Using Generative AI to Boost Your Sales Team’s Productivity

Riley Clark
May 2, 2023
 min read

Leaders have a responsibility to help their teams navigate change brought on by micro trends and macro movements. For instance, as buyer sophistication and preference for personalization skyrocketed over the past decade, we’ve all had to rethink our tried and true methods and channels for reaching and engaging with them.

Simply look to the growth of the MarTech 5,000 to 8,000 and beyond for quantitative evidence of the evolving landscape. 

Technology can certainly revolutionize sales playbooks, but it's not a silver bullet. What it can offer, however, is improved productivity and efficiency for front-line teams in their day-to-day activities, freeing up more time to experiment with new approaches and focus on what they do best - fostering relationships and initiating conversations with buyers. 

Recently one attention-grabbing technology has been dominating the B2B SaaS scene. It almost doesn’t even need an introduction.

Generative artificial intelligence is a highly sought-after technology that has caught the attention of go-to-market teams looking to engage their audiences more effectively and efficiently. The widespread adoption of AI in daily operations has created a sense of urgency for companies to embrace it, lest they fall behind. 

Whether you've already experienced its impact or not, it's likely that AI will soon play a more prominent role in your work.

To make the most informed decision about the benefits of AI for your sales reps, it's important to approach your exploration with research and clear expectations. Taking the time to prepare in this way will ensure that you choose the best option for your team.

This blog provides a roadmap for sales leaders interested in AI and its potential applications for their teams. We’ll go over what you can expect from AI solutions for sales specifically and discuss examples of how those capabilities can manifest within features, tools or an entire platform. 

Short on time? Check out this blog's layout to find the section most relevant to you:

- Do You Really Need AI?

- Expectations for Generative AI Tools 

- General Data Sets Versus Private Data Models

- Sales Workflows

- Content Storage and Management

- Content Performance Insights

- Data Protection

Do You Really Need AI?

With every technological advancement, familiar problems are solved and novel problems arise.

Take Co-Founder and President Matt Millen’s time at Outreach as an example. Millen and his team focused on scaling rep activity by giving them a way to reach more of their prospects at once through persona-based sequences. 

But that exposed a new problem. Suddenly, content was essential to sales teams in a way it wasn’t before. 

The abrupt importance of content in the outbound sales process presented a challenge for teams, who now needed to produce a larger volume of high-quality content for their outreach strategies, but weren’t equipped to generate it.

We’re here because sales engagement platforms spawned the need for organizations to find a better way to generate high-converting content at scale and First Movers quickly turned their eyes to AI as a potential solution.

It’s a bottleneck that’s still the norm and as a result, GTM teams today face three choices for creating sales-ready content:

- Writing their own sequences, which can be time-consuming for those who are not strong researchers and writers

- Relying on content provided by marketing that may not align with the team's style or brand

- Outsourcing the process, which can be expensive and require extensive internal approvals

Each approach has its drawbacks, especially as organizations look to scale their outbound prospecting efforts.

In short, we’re here because sales engagement platforms spawned the need for organizations to find a better way to generate high-converting content at scale and First Movers quickly turned their eyes to AI as a potential solution.

Today, Generative AI has reached a level of maturity where streamlining and optimizing workflows is possible, cementing the tech as a crucial part of every team’s go-to-market strategy. 

Given these advancements, it’s safe to say that incorporating AI into your operations is essential.

Expectations for Generative AI Tools and Platforms

Previously, we discussed the solution and its accompanying challenges. In this section, we aim to highlight the potential pitfalls for GTM teams that overlook the full implementation of Generative AI capabilities within their organizations.

General Data Sets versus Private Data Models

Odds are you’ve seen what AI can write and you’ve likely already played around with a free Generative AI tool for general purposes like ChatGPT. It’s an excellent solution for creating in-the-moment content.

However, very few platforms have been optimized for sales messaging, meaning they’re unable to take your company’s brand tone, voice, sales posture and industry best practices into account. 

