Friendly Upselling One Call at a Time

Jan 29, 2018

There are many ways to upsell in today’s world, yet before talking about upselling, there is a foundation to dig into. Are your sales representatives comfortable with the pricing they are quoting currently? If they are not at ease with the base price, they are not going to be comfortable upselling, whether it is friendly or not.

Recently, I listened to a reservation sales call in which the caller asked the sales representative to clarify whether the price on the website was per night or for the total stay. When the representative confirmed that the price was for the total stay, it was challenging to tell by her tone whether the caller felt it was too much or a deal. The next recommended step in such cases is to ask what price the caller had in mind. Instead, the representative made an assumption that the price was too much and offered a price reduction. Afterward, the caller shared that she thought the overall pricing was a deal and was excited. This is a perfect example of when not to assume and to ask more questions.

I often come across situations in which sales representatives don’t feel like they personally can afford such a stay, so they are not comfortable quoting higher prices. I find that lack of value building and overall confidence in the homes they are selling come out in the sales representatives’ tones when quoting pricing. The reservation sales agent often will also be quick to discount or will not ask for the reservation and quote only the lowest pricing available. In these situations, I recommend coaching the sales representative to give three pricing options. Start with a home that is an extra treat for the caller—maybe the home has a game room, mountain view, or hot tub—followed by quoting the price, being careful not to pause, and asking the caller how the home feels for his or her family. Callers will then share if the price is more than they are looking for or not. The next step is to go to the second pricing level based on the caller’s response, and then follow the same steps until getting to an agreed-upon fit for the caller.

Once you are confident that your team is proud of the product and the pricing, move on to coaching on friendly upselling. As consumers we are used to the occasional upselling technique when making purchases. I usually think of the upsell offering insurance on products or complementing products to the one being purchased. I am the consumer who is quick to deny the upsell because I usually have done my research and already have a specific price in mind; I don’t want to spend more. How do we overcome the mind-set of a set price?

Sales guru Jeffrey Gitomer, author of The Sales Bible, The Little Red Book of Selling and The Little Gold Book of Yes! Attitude, shares that when upselling is done right, it builds deeper relationships with your customers. His quote is:

“Tell me how I win. When I win, you win.”

I absolutely agree with Jeffrey and believe in relationship-building sales. If we educate the consumer on the benefits of the upsell, our ability to overcome the price objection solidifies. Here is an example based on traveler’s insurance when renting a vacation rental. The Mt. Hood Vacation Rentals team in Oregon quotes the final price, with and without the insurance, followed up with why it would benefit the guest (talking about older family members who are ailing and taking them for a final vacation). When you speak to the specific benefit for the potential guest, the situation shifts to relationship sales, and guests feel taken care of.

Another example of an ideal upsell is during the redemption of a vacation rental stay gift certificate purchased at a nonprofit, black-tie gala (Geronimo Solutions partners with Vacation Rental Management companies to facilitate such gift certificates). Instead of jumping straight to redeeming, ask how many people will be joining during the stay, and offer the option of a larger home, more desirable dates, or an upgraded home with a better view. This is a great way to leverage nonprofit fund-raisers, especially post slow-season and with middle-tier offerings. Have a menu of upgrades to offer to holders of these certificates, with each upgrade carrying an associated fee. Certificate holders often welcome these upgrades, and this creates incremental revenue for companies and homeowners.

Some vacation rental companies offer concierge services. Stony Brook Cabins in Tennessee offers rose petals sprinkled in the bedroom along with a bottle of champagne chilling in the refrigerator. A guest planning a wedding proposal was thrilled that he didn’t have to run around getting items and hiding them for the surprise proposal.

I remember traveling and staying at a vacation rental with Sea to Sky Rentals in Washington; they offered early check-ins and late checkouts for an additional fee. They made this offer in their online agreement and then followed up with a phone call, including additional upsell services.

Steve Strauss, author of The Small Business Bible, recommends additional suggestions for upselling:

• Make it affordable – Offering a 5 percent upsell feels manageable, whereas a 30 percent increase in an offer might not. It is important to think about the percentage of the upsell instead of the dollar price.

• Be casual about it – You are extending an offer in a friendly, non-pressuring way. Keep in mind that doesn’t mean you say, “No pressure.” Instead, have an upbeat tone and extend the offer.


Jeffrey Gitomer recently shared in an article that “the customer is in a buying mood and has already made up his mind and is open to suggestions that will help him. It all rests on the ability to engage, combined with how much trust you have built.

He speaks to breaking it down into forms or elements:

I think you should also consider . . .

You might also want to add . . .

I have personal experience with this, and I recommend you . . .

Have you thought about . . .?

Use power phrases:

    • My experience has shown me . . .
    • the best value is . . .
    • the most profitable way is to add . . .

Make it a deal. If you extend your stay to five nights, there is a deal to get the sixth night free . . .

Comfort them. Most people like . . .

Do you want . . .? Would you like . . .?

When we can step back from thinking about the next call coming in or the customer in front of us, we can be more strategic in our relationship building and make the guest feel taken care of as well as generating additional revenue.

Get closer than ever to your customers. So close that you tell them what they need well before they realize it themselves” – Steve Jobs