AI Won’t Replace SDRs—It’ll Supercharge Them

AI isn’t coming for your Sales Development Reps—it’s coming to upgrade them.

At SaaStr Annual, Carta’s CRO Jeff Perry and LinkedIn’s first VP of Sales Brendon Cassidy made one thing clear: the smartest sales teams are using AI to make SDRs faster, sharper, and more effective—not redundant.

Here’s the takeaway that says it all:

“The real playbook: Use AI to make SDRs 2x more efficient, not replace them.”

Instead of wasting hours on manual prospecting or repetitive follow-ups, AI is doing the heavy lifting—surfacing the right leads, crafting personalised outreach, and streamlining workflows. That gives SDRs more time to do what humans do best: connect, influence, and convert.

The future isn’t about choosing between reps and robots. It’s about building teams that use both to win faster.

Reference: Lemkin, J. (2025, May 12). Not Using AI to Replace Your SDRs, But to Make Them 2x Better: A Deep Dive with Carta’s CRO and LinkedIn’s First VP Sales. SaaStr.

Average Reps Beware—AI’s Coming

If you're relying on autopilot in sales—AI may soon outpace you.

By 2026, AI won’t just assist with admin tasks like CRM updates and email follow-ups—it’s projected to replace the bottom 30–40% of sales reps entirely. These are the reps who lack product knowledge, fail to follow up, and struggle to build meaningful rapport.

One quote from the article makes it crystal clear:

“AI will replace the bottom 30%-40% of sales reps — those who don’t know their product well, who don’t follow up, who don’t build rapport.”

But here’s the opportunity: high-performing reps won’t be replaced—they’ll be amplified. AI can manage the repetitive, time-consuming tasks, freeing you to focus on what truly drives revenue—problem-solving, strategic conversations, and relationship-building.

The message is simple: don’t compete against AI—partner with it. The future belongs to sales professionals who combine human insight with AI-powered execution.

Reference: Lemkin, J. (2025, May 12). Where AI Will, and Won’t, Replace Sales Reps in 2026. SaaStr. https://www.saastr.com/where-ai-will-and-wont-replace-sales-reps-in-2026/

AI That Works: Calendly’s 10 Lessons

Calendly's journey into AI offers valuable insights for sales professionals aiming to integrate AI effectively into their workflows. Here are the key takeaways:

• Address Real Problems: AI should enhance productivity by solving specific, high-friction issues users face daily.(SaaStr)

• Avoid Parallel AI Products: Creating separate AI experiences can lead to low adoption. Instead, integrate AI seamlessly into existing workflows.(SaaStr)

• Evaluate AI Investments Carefully: Assess AI initiatives based on customer value, cost structure, data quality, and user experience impact.(SaaStr)

• Personalization at Scale: Use AI to personalize user experiences across all touchpoints, enhancing engagement and retention.(SaaStr)

• Measure Meaningful Metrics: Focus on metrics like user engagement with AI features, task completion rates, and impact on core product metrics.(SaaStr)

• Ensure Robust Data Architecture: A unified data infrastructure is crucial for consistent and effective AI experiences.(SaaStr)

• Maintain Consistency Across Channels: AI should provide a consistent voice and experience across support, marketing, and product interfaces.(SaaStr)

• Manage AI Costs Strategically: Be mindful of the costs associated with AI, especially at scale, and consider hybrid approaches for cost-intensive features.(SaaStr)

• Implement 'Invisible AI': AI should operate seamlessly in the background, enhancing user experience without being obtrusive.

• Prioritize Continuous Education: Offer AI-powered, contextual learning experiences to keep users engaged and loyal.

These lessons underscore the importance of integrating AI thoughtfully to enhance user experience and drive business growth.

Reference: Lemkin, J. (2025, April 17). Building AI That Actually Works: 10 Key Lessons from Calendly’s CPO and Head of UX. SaaStr.

