You know AI sales tools help your team work smarter, faster, and more effectively. You know not adopting these tools puts you behind your competition. But the flood of available GenAI and agentic AI sales products is overwhelming.

The pressure to rapidly adopt these tools is real, setting a trap for today’s sales enablement leaders: the belief any AI tool is better than none. 

Luckily, knowing how to choose the right AI sales tool doesn’t have to feel like guesswork.

You’ve probably noticed AI showing up in more and more tools—and for good reason. GenAI is already an engrained, nonnegotiable part of the sales process. Allego found 100% of surveyed revenue enablement leaders now use GenAI to support the end-to-end sales process, and Gartner predicts that by 2027, “95% of sellers will initiate their research workflows with AI.” 

Choosing the right AI sales tool starts with asking the right questions. But first—let’s talk about why this choice is so critical.

Why Choosing the Right AI Sales Tool Matters

An AI sales tool is any software that uses artificial intelligence (AI) to automate or enhance one or more aspects of the selling process. That includes:

• Email generation
• Sales proposal (RFP) automation
• Sales forecasting
• Sales coaching (via conversation intelligence)
• Dialogue simulators and role-play tools
• Sales content creation and management (including digital sales rooms)

These tools can drive efficiency and performance—but only if you know how to choose the right AI sales tool for your team’’s needs.

By 2028, 60% of B2B seller work will be executed through conversational user interfaces via GenAI sales technologies.—Gartner

AI tools vary widely in accuracy, usability, security, and how well they integrate with your current systems. Choosing the wrong one can lead to wasted time, wasted budget, and frustrated reps. Worse, if your competitors choose wisely, you risk falling behind as they gain speed and market share.

And make no mistake: AI in sales isn’t a passing trend. You can’t ignore it or hope it will go away.

Gartner writes in its “Navigate GenAI in Sales Tech” report:

• “By 2027, median sales technology spending will exceed $10,000 per seller annually as B2B sales organizations shift spending from additional headcount to AI and hyperautomation to achieve revenue growth targets.
• “By 2028, 60% of B2B seller work will be executed through conversational user interfaces via GenAI sales technologies, up from less than 5% in 2023.
• “By 2030, 80% of sales leaders will consider AI integration in sales workflows as a critical factor for gaining a competitive advantage.”

The future of sales is already here—and it’s powered by AI. Choosing the right tools today means setting your team up for smarter workflows, faster ramp times, and stronger results tomorrow. In a fast-moving market, strategic adoption is how you lead the pack.

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Unlock AI’s Impact in Revenue Enablement

Dive into the 2025 AI in Revenue Enablement Report and discover how 100% of enablement leaders now use GenAI, plus the strategies earning measurable gains in sales, onboarding, and efficiency.

Read the report.

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Ask These 9 Questions Before You Choose an AI Sales Tool

You’re ready to bring AI into your sales process, but choosing the right tools is where things get tricky. With so many options flooding the market, it’s easy to feel overwhelmed or unsure about what truly works.

That’s why we created this framework. Rooted in Gartner’s trusted recommendations and real-world insights from Allego’s 2025 AI in Revenue Enablement Research, these nine questions will help you vet vendors, avoid costly mistakes, and choose the right AI sales tool for your team.

1. What specific sales workflow will this tool support?

It’s easy to fall for “shiny object syndrome” when exploring AI tools. But novelty alone isn’t a reason to buy. The right AI sales tool should support a specific workflow your team is actively trying to improve.

Maybe the workflow relates to:

• Onboarding
• Creating sales content
• Forecasting pipeline or revenue projections
• Coaching sales reps

When AI is aligned to a real need, the impact can be significant. Allego’s 2025 AI in Revenue Enablement Research confirms this. Of the 246 revenue enablement leaders surveyed, 51% said AI shortened the sales cycle. That’s up from just 28% in 2024.

51% of revenue enablement leaders said AI shortened the sales cycle.—Allego

And 63% said AI “definitely improved” sales rep coaching, making it more targeted, efficient, and scalable. This includes the host of benefits from a growing trend: AI sales training role-playing. A full 43% of those surveyed now use AI-powered role-play to improve sales coaching.