Sales-Optimized AI. Is the AI trained to speak in a sales context and able to recognize differences in tone between email types and buyer personas? Can it incorporate your own sales data?

Understanding which solutions are designed specifically for sales messaging is crucial. Otherwise, you might end up paying for what’s essentially a rebranded ChatGPT, where the AI models are borrowed “as is” without additional fine-tuning. 

To see the difference, try writing a few emails with You can create a free account and get started here

Exploring this angle further, a sophisticated AI tool can distinguish between different sales email steps, such as introductions, follow-ups, break-ups, referrals and more. AI with an understanding of an email’s placement in a sequence enables more contextual email generation. The alternative is to request "write me this email" in ChatGPT or something similar to generate a stand-alone email with only superficial reference points. 

To achieve this, utilize an AI platform that comprehends the intricacies of messaging architecture and can seamlessly arrange emails in a sequence or cadence for you.

Sales Workflows

Most generative AI-powered tools excel at producing singular pieces of content. But, a fundamental flaw is their lack of integration with sales workflows. This challenge is most apparent when you consider sales sequences. 

AI with training limited to writing single emails can only fulfill the latter, disjointing teams from optimizing other equally crucial sales steps.

Typically, sales sequences rely on the context of the previous message or are one-to-one using recipient research for highly-personalized communication. AI with training limited to writing single emails can only fulfill the latter, disjointing teams from optimizing other equally crucial sales steps.

Sequence Creation. There are many AI solutions that can write an email, but your team's efficiency will be limited. Instead, search for solutions with the ability to write an entire email sequence in the same amount of time.

The primary way we see AI helping improve sales messaging speed and accuracy is twofold:

  1. By streamlining the 3x3 workflow; in other words, finding three relevant points of personalization in under three minutes for a first-touch email. The challenge here is that in most teams, that doesn’t happen in three minutes, and they give up on it. AI allows SDRs to do the 3x3 in about 40 seconds. That’s the productivity level possible when Generative AI is used thoughtfully in a seller's workflow today.
  2. For sellers not living in their inbox but rather in a sales engagement platform like Salesloft or Outreach, personalization at scale can be unlocked by platforms like that can write sequences in minutes, personalize them ​in seconds and sync them to your SEP instantly.

Generative AI can unequivocally create better sales messaging when the workflow is considered. The messaging is crisper, tighter and more contextually relevant, making it more engaging, credible and less likely to get held up on deliverability. 

This helps significantly with the tightening of email deliverability and compliance, spurred partly by Google canceling access to their API to warmup services.

Sales teams relying on warmup services have responded by establishing domains, obtaining valid licenses, and creating ESP-specific emails - but these measures merely mask the underlying problem. 

The real issue is sending sequenced email templates in mass. It simply won't work anymore, and email deliverability is just one of the reasons why.

Apart from impacts on deliverability, questions to consider when evaluating which AI tools can help improve your sales workflows include:

  • Can you build a sequence for me using inputs relative to my business? 
  • How easy is collaborating with my teammates on that sequence or other generated content?
  • Can you push sequences created directly into my SEP?
  • Can you support messaging directly in my inbox?
  • How can I ensure my messaging is unique and not templated, to prevent it from getting caught in spam filters?

You’ll know you’re thinking about AI for your team the right way if you’re questioning whether its power can be accessed in the places your team is already working natively, like Linkedin, Outreach, SalesLoft, Hubspot, the email inbox, and more.

Integrations. Does the platform seamlessly integrate with your sales engagement platform (SEP) and email inbox? Evaluate how the platform integrates with the rest of your tech stack.

Content Storage and Management

Those aware of the quality and speed that characterizes AI generation should have no trouble imagining the mountain of content teams will be able to draw from in the near future. But inevitably, questions of what to do with it will arise. How will you effectively manage, access and utilize this abundance of content? Should you expect to just pass it around your team or publish it without human intervention? 


An AI content tool should have a built-in plan for its creations.

Data Storage. Where will the AI-generated content be stored and is it easily accessible to everyone on your team?

It’s crucial for individuals seeking AI solutions for their team to consider the manageability of the output. Avoid investing in a solution that necessitates additional tools to manage the influx. Instead, opt for an all-in-one content platform that streamlines your technology stack.

Suppose your AI platform is equipped with a built-in content management system. In that case, you can store every piece of content created across your team while leveraging built-in collaboration features like sharing and commenting, even for content elements as small as subject lines or CTAs. 

Content creation no longer needs to be a segmented process, so look for options that integrate with your existing workflow. If an effective CMS is not built into your AI platform, it may be difficult to quickly or easily access and collaborate on your creations in real-time.

Collaboration. Does the platform facilitate collaboration across your team and departments, with features such as commenting and sharing?

Content Performance Insights

Another expectation you should have is insight into content performance. Just like your SEP gives you feedback on your sales activities and your call recorder lets you know how conversations are going, you should expect the same from your sales content creation platform. 

Analytics. Evaluate the level of detail and granularity of the analytics, including feedback on entire sales sequences and individual emails, including the subject line and call-to-action.

Similar to the feedback you receive from your sales performance metrics or call recording system, AI platforms can provide a comprehensive view of how your content is performing.

Access to dashboards containing details like message length, readability, biases, highest-performing subject lines, tone and more, is necessary for iterating, optimizing, and improving your sales messaging. 

Analysis at this granular level is possible and should be an expectation.

Data Protection

Finally, when evaluating Generative AI solutions, ensure that you’re working with products that not only amaze you with their output but are also SOC 2 and GDPR compliant. Organizations across industries will look to this as they adopt and embrace these new technologies. 

Data Protection. Ensure the AI platform is SOC2 and GDPR compliant. Don't compromise on this one!

Still Unsure About AI?

If you’re still unsure about using AI in the sale process, take a minute to look back at the evolution of sales messaging. The utilization of AI in enhancing sales teams' messaging capabilities hasn’t come out of nowhere. Instead, it’s been a gradual progression.

We expect to see AI adding value across all the workflows of the modern revenue organization.

In the past, sales messaging was a one-to-many approach, akin to the broad strategy some marketing teams use today (although AI can positively impact marketing too).

However, in the last decade, sales engagement platforms have enabled salespeople to engage in one-to-one messaging with their buyers. Still, the catch was that these interactions were based on templates built for generalized personas.

It was considered one-to-one, but the message was the same for everyone that met the predefined criteria.

Today, we have advanced from one-to-one with templates to truly personalized one-to-YOU messaging, allowing it to be tailored to specific individuals.

This evolution in messaging is significant, as companies have long sought to achieve personalization on a large scale, but only recently has that become a reality with the advent of AI.

As technology improves, Generative AI represents the next frontier for even better, more contextual, messaging. We expect to see it adding value across all the workflows of the modern revenue organization.

While you familiarize yourself with these changes, don’t be deterred if the process requires a little time to get right. Talking to AI is like a dance; the more you do it, the better you’ll understand its rhythm and motions, just as the AI will, in turn, learn your moves and preferences.

Overall, we like to say Generative AI can get you to an editable state more quickly. Rather than replacing humans, AI enhances the human and computer partnership. To leverage that partnership fully, it’s up to the human to massage the inputs and yield the strongest outputs from the tech- not to expect every piece of AI-generated content to be final draft ready. 

This is precisely why choosing the right AI platform for your team requires preparation, thoughtfulness and human partnership. Your sales team is unique and so are its needs. 

But regardless of what you’re currently prioritizing, whether it's inbound sales, the sales-marketing relationship, sales training, conversion rates, reaching more decision-makers or anything in between, expect to see AI playing a role. 

After all, the debate on whether AI can unlock efficiency is over. Now the question is- which AI platform will you use to do it? 

We hope the information shared here brings you a step closer to finding your answer.

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