Simon Gerstler on Go To Market, Pipe Global

When you strip away the buzzwords and frameworks, startup survival comes down to one thing. Revenue.

As Simon Gerstler, Co CEO of Pipe Global, put it in our conversation:

“Everything comes down to one question: is your revenue growing or not. If you are not selling, you are dying as a startup.”

Simon Gerstler, Co CEO, Pipe Global

Simon has spent close to three decades in sales, with more than twenty five years in tech. He has co founded two tech companies that both reached acquisition. Today he helps founders around the world land their first fifty customers, build repeatable go to market engines, and avoid the most painful early mistakes.

This episode of Startup Sales Talks breaks down his playbook. Here is the story behind it and the lessons you can steal.

From door to door to two exits

Simon did not start in modern SaaS with a full tech stack and remote selling. His first sales job was very physical. He walked from jewelry shop to jewelry shop with a heavy bag of products, knocked on doors, read body language and learned how to handle rejection face to face.

Later he moved into tech, co founding a legal recruitment platform in the United Kingdom, then an education technology company in Israel that scaled to about two thousand clients before selling to a private equity firm in the United States.

In both journeys he led sales, built teams, and kept selling personally from day one until exit.

That experience shaped his view of what matters in go to market. It is not only about tools. It is about structure, clarity and dozens of small improvements executed consistently.

The marginal gains approach to sales

Pipe Global borrows the concept of marginal gains from elite sport. British cycling used this method to turn a previously weak national team into an Olympic powerhouse. They looked for tiny improvements everywhere: better pillows for sleep, cleaner bikes, smarter recovery. Each tweak added a fraction of a percent. Together they produced a massive performance jump.

Simon and his team apply the same thinking to startup sales.

“We looked at every little aspect within the sales process. CRM setup, demo structure, marketing assets. You do not need one miracle fix in sales. You need dozens of tiny optimizations that compound into real growth.”

Simon Gerstler, Co CEO, Pipe Global

They start with a deep sales audit. How are leads generated today. Which channels are in use. How does the team run demos. What happens after a prospect says no.

From that audit they pull out six or seven fast wins. Maybe the follow up rhythm is weak. Maybe LinkedIn profiles are bland and do not show any expertise. Maybe the product value is explained in technical language that buyers do not understand.

Nothing looks dramatic on its own. The power comes from stacking these marginal gains together.

Value proposition and ICP before anything else

Ask Simon where to start with go to market and he will not say tooling. He will say clarity.

Too many founders jump into outbound, content and ads without having a sharp answer to two questions:

• What specific problem do we solve
• For whom exactly

“Most founders blame go to market when the real issue is unclear value proposition and a vague ICP. You cannot scale if you do not know exactly who you help and why.”

Simon Gerstler, Co CEO, Pipe Global

For early stage teams Simon recommends:

• Write one simple value statement in plain language, not feature language
• Test it with several segments instead of locking into one narrow profile too early
• Avoid chasing only huge logos at the start, and focus on smaller companies where the sales cycle is shorter

The aim is to get real market feedback fast. If everyone ignores your outreach, it might not be a channel problem. It might be that the story does not land or that you are talking to the wrong people inside the account.

Using rejection as research

When an outbound motion does not convert, many teams go quiet and move on. Simon suggests the opposite.

Every no is a chance to learn.

He recommends replying to negative responses with a simple, humble ask. You can say you are an early stage startup, you appreciate their time, and you would love two or three honest pointers on why the product was not a fit.

People who have already turned you down often feel more relaxed and are surprisingly generous with feedback. Sometimes they will even introduce you to a colleague in another department who might benefit from your solution.

It is a small behavioral change that can uncover blind spots in your ICP and value proposition without paying for formal research.

Personalization that is actually personal

Everyone knows they should personalize outbound. Very few do it well.

Simon sees the same mistake across many teams. They add shallow references like “I saw you are based in Boston” or “Congrats on your recent funding” and call it personalization.

Buyers can smell that in two seconds.

Instead, he pushes teams to block time every day to craft a handful of truly tailored messages. That might be based on a panel the person spoke on, a white paper they wrote, a recent initiative their company launched or a shared connection who can anchor the outreach.

The test is simple. Does this line add any value to their day. Or is it only helping you feel better about your cold message.

Where AI really helps in go to market

We covered AI from several angles. Simon is clear that AI will have a huge role in sales, but he is also wary of teams that over automate and lose the human element completely.

He is especially excited about AI in two spaces:

• Conversation intelligence that reads tone, body language and non verbal cues on calls, not only transcripts
• Content and research tools that help sales teams move faster, but still keep a person in the loop for quality and empathy

At the same time, he believes we will see backlash against purely robotic outreach. Inboxes are already flooded. Buyers will gravitate back to people who feel real, who show up consistently with useful insight, not just perfect grammar.

Why social presence is part of go to market now

One area Simon feels is heavily underused is social selling. Not in the spammy sense, but as a way for leaders inside the company to show expertise and build trust.

Many startup pages on LinkedIn are full of corporate announcements. New logo. New feature. New hire. That content has its place, but it does not build real connection.

“You want people buying from people, not from a logo. Your company page is the news channel. Your founders and commercial leaders are the faces that create trust.” Simon Gerstler, Co-CEO, Pipe Global

Simon recommends that founders and sales leaders post regularly from their personal profiles, sharing lessons, opinions, stories and even failures. AI can help draft ideas, but the tone should still feel like a human talking, not a press release.

Podcast appearances, like this conversation, are another way to do that. Audio and video are hard to fake. Listeners build a different level of trust when they hear unpolished discussion rather than polished copy.

The future of teams in a noisy world

Finally, we touched on the structure of sales teams. Many early startups still hire one generalist sales rep, tell them to “do sales” and hope they prospect, run demos and close deals all at once.

Simon sees that as a risk. Prospecting and closing are different skills. Most account executives do not enjoy generating their own pipeline and will quietly avoid it.

Where budget allows, he recommends specialization as soon as possible. Dedicated SDRs for top of funnel, dedicated AEs for discovery and closing, and clear ownership of each stage.

The market will only get noisier as AI makes mass outreach easier. The companies that will win are not the ones with the most automation. They will be the ones that combine sharp positioning, thoughtful personalization, social proof from real humans and a disciplined, specialized team behind it.

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