How to choose the right AI sales assistant for smarter selling

Today’s sales representatives—including yours—face many challenges. Notably, they:

• Lack time to effectively plan for and analyse their sales calls
• Worry about meeting quarterly sales targets and quotas
• Have too many time-consuming tasks that prevent them from completing the work that matters: building relationships with potential customers

The good news? Artificial intelligence (AI) assistants can improve your reps’ productivity.

What is an AI sales assistant, and how does it work?

An AI sales assistant automates daily activities, summarises conversations, recommends next-best steps, and serves up relevant content for sales reps.

In short, the newer type of sales technology acts as a virtual assistant that streamlines workflows so sales reps can maximise their time and close more deals.

An AI assistant doesn’t replace your team. Rather, it augments your reps’ work.

Great sales still requires a human touch. The right AI tool simply supplements your reps’ role as a trusted partner and empowers them to work faster, smarter, and more efficiently.

Top benefits of using an AI sales assistant

The best AI sales assistants automate repetitive tasks (think data entry and follow-ups) so your reps can focus on selling. They also use sales analytics to help your reps identify at-risk deals and find valuable sales enablement content to share with specific leads.

Using AI in sales can also personalise outreach, shorten sales cycles, and enhance buyer experiences and customer interactions.

For example, AI assistants for sales teams can highlight key points and use content automation to deliver a relevant case study to share with leads. This leads to more intelligent decision-making for sales outreach and accelerates buyers through the sales pipeline.

Our State of Sales Enablement Report 2025 found 49% of GTM teams use AI like sales assistants to enhance their work, and 41% intend to adopt it in 2025. The use of AI assistants is leading to strong results: They help these teams see up to 20% better revenue outcomes.

What the best AI sales assistant tools offer

Whether you’re a mid-market and enterprise company, the best sales tools today offer intuitive generative AI, advanced natural language processing (NLP), and cutting-edge sales intelligence capabilities, the combination of which can help your team find, engage, and convert high-quality leads faster.

When it comes to AI sales assistants, in particular, your sales organisation needs the following six capabilities:

1. Content automation

Using AI-driven content automation, your reps can tag, categorise, and personalise sales materials automatically. Everything from case studies to pitch decks are tailored to the specific buyer’s needs.

For example, AI might quickly find a healthcare-focused case study for a hospital prospect and an ROI analysis for their CFO. This means your reps don’t have to sift through potentially hundreds of files to unearth the most up-to-date, relevant content to share with the lead.

Questions to ask:

• What content formats does the tool support?
• How does it organise content for fast, accurate search?
• Can it surface content automatically, based on deal stage, persona, or industry?

2. Conversation intelligence

Conversation intelligence examines calls and meetings to assess tone, talk-to-listen ratios, and detect possible objections early. It identifies patterns, like what top performers do that under-performers don’t.

For example, call analysis might flag a sales rep talking about pricing too soon and suggest adjustments. It also generates call summaries and recommends next steps, such as a follow-up email that addresses unresolved questions.

Questions to ask:

• Can it analyse conversations and suggest specific improvements?
• Does the tool tag content based on the topics discussed during the call?

3. Customisable playbooks

Generic recommendations don’t help your reps deliver stellar buying experiences to prospects.

A strong AI assistant adapts to your company’s sales process, messaging, and ideal customer profile. This requires training the AI with your own customised playbooks so it learns your internal strategies, ensuring context-aware suggestions.

For example, an AI virtual assistant will learn your team’s objection-handling scripts and suggest talking points, like those tied to competitors’ offerings, to bring up on tough calls in which prospects push back.

Questions to ask:

• How does the AI tool learn our processes, ICP, and knowledge?
• Does the AI come pre-built with standard sales workflow processes?

4. Rep-level coaching and training insights

Developing reps to their full potential will help you close more deals. Look for AI tools that provide performance insights and simulate real sales conversations through role play.

These features give sales managers a clear view of where each rep needs support, along with tailored coaching tips to speed up their growth.

