14 Challenges and 18 AI Innovations in Sales Outbound
From AI-powered account insights and prioritization to hyper-personalized emails and social media engagement, this guide shows how sales leaders can leverage AI to stay ahead. Learn actionable strateg
Outbound sales have become more complex than ever. Sales teams are switching to multiple channels, and touchpoints, and trying to get a meeting with prospects.
No matter if you are a Sales Rep or a Sales Leader, the challenge is quite intense.
Here is a set of steps that sales teams (including yours) traditionally follow:
1. Getting a list of ICP accounts
Traditionally, this involves a mix of market research, data analysis, and getting a dump from database tools. Sales teams spend hours, if not days, combing through databases, tweaking their ICP criteria, LinkedIn profiles, and industry reports to curate a list of potential accounts.
2. Prioritize them as per Intent Signals
The next challenge is prioritization. Some accounts might be showing strong buying signals or are planning to look for solutions, while others are just browsing.
Traditionally, sales teams rely on a mix of past interactions, 3rd party intent signals, manual research, website visits, content downloads, and social media interactions to prioritize these accounts.
3. Send Personalized Emails
Personalization is no longer a choice in outbound sales—it's a necessity. Generic emails are not working anymore.
4. Cold call Target Accounts
Cold calling has been, and still is, one of the preferred ways to reach prospects. However, it’s a numbers game, with only a percentage of calls being picked up and leading to meetings. Unfortunately, this number is declining over time.
5. Reach them on Social Media or Communities
Social media platforms like LinkedIn and Twitter have become essential for engaging with prospects. Sales reps are going for multi-channel prospecting to get a meeting.
6. Follow up or nurture through Insights
Sales reps have to follow up consistently to get attention and be on the top of their mind. They use pre-built follow-up and nurturing sequences for pipeline prospects.
Challenges with Outbound Sales
Outbound sales have always been challenging and new obstacles keep coming to even sales champions.
Based on our interaction with 120+ sales teams, we have identified the following challenges with the existing workflow steps.
1. Getting a List of ICP Accounts
Your outbound starts with identifying the right accounts. The sales team even faces challenges at this step.
Challenge #1 - Incorrect email and phone data:
The ICP account list is only if the contact data associated is correct. If that data is outdated or wrong, sales teams end up targeting the wrong people and wasting time and resources.
Challenge #2 - Relying on a single tool for data enrichment:
Many sales teams depend heavily on one tool to enrich their data. But no single tool can guarantee complete accuracy.
2. Prioritizing Accounts Based on Intent Signals
Challenge #3 - Intent signals not relevant i.e. False Positives:
Not all intent signals are indicators of interest. What looks like strong interest in your product might be misleading and you will end up wasting time on prospects who aren't interested.
Challenge #4 - Relying only on job changes, acquisition announcements, and other intents:
While these are important signals, they aren’t indicators of exact pain. Only focusing on them can make you overlook other important signs that show a prospect’s interest in a solution like yours.
Challenge #5 - Not recent:
If your intent signals are outdated, they’re essentially useless. A prospect who showed interest months ago might no longer be in the market.
3. Sending Personalized Emails
Personalization is key to breaking the ice and getting meetings, but it’s not as simple as it sounds.
Challenge #6 - Emails are a mix of value proposition and offering:
Many sales emails are “me” focused and are verbose, covering everything. This dilutes the message and goes to the trash.
Challenge #7 - Emails contain name, company, and a couple of recent news items rephrased:
While it’s important to show that you’ve done your research, just rephrasing recent news also doesn’t work. Prospects identify this easily and mark it as “Junk”.
4. Cold Calling Target Accounts
Cold calling is still a key strategy in outbound sales, but it's becoming more difficult to execute effectively.
Challenge #8 - Connection not leading to conversation because of generic scripts:
The problem with generic scripts is that prospects are already bombarded with those. If you can’t engage the prospect in those first few seconds, the call is essentially over before it starts.
Challenge #9 - Call pick-up rate is impacted – power dialer came as a solution but did not lead to meetings:
Power dialers have increased the number of calls reps can make, but they haven’t increased the quality of those interactions. More calls don’t always translate to more meetings.
Challenge #10 - Sales reps don’t know who is going to pick up the call:
Without knowing who’s on the other end, reps are forced to use generic scripts. This lack of context can make the conversation feel impersonal and robotic. It reduces the chance of a meaningful connection.
5. Reaching Prospects on Social Media or Communities
Social media is the platform to engage and build repo with prospects even before you reach out, but it’s becoming increasingly difficult to stand out.
Challenge #11 - It’s overcrowded… requires serious time commitment:
With everyone trying to connect on platforms like LinkedIn and Twitter, it’s harder to break through the noise. Meaningful engagement with prospect activities requires a significant time investment, which many reps don’t have.