Scaling AI the Monday.com Way

Monday.com’s rise from $10M to over $1B in ARR in just eight years wasn’t just about product-market fit—it was about embedding AI as a strategic growth lever.

Co-founder and Co-CEO Eran Zinman shares a perspective that every sales and product leader should note:

“AI is not just a feature; it's a core part of our product strategy.”

That mindset shaped how Monday.com approached everything—from customer workflows to product innovation. Instead of treating AI as a bolt-on or gimmick, they made it integral to the user experience. The result? More intuitive automation, smarter insights, and a platform that adapts to the way teams really work.

Here are three key lessons from their journey:

1. AI is Infrastructure, Not Add-on They invested in making AI foundational. This allowed their features to scale across multiple verticals and use cases without having to rebuild core logic for every department.

2. User Empowerment at Scale AI wasn’t used to replace human decisions—it was designed to amplify them. Features like AI-powered task suggestions and workflow automation helped users move faster with less friction.

3. Speed Fuels Product Velocity By deploying AI across teams internally (not just in the product), Monday.com improved their development cycles and operational efficiency. That internal AI adoption was just as critical as customer-facing innovation.

For sales professionals and startup founders, the takeaway is clear: the companies that win with AI aren’t just using it—they’re designing around it. That means aligning teams, building with scale in mind, and constantly asking: how can AI make this better for the user?

Reference: Lemkin, J. (2025, February 28). AI at Scale: 8 Learnings from Monday.com Co-Founder and Co-CEO Eran Zinman. SaaStr.

AI Tools for Marketing Scorecard (May 2025)

Every B2B sales leader wants to know: where is AI delivering real value in marketing—and where is it still a science experiment?

A new 2025 scorecard based on insights from 50+ top CMOs gives us the clearest picture yet.

Here’s the TL;DR for sales pros:

🚀 What’s Working

• Analytics & Insights (⭐⭐⭐): AI is great at finding patterns humans miss. Think of it as your secret pre-call briefing—now smarter and faster.

• Ad Creation/Optimisation (⭐⭐⭐): Creative variations and smarter targeting are saving time and boosting campaign ROI.

• Budget Optimisation (⭐⭐): Tools are improving—soon you’ll see AI helping marketers put their money where the results are.

🤖 What’s Still Maturing

• Customer Journey Mapping (⭐): AI’s not yet reading buyer minds, but it’s starting to track the breadcrumbs.

• Event Marketing (⭐): In-person events? Still mostly human. Virtual ones are starting to feel the AI touch, but we’re early days.

🔎 What It Means for Sales

If marketing isn’t leveraging AI in analytics or ad targeting, they’re leaving conversions on the table—and you’re losing sales momentum.

This isn’t just a martech issue—it’s a pipeline issue.

🧠 Sales Insight

The smartest sales teams aren’t just asking for MQLs anymore. They’re partnering with marketing to guide AI investments toward high-impact outcomes—like better qualified leads and real-time account intelligence.

Source: Based on insights from Carilu Dietrich’s 2025 State of AI in B2B Marketing Scorecard, reflecting conversations with 50+ tech CMOs.

Make it stand out

Whatever it is, the way you tell your story online can make all the difference.

A Practical Guide to AI Agents

Agents are the next evolution of automation—and they’re a big step up from chatbots or basic workflows.

This guide unpacks how to design, deploy, and scale AI agents that can think through complex decisions, take action across systems, and actually complete real-world tasks for your users. It’s written for product, engineering, and AI teams, but any forward-thinking business leader should pay attention.

What’s an Agent (and Why Should You Care)?

Agents don’t just respond—they act. They use AI to make decisions, choose tools, and run multi-step workflows. Think customer support, fraud analysis, or triage—jobs that used to need human judgement.

When Should You Build One?

If your rules-based automations are breaking down—or your team is drowning in edge cases—it might be time. Agents shine when there’s ambiguity, messy data, or high-context decisions.

