Jessyka Bailey

Tag: AI

  • Account Scoring System: Three Weeks In

    Hi team. Can I call you team?

    I know I’ve been a little quiet, but if you’ve been following along, you probably get it. We’re getting close to the end of Q3, so I’ve been auditing my sales process, working deals, and trying to get things wrapped up before Q4.

    What I’ve Been Building

    If you’ve read some of my other posts, you also know I’ve been thinking a lot about account selection. Not just who fits an ICP, but who actually deserves my attention right now. For the last three weeks, I’ve been turning that thinking into an actual system that will ultimately take my large territory and tell me where I need to focus.

    If I can be completely honest, I genuinely thought this would be easier.

    Getting a System to Apply the Same Rules Every Time

    There are so many variables and situations that have to be considered. The hardest part so far hasn’t been finding a great account. It’s been getting the system to apply the same rules consistently and surface the same accounts for the same reasons every time.

    And I think what’s surprised me the most about building this is that you can make something, test it, and something weird can happen. Then you figure out why, make some changes, and run it again. And after all of that, something else breaks. So you start from the beginning and run it again.

    When the System Works but the Rules Are Wrong

    You can even have a system that works exactly how you told it to, and the problem isn’t anything the system is doing. It’s the rules you gave it.

    That’s basically what I’ve been doing for the last three weeks.

    How Long Does It Actually Take to Build Something?

    It’s given me a new appreciation for how long it actually takes to build something. Three weeks ago, I probably would have heard that something took six months to a year to build and wondered what could possibly take that long.

    I get it now.

    Making something work once is one thing. Making something that keeps working when you throw different situations at it is a completely different problem.

    Heading Into Q4

    Anyway, Q3 has given me a lot to think about: what worked, what didn’t, where I wasted my time, and where I should be spending more of it. So I’m heading into Q4 with a slightly different sales process, a system I built to support it, and a few things I want to test. Hopefully I’ll have some interesting results to share.

    Until then ✌️

  • Selling in an Age of Abundance

    What makes you trust someone when you know they’re trying to sell you something? And what’s that feeling when you’re being sold something and you feel like something is off? Would you call that intuition? A gut feeling? Vibes???

    Now think about the opposite and remember a time when you had a great experience being sold something.

    I like to relate this to serving because, just like a majority of the products we’re trying to sell, eating out is a nice to have, not a need to have. And the server is quite literally trying to sell you something. Whether that’s an experience, that osetra caviar, or even an idea of how that food is going to taste.

    The best servers will paint the picture for you. But what really makes you believe them?

    Is it the reputation of the restaurant?

    Is it everything that happened between walking through the door and sitting down at the table?

    Or is it something about the person standing in front of you? The way they talk about the food, the way they listen to you, or the confidence they have when answering your questions?

    Because anyone can tell you that the hanger steak is amazing but a great seller makes you believe that you’ll think the hanger steak is amazing.

    As I’ve been thinking about what selling will become in the age of AI, this difference really matters. A great seller isn’t just repeating everything they know. They’re paying attention to you, asking the right questions, picking up on what your preferences are and using that evidence to make recommendations specific to what you need.

    A lot of skills we’ve historically valued in sales are getting cheaper. I don’t think they’re becoming less important. Research, product knowledge and being prepared still matter. But the effort that it takes to do those things well is changing.

    If everyone can walk into the room prepared, what becomes the most valuable asset?

    Maybe it’s your ability to make the person sitting across from you believe you.

  • How Many Accounts Should You Actually Work?

    When I think about outbound sales, I think about touchpoints. Emails, LinkedIn Connections/Messages, calls, and all of the ways that you’re trying to get in front of somebody to create awareness.

    But I think that we’re putting way too much emphasis on whether one of those individual touchpoints books a meeting. I can say from experience, a lot of the time, that isn’t how it happens.

    What outbound actually looks like

    What really happens is this:

    Someone gets an email from you and they don’t reply. A little bit later, you send them another email and marketing is also touching that same account. Then they go to your company’s website, where they start doing their own research, and a few days later, they fill out a demo request form.

    To me, this is outbound working.

    The outbound didn’t necessarily create the lead on its own, and neither did the marketing. What they did was work together. They told someone the same story in different ways enough times that eventually that person became curious enough to think, “this might actually help my business.”

