5 AI Tools That Will Transform Your Sales Process

Almost not a day that goes by when the topic of AI—specifically, AI tools—doesn’t pop up in everyday conversation. 

I was reminded of this again on Halloween when I was at a friend’s party, dressed as a circus performer, chatting with the Queen of Hearts and Deadpool (Wolverine was MIA). We were standing around the kitchen island, discussing our various levels of AI adoption (clearly we’re a fun crowd). While Deadpool was a big fan (he works for a major gaming company), the Queen was still taking small steps in her role as an attorney… and for good reason. 

At Masthead, I’m the head of Sales and Marketing, and over time I’ve come to not only embrace AI for my role, but become a huge advocate for its use across our company (though my colleague Calia officially holds the title of Masthead’s AI czar).  

My passion for AI tools has come as I’ve seen how immensely helpful each one has been to me as I’ve tried them out. Even aspects of my day I didn’t entirely realize were so time-consuming or hands-on have become more streamlined, freeing me up to do more proactive or creative work.

I always find it helpful to read firsthand accounts from people who’ve already used the tools (instead of high-level editorial profiles), so I’m sharing my experiences, along with those of our team at Masthead, below. 

Otter.ai

I don’t have an actual virtual assistant, but for now, Otter.ai is the next best thing. I originally used the free version to join, record, and transcribe my meetings with prospective clients—but quickly upgraded once I realized how it transformed my whole approach to virtual meetings. 

Otter automatically joins every call scheduled in my work calendar, working seamlessly across Zoom, Microsoft Teams, and Google Meet. Not only does it record the audio, and provide a real-time transcript of the conversation and screenshots of any slides presented, but it also provides meeting summaries, key takeaways, and action items immediately afterward. 

Knowing that all of these are captured (without me madly trying to keep up as I type!) has enabled me to stay fully focused on the conversation and ask better questions. A lot of times, I’ll ask questions during my meetings that I plan to use in a follow-up email or proposal, and Otter will remind me what to include. Everything is immediately stored with the Otter.ai tool, and ready for me to access minutes—or months later. This part is invaluable, as the context might otherwise be forgotten. 

Most prospects are okay with my AI notetaker showing up, but if they ever ask, I turn it off to respect their company’s policies. 

Waldo.fyi

This tool was designed specifically for agencies—but almost anyone in sales or marketing can use Waldo.fyi to research companies at lightning speed ahead of calls and in advance of making pitches to brands.

Waldo comes with several purpose-built-workflows that almost instantly serve up background information on a brand, competitive insights, and the latest news about an industry. The amount of information that Waldo provides would typically take me or one of my team members hours to pull together by combing through websites on Google. And, considering the number of new business calls I have, that’s just not practical from a time-management standpoint. 

You can use Waldo’s pre-built workflows to pull info into a concise mini-report, or ask more customized questions (a lot of mine are around a brand’s content marketing related efforts) and it will deliver the information you need to gain up-to-date business intelligence quickly.

One thing I love is that Waldo provides links to all of its sources, so I can verify the information myself. That gives me the confidence to speak knowledgeably on topics that matter most to potential clients. I’ve also used Waldo on numerous occasions to support me in building capabilities and sales decks that are customized to a specific brand. I can see this really impresses prospects, especially when I’ve had a very quick deadline to get the info together. 

We’ve won business this year specifically because of Waldo: I had one client asking to invest even more money than we’d pitched! That’s when I knew this technology was a win for Masthead.

Gemini and ChatGPT 

I would be remiss not to include the dynamic AI duo here—they’re still strongly worth mentioning for sales and marketing folks. At just one and two years young, respectively, Google’s Gemini and ChatGPT already feel like the “establishment” when it comes to AI support, but they’re tools that I personally use throughout the day, and recommend for support with sales, marketing, and dozens of small tasks during your week.

Just when I think one’s better than the other at brainstorming, organizing, or quick research, I’ll find that’s not the case—so I’ll often ask them both the same question, provide a highly detailed prompt, and see which gets closer to what I’m looking for. They’re great for getting ideas going or tackling ‘blank page syndrome,’ but they’re just a jumping-off point; I still end up doing all the heavy lifting for most types of writing. 

Of all the tasks I give Gemini and ChatGPT, I find that it’s most helpful in summarizing white papers, and in creating bullets (AI lovessss bullets!) for decks. I always use Gemini or ChatGPT to proofread important documents and emails before they go out to prospects. You’ll need to prompt them in the right way (“Go line by line and point out any proofreading and grammatical errors, but don’t make any changes to the tone”), but it can be a real time saver.

Hublead

For years, I lamented that all of my LinkedIn activity couldn’t be mapped back to our CRM, Hubpsot—and it was too labor intensive to do it manually. That’s why our recent adoption of Hublead has been a game changer for my workday, and my company. Although Hublead doesn’t brand itself purely as an AI tool, it leverages AI-driven automation to bridge LinkedIn-HubSpot connections and keep track of every interaction without having to type them by hand.

Now, Hublead’s AI-enabled Chrome extension lets me add a contact directly from LinkedIn into HubSpot with a single click (I can’t even believe this magic after years of porting in selected contacts!). I’ve customized the process to carry over specific fields—conversation details, role, industry—that are most relevant to my future outreach. Another huge bonus is that the tool's AI helps pull in and organize LinkedIn messages and conversation context, which isn’t the easiest to navigate on its own.

Hublead's intelligent organization of LinkedIn activity is especially useful for sales reps or marketers like me who interact frequently on the platform. This integration has freed my team up to focus on strategizing and building deeper connections with prospects, rather than managing data entry.

Google’s NotebookLM

NotebookLM is a recent addition to Masthead’s AI toolset—and I know our editorial team really loves it. It’s essentially our own GPT, but one that’s trained specifically on our company’s resources—things like project briefs, process documents, research, internal reports, and even transcripts from key internal meetings (recorded on Otter.ai or through Zoom). 

And the best part? As a Google tool, NotebookLM works seamlessly with the Google Suite. So, as we make updates to any process documents, those updates reflect in answers to future queries in NotebookLM—exactly how AI should work!

NotebookLM has been invaluable for Masthead’s new and existing team members alike. 

For newbies, it makes onboarding and taking on a new project seamless. For example, they can query NotebookLM, and it will reference transcripts from past training sessions or notes from similar projects, helping them navigate the task with confidence. I can see myself using this to help future sales assistants to train and put together “grids” (budgets) for new prospects and contracts for future clients. 

On the editorial side, our team has created Notebooks for each client where they store resources like style guides, budgets, and branding documents—this is where the privacy settings are so key. 

“It’s amazing how much more room for thinking you can make when you leave remembering client preferences to AI,” Masthead’s VP of Editoiral Operations said. “We now no longer need to remember which client prefers Zoom vs.Google Meet, who shudders at a serial comma, which clients can’t access Google Docs, and which individuals like to be CCed on emails. It’s become a true game-changer in our day-to-day work.”