How to Design a Great Agent

Three key ingredients:

• Model: The brain (usually a large language model)

• Tools: APIs or functions to take action

• Instructions: Clear prompts and guardrails to keep it on track

Start with one strong agent and expand from there. Multi-agent systems come later—only when things get complex.

Guardrails Matter

Agents need boundaries. You can use filters, classifiers, and human overrides to prevent chaos. Safety isn’t optional—it’s built in from day one.

Start Simple. Build Fast. Scale Smart.

Don’t over-engineer. Launch a single use case, test with real users, and expand as you learn. Done right, agents can transform how your business handles everything from support to operations.

📘 Read the full guide here: A Practical Guide to Building Agents – OpenAI

How AI Will Flip Sales in the Next 12 Months

It’s already happening. AI isn’t coming to sales — it’s in the room. And over the next year, it’s going to shake things up fast.

Sales leaders used to ask, "How do we scale the team?" Now, they’re asking, "How do we scale with fewer humans?" That’s not about cutting heads. It’s about using AI to handle the heavy lifting — and freeing up humans to do what they do best: influence, connect, and close.

Here’s what to expect.

1. AI Will Be on Every Sales Call

AI note-takers are just the beginning. We’re about to see AI tools actively participate in calls — answering questions, pulling up data, summarising next steps, even coaching the rep in real time. It’s not just call support; it’s a co-pilot.

2. Your BDR Might Be a Bot

BDRs powered by AI are already generating leads, qualifying them, and booking meetings — 24/7, no burnout, no holidays. We’ll see a surge in AI-led outreach that actually gets replies because it's tailored, fast, and consistent.

3. Low-Dollar Deals? Let AI Handle It

For deals under $10K, AI can now manage most of the process — from first touch to close. Think auto-generated quotes, contract workflows, follow-ups — without a human ever jumping in. That leaves sales teams to focus on strategic, complex deals.

4. Sales, Support, Success = One AI-Powered Flow

The handover mess between sales and CS? Gone. AI will bridge gaps, sync systems, and keep context — so the customer feels like they’re dealing with one team, not three departments.

5. Expectations Are Getting Harder to Meet

Here’s the kicker: AI isn’t just changing how we sell. It’s changing how customers buy. They now expect real-time answers, ultra-personalised experiences, and instant follow-up. If you can’t deliver that, someone else will.

Wrap-Up

Sales isn’t dying. It’s levelling up.
The reps who win won’t be the loudest or pushiest. They’ll be the ones who know how to work with AI — using it to be faster, smarter, and more helpful than ever.

The next 12 months will separate those who adapt from those who stall. Time to get ahead of it.

Based on insights from SaaStr’s article and video series: 10 Ways AI Will Change Sales in the Next 12 Months.

AI Just Blew Up the Sales Rulebook

AI isn’t just tweaking the sales process—it’s overhauling it. According to a recent deep dive, we’re now entering the era of AI-native sales. That means less admin, faster decisions, and sharper customer conversations. Here’s what stood out:

1. CRMs Are Getting a Brain

Old-school CRMs were basically graveyards for call notes. AI flips that—listening to calls, reading emails, and turning raw conversations into structured insights. Sellers don’t need to enter data. It’s captured and analysed automatically.

2. Coaching Happens in Real Time

Instead of post-call reviews, AI gives reps guidance during the conversation. Think prompts, reminders, and nudges to ask the right questions while the deal is live.

3. Sales Is Becoming a Team Sport

AI makes the whole go-to-market team smarter. Sales, marketing, and product teams can see the same insights—what’s resonating, what’s not, and what buyers actually care about.

4. Reps Can Spend Time Selling Again

With AI handling note-taking, research, and task follow-up, reps spend more time doing what they’re paid to do: talk to buyers and move deals forward.

Final Thought

This shift isn’t about replacing reps—it’s about removing friction. The best sales teams won’t just use AI tools—they’ll be built around them. If you’re still stuck in CRM admin hell, now’s the time to upgrade how you sell.

