Great subject. Would love to hear from someone on the property management side.
My short take is this: patient persistence.
The long take--
Our prospect/client base is structurally distracted. They have people coming at them from above (investors/owners), on the same line (peers) and below (their employees). Enter the vendor, and there is clearly a clash for the finite amount of time that exists in a given day.
My keys to success are as follows:
1. Patient persistence.
2. Deliver value--do homework in advance, know the mix of their properties/residents, current vendors, and the like. Spend 3-4 hours understanding the prospect before calling so that you can speak with authority and expertise on their company.
3. Hang around---this means staying on their radar without being a pest. Send newsletters, books/articles of interest, new client updates, and other things that they may value. This way, when it comes time to seek out a potentially new vendor, you will come favorably in mind.
4. Develop a robust funnel. When you have plenty of prospects to work with, you do not have the "inverted pyramid" of needing a sole sale with one particular prospect. When you have all of this upside-down pressure, you tend to press, and then squeeze the life out of the prospect--causing you to lose the deal, and maybe the respect of the prospect (now you can't get back in again later).
5. Be generous. Genuinely give of yourself. You know the people out there that do stuff for others because it is the right thing to do. When you genuinely care about your prospects, it comes through. Think about your own personal relationships, do you do stay friends with those that are just "takers"? Probably not. Well, do not be one yourself.
6. Tell the truth. (especially you software salespeople out there) If you know that your product cannot do something, and the client asks, tell them. If you honestly feel that the product you are selling is not right for them, tell them. If you do not know if something does a certain thing that the client deems important, do not reflexively say "Oh, it can do that." I remember going out on a sales call with a VP of a major software company. Before the meeting, he said "what lies am I going to tell today." I cannot tell you how many of his clients have told me that they know he is a liar.
7. Ask the client how they want to be sold to. Ask them how they make these kind of decisions, talk to other vendors see how they do this. This way, you have a much better chance of success.
8. Remember what we all do here for a living---we work to give people a place to call home. Treat each and every part of your daily professional life with that same level of respect. Every single day, in every property that we have ever influenced (either on the vendor side or the property management side) there are people who come home at the end of the day, put their feet up and say "boy, it is sure nice to be home."