5 Questions to Reveal the Truth About Your Potential Virtual Assistant for Sales

When you browse through websites selling AI sales assistants, you naturally pay attention to features and pricing structures first. And these do matter.

But other factors also determine whether your investment will pay off in the long term: The adaptability of the AI model, the pace of product updates, and platform flexibility, to name just a few.

That’s why we go further than comparison articles that look at features and price. Here are some critical questions to ask vendors before you “hire” a virtual sales assistant.

Question 1: How do you keep your AI up to date?

A lot of sales technology today relies to some degree on artificial intelligence. But without regular updates, AI tools tend to age poorly. Within a few months, the model you’re using may stop performing like it used to.

Most AI sales software is powered by LLMs from tech giants like OpenAI (ChatGPT), Anthropic (Claude), and Google (Gemini).

And these companies update older models and release new models often.

OpenAI frequently introduces new models. For instance, less than a month after it released GPT-4.1, OpenAI launched o3. Each one has its strengths, and they’ve come a long way from GPT-3.5.

If your platform doesn’t stay on top of these updates, your virtual sales assistant will start falling behind. Its emails will sound less natural, its responses to objections will feel off, and it might miss buying triggers.

Another factor that makes AI age quickly is the data it learns from. 

They need to be trained on fresh data.

This helps the AI stay sharp, respond better, and sound more natural.

How to evaluate

The features vendors emphasize on their sales webpage may not mention which LLM powers their virtual sales assistant or how often they train the AI tool on new data. 

Here are specific questions to ask to ensure you invest in future-proof AI tech:

• Which LLM do you use under the hood?
• How extensively do you fine-tune your models for sales-specific scenarios? 
• Do you use a retrieval-augmented generation (RAG) pipeline for real-time data integration? RAG allows an AI sales assistant to incorporate current information, like recent customer interactions, pricing changes, and new product features, in its output. Without RAG, the virtual assistant is limited to what it learned during its initial training.

Red flags

Your AI sales assistant will probably not provide decent results if your vendor:

• Won’t reveal which LLM they use. In this case, you’re investing blindly.
• Updates its LLM infrequently. You’ll keep paying a subscription fee, but miss out on months of improved AI capabilities you could get from another sales platform.
• Boasts about always having the newest LLM. Yes, this is a problem, too. Software providers must find an optimal balance when updating their LLM. The most recent version isn’t always the most effective. The latest update of a virtual assistant for sales may suddenly become buggy and push away prospects with confusing messages. LLM providers might also roll back versions if they discover critical bugs, meaning your sales platform might temporarily lose capabilities you depend on.

AiSDR is LLM-agnostic, and you can select the LLM you want to use. Currently, our virtual assistant for sales supports:

• GPT-4o
• GPT-4.1
• OpenAI o3
• Claude Sonnet 3.5
• Claude Sonnet 3.7
• Claude Sonnet 4
• Claude Opus 4

You can even switch models mid-campaign if you feel one model is underperforming in message quality.

Question 2: How regularly do you release feature updates?

AI is just one component in the tech stack that requires regular updates. Next, you also need to ask how often the vendor updates features or introduces new ones that wrap around AI. 

Any improvements that make your sales reps’ lives easier and help your outreach cut through the noise matter. Software providers that regularly ship something new keep their users one step ahead of the competition.

Even the smallest innovations, like AI-generated memes, can take your outreach to the next level. For example, we recently implemented this feature, and memes have already improved our outreach with multiple leads. Sometimes prospects go silent for weeks, but the moment we send a humorous “goodbye” meme, they suddenly re-engage and schedule a call.

How to evaluate

You can visit an AI sales assistant vendor’s website, where they may highlight their recent releases in their blogs. Or you can request release notes to assess not only the frequency of major upgrades, but also current feature optimizations.

In addition, get acquainted with the software provider’s public roadmap. This is a document where they share a timeline for planned features and upcoming improvements.

Vendor’s C-level execs may also discuss their recent releases and updates on social media.