Challenge #12 - Social media DMs are not eliciting a response:
Sales reps are not able to get responses from direct messages. Prospects are already bombarded with messages. This makes it extremely hard for your message to stand out unless it’s highly relevant and timely.
6. Following Up or Nurturing Through Insights
Challenge #13 - Templatized follow-up sequences are generic and don’t elicit a response:
Using the same follow-up sequence for every prospect might save time, but it often comes at the cost of engagement. Prospects can tell when they’re receiving a generic message, and it’s a major turn-off.
Challenge #14 - Account research takes time—around 40-60 minutes—to find insights for follow-up communication:
Personalized follow-ups require in-depth research, which can be time-consuming. This often leads reps to either skip the research or rely on generic templates, both of which reduce the effectiveness of the follow-up.
The challenges of outbound sales are evolving, making it harder to connect with prospects in meaningful ways. Whether it’s the accuracy of your ICP list, the relevance of your intent signals, or the effectiveness of your outreach methods, each step in the process has potential pitfalls.
Innovation in Outbound Sales
AI is revolutionizing outbound sales by bringing innovation to key areas of the process. Let’s explore how these advancements are making outbound sales more efficient and effective.
We will categorize the innovations as per the sales workflow steps we defined earlier…
1. Getting a List of ICP Accounts
Creating an accurate list of Ideal Customer Profile (ICP) accounts is the foundation of successful outbound sales. AI is making this process smarter and more reliable.
Innovation #1 - Aggregation of data providers and private APIs for enrichment:
AI tools now aggregate data from multiple sources, including data providers, standard aggregators and private APIs, to enrich your ICP list. This ensures that the information you’re working with is comprehensive and up-to-date.
Tools - Clay, ZoomInfo
Innovation #2 - Email and call verification tools:
Alongside list enrichment, AI integrates email and call verification tools to cross-check and verify the data in real time. This step helps prevent outreach to incorrect or outdated contacts, improving the accuracy of your targeting.
2. Prioritizing Accounts Based on Intent Signals
Data-backed prioritization is possible now, thanks to AI’s ability to analyze massive data points.
Innovation #3 - Account Insights:
AI scans through 10K Reports, Earnings calls, other reports and relevant online sources for account insights to identify relevant pain points based on business milestones, roadmaps, and preferences. This deeper understanding helps to prioritize accounts more effectively.
Tool - Evabot
Innovation #4 - Mix of account insights and intent signals:
AI prioritizes accounts by combining account insights and intent signals based on relevance. This holistic view ensures that sales teams are focusing on the most promising prospects.
Innovation #5 - AI-led Scoring:
AI evaluates these insights and signals according to their relevance and continuously improves its accuracy by learning from sales reps' feedback. Over time, this results in more precise account scoring.
Tool - Evabot
3. Sending Personalized Emails
Innovation #6 - Emails crafted with relevant pain points:
AI can help you craft emails that go beyond surface-level personalization i.e. just stating your value proposition. It can highlight the specific pain points of the prospect, adding a personal touch that breaks the ice and makes the message more relevant.
Tool - Evabot, Regie
Innovation #7 - Leveraging expert frameworks:
Tools like Evabot AI utilize proven frameworks like PSA (Problem, Solution, Ask) and OPPS (Offer, Problem, Proof, Solution) to structure emails in a way that’s more likely to elicit a response.
Innovation #8 - Integrating insights and signals into email drafts:
Now, AI can directly incorporate account insights and intent signals into your email drafts, making them more compelling and personalized to prospects.
Tool - Evabot
4. Cold Calling Target Accounts
Cold calling has started working once again, thanks to AI-driven insights.
Innovation #9 - No more generic conversations:
AI provides real-time insights and research on any account a rep is targeting. This information makes each call more relevant and engaging.
Tool - Evabot
Innovation #10 - Automatic script crafting:
For large-scale cold-calling campaigns, AI can automatically craft call scripts for thousands of target accounts. These scripts are based on account insights and are tailored to each prospect. This increases the chances of a successful conversation.
Tool - Evabot
Innovation #11 - Power Dialer integrations:
AI integrates with Power Dialers, automatically pulling up call prep notes as soon as someone picks up. This allows reps to start the conversation with hyper-personalized context and book meetings.
Tool - Evabot
5. Reaching Prospects on Social Media or Communities
Social media is a crowded space, but AI is helping sales teams navigate it more effectively.
Innovation #12 - Engagement suggestions:
AI pulls relevant posts from prospects and suggests ways to engage with them in your tone and style.
Tool - Evabot
Innovation #13 - Automated DMs:
AI can automatically send direct messages to prospects based on their recent posts. These messages are hyper-personalized and relevant, increasing the likelihood of a response.