Questions to ask:

• Does the tool provide detailed, individual performance analysis?
• Can sales managers use AI to role-play training sessions?
• Can reps role-play specific negotiation and complex conversations using AI?

5. AI-powered analytics

Predictive analytics powered by machine learning and AI analyses sales rep performance, buyer engagement, content usage, and deal velocity without extra manual effort.

Sales technology that delivers predictive insights can provide actionable feedback and suggestions. For example, it can recommend actions like, “Discuss ROI earlier with IT financial buyers,” or, “This case study influences closed-won with 40% of leads,” rather than leaving you digging through volumes of historical data to examine past performance.

Questions to ask:

• Can it track content usage and suggest resources to update, keep, or retire?
• Can it suggest deal strategies based on real-time sales data?

6. Asynchronous selling

Buyers don’t always want a sales call. In fact, many prefer self-guided interactions. That’s why your sales virtual assistant should work across every channel. The best AI assistants support email, chat, telephone, and in-person meetings. These features enable you to meet buyers where they are.

Questions to ask:

• What communication channels does the AI tool support?
• Does the tool create content and communications without live meetings?
• Can it track buyer engagement across different channels?

AI sales assistant feature checklist

Do you know what your must-have features are? Before evaluating AI sales assistant software, review this list and note the features your team will benefit from most. Use those as your must-have evaluation criteria.

Feature	Why it matters	Must-have (Y/N)	Notes
Content Automation	Organises and personalises content for buyers, saving time
Conversational Intelligence	Analyses calls to improve pitches
Customisable Playbooks	Aligns AI suggestions to your sales process
Rep-Level Coaching & AI Role Play	Provides scalable personalised training and feedback
AI-Powered Analytics	Delivers actionable insights to optimise strategies
Asynchronous Selling Support	Creates content to engage buyers without live meetings
AI Training	Ability to train AI with your expertise, product specifications, processes, and workflow
Automated Lead Scoring	Prioritises leads based on buying intent, engagement, and fit so reps focus on high-potential opportunities

What AI success looks like for modern sales teams

It’s clear AI is already transforming how sales functions operate.

But what does success look like?

How Juniper Networks leverages our AI sales tools

Juniper Networks, a leading global network provider, wanted to build an AI-powered sales force. The business had ungoverned content from 90 different administrators and countless publishers. This led to inconsistent messaging and a fragmented experience for their global team.

Onboarding Highspot’s AI-powered sales enablement platform that integrates directly with its workflow and automated content governance proved to be the ideal solution for Juniper Networks. Highspot Copilot, in particular, generates descriptions and fills metadata gaps for the company’s sales staff. This reduced reps’ content search time by 95%.

Instant Answers, which integrates with Salesforce, provides just-in-time content recommendations at specific opportunity stages. This resulted in 20% more platform usage. What’s more, AI analytics gives sales managers valuable insights they need to standardise top-performing sales strategies.

Why Elsevier trusts our AI sales assistant software

Elsevier, a leading scientific publisher, started their sales enablement journey from scratch, only to find inconsistencies in their sales training processes along the way. The business needed to align managers to a consistent coaching strategy that would scale across their entire GTM motion as it evolves.

So, Elsevier began with Highspot’s content management capabilities. After getting positive feedback from sales reps and achieving 90% adoption, though, the business expanded to include other sales enablement features, including our unified platform’s training and coaching capabilities.

Using AI features such as meeting intelligence and call recording simplified coaching so much that Elsevier was able to reduce its tech stack by 50%. Seamless access to content, training, and coaching in one platform also resulted in 30% more buyer engagement and 65% more sales rep confidence.

Let AI do the heavy lifting—so your reps don’t have to

Best-in-class AI sales assistants lighten the workload. They handle repetitive tasks, deliver data-driven feedback, provide predictive analytics, and tackle other critical tasks so reps can focus on closing more deals and contributing to revenue goals for their companies.

As you explore AI-powered solutions, prioritise features like content automation, sales intelligence, machine learning, and analytics. This will give your team the edge they need.