Episode 450: LinkedIn and AI for Sales Leaders

Bob Woods (00:22)
Hey there, everyone, and thanks for joining us for Making Sales Social LIVE, coming to you from the Social Sales Link virtual studios. I’m Bob Woods. Brynne Tillman is off, but Stan Robinson Jr. is here. What’s happening, Stan?

Stan Robinson Jr. (00:56)
Hey, Bob. All is well.

Bob Woods (01:01)
Excellent, excellent. Good to hear. If you’ve joined us for the past couple of weeks, we’ve been discussing at length how sales leaders can help their teams perform at their highest and best levels. Up until now, we’ve focused on how sales leaders must model the behavior they want to see.

In recent sessions, we’ve talked about using Sales Navigator, the different types of sales campaigns that can be used on LinkedIn, and how sales leadership can support their teams — even modeling those strategies themselves. It’s the modeling, people!

Today, we’re going to take a step back and discuss using LinkedIn and AI in a broader sense — and how to model those behaviors for sales teams. As a sales leader, if you’re not active on LinkedIn — sharing content, engaging with others, and building your network — guess what? Your team won’t do it either.

Your activity as a sales leader sets the tone for what’s expected and what’s possible, which is really important, Stan.

Stan Robinson Jr. (02:11)
Exactly. You nailed it, because the sales team looks to their leader to set the pace and example. That includes using LinkedIn for search, research, and networking.

If you’re using a tool like Sales Navigator, regularly save accounts and leads of interest. Keep in mind that as a sales leader, eyes are on you — not just for giving directives, but for leading by example.

Bob Woods (03:07)
Absolutely. You’re in the spotlight if you’re a sales leader.

Before we get rolling, we have a free ebook for this session called LinkedIn and AI for Sales Leaders. Everything we talk about today is also in that ebook. If you’re watching live, we have a QR code in the upper right corner and a URL in the lower left.

If you’re listening on the podcast replay, you can grab it at socialsaleslink.com/salesleaders.

So with that, Stan, let’s talk about leading by example.

Stan Robinson Jr. (03:48)
That was the first point we touched on, but let me give a few examples. If a sales team is pursuing specific accounts — say, a top ten list — every week or at least monthly, sales leaders review those accounts and make suggestions.

As a sales leader, use LinkedIn or Sales Navigator to gather business intelligence about those accounts. Identify where you can bring value rather than just talking about your product.

Sales managers should use these tools not only to review analytics or reports but also to research leads and accounts. Connect with top-tier accounts — sometimes you can add to the conversation by engaging with peers at target organizations that your reps can’t easily access.

Those are examples of how sales leaders should lead by example.

Bob Woods (05:44)
Exactly. It’s about putting yourself in your sales reps’ shoes and setting the example through your own actions.

Next, let’s talk about aligning LinkedIn and AI activity with sales outcomes. As a sales leader, you need to make it clear how LinkedIn and AI usage supports sales goals — whether it’s building pipeline, nurturing relationships, or shortening sales cycles.

AI can help with content and message ideation, but don’t let it do the work for you. People can tell when something is fully AI-generated. Use AI for inspiration, not automation.

When you focus on relationships, you’ll likely close deals faster because you’re showing genuine interest, listening actively, and providing relevant content. That builds trust not just with one stakeholder but across the organization.

And of course, AI can help with writing — just make sure your tone sounds like you and always leads with value, not a sales pitch.

When your team sees how these activities directly tie to outcomes, they’ll be more consistent and successful.

Stan Robinson Jr. (09:49)
And I think the phrase we were looking for was, “Slow down your outreach to ramp up your outcome and income.”

Bob Woods (09:57)
Yes! Exactly. Outcome and income follow from that.

Stan Robinson Jr. (10:04)
Right. Next, we’ve been touching on number three — integrating LinkedIn into the sales process.

When working through your sales pipeline, make it a habit to look up target accounts and prospects on LinkedIn. The good news is people can see when you view their profiles, which often prompts them to look back at yours. That’s a perfect opportunity to send a connection request.

When they accept, follow up with a welcome message — not a sales pitch. Something like, “Thanks for connecting! Looking forward to staying in touch and providing value to each other.”

At each stage of the sales process, use LinkedIn consistently — not sporadically — and make it part of your everyday rhythm.

Bob Woods (12:01)
Yes. And to add to that, if you want to take it a bit further, you could mention an educational ebook or resource — as long as it’s not salesy.

Say something like, “If you’re interested, I have an ebook on [topic]. I think you’d get a lot out of it. Let me know if you’d like the link.”

Don’t send the link immediately — ask permission first. That makes it feel helpful, not spammy.

It’s a great way to provide genuine value and position yourself as an expert.

Stan Robinson Jr. (13:30)
Exactly.

And I see Paul Smith has a question. Paul, can you expand on it? When you say people are still against it — do you mean LinkedIn, or using AI?

Bob Woods (13:57)
We’re a bit behind the chat since it’s just me and Stan today, but while we wait for Paul’s clarification, let’s move to number four — setting clear and measurable KPIs that drive the right behaviors.

If you don’t have realistic, trackable goals, none of this matters. Define activity-based metrics that focus on building relationships and creating conversations.

Examples include:

• Weekly targeted connection requests
• Strategic comments on buyer or influencer content
• Personalized, value-based direct messages
• Referral introductions requested and received

These KPIs encourage consistency and reward behaviors that drive pipeline growth. And as the sales leader, you have to set them — not your team. You can adjust over time based on feedback, but you set the benchmarks.