Tool - Dripify
Innovation #14 - Tracking job changes and announcements:
AI keeps track of prospect’s job changes, announcements, and other relevant news. It then recommends personalized messages or comments. This helps you stay top-of-mind with your prospects.
Tool - Evabot
Innovation #15 - Personalized video DMs:
AI can also help you craft personalized video direct messages to send over social media. This adds a unique, human touch to your outreach that can set you apart from other reps.
Tool - Sendspark
6. Following up or nurturing through insights
Following up is crucial, and AI is making it more strategic and data-driven.
Innovation #16 - Contextual account insights:
AI gathers account insights from a wide range of reports (10K, 8K, 4Q etc), earnings calls, and other online sources. This helps you keep the conversation contextual and relevant, which is key to successful follow-ups.
Tool - Evabot
Innovation #17 - Auto alerts for follow-ups:
AI sends automatic alerts to reps based on the priority of account insights. This ensures that you follow up at the right time, with the right message, keeping the prospect engaged.
Tool - Evabot
Innovation #18 - Keyword-based insights:
AI also alerts you to account insights related to other keywords linked to your product or service offerings. This allows you to introduce additional solutions that might interest the prospect, expanding your opportunities.
Tool - Evabot
AI is driving innovation in outbound sales by making each step of the process smarter and more efficient. From refining your ICP list to crafting personalized emails and making data-driven calls, these innovations are helping sales teams connect with prospects in more meaningful ways.
What Sales Leaders Are Expecting from AI
Sales leaders today have high expectations when it comes to AI in outbound sales. They’re not just looking for tools that automate tasks—they want AI to drive real results by enhancing every step of the sales process. Here’s what sales leaders are expecting from AI:
Sales leaders expect AI to provide accurate and up-to-date Ideal Customer Profile (ICP) data. This means AI should not only identify the right accounts but also ensure that the data is current and reliable.
Sales leaders want AI to do more than just provide a list of potential accounts—they want it to prioritize those accounts based on relevant signals and insights.
AI should not only identify the right accounts but also provide detailed insights for each one. Sales leaders expect AI to deliver relevant, actionable insights (Whether it’s understanding a prospect’s pain points, business challenges, or recent activities) that can be used in outreach.
Sales leaders are looking for AI to help craft hyper-personalized emails that stand out in a crowded inbox. They want AI to use top-scored account insights and proven frameworks to create emails that resonate with each prospect on a personal level.
Sales leaders expect AI to generate personalized call prep notes for each account, providing sales reps with the information they need to make meaningful connections. Additionally, they want AI to integrate with power dialers to improve the connect-to-conversation ratio, ensuring that every call has the potential to turn into a productive conversation.
Social media is a critical platform for engaging with prospects, and sales leaders want AI to help them do it effectively. They’re looking for AI to suggest ways to engage with prospects on platforms like LinkedIn and Twitter, whether through post engagement, personal DMs, or other means.
Follow-ups are a crucial part of the sales process, and sales leaders want AI to help them do it better. They expect AI to use relevant account insights to guide continuous nurturing, ensuring that follow-up communications are timely, personalized, and value-driven.
Finally, sales leaders are looking for AI to help them explore upsell and cross-sell opportunities. By analyzing account insights and identifying areas where additional products or services might be needed, AI can help sales teams expand their reach within existing accounts.
Sales leaders expect AI to be a powerful partner in outbound sales, driving higher efficiency, hyper-personalization, and conversion effectiveness at every stage.
Evabot taking the Innovation Leap
Among the many outbound tools available, Evabot stands out as a pioneer in delivering a cohesive, AI-led outbound solution.
It’s not just about automating tasks—Evabot is transforming the entire outbound workflow with smart, data-driven insights and personalized engagement multi-channel strategies.
Here are the innovations that Evabot is spearheading with…
1. Account Insights Using AI
2. AI-Led Account Scoring and Prioritization
3. Hyper-Personalized Emails Using Insights and Frameworks
4. Call Prep 2.0: Integrated Account Insights for Power Dialers
5. Social Media Engagement with Prospects Using Account Insights
6. Upsell and Cross-Sell Opportunities with Customers Using Account Insights
7. Follow-up and Nurturing Opportunities with Pipeline Prospects and Cold Leads
Evabot is taking the innovation leap by integrating AI-driven account insights, smart prioritization, and personalized engagement strategies into every step of the outbound sales process.
From initial account prioritization to research to multi-channel engagement to follow-up and beyond, Evabot is innovating what’s possible in outbound sales, helping sales teams achieve better results with less effort.
Would you like to evaluate “Evabot AI” for leveraging AI in your outbound efforts? Book a meeting on the button below.
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