    AI changed the volume, not the job

    Now, AI has made it possible for sales reps to create more touchpoints than ever. We can research faster. We can write and personalize emails at a scale that would have never been possible for one person to do manually. Today’s SDR can get in front of more people than they ever could before.

    But so can everybody else.

    So, I don’t think the answer is to use AI to create more touchpoints. I think the opportunity is to make the touchpoints we do create better.

    Find the right company. Find the right person. Find an actual reason why that person might care right now. And then be persistent enough to actually get in front of them.

    To get there takes judgment. And this is where I think the role of the SDR starts to get more interesting as AI does more of the work.

    Find your key accounts

    Right now, I don’t think any manager should be having their reps try to meaningfully work hundreds of accounts. If you’re responsible for touching hundreds of accounts, somebody is getting missed. I’m sorry, there just isn’t enough time to actually think about all of them.

    So hear me when I say this: you need to find your key accounts.

    If a rep has a smaller group of accounts to really focus on, they can actually spend time figuring out how to get into them.

    They can research the company. They can find the right people instead of just going after the most obvious title. They can look through LinkedIn and see if they know somebody who knows somebody. They can figure out what’s happening at the company right now and whether there is actually a reason to reach out.

    And most importantly they can start looking beyond the obvious ways of getting in front of someone. They can get creative.

    That’s the piece I think gets missed when we talk about outbound.

    Good outbound takes thinking.

    Especially now, as we’re asking AI to do more and more of the execution while we give it the direction. We’re telling it what companies to look for, what matters, who a good prospect is, how we want to sound, and what kind of message we want to send.

    So it actually matters whether the person directing the AI knows how to think through those things.

    The basics don’t change

    When we really think about it, the basics of outbound don’t really change.

    You still need to find the right company. You still need to find the right person. You still need a reason to reach out. And you still need to figure out how to actually get in front of them.

    What changes is how much of the work around outbound can now be done for us.

    What I’m doing for the next 30 days

    So what I want to do is this: I want to see what happens if I go the other way.

    For the next 30 days, I’m going to work five key accounts at a time. Although I won’t be able to tell you what accounts I chose, I will be able to give you the logic behind my decisions.

    These will be five accounts that I think are genuinely worth my time, and I’ll work them through the entire sequence. I’m going to spend more time figuring out who I should actually be talking to, why I should be talking to them now, whether I have a way into the account, and what else I can do besides just sending another email.

    If someone gives me a no, I’ll move another account in and take note.

    What I want to know is pretty simple: can I get more meaningful engagement by going much deeper on fewer accounts? Or are people just truly burnt out from all the outreach they get?

    I’ll let you know what I find.

  • The Content AI Learned From

    Maybe I’m biased because I work in affiliate marketing, but the way I see it, affiliate built the incentive for publishers and creators to make a huge amount of commercial content.

    Think reviews, comparison sites, buying guides, product recommendations, tutorials — all of the things people create based on actually using, researching, or caring about something.

    Take the money out and I don’t think that content disappears. People love writing about the things they buy, their hobbies, and their experiences. But I do think, without the incentive, it would have happened a lot slower.

    Affiliate didn’t create that content as much as it set the pace for it to be created.

    It fueled and gave life to something that might have just smoldered along slowly on its own.

    And then AI shows up.

    Suddenly, there’s this massive library of years and years of reviews, recommendations, comparisons, forums, articles, videos, and niche expertise for these models to learn from and draw on.

    For the most part, it’s all content AI didn’t create. And in most cases it’s content it isn’t paying for.

    So what happens when the people creating that information decide that exchange doesn’t work for them anymore?

    Lately I’ve been seeing more publishers talk about blocking AI crawlers or putting content behind paywalls. And really, it’s not just talk anymore.

    Cloudflare already lets website owners block AI crawlers or actually set a price for them to access their content.

    Others are going the licensing route instead — essentially saying: you can use our content, but you need an agreement with us and you need to pay for it.

    So, I don’t think this means affiliate goes away — I actually think it’s more important than ever now. I also don’t necessarily think there’s going to be one new model that suddenly replaces it.

    I think we’re watching the value exchange around content change in real time.

    What I keep coming back to is the incentive.

    I’m on both sides of this. I work in affiliate marketing, and I’m also building with AI constantly.

    But somebody still has to create the information that makes it useful.

    If publishers and creators are being asked to keep producing that information while getting less traffic, fewer clicks, and potentially less money back from it, at some point you have to ask:

    What keeps the incentive going?