How to Do Enterprise SaaS Sales

Enterprise SaaS sales is a different sport. Not a harder version of SMB sales. Not a slower version of mid-market sales. A different game entirely, with different rules, different risks, and very different ways deals actually get done.

I’ve watched a lot of founders struggle with this transition. They have a solid product. They’re closing $5k–$20k deals. Then they land their first shot at a $100k+ enterprise opportunity and assume it’s just a longer sales cycle with more meetings.

That assumption is where a lot of time, energy, and pipeline goes to die.

This post is based on a SaaS CEO mastermind conversation where we spent time unpacking what actually works in enterprise sales — not what sounds good in theory, but what closes deals in the real world. If you’re selling to companies with 500 to 10,000 employees, this is the mindset shift that matters.

First, understand what you’re walking into

Before you get excited about logos, deal size, or ARR math, you need to understand the reality of the buying situation you’re stepping into.

One of the most important questions you can ask early is whether you’re replacing an existing solution or if this is a first-time purchase. That single distinction changes everything. As one CEO put it in the discussion, “I always want to know if you’re replacing a technology or if it’s their first-time buy, because it’s vital. If you’re replacing a technology, there’s typically a contractual period, so we want to know when that agreement is over.”

If they’re mid-contract with an incumbent, the odds of anything closing soon drop dramatically. You’re either early-stage education for a future cycle, or you’re about to spend months acting as an unpaid consultant.

That’s why you need to ask uncomfortable but necessary questions early. Who else needs to be involved? What does the buying process actually look like? What were the steps the last time they bought something similar? What are the real timeframes?

One of the strongest warnings that came up was this: “You want to ask up front who else needs to be involved, what the buying process is, and what the timeframes are. Otherwise, you could spin your wheels being an unpaid consultant without ever getting close to the finish line.”

Enterprise sales punishes ambiguity. If you don’t define the process, the process will quietly define you.

Know the three buyer types — and who really matters

Enterprise deals don’t get decided by one person, but they do get pushed through by one person. Understanding who’s who inside the account is non-negotiable.

There are three buyer types that show up in every enterprise deal.

First, the economic buyer. This is the person who controls the budget and ultimately decides whether the deal happens. They can say yes. Everyone else just influences them.

Second, the technical buyers. These are procurement, legal, compliance, security. They don’t wake up wanting to buy your product. Their job is risk reduction. As one founder said very bluntly, “There’s the technical buyer — they can say no, but they can’t say yes.”

Third, the user buyers. These are the people who will actually live in the product. They matter because they influence the economic buyer, but they don’t close deals on their own.

Where founders often get stuck is confusing support with power. A champion who loves your product but can’t move budget isn’t enough. The real unlock is a champion who can push the organization forward.

Ideally, that champion is the economic buyer. When that happens, things move fast. One of the strongest quotes from the session captured this perfectly: “If you can get your economic buyer to be a coach, they will basically trump everybody else inside the organization. I’ve had $100,000-plus agreements go through in three, four, five days.”

That’s not hype. That’s how enterprise actually works when you have the right person on your side.

Get decision makers involved earlier than feels comfortable

One of the most expensive mistakes in enterprise sales is waiting too long to surface real objections.

A simple question came up in the discussion that does a lot of heavy lifting: If the decision maker were to say no to this, what do you think the reason would be?

That question does two things at once. First, it forces your contact to think honestly about what could kill the deal. Second, it gives you a clean opening to say, “That’s probably a conversation we should have with them directly.”

As one founder explained it, “If the decision maker was to say no to this for any reason, what do you think that would be? You’re able to override some of those potential objections and ideally get the decision maker on the phone.”

If you can’t get direct access, you still need a path forward. Short, focused 3–5 minute videos sent to decision makers can work surprisingly well. You’re not pitching. You’re giving context and framing the problem in a way that makes it easier for them to engage when the time comes.

What doesn’t work is hoping your internal contact will “handle it.” That’s how deals stall quietly for six months.

Prepare for the enterprise gauntlet

Enterprise sales isn’t just selling. It’s surviving procurement, legal, security, and finance without losing momentum.

You should assume you’ll be asked about SOC 2, data handling, uptime, indemnification, and terms you’ve never heard of before. You should also assume procurement will ask for a massive discount.

Sixty percent off is not uncommon. That’s not an insult. That’s procurement doing their job.

The key is knowing your walk-away point before you get there. If you don’t know your floor, you’ll negotiate against yourself. If the deal doesn’t work at a certain price or structure, it’s better to find that out quickly than to drag it out for months.

Every enterprise deal should also make you smarter. Document the requirements. Save the redlines. Capture the objections. Each deal should lower the friction for the next one.

The golden rule: lose fast

This was the most repeated theme in the conversation, and it’s the hardest one for founders to internalize.

Enterprise sales rewards speed to clarity, not just speed to close.

As one founder said flat out, “The name of the game is get to yes or no as quickly as possible. I’d rather have somebody tell me no than maybe and just drag me out for six, eight, ten months.”

Another added, “Lose fast. Your most precious commodity is your time. If you don’t lose fast, you end up really losing opportunities that you haven’t even met yet because you were fixated on junk in your funnel.”

This is especially hard early on, when every enterprise logo feels precious. But slow maybes are far more dangerous than clean no’s. They consume founder attention, distort pipeline forecasts, and crowd out real opportunities.

One practical tactic that came up was setting expectations in the very first conversation. Something as simple as: Our job on this first call is to figure out why we don’t fit. Life is too short to waste each other’s time.

That framing changes the dynamic immediately. It gives you permission to qualify hard, ask real questions, and move on if it’s not real.

Don’t be intimidated — use humility instead

Big titles can mess with your head if you let them. But one of the best reminders from the session was this: enterprise buyers have less autonomy than you do, not more.

“They put their pants on one leg at a time,” someone said. “They’ve got a lot of people they’ve got to ask for permission.”

There’s real power in humility here. Being honest about where you are as a company can actually increase trust. Saying, You’d be a big fish for us — help me understand what you need doesn’t weaken your position. It often strengthens it.

Enterprise buyers are tired of being oversold. Authenticity cuts through faster than polish.

The bottom line

Enterprise SaaS sales isn’t about perfect decks or clever negotiation tactics. It’s about understanding organizational dynamics, getting the right people involved early, and protecting your time aggressively.

Find out what you’re replacing. Map the buying process. Identify the economic buyer. Turn them into a champion if you can. Prepare for procurement without being naïve. And above all, don’t let your funnel fill up with false hope.

When enterprise deals are real, they move. When they don’t, you should move on.

Master that discipline, and enterprise sales stops feeling mysterious and starts feeling predictable — which is exactly what you want as you scale.