Proposify logo Proposify logo
  • Product
    • Product OverviewProposify is the all-in-one platform that makes every deal a closed deal.
    • IntegrationsChoose from hundreds of third-party tools to connect with
    • Document AutomationAccelerate your sales cycle by sending professional, on-brand documents.
    • Interactive QuotesCreate interactive and error-free quotes that will quickly seal the deal.
    • Contract ManagementMark up and sign on any type of contracts, quotes, and agreements.
    • E-Signatures & PaymentsGet all your sales documents legally locked down right within Proposify.
  • Solutions
    • Roles
      • Sales
      • Marketing
      • IT/Operations
    • Industries
      • Agencies and Consulting
      • IT and Software
      • Landscaping and Janitorial
      • Construction and Restoration

    Want help from the experts?

    We offer bespoke training and custom template design to get you up and running faster.

    Learn more
  • Templates
  • Pricing
  • Resources
    • LEARN
    • Case Studies
    • Self-Guided Tour
    • Webinars
    • Blog
    • Newsletter
    • SUPPORT
    • Help Center
    • Getting Started
    • Product updates
    • API Docs
    • Refer a Friend

    State of Proposals 2025 Report

    We’ve dug deep into our data and extracted the information that sales and marketing leaders can use to make their proposals better and boost their business.

    Read the Report
  • Log in
  • Book a demo
  • Sign Up Free
  • Product
    • Product OverviewProposify is the all-in-one platform that makes every deal a closed deal.
    • IntegrationsChoose from hundreds of third-party tools to connect with
    • Document AutomationAccelerate your sales cycle by sending professional, on-brand documents.
    • Interactive QuotesCreate interactive and error-free quotes that will quickly seal the deal.
    • Contract ManagementMark up and sign on any type of contracts, quotes, and agreements.
    • E-Signatures & PaymentsGet all your sales documents legally locked down right within Proposify.
  • Solutions
    • Roles
      • Sales
      • Marketing
      • IT/Operations
    • Industries
      • Agencies and Consulting
      • IT and Software
      • Landscaping and Janitorial
      • Construction and Restoration
  • Templates
  • Pricing
  • Resources
    • LEARN
    • Case Studies
    • Self-Guided Tour
    • Webinars
    • Blog
    • Newsletter
    • SUPPORT
    • Help Center
    • Getting Started
    • Product updates
    • API Docs
    • Refer a Friend
  • Log in
  • Book a demo
  • Sign Up Free
Proposify Blog
    • Sales
    • Proposals
    • Business
    • Tools
    • Product
    • Marketing
  • Proposals
6 min read

How to Automate Your Proposals Without Alienating Your Prospects

August 18, 2020
Lauren d'Entremont Lauren d'Entremont
  • Share
  • Share
  • Tweet
  • Copy

    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.

    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:

    • data entry and retrieval;
    • deal tracking and follow-up;
    • and coordinating digital sign-off.

    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.

    Lauren d'Entremont
    Lauren d'Entremont

    Subscribe via Email

    Related Posts

    Why It Pays to Disqualify More During Your Lead Qualification Process
    Sales 8 min read October 16, 2018
    Why It Pays to Disqualify More During Your Lead Qualification Process A well-qualified lead is worth its weight in gold. But how much is letting poorly-fitting leads into your funnel dragging your sales team down?
    Read Post
    Where to Slow Down Your Sales Process to Close Deals Faster
    Tools 9 min read August 14, 2018
    Where to Slow Down Your Sales Process to Close Deals Faster A super-speedy sales cycle is great—until it isn’t. Here’s where haste makes waste in the sales process and how to slow down while staying proactive …
    Read Post
    Proposify logo
    • Platform
      • Proposal Automation
      • Quoting
      • Contract Management
      • E-Signatures & Forms
      • Integrations
      • API
      • Security
      • Our Professional Services
    • Solutions
      • Sales
      • Marketing
      • IT/Operations
    • Resources
      • Blog
      • Templates
      • Webinars
      • Books & Guides
      • Knowledge Base
      • AI Proposal Generator
    • Company
      • About
      • Diversity
      • Careers
      • Customers
    ©2025 Proposify Inc. All rights reserved.
    • Contact Us
    • Privacy Policy
    • Terms & Conditions
    • Status
    • LinkedIn
    • Facebook
    • Instagram

    Basic

    Start free trial

    Team

    Start free trial

    Business

    Book a demo

    Brand customization

    Unlimited templates

    All accounts allow unlimited templates.

    Content library

    Create and share templates, sections, and images that can be pulled into documents.

    Embed images & videos

    Images can be uploaded directly, videos can be embedded from external sources like YouTube, Vidyard, and Wistia

    Custom domain

    You can map your domain so prospects visit something like proposals.yourdomain.com and don't see "proposify" in the URL

    Content authoring

    Basic Team Business
    Online signatures

    All plans allow you to get documents legally e-signed

    Interactive quoting

    Allow prospects to alter the quantity or optional add-ons

    Client input forms

    Capture information from prospects by adding form inputs to your documents.

    Document Sends

    You can create unlimited documents but some plans limit how many you can send per month.

    info

    5 sends / mo

    Unlimited

    Unlimited

    Collaborator seats

    Collaborators are users who only have access to specific proposals, and can edit or approve, but not create or send.

    info

    1 collab seat included

    3 collab seats included

    5 collab seats included

    Visibility

    Basic Team Business
    Notifications & metrics

    Get notified by email and see when prospects are viewing your document.

    PDF export

    Generate a PDF from any document that matches the digital version.

    Reports

    Get a full exportable table of all your documents with filtering.

    Integrations & API

    Basic Team Business
    Payments

    Connect your Stripe account and get paid in full or partially when your proposal gets signed.

    Integrations

    Integrate with popular CRMs, invoicing, and project management tools.

    Automations

    Set up automations using pre-built connectors or customize using the workflow builder

    Single sign-on (SSO)

    Our SSO works with identity providers like Salesforce, Okta, and Azure

    Salesforce integration

    Use our managed package and optionally SSO so reps work right within Salesforce

    $9/user/mo

    Aspire integration

    Import contacts and field data from Aspire into documents in Proposify

    $9/user/mo

    Process & control

    Basic Team Business
    Custom fields & variables

    Create your own fields you can use internally that get replaced in custom variables within a document.

    Auto reminders

    You can automatically remind prospects who haven't yet opened your document in daily intervals.

    Roles & permissions

    Lock down what users can and can't do by role. Pages and individual page elements can be locked.

    Approval workflows

    Create conditions that if met will trigger an approval from a manager (by deal size and discount size).

    Workspaces

    Great for multi-unit businesses like franchises. Enables businesses to have completely separate instances that admins can manage.

    API Access

    Integrate with external systems, or enhance customization, our API provides the tools you need to succeed.

    Customer Success

    Basic Team Business
    Email & chat support

    Our team is here to provide their fabulous support Monday - Thursday 8 AM - 8 PM EST and on Fridays 8 AM - 4 PM EST.

    Phone & Zoom support

    Sometimes the written word isn't enough and our team will hop on a call to show you how to accomplish something in Proposify.

    Success manager

    Your own dedicated CSM who will onboard you and meet with you periodically to ensure you're getting maximum value from Proposify.

    Premium integration support

    Our team of experts can perform advanced troubleshooting and even set up zaps and automations to get the job done.

    Custom template design

    Our in-house designers will design an on-brand, professional proposal template to your satisfaction.

    info
    Learn more Learn more Learn more

    Subscribe via email