I'm not talking about those secret lairs we created out of kitchen chairs and blankets when we were nine years old, though that sounds fun even at my age. No, I'm talking about F.O.R.T. Friction. Options. Reinforce. Timing.
Let me explain.
Within your base, you have customers and prospects. Prospects are over 3x more difficult to sell than current customers which makes expansion your golden goose. Check out this graph from the 2019 KBCM SaaS Survey.

In this graph, notice the average % of new ARR from upsells climbs to 50%, and even grows as ARR grows. Takeaway: Expansion is the key to breakout growth, whether you're big or small.
F is for Cow
Let's address the F in the room... friction. Momentum is the pathway to any expansion and friction is the herd of cows crossing said pathway at a very, very slow pace. The willingness to buy more stuff is higher when we’re making forward progress. Friction stops or slows down momentum making the buyer second guess, hesitate, or rethink and ultimately fall back into a complacent state. This is why the suggested add-on during a sale on Amazon is so darn effective. Ever been suggested dessert after a meal, or offered a promo in a game after reaching a certain level? These are examples of sellers taking advantage of forward movement. FRICTION - keep it low with focused plans that ignite momentum.
This or that?
Or what about those? Maybe these? People love options (that's the O), just not too many. Beyond 5 choices, customers may begin to feel overwhelmed which kills momentum. Not enough options can lead customers to feel out of control of the buying process which, you guessed it, kills momentum. The idea is for them to have clear options to buy more of something, whether it’s by volume, type, or term, so the buyer feels like they are still in control. The sensation of control, coupled with momentum achieved with less F, makes it easy to buy more stuff. OPTIONS - keep them short, sweet, and to the point.
Positive Reinforcement
It's not just for toddlers and well-behaved husbands! Recurring revenue hinges on recurring behavior. Regular reinforcement of favorable behavior drives more steam in the momentum locomotive. Send a reminder if you see activity fall off, or better yet, congratulate an action or outcome in the software. Proposify sends a string of encouraging and motivational felicitations to closers who sealed the deal; there's confetti and everything. This simple action made users want to close more deals. Reinforcement drives a stronger force behind building momentum, which goes farther with low friction, and acted upon with the sensation of control...see what we're building up to here? REINFORCE - keep it consistent and meaningful.
Right On Time
The best upsells happen when the client is ready to buy, not when you are ready to sell. So how do you have pro-comic-level timing? You tie your upsell offers to a well-defined milestone or event in the application. When the customer reaches W number of users, performed X number of downloads, sent Y emails to Z contacts is when you through confetti and upsell. Avoid bad timing such as when the customer is just getting started, struggling, or worse, deciding to churn (more on saving customers with pricing in a different blog). TIMING - keep it data-driven and thoughtful.
If you Reinforce the repeated behavior that leads to value, grease the skids with low Friction, create the feeling of control with Options, and make the offer when the Time is right,...that is when the expansion mansion is built. In other words, you got yourself a F.O.R.T.!