2. What data does the tool need and how secure is it?

GenAI tools are only as good as the data they’re fed. Generic prompts yield generic answers. For meaningful, personalized outputs, AI tools often need access to your CRM, customer lists, proprietary sales content, pricing, IP, and historical performance data.

That level of access raises serious questions about data security. Many tools rely on externally hosted large language models (LLMs), which can create risks if your data is shared, retained, or used to train public models. Gartner highlights this as a key concern, especially when vendors aren’t transparent about how prompts and content are handled.

As a buyer, it’s essential to dig into the details. So, make sure you ask these questions:

• What third-party vendors are involved, and how compliant are they?
• Will any of your data be used to train public models? Is there an opt-out?
• Who owns the data once it’s processed?
• What encryption is used in transit and at rest?
• Who has access, and what controls prevent unauthorized use?

3. Does the AI sales tool generate accurate, relevant outputs—or hallucinations?

AI hallucinations—fabricated or inaccurate outputs—can be hard to spot and easy to believe. That’s what makes them so dangerous. If your team isn’t deeply familiar with a topic, it’s easy to mistake false information for fact. The result? Off-brand messaging, made-up data, or outright misinformation.

According to Gartner, vendors should “offer functionality to eliminate hallucinations, false outputs, and verify sources’ provenance.”

To reduce the risk, prioritize tools that use:

• Retrieval-augmented generation (RAG): Combines real-time data retrieval with generative AI to ground outputs in trusted, up-to-date sources. This reduces the chance of hallucinations.
• Grounding: Ensures AI outputs are based on verified internal data, such as company documents, CRM content, or product materials—rather than open-ended language prediction.
• Windowing: Limits the scope of an AI model’s response to a defined set of inputs or context windows, helping it stay focused and accurate.
• Human-in-the-loop: Incorporates human review and feedback into the AI process to catch errors, improve accuracy, and maintain brand alignment over time.

Ask vendors directly what they do to prevent hallucinations and how they ensure output accuracy, especially in complex or regulated industries.

4. How customizable is the experience for sellers and managers?

The best AI tools don’t just generate content—they adapt to your team’s unique workflows, personas, and sales stages. Look for tools that let you customize:

• Outputs
• Workflows
• Prompts based on specific personas or sales stages

Rigid, one-size-fits-all AI tools lead to poor rep experience, low adoption, and low ROI. On the other hand, when AI tools align with how your sales reps operate, usage goes up—and so does impact.

To ensure customization, ask vendors if the AI tool allows for admin-level configuration of prompt templates, integrations, and output formats. The more flexibility it offers, the more value it can deliver.

5. What kind of AI literacy and training does the vendor offer?

GenAI-powered sales tools are evolving quickly, and new ones enter the market every month. However, most sales teams are still just getting up to speed. That’s why vendor-provided training and support are critical to successful adoption.

To see the best adoption, look for vendors that provide clear, easy-to-understand resources, such as:  

• Guided onboarding
• Step-by-step user guides
• Practical templates and examples
• Peer communities or forums for shared learning

The organizations gaining the biggest boost from AI aren’t the ones blindly investing in random solutions. They’re the ones investing in strategic enablement.

With 100% of revenue enablement leaders now using GenAI to support sales, marketing, and customer success, the competitive edge comes from knowing how to use these tools well, not just having them. That means selecting the right tools and then ensuring your team has the AI skills and literacy to use them well.

6. How does this tool fit into your existing sales tech stack?

A good AI tool doesn’t just work. It works with the systems your team already uses. According to Gartner, “Integrating GenAI with existing sales tech AI investments transforms the perception of technology from a tool to a teammate.”

If the tool creates friction or lives in a silo, adoption will suffer—and so will your ROI. Look for solutions that integrate seamlessly with your: 

• CRM (Salesforce, HubSpot, Pipedrive)
• Sales content management systems
• Conversation intelligence platforms

When integrated properly, AI can automate manual tasks, personalize outreach, and boost seller productivity:

• Surface the right content at the right time through your CMS
• Deliver real-time, personalized coaching through call analysis
• Generate relevant follow-ups using insights from your CRM

The smoother the integration, the faster your team sees results.

