From Transactions to Strategy: A Notion Sales Lead's View on the B2B Growth Engine | Yunqi Tech π

云启资本·July 15, 2025

The Path from PLG to Enterprise Sales

In the development of B2B products, the replicability and scalability of the sales team are critical factors for product growth. Recently, the "20 Sales" column under the podcast brand 20VC hosted a conversation with Kim Graves, Go-To-Market Sales Lead for the Americas at Notion, discussing how to build a replicable B2B growth engine in the AI era.

As a well-known collaboration platform, Notion currently has over 6 million paying users, with global revenue exceeding $500 million in 2024, and its North American sales team achieved 50%+ annual growth.

In this episode of "Yunqi Tech π", we share a compiled version of this conversation, exploring Kim Graves's practical experience and insights from Notion's transition from PLG to enterprise sales.

Content adapted from 20 Sales, compiled by Yunqi

🎤 [Guests] Harry: Founder of 20VC, host of 20 Sales Kim Graves: Currently leads sales, solutions engineering, customer success, and renewals at Notion. Recently led the team in driving Notion's AI-powered go-to-market strategy expansion in North America, delivering record-breaking growth in 2024. Previously at Slack and Salesforce.

💡 Part 1: Kim's First Steps into Sales

Kim recalls that her first "sales" job was working reception at her mother's beauty salon, answering phones and booking appointments. After studying marketing in college, she sent her resume to a small local startup in Vancouver for a marketing role. Later, Kim discovered Slack was hiring its first account manager and landed the job through a cold application. Only after joining did she realize the role combined AE, SE, and CSM functions into one hybrid position.

Kim: Honestly, my first real sales job wasn't something I actively sought out. My first time facing customers was at my mother's beauty salon. I answered phones, responded to questions, and helped with bookings. Later I went to university for marketing and, after graduating, joined a tech startup in a marketing role.

It was at that company that I first heard about an entrepreneur in Vancouver starting a new project. That person was Stewart Butterfield, founder of Slack. I was immediately drawn to the project and started researching Slack: reading their blog, following every customer tweet. Then I saw on their website — they were hiring their first Account Manager.

To be honest, I had no idea what an Account Manager actually did at the time. But they said they wanted someone with strong communication skills, and I thought: "Well, I've got that." So I blindly submitted my application through their website — no referral, no connections. After several rounds of interviews, I got the job.

Only after joining did I discover that this so-called "Account Manager" was actually a three-in-one role combining Account Executive, Solutions Engineer, and Customer Success Manager — serving customers from every angle. From then on, I've stayed in sales roles. Now, I'm the head of go-to-market for the Americas at Notion.

💡 Part 2: Building Confidence and Sharing Discount Negotiation Tactics

Kim shares her experience: when customers ask for discounts, don't panic. Confidently state your value, use open-ended questions to understand their real concerns. As she puts it, "Stay confident, and don't treat discount negotiations as awkward."

Harry: If you could go back to the day you first got your Slack email address, what would you tell yourself?

Kim: I'd tell myself to have confidence. Especially on customer calls — in the beginning, it was fine. Chatting with customers who loved Slack was easy and enjoyable. But once customers started raising objections, like asking for discounts or saying they were comparing competitors, I'd start to get a little uneasy.

I'd tell myself: "You've got this. It's all about how you present yourself — be confident. You got this job for a reason. Now it's about learning as much as you possibly can."

Harry: I couldn't agree more, especially about "confidence." It's like when I'm fundraising — seriously, confidence is everything. I'd add one more thing: "What's the worst that can happen? You just don't close this one deal — that's fine, there are plenty more customers out there."

Kim believes that when discussing discounts with customers, she recommends listening carefully and asking questions rather than immediately defending your position. Seek win-win solutions. After stating value and solutions, pause to listen and guide with questions like "What feels expensive to you? What's your ideal price?"

Harry: Price negotiations are genuinely awkward, especially early in your career. The moment a customer asks for a discount, the atmosphere instantly stiffens. How would you advise young salespeople to handle this?

Kim: My advice is don't treat it as an awkward conversation. Just like when you're doing discovery with a customer in the early stages of a deal — everyone is relaxed, the vibe is good. When you enter the price negotiation phase, don't let the atmosphere suddenly become tense. Treat it as naturally as any other conversation. Because customers can feel your energy.