Read the original article

Small Deals, Big Automation

AI isn’t coming. It’s already here—and it’s reshaping how we sell.

In a recent podcast I listened to, the speaker laid out 10 ways AI is changing B2B sales. It wasn’t theory—it was grounded, practical stuff that every sales team should be thinking about right now.

Here are the five changes that stood out to me:

1. AI is joining your calls

AI tools are already showing up in customer meetings, answering technical questions on the spot. No more “I’ll check and get back to you.” That changes the rhythm of the whole sales conversation.

2. It’s the new BDR

AI doesn’t sleep. It’s polite, accurate, and always on. It can respond to inbound leads instantly, book meetings, and keep the conversation moving—even outside business hours.

3. It handles small deals

For lower-value transactions (say, under $10K), AI can qualify, follow up, and even close. That frees your team to focus on strategic accounts that actually need a human.

4. It blends departments

AI doesn’t care if a question is “sales” or “support.” It just answers. That means your customer gets a consistent experience—faster and with less friction.

5. Buyer expectations are shifting

Once customers experience AI-driven speed and clarity, they won’t go back. If your response time is slow or your answers are vague, they'll move on.

Why This Matters

This isn’t about replacing people—it’s about removing friction. Sales is still about trust and timing, but AI is taking care of the boring bits so we can spend more time where it counts: in real conversations with real decision-makers.

If you’re not already using AI to speed things up or sharpen your sales process, now’s the time to start.

🎧 Here's the podcast that inspired this:
Listen here

The Questions that Close

That’s what kills deals before they even get going.

There’s a better way — one borrowed from the CIA.

Here’s what most sales training leaves out:

Top performers don’t focus on what they’ll say. They focus on what they’ll ask.

Forget the polished pitch or clever comeback. That’s not what wins deals.

What wins is asking the right question at the right time — and doing it with intent.

I learned this the hard way.

For years, I’d ask safe, friendly questions:

“How was your weekend?”

“Got any holidays coming up?”

Nice? Sure.

Useful in a B2B sales process? Not really.

Then I came across how CIA operatives prep conversations.

They build what’s called a Conversation Map.

Before they walk into a meeting, they map out:

• “If the person says this, I’ll go there…”

• “If they push back, I’ll pivot here…”

It’s not a script. It’s strategy. And it works.

Great salespeople do the same.

They know their critical decision points.

They prepare questions that uncover real needs.

And every question moves the buyer one step closer to clarity.

No fluff. No guessing. Just purpose-driven conversation.

Here’s the mindset shift:

Don’t ask questions to sound smart. Ask to serve.

Most reps ask like they’re testing the buyer.

But when buyers feel dumb or cornered, they either buy small — or not at all.

The fix?

Ask questions that help buyers feel confident and in control.

Examples:

• “What’s stopping this from moving forward today?”

• “How does this impact your bigger priorities this quarter?”

• “What happens if nothing changes?”

These are easy to answer, but packed with insight.

They move the conversation forward — without pressure.

Here’s a simple way to build your own Conversation Map:

1. Pick 3-5 key decision points in your deal

2. Plan responses based on possible answers

3. Craft questions that uncover what matters most

4. Prepare follow-ups that show you’re really listening

For example:

• If they raise budget concerns — talk about the cost of doing nothing.

• If they mention needing leadership approval — offer a plan to get it.

Now it’s no longer a sales pitch. It’s a two-way discussion.

You’re solving problems together.

After every call, review:

• What landed well?

• Where did it get stuck?

• What surprised you?

Tweak your map. Keep getting sharper.

Elite sellers don’t wing it. They work from a playbook.

And this is one worth building.

Because when you ask better questions, you lead better conversations.

You reduce pressure, build trust, and help your buyer make the right call.

That’s real influence.

And it starts by letting your questions do the heavy lifting!