Proposal automation for SaaS: Best practices

Proposals are a timesink, but it’s not like you can just eliminate the time you spend on them. SaaS proposals are especially complex, since custom pricing, technical details, and even promised development work need a lot of time and work to put together.

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That’s why proposal automation is so essential in SaaS. Your proposals are constantly getting longer and more complex (especially as your org grows), but you need significant personalization and technical detail to close a deal.

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In this guide, you’ll find out what proposal automation is, what it needs for sellers in SaaS, and how you can integrate it into your process.

Why SaaS proposals are different (and harder)

SaaS proposals abide by a set of constraints that other industries don’t have to. Your team will run into unique challenges that every SaaS founder knows, without necessarily realizing their impact on the proposal process.

Unique challenges of selling software-as-a-service

Selling a SaaS product comes with significant challenges:

• More stakeholders: A SaaS product needs to be reviewed by technical stakeholders, stakeholders representing end users, finance teams scrutinizing contracts, and executives who need to see a clear business case.
• Shelf life: SaaS products are updated constantly, and just keeping up with product updates can make your proposal creation process so much more complex.
• Specificity: All proposals need customization, but SaaS proposals need to account for specific ROI calculations that can vary with each prospect, security concerns, integration requirements, and more.

The complexity problem: Features, tiers, add-ons

SaaS products can be technical and complex, and nowhere is that more true than pricing. Pricing tiers can cover a wide range of features and add-ons, and you need to strike a balance between accurately describing these without overwhelming a prospect. Proposals always need a significant amount of customization, but the pricing alone can make SaaS proposals significantly more time-consuming.

What SaaS companies need from proposal automation

Generic proposal software won’t cut it for SaaS sales. Here’s what you should be looking for.

Essential features for SaaS sales

Proposal automation software should cover the following features at a minimum:

• Natural language editing: Your sales reps should be able to generate proposals, make changes, and fine-tune specific sections the same way they would when talking to a colleague.
• Role-based content generation: The ability to produce different proposals (or different sections in the same proposal) for stakeholders in various roles.
• Version control: SaaS products are constantly being updated, and your proposal automation software should be able to handle this.
• Integrations: Integrating with the right platforms prevents sales reps from having to manually extract content.
• Uploading files: Covering anything from existing proposals to documents from prospects.
• Brand extraction: For both your company’s and the prospect’s branding.
• Machine learning: Proposal software that can understand deal content, challenge sales reps, and know how to ask the right questions to identify missing sections in proposals.
• Export options: Allowing for exporting of proposals to file types like Word documents and PowerPoints.

Integration requirements (CRM, billing, product)

When evaluating proposal software, make sure they cover the following integrations:

• CRM: Your CRM is the beating heart of your customer-facing teams, and proposal software needs the ability to pull data from conversations, company details, prospect profiles, and more.
• Billing and payment integration: Integrating with apps like Stripe and Chargebee allows your proposals to reflect actual billing logic, while facilitating e-signatures and payments.
• Contact management tools: Whether you’re using Google Contacts or another platform, you need prospect information at your fingertips.
• Knowledge base: Tools like Notion and Confluence are essential for more accurate, customized proposals.
• Chat apps: For sharing progress, updates, and more.

Best practice #1: Dynamic pricing configuration

Proposals with pricing tables are 54% more likely to lead to a closed deal, and the pricing section is the second-most consulted section (in time spent reading) for your proposal. It’s where you’ll spend a significant portion of your time, and where you can see the most gains from proposal automation.

Automating multi-tier pricing presentation

SaaS involves multiple pricing tiers, carefully designed to optimize conversion and ARPU (average revenue per user). These tiers can be complex, with long lists of features that are only available in some tiers. They also tend to change from quarter to quarter (if not faster). Proposal automation software can save you tons of time researching pricing tiers for every proposal by learning your pricing and staying up-to-date for you.

Add-on and module management

Does every seller in your team have a list of available add-ons and modules on hand? Do they need to comb through every conversation they have with prospects to find the add-ons that were promised? Automated proposal software integrates into your stack and remembers pricing information from previous deals. That means it can automatically pull context and product features from what it knows and include them in your proposals.

Volume discounting and annual vs. monthly

These pricing details can often make the difference between winning and losing larger deals, and constantly going to a sales leader for approval can slow down your sales cycle unnecessarily. AI-powered proposal software can be trained on the requirements and patterns for these pricing elements, while the human in the loop can share proposals for approval if anything gets flagged.

