensi could see a clear pipeline path to $1M ARR. By onboarding early customers for free, fixing product chaos, and building momentum in stealth, they went from zero to $1M in seven months once the switch flipped.

This is the most counterintuitive move Merge made. While most founders rush to show revenue, Shensi held off. Their first customer, Drata, used Merge free for two months. Two others joined under the same arrangement. The goal wasn't charity — it was proof. Prove reliability, prove quality, and fix the inevitable early chaos before money was on the table.

The logic: revenue is a momentum signal. A chart showing $0 to $1M in seven months is a completely different story than a chart showing $0 to $1M in two years with a slow ramp. Investors, future customers, and your own team all respond to momentum differently.

Shensi frames stealth as a strategic asset that most founders waste. Taking on paying customers too early creates support burdens that pull you away from the product vision. The controlled onboarding window lets you fix what's broken before the clock is running.

"Startups are all about momentum." — Shensi Ding

"I think you should not collect revenue and not onboard customers until you know that you are going to get a million of revenue as quickly as possible." — Shensi Ding

Outbound Sales From Zero to $10M: The Only Strategy That Worked

Merge's entire go-to-market from zero to $10M was outbound. Shensi ran demos from 9am to 9pm, hired a college intern to source prospects via Crunchbase, and kept her calendar fully booked every day. There was no marketing strategy — just volume and execution.

Shensi's sales motion was simple and brutal: cold LinkedIn, cold email, book the demo, run the demo, repeat. She hired a summer intern to pull prospect lists from Crunchbase and send outbound messages on her behalf. Her only metric that mattered was a full calendar.

When they lost a major deal to a competitor who had copied Merge — and that competitor used the logo as a reference in every subsequent sales conversation — it nearly broke their momentum. But Shensi is clear: they won that customer back. Years later, they're a Merge customer.

Marketing didn't become a real function until roughly a year and a half before the episode recorded, when Merge hired their first VP of Marketing. Before that: light SEO, minimal paid ads, and pure outbound. The lesson is stark — you don't need a marketing budget to get to $10M. You need founders who will do the uncomfortable work.

"Anyone who is too lazy to outbound, you're just not going to make it. You just got to get over that. You have to be embarrassed, you have to do all these really awkward things." — Shensi Ding

"My co-founder and I, we still think to get to $10 million. You just have to work really hard. That's really it, it really sucks and it's a lot of pain. But you can just work your way to $10 million." — Shensi Ding

• Cold LinkedIn was the source of their first customer, Drata
• Intern sourced prospects via Crunchbase; Shensi ran all demos herself
• 9am–9pm demo schedule to maximize pipeline volume
• No marketing investment until VP Marketing hire ~1.5 years ago
• Lost a major deal to a copycat competitor — won them back years later

What Changes After $10M: Scaling Beyond Founder Will

Getting to $10M is a willpower problem. Getting to $100M is a leadership and systems problem. Shensi is direct: you cannot will your way past $10M. It requires enterprise motion, a strong leadership team, and great decision-making at every level of the org.

Shensi is unusually honest about the transition. Everything that got Merge to $10M — founder hustle, outbound brute force, personal relationships — stops scaling. The company that hits $100M looks fundamentally different: enterprise sales cycles, a real leadership team, structured decision-making.

The 9am–9pm work schedule hasn't changed for Shensi personally. But what that time goes toward has. Building products, developing leadership, and navigating enterprise deals require different muscles than cold-messaging prospects and running product demos all day.

Her advice to founders eyeing that next phase: hire for leadership quality early, move upmarket deliberately, and accept that the founder's job description changes completely.

"You need people making really good decisions. You need to move to enterprise. It's a very different type of company. It's all about the leadership team then. You can't as the founders, just will your way to get to there." — Shensi Ding

"We really willed our way to get to $10 million, which was really exciting. But to get past it, it's a completely different process." — Shensi Ding

Zero to $10M vs. $10M to $100M: What Changes at Merge