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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:
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.
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.
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.
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:
Pick 3-5 key decision points in your deal
Plan responses based on possible answers
Craft questions that uncover what matters most
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!
10 Quick Pricing Wins to Boost SaaS Revenue
SaaS growth isn’t just about flashy new features or perfect pitch decks. Sometimes it’s about clever tweaks to your pricing and packaging that quietly move the needle – fast.
Here are 10 monetisation plays your growth or product team can run this week without engineering support or board approval.
1. Reverse Trial It
Give freemium users the good stuff first. Unlock premium for 7 days at signup (no credit card). Then take it away. Cue FOMO. Cue conversions.
2. Re-trial Like a Pro
One-and-done trials are dead. Bring them back every 6 months. Tie them to new features, product milestones or when someone bumps into a paywall. “Surprise! You’re trialling again!”
3. Default to Annual... or Not
Annual plans = retention. Monthly = more signups, more churn. Smart SaaS teams geo-segment: mature markets → annual. New markets → monthly. Let the data decide.
4. Upgrade Monthly Users (Gently)
After their first monthly renewal, hit them with: “Get 3 months free if you go annual.” It’s the SaaS equivalent of: Would you like fries with that long-term contract?
5. Fix Your Pricing Page
Your pricing page isn’t a billboard—it’s your cash register. It should convert, not confuse. Benchmark: 15% should click through to checkout. If not, it’s broken.
6. Localise or Lose Them
Emerging markets don’t want your $4,000-a-month “Enterprise” plan. Strip it. Simplify. One plan. Local pricing. Lower barrier. More conversions.
7. Smart Feature Wall Redirects
If a user hits a feature wall, land them on a pricing page with that exact feature highlighted. “Hey, that shiny thing you wanted? It’s in Plan B.”
8. Monetisation Awareness FTW
Highlight premium features everywhere. Use icons, colours, pop-ups—anything that says “This button = pro plan.” Make upsell visual and obvious. Slack did it. You should too.
9. Use Overage as Leverage
Don’t block users who hit their usage limit. Let them go a little over, then offer a deal: “Pay for overage or upgrade to a bigger plan and we’ll forgive it.” That’s SaaS judo.
10. Discount with Purpose
Startups, students, and schools are not just nice-to-haves. They're future revenue. Discount 25–50% now. Watch them come back later with budgets and buying power.
Keep Testing. Keep Charging.
These aren’t wishlist items. These are high-impact, low-risk levers you can pull today. SaaS monetisation isn’t a one-time set-and-forget—it’s a constant experiment.
Now go give your MRR a nudge. Or ten.
Unlock Strategies for Growth
Navigating the world of B2B sales can be both exciting and challenging for startups. Establishing a strong sales foundation is crucial to a company's success and growth. This guide provides an overview of effective B2B sales strategies to help startups unlock their sales potential and achieve long-term growth. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Identifying Your B2B Target Market
The first step in any B2B sales strategy is to define your Ideal Customer Profile (ICP). Your ICP is a detailed description of the type of company or organization that is most likely to benefit from your product or service. By narrowing down your target market, you can focus your sales efforts on the most promising prospects and avoid wasting time and resources on low-value opportunities. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Conduct thorough market research to gain a deep understanding of your target customers' needs, preferences, and pain points. This information will help you craft tailored sales messaging, positioning, and value propositions that resonate with your target audience and increase your chances of closing deals. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Crafting a Compelling B2B Startup Value Proposition
A strong value proposition is essential for standing out in a crowded B2B marketplace. This concise statement should clearly communicate the unique benefits of your product or service and why it's better than competing solutions. It should be targeted at your ICP and directly address their most pressing pain points. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
To craft a compelling value proposition, first identify the key features and benefits of your product or service that set it apart from the competition. Then, focus on translating those benefits into customer-centric language that demonstrates how your solution will help your target audience solve their problems, save time or money, or achieve their goals. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Building a High-Performing Sales Team
The success of your B2B sales growth efforts largely depends on the strength of your sales team. Hiring the right talent is critical, so look for individuals with a proven track record in sales, strong communication skills, and a deep understanding of your target market and industry. A diverse team with complementary skills and backgrounds can also help drive innovation and collaboration. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Providing ongoing training and support to your sales team is essential for maintaining high performance. Regularly invest in sales training, coaching, and professional development to keep your team up-to-date on industry trends, best practices, and new sales techniques. This will ensure they have the skills and knowledge needed to close deals and achieve your company's growth objectives. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Implementing a Multi-Channel Sales Approach
In today's highly connected world, a multi-channel sales approach is crucial for maximizing your reach and engagement with potential customers. Leverage various sales channels, such as email, social media, phone calls, and in-person meetings, to connect with prospects and build relationships. Each channel has its strengths and weaknesses, so be sure to tailor your sales approach accordingly. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