Best practice #2: Multi-stakeholder proposal journeys

Proposals typically go through multiple stakeholders in all industries, but SaaS creates an especially important divide: technical buyers vs. end users.

Technical vs. end-user content

Technical stakeholders need to dig into detailed product information before they can make a decision. They might have concerns around security certifications, cloud infrastructure, or available integrations. Stakeholders representing end users are typically more concerned with ease of use, feature availability, and pricing. Proposal automation software needs to support your efforts to appeal to both types, whether that’s by creating distinct proposals or integrating multiple perspectives into one.

Champion enablement: Arming internal advocates

Champions have a significant role to play in helping you close deals, especially in SaaS, where they can try your product before they buy it. Proposal automation software can customize enablement documents and arguments based on past conversations, as well as product information, your roadmap, and more.

Executive summary automation for C-Suite

Leaders rarely have time to go through proposals in their entirety, and executive summaries allow them to get a quick sense of what you’re offering. Properly summarizing a proposal requires skill and time, and proposal automation software can streamline this without sacrificing precision or personalization.

Best practice #3: Security and compliance automation

Because SaaS products deal with personal data, customers expect a certain level of data security and different jurisdictions enshrine these requirements into law. Answering questions about your product’s security and compliance in a proposal has to go beyond linking to your security page.

Compliance badge integration (e.g., SOC 2, GDPR)

While your sales team likely already knows how to reference the certifications and compliance badges your product has earned, they may not have the knowledge to answer specific questions from technical stakeholders. Proposal automation can automatically fill in these answers, even noting places where additional product documentation might be needed.

Data privacy and protection documentation

Turning data privacy and protection information or boilerplate copy into longer documentation can be a taxing task to add on top of drafting a regular proposal. AI assistants can cross-reference the documentation you have access to with legislation, compliance documents, and other sources, automating the creation of extra documentation for more discerning prospects.

Best practice #4: Integration showcase automation

SaaS prospects want to know if the products they purchase integrate natively with their existing tool stack. Not only that, but technical stakeholders need to know how these integrations happen, what technology lies behind them, and what holes they’ll have to plug.

Dynamically showing relevant integrations

Adding a link to your integrations page doesn’t make for quick reading, and manually identifying the integrations your prospects need and adding them to your proposal creates significant admin work. AI-powered proposal software can review past conversations, identify integration needs, and automatically update proposals with relevant integration information.

API capabilities documentation

APIs (Application Programming Interface) are the connective tissue between SaaS apps, and your product’s API can make the difference between winning or losing a deal. Front-line sellers might not know all of their API’s capabilities, and API documentation can be particularly dense. Proposal software trained on your API documentation can tell sellers what is and isn’t possible, as well as inject these answers into proposals.

Ecosystem partner integration

If your org partners with providers of other SaaS tools, highlighting these integrations can have a significant impact on a potential deal. Highlighting these relationships requires deep knowledge of your partner ecosystem, which isn’t always realistic for salespeople in orgs that move fast and break things. Proposal automation equipped with an AI layer can keep that knowledge at their fingertips.

Best practice #5: ROI and business case automation

Demonstrating ROI in your proposals allows prospects to go beyond pricing tiers to see the benefits they’ll get from your product in hard numbers. Stats from existing customers are a good place to start, but proposal automation software can help you augment this section of your proposals.

SaaS-specific ROI calculator templates

Calculating ROI in a way that’s impactful for prospects means picking variables that matter to them and demonstrating value. In Cobl’s Sales Proposal ROI Calculator, for example, we use time spent on proposals, proposals sent per week, number of sales reps involved, and similar metrics to demonstrate ROI. Proposal automation software can help you identify these variables, run the numbers, and show prospects how your tool delivers value.

Time-to-value modeling

Some prospects need a bit more convincing. Time-to-value modeling can chart what a prospect will gain after they first buy your product, after they’re fully onboarded, and after they’ve expanded it to all their relevant workflows. Charting this out without AI-powered proposals software would mean working with a data analyst or performance marketer, slowing down your proposals.

Competitive TCO comparison

TCO (total cost of ownership) covers everything from initial subscription prices to infrastructure upgrade and maintenance costs. Proposal automation software can source that information from past deals, case studies, and other documentation.

Best practice #6: Version control and product updates

Salespeople are among your most knowledgeable product experts, but even they can’t always keep up with your product as it evolves. Because proposals need to reflect your product as it is right now (and how it will be in the near future), having up-to-date product information is essential.

Keeping proposals current with product releases

Templates, by definition, can’t keep up with product releases. By the time you’ve updated them, you might be dealing with a completely different product. Proposal automation software can automatically source product updates from across your organization, comparing them with prospect priorities so proposals always reflect what they need (and the work you’ve done to meet those needs).