7. What kind of outputs does the tool deliver and how are they reviewed? 

If you’ve used GenAI tools, you know the quality of outputs can vary wildly. Some generate vague, generic content, while others produce targeted, relevant messaging that sounds like your brand.

When evaluating tools, ask vendors how they ensure their tool delivers brand-aligned, high-integrity outputs. 

When evaluating tools, ask vendors how they ensure their tool delivers brand-aligned, high-integrity outputs.

Look for AI sales tools that:

• Provide prebuilt prompt templates
• Use reinforcement learning or human feedback loops to continually improve
• Offer administrative control over output quality and tone

Not only do strong output controls protect your brand, but they also drive trust and adoption across your sales team.

8. What’s the pricing model, including hidden costs?

Before investing, understand the AI tool’s full pricing model. Here are points to consider with two common pricing methods:

• Token-based pricing. This is a straightforward pay-as-you-use-it system. However, as your usage becomes more integrated into processes and tasks become more complex (generating full emails, playbooks, or summaries), that usage—and expense—can grow quickly. It’s common for vendors to pass on any AI-related costs to the customer.
• Freemium model. With this pricing structure, you get in at a low or free cost, but essential features often aren’t included. (Think CRM integration, multi-user access, or administrative tools.) An upgrade to full functionality can be expensive.

As Gartner’s report points out, many AI vendors are actively competing for early market share by enticing users with low initial pricing or by bundling GenAI features into existing subscriptions. But as adoption and use increase, “pricing is likely to evolve.”

To avoid surprises, ask vendors about:

• Usage caps and overage fees
• Whether credits expire
• How pricing changes as your team grows or scales usage
• Real-world examples of what similar companies pay

A clear understanding of cost today—and tomorrow—will help you avoid budget blowouts later.

9. How will you measure ROI from this tool?

Don’t implement an AI tool now and figure out success later. Define what success looks like before you invest in an AI sales tool, then choose a solution built to deliver on those goals.

Focus on the outcomes that matter most to your organization, such as:

• Shortening onboarding time
• Increasing sales rep productivity
• Speeding up proposal creation
• Improving conversion rates
• Boosting forecasting accuracy

The right AI tools have the capability to achieve those outcomes. And Allego’s research report confirms that top-performing organizations are seeing benefits. Over half saw a shortened sales cycle, while 51% saw faster onboarding and training with AI-powered coaching. Overall, 48% of these leaders said AI contributed to their revenue growth.

Before purchasing the flashiest tool, ask vendors for case studies and benchmarks that show how others have achieved ROI using their tool.

These aren’t gut feeling benefits. They’re measurable, trackable, and objective.

Before purchasing the flashiest tool, ask vendors for case studies and benchmarks that show how others have achieved ROI using their tool. That evidence will help you connect performance metrics to your business goals. And it will help you make a confident, well-informed decision.

How to Choose the Right AI Sales Tool Comes Down to Strategy

Don’t let the excitement about new AI sales tools blind you. Be strategic in how you choose the right AI sales tool. 

Ask tough questions. Involve your sellers early. Pilot before you purchase. And prioritize platforms that support enablement, not just automation.

The reality is clear: AI is reshaping how sales teams operate. And those who don’t adapt risk falling behind. But success doesn’t come from adopting every tool. It comes from selecting the right ones and using them intentionally to drive real impact. A few wise, measured, strategic investments will position your team for long-term success.

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About the Author: Michelle Davidson is a content marketing manager at Allego, where she partners with sales and enablement teams to create content that helps reps engage customers and prospects in meaningful conversations.

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Unlock AI’s Impact in Revenue Enablement

Dive into the 2025 AI in Revenue Enablement Report and discover how 100% of enablement leaders now use GenAI, plus the strategies earning measurable gains in sales, onboarding, and efficiency. Read the report.