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Red flag

If an AI sales tool hasn’t shipped updates in over three months, that’s a major red flag.

And we’re talking about both major feature releases and regular bug fixes. When vendors skimp on updates, they accumulate technical debt: outdated code, deprecated APIs, and security gaps.

Eventually, this becomes your problem as technical debt directly translates to slower performance, software downtime, and security risks.

We constantly work on improvements for both our AI tools and other B2B sales automation features, with small releases published weekly and large features released nearly every month.

Question 3: How do you handle feature requests from customers, and what ongoing support do you provide?

Not all providers are sensitive to customer feedback. They may release new features based on their team’s opinion or on what their competitors do. Or they may follow trends just to attract customers, without considering whether updates bring tangible benefits.

B2C software is created for millions of users, and vendors can’t possibly satisfy the preferences of each client. The most they can do is segment users into large groups and make features for entire segments. 

In contrast, B2B sales tools have a more specialized audience. B2B sales automation software providers can and should satisfy each client’s preferences. Vendors must address clients’ unique needs and treat enterprise customers as partners, rather than just subscribers.

Plus, some vendors set up your digital sales assistant, then focus on collecting subscription payments and offer only occasional support. Instead, look for providers that position themselves as more than software vendors and are ready to spend as much time as needed supporting clients. 

How to evaluate

It may be harder to evaluate the basis of their feature releases until you become a client and make several feature requests. 

Your best bet? Get some guarantees up front. 

Ask your potential vendor the following questions:

• Do you have a public roadmap? If they do and they actually plan features that can help you solve your current pain points, that’s a good sign. They understand your needs and are worth considering.
• Do you offer dedicated feedback channels? Ask how often they request feedback and how they actually gather it. Some providers may offer generic support and annual surveys, which can feel a bit distant. Others prefer direct conversations through Slack channels or feedback calls.
• What client feature requests have you already addressed? It’s great if a company says it listens to customers, but see if they can actually show you examples of features that clients requested that made it into their AI sales assistant solution.
• Will I receive a dedicated customer success manager or implementation engineer? It will make a big difference in how quickly you start seeing value. A dedicated manager will ensure your setup is tailored to your workflows, help with onboarding and adoption across teams, and act as your go-to person for troubleshooting or future feature needs. This kind of support shows the vendor is invested in your long-term success, not just in closing the sale.

Red flags

Detecting unresponsive vendors before you sign a contract requires more than checking how often they publish updates. Look for some warning signs during the demo:

• The demo is too generic. It doesn’t clearly show how their product aligns with your business goals and solves your core pain points. They may be interested only in closing another deal rather than figuring out how to make their solution work for your specific situation.
• The vendor uses pushy sales tactics, and they don’t fully address any of your concerns. This interaction is likely to continue when you become a paying customer.
• They’re vague about who will actually help you after the sale. If they can’t explain who you’ll work with post-implementation or how technical issues get escalated, you’ll likely be left to figure things out alone.

At AiSDR, we enjoy working with our clients and are enthusiastic about their feedback. We have a dedicated Slack channel for each client where anyone can reach out, share their thoughts and ideas for improvements, and directly request features. We introduced our LinkedIn outreach automation feature based on client requests.

We also provide each customer with a go-to-market (GTM) engineer they can go to. The engineer assists with the initial setup and guides customers until they see their first ROI, and continues assisting them as needed thereafter.

Question 4: Can your platform adapt to my sales process?

Even if your potential vendor checks all the boxes above, their digital sales assistant software might still be missing essential features or not offer enough flexibility and automation. The platform might force you into an AI outreach sequence logic that they consider perfect for everyone, but your needs might go beyond what it can handle.

In these cases, you’re left with two options: Either squeeze your processes into the software’s functionality or abandon the platform after a few frustrating months of trying to make things work.

How to evaluate

Don’t just take your provider’s word for it. You should test the platform’s adaptability during a demo. Vendor’s sales teams may promise customization and automation, but to what degree? 

