twitter linkedin
Andy Hattemer > Posts

Buying B2B SaaS at a company is like playing a hand of Poker

The dynamics around the process of buying multi-user business software tools like Trello at a company are similar to a poker hand.

Image credit: Card and Backgammon Players. Fight over Cards, Theodoor Rombouts (Flemish, 1597–1637)


I worked in a variety of teams at a tech company as it scaled from 150 to 600 people. As a company, we tended to be early adopters and big users of B2B SaaS Tools like GitHub, JIRA (Atlassian), Trello, Basecamp, Segment,, Looker and many many more. This meant adding and changing tools quite often. As a result, after watching many iterations of the “SaaS tool buying process” I started to think of it like a Poker hand.

This is even more relevant today. Five years ago, there were often scenarios where the SaaS tool had created it’s own category and had no competition. For example, when we decided to use Segment, there wasn’t really a competitor so there wasn’t a poker hand. Times have changed. Nowadays, there are 11 SaaS tools in every imaginable permutation of category, every multi-user SaaS tool purchase decision is a poker round. Not only that, but they can get pretty heated because often different employees will bring years of experience with competing tools.

I found the Poker analogy to be a useful way of understanding the influencing factors and outcomes of a process that is anything but rational.

The buying factors, explained via Poker

B2B SaaS tool buying process = A hand of poker

In our analogy, the buying process is the Poker hand, or one round of Poker. It starts when someone says: “We should all use [tool X]” or “We need a [category] tool”. Sometimes the decision is new tool vs existing tool, sometimes it’s new tool A vs new tool B, sometimes new tool vs in-house tool.

Groups of supporters for a specific tool = the players

Starting a hand forces employees into groups (players) backing a specific tool (their cards, more on that later). As you can imagine, groups can be made up of one person (VP wants us to use Salesforce), homogeneous teams (infrastructure doesn’t want to outsource monitoring), or a motley assortment of employees (people at the company are starting to prefer AirTable over Google Sheets).

A group’s authority in the process = Their stack of chips

One group might have more authority (a larger stack) purely due to seniority, another might have more because it is their area of expertise. Big, intimidating stacks, when combined with other factors, can cause other people to fold early and not voice disagreement.

The needs of the business = The community cards

The community cards that everyone can see on the table (i.e. the flop, turn, and river cards) are the specific needs or requirements your company has, presumably what caused you to start looking for a tool in the first place. A forceful player can end a hand before all the community cards are out, before all the requirements are well known.

The SaaS tool = The cards in your hand

How well does the SaaS tool you are pulling for actually solve the problems at-hand. The actual quality and capabilities of the tool really only matter in extraordinary cases, where a tool is just instantly recognizably better or worse than the competition.

A group’s appetite for pushing their tool = Bluffing

How hard are you willing to push your hand? You almost don’t need an analogy here, a group’s ability to influence the outcome by bluffing can manifest in a couple ways: Maybe that’s just their personality, whatever cards they come to the table with, whatever the flop, without a second thought say: “My hand is the best, you’re all going to lose so give up now.” Or maybe they just really love their cards, and only in this particular hand of poker do they really push it.

Where the analogy falls short

I’ve also seen that “just working circles around people” is a decently effective way of short-circuiting the Poker round. What I mean by that is: If it’s clear the company needs a tool for feature flagging, one team wants to use X and the other wants to use Y. Sometimes the team that integrates, ramps up usage and does effective internal evangelism of the tool fastest wins.

Implications of B2B SaaS Poker

  • The process is anything but rational, “Bluffing” and “Intimidation” behind a tool that is poorly suited for the requirements will often beat the best tool.
  • “Superfans” are extremely valuable because they will “bluff” or push a tool and everyone else will fold.
  • “Executive Support” for a tool is the equivalent of a fat stack of chips.
  • Self-serve SaaS tools often think about growth in three stage: Singleplayer mode, Team usage, and Enterprise. In that setup the Poker round doesn’t start until Teams or Enterprise decision. (Which is part of the reason why self-serve is so popular.)

What’s the buying process like at your company? Does it feel like a round of poker? Send me your stories on twitter.