If you're thinking to yourself, "Ah, this price might be too expensive, I'm so afraid they'll reject it," customers will pick up on that tension. On the other hand, if you calmly and confidently say: "We've talked for so long now — this is the value I understand we can bring you, and this is the problem we're solving — and this is the corresponding price." Then pause and listen to their reaction. Their first reaction might be: "Wow, that's expensive."

But at this point, don't rush to defend your pricing as reasonable. Instead, return to question mode: "Oh? What feels expensive about it?" "So in your view, what would be a more reasonable price?" Continue the conversation, to understand their real thinking and see if there's a way to find a solution that feels valuable to both sides.

💡 Part 3: Stages and Corresponding Mindsets in the Sales Process

Notion divides its sales process into multiple stages, but doesn't call them "stages" — instead, it labels them with "mindsets." Kim believes that replacing "sales stages" with "sales mindsets" helps salespeople build emotional awareness and behavioral standards, emphasizing "mindset over process" to help teams respond flexibly to customer needs.

Harry: I especially agree with what you just said — "after stating the price, pause and wait for the customer's response."

Many people can't do this. The moment there's silence, they can't help but jump in: "Ah... but we can actually negotiate!" "We definitely have room to adjust!" "If it feels expensive, we can think of something else..."

Kim: This is actually a concept we've introduced into our sales process at Notion. Traditional sales processes are often "stage-based" — for example, stage one is Qualify, stage two is Discovery, stage five is Negotiation, stage seven is Closed Won.

But at Notion, we've chosen another approach — we don't call these stages "actions," we define them as "mindsets." Because what we really want salespeople to "play" and "internalize" is the role-based thinking behind each stage. This way, sales responses become more flexible, more human, and not just mechanically completing a checklist.

For example:

  • Stage two: we don't call it "Discovery," we call it "Curious Investigator." We want salespeople to deeply research the customer at this stage, figure out how they make money, and ask questions with genuine curiosity.

  • Stage five: traditionally called "Negotiation," but we call it "Value Articulator." At this point, the salesperson's job isn't to give discounts, but to clearly articulate the real value the product brings.

This sounds like a small word change, but it changes a person's entire expression and state. Just like when you're hosting a podcast — maybe you don't just prepare what questions to ask, but think: "What tone do I want this conversation to have? What feeling? Can my body language, my tone, help the guest relax?"

After all, people always remember how you made them feel more than exactly what you said.

💡 Part 4: From PLG (Product-Led Growth) to Enterprise Sales

  • PLG companies often mistakenly target their highest-usage users, when they should actually focus on B2B customers with the strongest willingness to pay and highest value.
  • Kim recommends starting with user interviews + firmographics, then working backward to define your Ideal Customer Profile (ICP). Having founders involved tightly connects GTM strategy with product development.

Harry: How uniform is your solution design across different customers? Is it like "playing from a sales script"?

Kim: At PLG companies like Slack and Notion, customer types are incredibly diverse: from students and communities to all kinds of enterprises, across every industry and department. So our initial sales messaging is broadly unified, but the real key is "focus" — focusing on the customer types most likely to convert successfully. Once that focus is clear, there are actually "common patterns" among these customers, and you can customize your approach for that type rather than customizing solutions for every single person.

Harry: So do you look at which PLG user segments are most active and have the most budget, then pick the largest industry to go after?

Kim: That logic sounds reasonable, but it's actually a common trap. Many PLG companies use product usage data to judge "whether to apply sales resources," like seeing a lot of community users and thinking about pushing for paid conversion. But our experience at Slack was: you can't just look at activity, you have to look at "whether it truly delivers value" + "whether they have budget."

For example, community users may use the product a lot, but they don't necessarily have budget, and they won't need your enterprise features — you'd have to invest significant resources developing specific features (like message moderation, reporting mechanisms, etc.). These users are fine on the free product, but not worth dedicating sales resources to "convert." So we deliberately abandoned community-type, high-volume, low-conversion segments and directed sales resources toward B2B customers that could actually drive revenue.

Harry: So if I'm a PLG founder, my product is growing organically pretty well, and now I want to launch a sales team — what's the first step?

