You know the feeling: It’s 3 p.m. You’ve been in the office for 7 hours. And you still have a couple dozen emails, tasks, and follow-ups to send your prospects.
A few of those emails require nuanced objection handling. One of them requires digging through a few different apps and internal resources.
To make things worse, it’s late in the quarter, so you can’t just call it a day and go home.
As an account executive, moments like this are the hardest part of my job. Sales is all about momentum. But humans aren’t wired to be productive at all hours of the day—especially not at 3 p.m. That makes it difficult to keep momentum throughout the day.
But imagine if you had a sales assistant that could help you throughout your day to get work done more effectively and efficiently. Now imagine that you didn’t have to pay that assistant, give them any vacation time, or manage them.
Recently I started leveraging artificial intelligence (AI) in my workflow to become a more effective account executive. In this blog, I’ll share how I’m leveraging Outreach’s AI capabilities such as Deal Health and Smart Email Assist—along with a collection of free AI tools—to create more pipeline and close more deals.
Keep reading to learn how I use AI to help:
Let’s be honest. No one gets into sales because they want to make cold calls every day. But sourcing pipeline is what keeps the lights on and puts food on the table. It’s also the difference between sellers that make the President’s Club and those that don’t.
I use three AI technologies to source pipeline more efficiently.
The Pareto principle tells us that 80% of results come from just 20% of activities. In sales that means 80% of your business will be met by working just 20% of your book.
But you know this already. The challenge is figuring out which 20% of accounts to focus on.
The Outreach + 6sense integration helps me do just that. Using its predictive model, I can score accounts based on three factors:
Once I’ve identified my highest-scoring accounts, I simply drop them into an Outreach sequence and start sending personalized emails.
In sales, there’s nothing I love more than an easy layup. I’m constantly looking for the lowest-hanging fruit on my way to beating quota. Outreach’s Email Sentiment capabilities help me identify these opportunities.
For example, I know from experience that one of the best ways to set up meetings is to go back through old leads and send follow-ups.
Using Outreach, I pick a time frame—4 or 5 quarters ago is usually my sweet spot—and select leads with the tag “Bad timing” or “Already has a solution.”
This is especially effective when we’ve released a new capability that is better than our competitors’ features. Why? Because I know that they have a pain point that our platform solves. And I can use this knowledge to tailor my outreach to be hyper-relevant.
This process used to take me days. Using AI, it now takes just a few hours to send several very targeted prospecting emails that oftentimes lead to a very high conversion rate… a slam dunk!
When I wrote down my daily activities, I noticed that I spend the first and last hour of every day answering emails.
But I noticed something else. The emails I send in the first hour of the day are of much higher quality than those that I send at the end of the day. This makes sense given that I’m a human that only has so much energy. By 3 p.m. my energy and effectiveness as a seller wanes.
Outreach’s AI-powered email response generator, Smart Email Assist, helps me get more emails out in the morning when I’m at peak productivity and it helps me push through and keep up the momentum at the end of the day.
How does Smart Email Assist do this? The generative AI capability analyzes all of the text in my email threads with a prospect and then makes recommendations on how to respond and handle objections.
This capability helps me get over the initial hurdle of writing an email and helps me shift into the much less cognitively intense role of editor.
Sourcing pipeline is essential. But as any account executive will tell you, it’s hard to meet quota if you don’t manage your pipeline effectively.
I use three AI technologies to manage my pipeline efficiently and close more deals.
One of the worst feelings as a salesperson is walking into a pipeline review unprepared for questions from your manager.
We’ve all been there. Your manager asks you about the next steps on one deal and when you last connected with another, and you respond with ‘ums’ and ‘ahs’. Frankly, it’s embarrassing.
Deal Health in Outreach has helped me avoid many of these embarrassing moments over the last year. Using information from other deals of similar size and stage, Deal Health provides an account score and indicates what’s working well, where to focus, and suggested actions.
I look at Deal Health every time I go into a pipeline review meeting, join my team for a cold call blitz, or set goals for myself at the beginning of a given week.
Deal Health helps me prioritize my time and focus on the right deals and the exact right next activity I need to take to move the deal forward.
I was born to be a salesperson, not a designer.
But I often find myself in situations where I need to customize a sales deck or build a business case for a prospect. Gamma is a free AI tool that helps me do that without bugging our design team or staying up all night picking fonts and colors.
The process of creating decks or documents in Gamma is straightforward and simple. The app asks you what you want to create and then prompts you to type an outline of the content. Then it creates a well-designed presentation for you in seconds.
Like some of the other AI technologies I mentioned, it’s not perfect. But again, it shifts you into the much easier role of presentation editor as opposed to presentation creator.
Another activity I spend a lot of time on each day is account research. I’m constantly asking what’s going on with an account, how Outreach can drive value, and how I can build rapport with a prospect.
In order to answer some of these questions, I use Bard, a ChatGPT competitor released by Google earlier this year.
Here are a few examples of prompts that I’ve used recently:
Pro tip: If you aren’t getting the results you want, try replacing an account’s company name with its domain (e.g. outreach.io instead of Outreach)
A mentor once told me that to build trust with a client, you need to be competent and likable. If you’re competent, but not likable, you’re not trustworthy. Conversely, if you’re likable, but not competent, you won’t have authority.
Outreach’s Kaia is an AI-powered virtual assistant that I use every day to help me be more competent and close more deals.
I use two capabilities more than any others: content cards and action items.
You can think of content cards as an assistant whispering in your ear on sales calls to help you answer questions and handle objections. For example, if a prospect asks if your platform integrates with another tool, Kaia will look that up in real time and present you with an answer on your computer screen.
Action items help me stay on top of the important task of following up with prospects after a call. On a call, if I say something like “I’ll follow up with X,” Kaia sends me an email and reminds me to send that follow-up item.
These capabilities ensure that I build and maintain momentum throughout each day and quarter. Whether it’s 8 a.m. or 3 p.m., Kaia helps me stay on top of the most important activities I need to execute in order to beat quota.
When I first started hearing about AI, I was hesitant to integrate it into my life and workflow. I thought it was a technology reserved for savants and PhDs.
But my biggest source of hesitation was my belief that there was a tradeoff between automation and personalization. I worried that in using AI, I would sacrifice the human touch that has helped me close so many deals.
But I was wrong.
Over the last year, I’ve learned that AI is most effective when it’s in the hands of a sales rep that can apply their human touch. It allows reps like me to spend less time on the things that distract us from our true passion: connecting with other humans.
And you don’t need to be Sam Altman or the CTO of Google to experience the value of AI for yourself. Whether you’re a college dropout or have a Master's degree, you can start using AI today and unlock more seller productivity.
Learn more about how account executives can create and close more deals in this ebook that discusses: