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How to Automate Your Proposals Without Alienating Your Prospects

There’s nothing like automation for freeing you and your sales team from time-consuming tasks like data entry. But can there be such a thing as too much of this tech in your sales docs? Here’s how to avoid overloading your proposal process with automation and turning off your customers.

6 min. read

Alexa, automate my deals.

We’re always talking about adding more automation into your sales and proposal process. It frees up your sales team from time-stealing tasks that take the focus away from selling.

But we’ve also all experienced frustration when the automated tasks designed to give us or our team less work end up being more work. Automation is only as good as the inputs and the oversight you give it.

Because robot assistants are *very* literal.

This post looks at four areas in the proposal process where automation can go awry if you’re not careful. First, let’s quickly look at automation in sales.

When is proposal automation great? And when is it not?

Automation isn’t a ‘nice-to-have’ anymore. It’s vital for connecting all the people and programs, the touchpoints and tech that your sales team needs to close deals. We all know that the more time salespeople spend on admin tasks, the less time they have for, you know, actually selling.

Automation is great for straightforward sales tasks like:

Now let’s look at four areas where automation needs a bit more human oversight.

4 proposal process areas to watch for over-automation

1. Remember to reassess your proposal content

Don’t just set it and forget it. Watch for updates or ways to make your content feel more personable. This is a great place to have automation helping you in the background to keep this from becoming a time-consuming task. For example, Proposify’s template batch update feature allows you to make a change once and then apply it to any or all of the templates in your account.

What kind of automated or pre-set content should you watch for update opportunities? We’ve found that there are two main types of content that need updating:

Content that can become easily outdated

In some cases, proposal content is evergreen. In others, information can become outdated fast.

For example, the marketing lead for one of our customers in the digital media space has set up alerts to check their team’s proposal content regularly. The company’s proposals include details, like audience data, that can quickly become outdated and obsolete.

It’s easy for the marketing lead to check and update their content on a regular schedule because it’s all housed in their content library. Each text snippet, graphic, and pricing table is clearly labelled with the last update date so everyone knows what they’re working with and when it’s time to reassess a piece of content.

An About Us page like this magazine advertising proposal example that includes audience statistics will need to be kept up-to-date.

Content that might not work in all situations

Context is everything. This is something that a lot of us discovered during the pandemic. Content that might normally be seen as humorous or cheeky could give the wrong impression now that the situation had changed.

For example, towards the end of 2019, I wrote an email that automatically goes out to folks who requested our sales playbook guide but hadn’t downloaded it yet. The subject line for the email was, “If you’re reading this, it’s too late,” a play on the Drake mixtape and a reminder that if your sales team doesn’t already have a playbook you need to get on that ASAP.

Anyway, as we did an evaluation of all of our marketing and outreach at the outset of the pandemic response in North America, we realized that a subject line like this, meant to be light, might not be received that way during heavier times. It was much easier to write a new subject line for that email than potentially add stress to someone’s day.

2. Re-evaluate your template strategy

Having one multi-purpose template definitely works in some cases. A one-template approach is a great way to streamline proposal creation, particularly if you have a large and/or spread-out sales team. It also relies heavily on an organized and up-to-date content library.

But if you feel like your main template has to be overly vague or too generic to fit all sales situations, consider a ‘template per’ approach. With this strategy, you create a template for each selling situation.

Here at Proposify, we’ve seen customers customize their templates in many different ways. Some of the most popular include customizing templates for:

  • Each product, service, or package offered;
  • Each buyer persona;
  • Each region or location they sell in.

That way you can still use boilerplate content but niche it down so it doesn't feel bland. Specificity is what keeps personalization from feeling creepy. Instead, your prospects will feel understood.

3. Monitor your metrics

Your proposal view metrics can be the ‘canary in the coal mine’, letting you know that you may have over-automated.

How many times are your clients viewing your proposals? Are there parts or places in your proposal that prospects skip or skim over? Our research has found that most winning proposals receive two to three views. If your proposals only get one view before the deal goes dark, it could be that it’s too automated and generic and it’s turning your prospect off.

The same goes for too many views. If your prospects are viewing your proposal more than three times, they might be having a hard time understanding how your proposal applies to their pain points.

4. Follow up on your follow-ups

What’s the antidote to over-automation? Smart customization. Automate the easy parts—adding in client company details, pulling in product descriptions—and customize the parts that matter more.

Automated follow-ups are a perfect example of a place in the proposal process where automation can be a double-edged sword. Sending a reminder email if your prospect doesn’t open your proposal within a specified amount of time works. Just make sure it makes sense.

Say your rep sends a proposal. The recipient says thanks, but—heads up—they can’t make a decision on it for 2 weeks. Your salesperson forgets to amend the automated follow-up email program and sends the prospect a follow-up three or seven days later anyway. Now your prospect feels like no one is listening to them. Awkward!

Automate everything?

On that note, it’s important to keep in mind that not everything that can be automated should be automated.

Yeah, it might be faster to use a boilerplate executive summary or cover letter. But that means you’re losing out on a great opportunity to really sell your solution by calling out the prospect’s specific pain points and showing how you solve them.

Ultimately, ‘good’ automation is not just robots doing things for you. Automation is only as good as the inputs you give it and the care you take to make sure it’s not alienating your prospects in the process.

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