Kim: I'd start with extensive user interviews. Don't go straight to outbound, don't look at usage data first — instead: deeply interview users who are already using your product. Understand how they discovered it, why they started using it, how they use it now, and what role it plays in their business.

Compile user profiles, but don't just look at product usage behavior — look at firmographic information: What industry? How big is the company? What region? Which roles/functions get the most value from it? Work backward from this information: Which customer segments have the strongest value perception and greatest budget potential? That's who you should dedicate sales efforts to.

💡 Part 5: Who Should You Hire for an Early Sales Team? "Renaissance Reps"

  • Early sales teams shouldn't look for "script-following" salespeople, but rather "Renaissance Reps" — adaptable generalists with cross-functional communication skills and a hunger to learn. They can drive sales while quickly feeding back market and product needs.
  • When hiring, define first month / first quarter key outcomes, accelerate training through simulated scenarios and small-scale live practice. First output key outcome metrics (like account prioritization, mock calls), then quickly get them on calls with customers.

Kim: My most important advice for early-stage founders is: think about building your sales team like manufacturing a "supply chain." This inspiration comes from a Harvard Business Review article I highly recommend, called The Sales Learning Curve. It points out that building a sales team is also a learning curve process, not about pursuing "high output" from day one.

The biggest mistake in early stages is rushing to hire traditional "coin-operated reps" and expecting them to build out your complete playbook for you — that's completely unrealistic. Imagine you're building a supply chain to manufacture swimsuits: your first 10 swimsuits will be expensive and inefficient, but you'll learn the most from them. Building a sales team is the same — your earliest 3-4 salespeople will be costly, processes will be fuzzy, but this is where your steepest learning curve begins.

We call these people "Renaissance Reps" — they're not good at just one motion, but are all-around players: they can talk and write, they communicate; they adapt to different roles, spanning product, marketing, engineering; they can work with customers and collaborate closely with internal teams. Their real value isn't "how fast can they close deals," but "can they help you understand customers, refine the product, and polish the process" — driving the entire go-to-market flywheel.

Harry: Where are these people usually in their careers? Entry-level newcomers, or more senior people?

Kim: Actually it's not about "seniority," but about "learning ability and willingness to build." You can hire young, fast learners, or mid-level people in transition who are passionate about participating in "building from zero."

But the key is: they have to be people genuinely passionate about learning and co-building, not salespeople who just want to use a fixed script to make quick money. Because in the early days of a startup, the point of sales is never "make money immediately," but "finding the connection between product and market through continuous iteration."

💡 Part 6: Pipeline and Prioritization Management

  • Implement a dual-track strategy: strategic large deals (≥ $100K) running parallel with fast-closing, high-win-rate SMB deals ($20-50K), building a multi-layered pipeline.
  • Sales must self-direct and own multi-channel development: email, phone, social networks, LinkedIn, warm channel collaboration, etc., with consistent weekly follow-up and persistent multiple touchpoints.
  • Trigger customer behavior. Cold calling is hard, but most differentiates from routine emails, creating differentiated exposure.

Harry: Some small actions have bigger impact than you'd think — like consistently commenting on LinkedIn. You might think it's just drive-by engagement, but when someone comments on 10 posts in a row, I subconsciously feel like I "know" them. If they message me later, I'm much more likely to respond.

Kim: Yes, this is actually a strategy very worth building into your outbound playbook. At Notion, our salespeople operate across multiple channels: cold email, cold calling, LinkedIn comments and DMs, Sales Navigator for mutual connections, etc. Sales needs to quarterback the entire process like a quarterback: Who should we reach? How do we divide responsibilities (like working with BDRs)? What's the best entry path for each lead?

Harry: You basically have to become a professional "stalker" (laughs). But I get the persistence you're talking about. Like when I sent 53 emails to get Salesforce founder Marc Benioff on my podcast — that kind of resilience is so important in outbound. It's not about giving up after the first, second, or even seventh email with no response.

Kim: You're absolutely right. That's why salespeople who've done door-to-door are so resilient. Nobody opens the door saying "Wonderful, please sell me your product." It's the ultimate "rejection training." And this experience also builds empathy for others.

Harry: How do you prioritize leads? By contract size, or is there a smarter way?

Kim: It's not just about deal size. We use a combination of firmographic + product signals:

  • Firmographic: industry, size, region, tech stack, etc.
  • Product signals: product activity, depth of usage, etc.

