How to get enterprise clients as a startup (enter through the CEO, land with the CMO)

Sunny Ray · Sep 2, 2026 · 7 min read

To get enterprise clients as a startup, get in front of a senior person with something they want, let them pass you to the person who owns the problem, and then find an internal champion who will sell you inside the company. Keep every stakeholder engaged, start with a contained pilot, and plan for a long cycle. You do not need an enterprise sales team to begin. You need the right entry point and the patience to follow through.

The usual advice is to hire an experienced enterprise account executive. That is expensive, slow, and premature for most startups. What I have seen work is cheaper. On September 2 we noticed that the companies arriving in our pipeline had changed size, and the reason was a forwarded email.

Why enterprise is a different sale

Selling to a large company is not a bigger version of selling to a small one. It differs in a few ways that matter:

• More people. Users, budget owners, signers and blockers are usually different people.
• Longer cycles. Procurement, security reviews and legal all take time.
• Less tolerance for risk. A startup has to prove it will not create problems.
• More upside. One enterprise logo can change your revenue, your credibility and your next fundraise.

Most startups lose enterprise deals not because the product is wrong but because they cannot get in the right door, or cannot keep the deal moving once inside.

The forward: entering through the CEO, landing with the CMO

On September 2, reviewing our pipeline with Charles, I noticed that inbound quality had been climbing. We were now regularly seeing companies with $50M to $100M in revenue. When we looked at how they arrived, a pattern showed up. CEOs were receiving our podcast invitations and forwarding them to their CMOs and marketing leaders. Those marketing leaders arrived pre-warmed.

Think about what that forward does. A CEO who forwards an email is effectively saying "take a look at this". The person who receives it has an endorsement from the top before they have said a word to you. That is a better entry than any cold email to the CMO directly could give you.

And it happened because the invitation was something a CEO could forward without embarrassment. Not "can we demo our marketing software?" but "would you like to be featured on a show about how leaders in your space grow?". The podcast angle landed especially well with companies that already ran a podcast or were planning one.

So the entry point for enterprise is often a level above the buyer, with an offer that is easy to pass down.

Write an invitation a CEO will forward

If the entry point is a senior person passing you down, the invitation has to be forwardable. A few things make that more likely:

• It is about the company's story, not your product. A CEO forwards things that make their company look good.
• It is short enough to read on a phone between meetings.
• It names a topic the marketing or growth leader would own, so the CEO knows exactly who to send it to.
• It asks for nothing that needs a budget or a decision.

Our own invitations are built this way, and the forward pattern showed up without us asking for it. Nobody wrote "please forward to your CMO". The invitation simply belonged on the CMO's desk, and the CEO could see that.

Find your internal champion

Once inside, you need someone who wants you to win. On the same call Charles shared the qualifier he now uses: ask whether they have a salesperson.

His logic works for any startup selling into larger companies. If there is a salesperson, that person becomes your internal champion. They understand what you are doing, they benefit from it, and they will sell it up to the CEO. If there is no salesperson, that is a signal that the CEO does not prioritize sales, which makes them a weaker fit for anything sales-related.

Adapt the question to your product. Who inside this company already does the job your product helps with? That person is your likely champion. Find them early and make them look good.

Multi-stakeholder deals without losing momentum

Enterprise deals die in the gaps between people. Some habits that help:

• Map the people. For every account, write down who uses, who pays, who signs and who can block.
• Book the next meeting before the current one ends, and invite the next stakeholder to it.
• Give your champion material they can forward: a short summary, a one-page business case, a relevant episode.
• Send a written recap after every call so nobody has to remember what was agreed.
• Never let a week go by without a dated next step.

When someone new joins, start them from the beginning. Do not assume they were briefed.

Pilots, procurement and patience

Large companies rarely sign a big contract with a startup on day one. They start with something small and safe.

• Offer a contained pilot with a clear goal and an end date.
• Agree upfront what success looks like and what happens if you hit it.
• Ask early about procurement, security reviews and legal, so they do not surprise you at the end.
• Price the pilot so it is easy to approve, ideally within someone's own budget.

How long does it take? Longer than you want. Plan for months, and keep smaller deals moving in parallel so your cash does not depend on one signature.

Can a small startup sell to enterprise companies?

Yes, and buyers are more open to it than you might think, as long as you do not act like a typical vendor. Gartner's survey of 646 B2B buyers, as reported by Distribution Strategy Group, found 67% prefer a buying experience without a sales rep. A startup that shows up as a host, an expert or a useful peer gets a different reception from one that shows up as a rep with a quota.

Who should I contact first at an enterprise?

Often one level above the buyer, with an invitation that is easy to forward. Then the person who owns the problem, with the senior endorsement in hand. Then the champion who does the work. In our pipeline, the CEO-to-CMO forward was the pattern that brought larger companies in.

Use the conversation to qualify the account

An interview or a senior conversation tells you more about an enterprise account than any data tool. Listen for who makes decisions, which projects have budget this year, what has already been tried, and what the company is under pressure to fix. By the end you should know whether this account is a real opportunity, a long-term relationship, or a polite dead end.

Treat all three as useful. Real opportunities get a pilot proposal. Long-term relationships get regular, low-pressure contact. Dead ends get a thank you, and they sometimes send you someone better.

What to do in the first 90 days

1. Weeks 1 to 2: pick 30 to 50 target accounts. Identify the CEO and the likely buyer at each.
2. Weeks 2 to 4: invite senior people onto your show, or to something else valuable, with an invitation built to be forwarded.
3. Weeks 4 to 8: run conversations. For each account that engages, find the champion and map the people.
4. Weeks 8 to 12: propose contained pilots to the two or three accounts with the strongest champions.

Keep the rest of your pipeline running in parallel. Enterprise is a long game, and the startups that win it are the ones still around when the deal closes.

Mistakes startups make with enterprise

• Pitching too early. Senior people forward invitations, not pitches.
• Relying on one contact. If they leave, the deal leaves with them.
• Waiting on procurement silently. Ask what the process is in the first serious conversation.
• Overpromising in the pilot. A pilot that misses its goal is worse than a smaller one that hits it.
• Letting the champion do all the work. Give them what they need to sell you inside.

If you want to land enterprise buyers as guests on your own show, see how it works.

Frequently asked questions