SaaS Proposal Templates That Convert

New Business Proposal Template

New business proposals have the heaviest burden. They need to establish credibility, articulate value, and justify cost for a buyer with no direct experience of your product. Here’s how you build these proposals:

1. Lead with a concise executive summary that frames a prospect’s problem in their language. Draw this from discovery notes in your CRM.
2. Follow with a solution overview that’s mapped to specific pain points, rather than generic features.
3. Present pricing options clearly, limited to two or three plans. Highlight one as recommended. Cover seat counts, billing cycles, and add-ons without overwhelming the reader.
4. Include a security and compliance section that mentions certifications and security measures.
5. Close with an ROI projection.

Trial-to-Paid Conversion Template

Prospects receiving these proposals already know your product, they just need to know that it’s worth their budget.

1. Skip the introductory pitch and lead with their usage data. Think of features adopted, time spent in the platform, and outcomes achieved during their trial.
2. The pricing section should be a natural next step, showing what the trial included and the pricing plans that match these the most closely.
3. Address the transition from trialing to paid plan, including what happens to their data, configurations, and workflows.
4. Acknowledge uneven feature usage during the trial if needed, framing it as an opportunity to unlock better ROI with a paid plan.

Renewal Proposal Template

Renewal proposals are rarely as thorough as other forms, but they still need to be more than a generic invoice with a signature field.

1. Start with a value summary that quantifies the gains customers have made in your current contract.
2. Present renewal terms clearly alongside any changes from previous contracts.
3. If adjusting prices, anchor the adjustment in increased value.
4. Include a section on what’s coming for your product, like relevant roadmap items, upcoming features, or planned integrations.

Expansion/Upsell Template

The customer already believes in your product, you just need to show that expansion is the best way to meet their evolving needs.

1. Lead with the customer’s current plan and usage data, showing the value they’ve received from your product.
2. Frame the expansion as a natural progress, based on evolving needs, rather than an additional purchase.
3. Show the gap between what they’re already using and what they could be unlocking.
4. Add an ROI section quantifying the difference between their current commitment and the gains from expansions and upsells.

SaaS Proposal Automation Tech Stack

Proposal automation software shouldn’t be a silo. In fact, it works best when it can learn from your existing documentation, pull data from your CRM, or even push signed contracts to your billing system.

Essential Integrations: CRM, Billing, Product

Integrating with your CRM is the bare minimum for any proposal automation software. It’s every customer-facing team’s database for contact information, past conversations, deals, and more. Billing integrations connect your proposal’s pricing section with actual invoicing and payment logic, automatically updating it as your product evolves. Finally, product integration, while not as common, can be extremely valuable. Product usage data, adoption metrics, and account health scores can be vital for trial-to-paid conversion proposals and renewal proposals.

Data Flow Architecture

Proposal automation tools should pull deal details from your CRM, pricing from your billing platform, and usage data from your product without any manual intervention. When a proposal is signed, that information flows back so your CRM is updated, an invoice is triggered, and customer success starts onboarding processes.

API Strategy for Proposal Automation

While built-in integrations can fit most of your team’s needs, a robust API can customize proposal automation platforms to your specific workflows. If you have the technical resources to build your own integrations, evaluate a proposal automation platform’s API to see if it supports custom development.

Case Study: How adista Automated Their Proposal Process

As a leading alternative telecoms operator and cloud services provider, adista needed a platform that could help them generate, update, and standardize hundreds of technical documents to support their proposal creation process.

The Challenge

The pre-sales team at adista handled a constant flow of RFPs (requests for proposal) and technical documents. Because so much customization was needed for each proposal, they took hours and hours to write. Technical requirements were intense, requiring input from multiple departments to keep things accurate and aligned.

The Solution

No-code proposal generation and AI-powered features, all in one platform: Cobl. With Cobl, adista’s pre-sales team could build their own automated workflows for RFP responses, technical memos, PowerPoint generation, and more.

The Results

• 150-200 page documents generated in five minutes or less.
• 90% of content is ready to use out of the gate.
• 35 users across four departments.

Read the full story here.

Purpose-built proposals for SaaS teams

Even with SaaS sales being more complex, proposal automation can save you hours of administrative work and increase your win rate. The key is to find software that can learn from existing proposals, allows sellers to build and edit proposals using natural language, and can parse through dense documentation and pricing tiers.

Want to see what proposal automation can do for your team? Try Cobl for free now.