Combined, which customers are most likely to close, launch quickly, or have growth potential in the future — this tells you where to put your resources.

Harry: So when it comes to actually "closing" these customers, how do you evaluate payback period for individual accounts? And how do you look at "return on investment"?

Kim: This is mainly set with RevOps (Revenue Operations), since ramp-up times differ by role:

  • Commercial
  • Mid-market
  • Enterprise

We set expected timelines, like ramping up within X months and starting to hit targets.

Harry: Founders often say "50% of sales hires work out." What's your actual attainment rate?

Kim: Our team goal is: 80% of salespeople achieve at least 80% of their quota. This is a core metric we use internally to measure sales team health.

💡 Part 7: How Will AI Drive the Future of Sales?

Human-Machine Collaboration

  • AI will take over a large volume of transactional go-to-market activities (scheduling, simple inquiries, small deal closure, data enrichment, information synthesis, etc.). "Machines do repetition, humans do strategy" will become the trend. Salespeople should return to complex deals and consensus-building among multiple stakeholders, focusing more on cross-functional, multi-decision-maker complex projects and deep relationships.
  • Notion's internal AI practice: Notion itself uses AI to automate data collection and preliminary insights, using Notion AI to aggregate customer-side data sources and instantly generate high-quality Executive Briefs, freeing up more energy for high-value conversations.

Harry: Are we entering an era where sales reps and leaders need to be more technically proficient than ever to directly demonstrate these more complex technical solutions to customers, especially in today's AI era? Or should we emphasize building deep human relationships more? Or both?

Kim: Yes, both are needed. Because as AI gets better at handling standardized, low-complexity transactions (like SMB deals, point solutions), human sales focus will concentrate on "complex sales":

  • Involving multiple stakeholders
  • Requiring consensus-building inside organizations
  • Requiring technical understanding to deeply match solutions with customer business

In other words, the more complex the sales scenario, the more irreplaceable humans become, and both technical literacy + empathy are key.

Harry: What are we doing in sales today that won't be needed in five years?

Kim: One thing I particularly hope to radically improve is data enrichment. What salespeople hate most is bad data in the CRM — employee counts that don't match, unfair territory assignments — this all affects customer prioritization. I deeply dislike manual entry and look forward to more high-quality automated data that doesn't require human maintenance.

Harry: Well said, I completely agree. I also think that customer research used to take an hour, and now you can basically get ChatGPT to handle it. The value of deep research is...

Kim: We actually use Notion AI internally, with underlying integration of top-tier models like ChatGPT, Claude, and the results are amazing. Take this week's executive customer meeting — they wanted an Executive Brief. In the past, sales would manually gather information from Slack, the customer's website, Salesforce, etc.; now we enable Notion's "Research Mode" and within seconds it aggregates sources and generates a polished brief.

Harry: So how do you ensure the sales team fully embraces AI? As a media company leader, I'm always pushing my team: should we set aside 30 minutes a week for AI play and experimentation? How do you drive new tools and new behaviors?

Kim: I believe you should start with the most impactful workflows. If brief writing is the bottleneck, optimize there first. Recognize internally the colleagues who use AI best — showcase their approaches in team meetings. A culture of celebration drives behavior change far more than criticism or mandates. Ask the team: "Where can we use AI? What new tools have you tried recently?" Get everyone involved in exploration. I even often say, we're not "eating our own dog food," we're "drinking our own champagne" — constantly discovering Notion AI best practices so we can demonstrate them more convincingly to customers.

💡 Part 8: Advice for All Salespeople:

Customer-Centric, Curiosity-Driven

  • Truly great sales isn't about being outgoing or having slick talk tracks, but about being customer-centric and driven by curiosity to ask deep questions and co-create value. Kim emphasizes that no sales technique beats being genuinely curious — truly caring about customers, willing to ask one more question, is the best sales method.
  • Any decision must answer "Why change? Why this product? Why act now?" — "Why Change / Why Now"; core pain points include revenue growth, cost reduction, risk avoidance.
  • Company culture: Build a learning and growth atmosphere through celebrating cold call wins, AI use cases, etc. within the team. Establish celebration rituals, treat failure as learning, and let real-world practice beat process dogma.