Stan Robinson Jr. (16:39)
Exactly. Collect data so you can figure out what’s working and what’s not, and tweak the process based on facts — not gut feelings.

Bob Woods (16:59)
Right. And before we get to number five, just a reminder about our free ebook, LinkedIn and AI for Sales Leaders, at socialsaleslink.com/salesleaders.

Paul came back with his clarification: he said some people on LinkedIn are afraid to trust what’s being written. He found that when he reuses similar AI-generated posts, engagement grows due to familiarity.

What do you think, Stan?

Stan Robinson Jr. (17:58)
I’d need more context, but the key is to make sure your content provides value to your target audience and isn’t self-serving.

Think like your audience — for example, if you’re reaching out to VPs of Sales, focus on topics like pipeline growth, revenue, or ROI from tools like Sales Navigator.

Also, curate content from respected voices in your industry and share it with your insights. That builds credibility and adds value to your audience.

Bob Woods (19:34)
Mark Crosby mentioned something interesting — he heard that sales reps should wait 60 days after connecting before engaging. I have to say, I completely disagree.

If you wait that long, you’ll be forgotten. Instead, stay on their radar by engaging lightly — comment on their posts, view their profile, or share something valuable. That way, you stay top of mind without being pushy.

Stan Robinson Jr. (21:00)
Agreed. The only time 60 days might make sense is if someone said they’re not ready for your solution and you’re following up later. But if they just connected with you, waiting that long is too much.

Bob Woods (21:52)
Exactly. Alright, let’s keep the ball rolling with number five — and this one’s a personal favorite of mine. It’s not as strategy-driven, but it’s fun.

Stan Robinson Jr. 22:10
It’s more people-driven, which is celebrating LinkedIn wins publicly. Some of you may have heard the adage: criticize in private, praise in public. Generally speaking, that is a good idea. When you’re trying to incentivize the right behavior in using LinkedIn as a fundamental part of your sales process, let people share their results and put a spotlight on them. In addition to money, most salespeople appreciate recognition. It doesn’t have to be a closed deal. For example, you could highlight someone connecting with a Chief Operations Officer at a large target company. Even connecting with a C-suite person at a target account is a win. The point is, don’t wait until people close deals to recognize them. Recognize the small steps along the way that lead to the outcomes you want. Bob, any other thoughts on that?

Bob Woods 23:56
Along those lines, celebrating wins publicly isn’t just recognition—it can also involve real incentives, like potential prizes. Several years ago, I was part of a LinkedIn social selling rollout for a company, and the company went absolutely nuts. They gave away several valuable items. One that sticks out in my mind was around 2017–2018—they were giving away iPhones. You don’t need to go that far now, given current smartphone prices, but you can tie big wins to KPIs that are valuable to your company. For example, a $100 gift card to a steakhouse works well. People compete for these rewards and see the benefits reflected in their numbers, reinforcing that the process works.

Moving on to number six: provide tools, training, and real-time coaching. Most salespeople haven’t been trained to use LinkedIn effectively. Many think their profile is a resume, but as salespeople, your profile is a resource. Shift it from resume-focused to resource-focused. Offer short trainings, profile makeovers, swipe files, templated AI prompts, and messaging frameworks for direct or instant messages. Teach the basics of AI prompting. We have a “Crispy Framework” for AI prompting that helps people understand what they need and why they’re using AI. Without guidance, people can easily go down rabbit holes.

Stan Robinson Jr. 28:13
Exactly. Coaching by leaders—individual one-on-one or small group sessions—helps your sales team learn by applying what they’ve learned to specific accounts. Training alone isn’t enough; it’s an ongoing process. Monthly coaching allows people to apply lessons in real time, which is how things stick.

Bob Woods 28:59
Speaking of ongoing reinforcement, you could hold a LinkedIn Power Hour every month or every other week. The team comes together in real time to get support and feedback while connecting, engaging, prospecting, or writing content. Power Hours help monitor activity and correct mistakes on the spot. You could also hold an AI Coffee Klatch where the team shares AI prompts, strategies, and successes. This helps build confidence in using LinkedIn and AI tools.

Stan Robinson Jr. 30:08
Yeah, good deal.

Bob Woods 30:13
Let’s move on to the last point. We are running a little over, so we’ll need to wrap up.

Stan Robinson Jr. 30:19
Lastly, encourage a value-first culture on your team, which is the opposite of pitching and leading with pricing. Encourage your team to have a value-first mentality by thinking about what brings value to the target audience and what helps them succeed. Bob always says: don’t talk about how you help people, just help them. This starts with your profile, providing information helpful to your audience. It also applies to commenting on others’ posts, which raises visibility. Add substantive comments that provide value and extend the conversation without mentioning your product. This positions you as a resource.

Bob Woods 31:41
Absolutely. Speaking of resources, don’t forget our free guide: LinkedIn and AI for Sales Leaders. That’s the correct guide this time. It’s available at socialsaleslink.com/sales/campaigns.

Stan Robinson Jr. 32:13
Yep, sounds good. That one is for last week’s session.

Bob Woods 32:19
Yes, thank you. The correct link for this episode will be socialsaleslink.com/sales/leaders. Whether you’ve joined us live or via podcast, thanks for tuning in to Making Sales Social Live. We do this every week, so join us regularly. If you’re listening via podcast and haven’t subscribed, hit subscribe or follow. We also appreciate likes and comments. Besides these live sessions, we interview leaders and experts in sales, marketing, business, and more. Catch those episodes at socialsaleslink.com/podcast. Make your sales social this week and every week. Thanks, everybody. Have a great week—we’ll see you back here next week. Bye!