For example, use email to provide informative content and schedule meetings, while utilizing social media to build brand awareness and engage with influencers in your industry. By adopting a multi-channel sales approach, you can reach your target audience more effectively and increase your chances of establishing B2B sales growth. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Utilizing Sales Automation and CRM Tools
Sales automation and customer relationship management (CRM) tools can significantly streamline your sales processes, save time, and improve the efficiency of your sales team. These tools can help manage leads, track sales activity, and automate routine tasks, such as sending follow-up emails or scheduling calls. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Implementing a CRM system allows you to centralize your customer data, making it easier for your sales team to access and update information on leads and prospects. This enables better coordination and collaboration among team members, ultimately leading to more efficient and effective sales efforts. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Developing Strong Sales Strategies and Processes
A well-defined sales process is essential for guiding your sales team through the various stages of selling, from lead generation to closing deals. Outline a step-by-step sales process that includes key tasks, goals, and milestones for each stage, as well as the strategies and tools your team will use to achieve them. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Regularly review and adapt your sales process based on customer feedback and performance data. This will help you identify areas for improvement, make necessary adjustments, and ensure your sales process remains effective and aligned with your target market's needs. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Nurturing Relationships and Building Trust
Building trust and nurturing long-term relationships with clients is key to driving repeat business and referrals in the B2B sales world. From the initial contact to post-sale support, consistently provide exceptional customer service and demonstrate genuine interest in helping your clients succeed. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Maintain regular communication with clients, keep them informed about new products or services, and be proactive in addressing any concerns or issues that may arise. By fostering strong relationships and consistently delivering value, you'll create a loyal customer base that will contribute to your startup's ongoing growth. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Measuring Sales Performance and Adjusting Strategies
Establish key performance indicators (KPIs) to track the success of your B2B sales efforts, such as the number of leads generated, conversion rates, average deal size, and sales cycle length. Regularly monitor these metrics to gain insights into the effectiveness of your sales strategies and identify areas for improvement. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Continuously refine your sales strategies based on the insights gained from your performance data. This may involve adjusting your target market, modifying your value proposition, or experimenting with new sales techniques. By staying agile and data-driven, you can optimize your sales efforts and maximize your startup's growth potential. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
Conclusion
Implementing effective B2B sales strategies is crucial for startup success and growth. By identifying your target market, crafting a compelling value proposition, building a high-performing sales team, and leveraging multi-channel sales approaches, you can unlock the full potential of your B2B sales efforts. Remember to measure your sales performance and continuously adapt your strategies based on data-driven insights. By staying proactive and committed to sales excellence, your startup will be well-positioned to achieve long-term growth and success. (Unlocking B2B Sales Strategies: Proven Practices for ... - Pitchdrive)
How Startups Can Build Real Communities, Not Just Customer Bases
In a recent HBR On Strategy podcast, Matt Mullenweg—founder of Automattic (the powerhouse behind WordPress)—joined host Sarah Green Carmichael to share how startups can transform their customer base into a vibrant, loyal community. It’s not about marketing fluff or building Facebook groups. It’s about genuine connection and contribution, from the inside out.
🛠️ Build Culture Like You Build Code
Forget ping-pong tables. For Matt, culture comes from the thousand small actions people see and repeat. Leadership sets the tone—if you walk past a problem, others will too. If you model care, others follow. Even in a fully remote team, culture shows up in rituals like "trash pickup day," where designers quietly fix UX details. These micro-decisions matter.
🎭 Hire by Audition, Not Assumption
Matt still champions hiring via auditions—actual trial projects—over resumes. Referencing his own write-up in Harvard Business Review, he highlights that skills, values, and culture fit are better revealed through doing, not just telling.
🧑🤝🧑 Community Starts with Generosity
Mullenweg compares building community to throwing a great dinner party: you’ve got to put out the snacks, pour the wine, and let people feel welcome. WordPress does this by offering multi-million dollar software for free—no strings attached. That gift creates goodwill. And in return, users often contribute back voluntarily. Like great guests, they help clean up after the feast.
💡 Control Is the Killer of Community
Many legacy brands struggle with community because they try to control it too tightly. Mullenweg warns against this. You’ve got to let go. Trust your users. Empower them. It's messy, but it's real.
💸 Freemium: If You Give, Make It Great
Automattic’s freemium model works because the free version is incredibly valuable. But the premium version? Genuinely next-level. Startups, take note: don’t hide basic functionality. Lead with value, and let your premium product earn the upgrade.
This episode is packed with insights for founders who want more than transactions—they want relationships. Community isn’t an add-on. It’s a strategic foundation.
📖 Inspired by Matt Mullenweg's conversation on HBR IdeaCast. For more, check out the full podcast at HBR.org.