You can ask the following:

• Can I customize prompts?
  
  Make sure you can input open-ended text instructions for AI. Some platforms only let you select from existing templates (e.g., dropdowns and fill-in-the-blank fields).
  
  Though don’t be surprised if you won’t be able to see the entire prompt, as this may be considered proprietary.
  
• Can I build my own outreach sequences?
  
  Maybe you need custom sales flows that combine email, text messaging, and LinkedIn in a specific order, or maybe you want to skip email entirely and only use LinkedIn for certain prospect segments.

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• Can I create custom webhook triggers?
  
  Webhooks are real-time alerts that inform your virtual assistant for sales about events happening in different channels, like your website and email, so that AI can then act accordingly: whether to send a ROI calculator to an interested prospect or pause outreach if someone unsubscribes. Webhook triggers offered by a platform may support specific scenarios only, like “email opened” and “link clicked.” But ideally, you should be able to design your own trigger scenarios, like “if a prospect views the pricing page AND downloads the case study within 24 hours, then send a personalized demo invitation.”

• Do you offer two-way sync with major CRMs?
  
  One-way sync means that your virtual sales assistant might log emails in your CRM tool, but if a salesperson updates a lead’s status, your tool won’t know. Two-way sync is much better because information flows both ways. 

• Do you support multichannel AI outreach by default?
  
  The channels vendors provide by default matter significantly. Some platforms, like Smartlead, offer email and SMS only, while others like Instantly, include email, SMS, and even calls. If you rely heavily on LinkedIn for prospecting, find platforms that offer this channel natively. And you might add another channel soon, so make sure the vendor already includes it or has plans to implement it in the near future.

Red flags

When it comes to flexibility, here are some red flags to watch out for:

• Rigid prompt templates
• No webhook support
• One-way CRM data sync
• Limited AI outreach channels
• Inability to adjust system-level AI prompts

AI sales platforms typically have their own underlying instructions that control how AI actually uses your information: whether it should sound formal or casual, how pushy it should be when closing, and how it handles objections. In some cases, all of this is predefined.

Why is that a problem? Because an underlying system prompt may be too generic or even conflict with your specific instructions.

AiSDR prioritizes your team’s flexibility. With our adjustable system prompts, you can be sure that your AI assistant behaves in line with your brand’s goals.

Whatever outreach workflow works for you, you can use our Sequence Builder to take full control of your AI outreach. And AiSDR users have total freedom in terms of outreach channels: email, LinkedIn messages, and SMS are all available by default.

In addition, native two-way HubSpot integration allows you to synchronize your active and static lead lists automatically and keep your CRM data up to date.

Question 5: Does your AI assistant deliver results?

Last but not least, ask for evidence about what tangible results the sales platform delivers. That’s what we’re here for, after all. If your AI sales platform doesn’t demonstrate a clear ROI, you’re just paying for the vendor’s marketing claims and hoping that one day it will help.

How to evaluate

Look for solutions with a transparent pricing model and flexible opt-out terms. It must be clear upfront what the platform will cost you and in which cases you’re entitled to a refund. Hidden fees and usage limits can eat into your ROI.

Also, when you visit software review sites like Capterra and G2, you may see satisfied clients saying things like, “The [platform’s name] helped us close more deals.” But that’s not enough.

Instead, you want to see comments with specific figures like, “We earned 1.8x more revenue in a month from deals using [platform’s name].”

The same goes for success stories on the websites. You want to see concrete metrics there; if you don’t, request real customer case studies directly. After all, any reputable vendor will be proud to boast about what their clients achieved using their digital sales assistant.

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Red flags

Some vendors structure their pricing in ways that make it hard to estimate the ROI their solution offers and thus, whether your business will actually benefit from it. Here’s what such vendors typically try to sell you on instead:

• Add-on fees for what should be core features. You may prioritize a solution thanks to particular features. But then they turn out to cost extra, which they didn’t mention during the sales process. 
• No free version, no seven-day free trial, and no monthly subscription. Providers who don’t offer these options try to lock clients into long-term contracts with few options to cancel early. This means you can’t assess whether the platform works for you until after you activate a yearly subscription, with no refund options. 

“Pricing available on request” isn’t AiSDR’s approach. Yearly subscriptions only? Not for us either. What you see on our pricing page is exactly what you get and what you’ll pay.

We prefer honesty, and all our marketing claims have solid evidence behind them. 

AiSDR does help clients book more meetings, and we can prove it with numbers. For instance, Metal generated 1.8x more revenue in one month using AiSDR to close deals.

How to measure ROI

Start evaluating the platform’s efficiency for your bottom line after 60–90 days of full use. This gives your virtual assistant for sales enough time to learn your processes and your team enough time to adapt to their new workflows.

Remember to document your current KPIs before implementing the sales platform so you have a baseline for comparison.

Here are some key metrics to track:

• Manual work (time saved): How many hours per week did your sales reps save on prospecting, writing emails, and follow-up tasks?
• Number of meetings booked (output per rep): How many qualified meetings did each rep book compared to pre-AI times?
• Cost per demo: You can calculate this by dividing total sales and marketing expenses by the number of qualified demos booked.

You want to get the highest ROI for your investment. Now that you know what to look for when evaluating virtual sales assistant vendors (and what to avoid), here are some platforms that show growth and innovation.

Tools that can keep up with you

Each of these solutions offers a decent degree of customization, regular releases of new features, and backs up their claims with real success stories and figures.

AiSDR

AiSDR is a virtual assistant that helps automate your entire sales process, from finding leads to scheduling meetings. The platform makes prospecting highly effective with a variety of intent data, like funding rounds, hiring activity, LinkedIn social signals, tech stack changes, and much more. Prospects showing the highest buying intent can be automatically added to your outreach campaigns.

Plus, you can customize the outreach to fit your unique sales style and brand voice by configuring sequences and adjusting prompts. 

AiSDR’s capabilities have proven highly effective in hard-to-reach industries like big pharma, where access to decision-makers is limited and sales cycles last for months. While the usual cost per demo in the industry starts at around $1,500, AiSDR managed to decrease customer acquisition cost to just $140, setting up 28 qualified meetings in only two months.

Clay

Clay is an AI-powered sales intelligence tool with data enrichment as one of its core strengths. It comes with over 130 premium data sources to expand your enrichment coverage.

Clay gives you the flexibility to set up different enrichment workflows depending on your needs. Whether you want to search for mobile numbers only when work emails can’t be found, need to use specialized data sources for certain industries or regions, or only enrich leads that meet specific criteria, Clay can handle it.

Smartlead

Smartlead is a budget-friendly cold emailing software. If your primary goal is to automate outreach, this is a solid option. It pays close attention to the technical side of email marketing and provides useful capabilities to help you manage your reputation as a sender: automated AI email warmup, automatic movement of emails from spam to the main folder, reputation tracking on 400+ blocklists, unique IPs for separate email campaigns, and much more.

Another thing we liked about Smartlead is that the vendor’s main page offers a convenient Smart Bot you can use to find specific information instantly, without having to browse through their entire website.

Outreach

Outreach is a comprehensive revenue orchestration platform that includes all the main outreach channels: email, phone, SMS, and LinkedIn. The platform puts a high emphasis on learning how your team actually works, which helps reps adopt the new process more easily and lets AI detect deal blockers in your sales funnel.

On top of that, Outreach has a Managed Services team that helps its clients configure the platform to match their business goals and successfully adopt new Outreach features as they become available.

Salesloft

Salesloft is another revenue orchestration platform. Its AI identifies buyer intent and highlights the most relevant sales plays and next steps, so your sales team can focus on the leads most likely to close. Plus, with Salesloft’s multichannel sequences, you can reach buyers through the communication methods they prefer most.

Salesloft’s core strength is integration. It offers more than 160 app connections so you can easily link it with your existing tech stack.