Strategies for Upselling Products

Hey Salespeople: Here is a collection of current use cases for AI in sales & CS: ** GenAI in Sales ** --> Draft messaging for personalized email outreach --> Generate post-call summaries with action items; draft call follow ups --> Provide real-time, in-call guidance (case studies; objection handling; technical answers; competitive response) --> Auto-populate and clean up CRM --> Generate & update competitive battlecards --> Draft RFP responses --> Draft proposals & contracts --> Accelerate legal review & red-lining (incl. risk identification) --> Research accounts --> Research market trends --> Generate engagement triggers (press releases; job postings; industry news; social listening; etc.) --> Conduct role-play --> Enable continuous, customized learning --> Generate customized sales collateral --> Conduct win-loss analysis --> Automate outbound prospecting -->Automate inbound response --> Run product demos --> Coordinate & schedule meetings --> Handle initial customer inquiries (chatbot; voice-bot / avatar) --> Generate questions for deal reviews --> Draft account plans ** Predictive AI in Sales ** --> Score leads & contacts --> Score /segment accounts (new logo) --> Automate cross-sell & upsell recommendations --> Optimize pricing & discounting --> Surface deal gaps / identify at-risk prospects --> Optimize sales engagement cadences (touch type; frequency) --> Optimize territory building (account assignment) --> Streamline forecasting (incl. opportunity probabilities; stage; close date) --> Analyze AE performance --> Optimize sales process --> Optimize resource allocation (incl. capacity planning) --> Automate lead assignment --> A/B test sales messaging --> Priortize sales activities ** GenAI in CS ** --> Analyze customer sentiment --> Provide customer support (chatbot; voice-bot / avatar; email-bot) --> Draft proactive success messaging --> Update & expand knowledge base (incl. tutorials, guides, FAQs, etc.) --> Provide multilingual support --> Analyze customer feedback to inform product development, support, and success strategies --> Summarize customer meetings; draft follow-ups --> Develop customer training content and orchestrate customized training --> Provide real-time, in-call guidance to CSMs and support agents --> Create, distribute, and analyze customer surveys --> Update CRM with customer insights --> Generate personalized onboarding --> Automate customer success touch-points --> Generate customer QBR presentations --> Summarize lengthy or complex support tickets --> Create customer success plans --> Generate interactive troubleshooting guides --> Automate renewal reminders --> Analyze and action CSAT & NPS ** Predictive AI in CS ** --> Predict churn; score customer health; detect usage anomalies, decision maker turnover, etc. --> Analyze CSM and support agent performance --> Optimize CS and support resource allocation --> Prioritize support tickets --> Automate & optimize support ticket routing --> Monitor SLA compliance

I turned 10,000 dead CRM accounts into meetings using Clay workflows. The results were a 20% reply rate, over $200K in pipeline, and zero cold outreach. Most sales teams are sitting on a goldmine, yet they don't even know it. Here's how you can do the same: 1. TURN PAST CUSTOMERS INTO NEW OPPORTUNITIES Look for companies where your contract has ended or gone inactive. Import these accounts from your CRM into Clay. Find the original champion plus new decision-makers who've joined since. Then send targeted messages like: → "We worked with your sales team last year - wanted to share how we've solved the X challenge they mentioned" → "Since our last project with Acme Corp, we've added features specifically addressing your scaling issues." This approach feels like reconnecting, not cold outreach. 2. USE CHAMPIONS AS REFERENCE POINTS Find accounts where you had a strong champion in the past. Use Clay to verify if they still work there and in what capacity. Then reach out to new contacts in that account: → "Saw you work with Sarah, who implemented our solution for your marketing team last year." → "Your colleague Jason mentioned your team is facing challenges with X." Always verify employment status before sending these messages. 3. TARGET RENEWAL WINDOWS Pull contract end dates from your CRM into Clay. Create auto-updating lists that flag accounts 60-90 days before expiration. Find both original buyers and newly added stakeholders. Time your outreach perfectly by saying something like: → "Your current plan comes up for renewal in September - perfect timing to share what's new." This timing creates a natural sense of urgency without being pushy. 4. CONNECT THROUGH OFFICE LOCATION Import location data for your contacts from your CRM. Use Clay to find new prospects at the same physical office location. Verify if both your champion and new prospect work on-site. Write messages that reference the shared location: → "Noticed you work with Sarah in the Austin office - we helped her team last quarter with X" This creates immediate familiarity and leverages existing presence. 5. BUILD LOOKALIKE ACCOUNTS Take your best-performing customers from your CRM. Run them through Clay + Ocean.io to find similar accounts. Target these accounts with messaging that references success patterns: → "Companies like Apple, Tesla, and Spotify saw 43% faster sales cycles using our approach." → "Based on our work with similar X teams, we've found Y works well for them" This combines the credibility of social proof with personalization. _____ The real edge comes from maintaining good CRM hygiene and regularly updating data. Most teams are sitting on gold, but still use outdated or incomplete information. Start using what you already have instead of starting from scratch.

In Q1 2025, LTI (Ongoing Equity) Programs Had 4x the “Pay for Performance” Differentiation for Promoted Employees Vs. Salary Raises Companies generally reward top performers through three types of compensation programs: [A] Salary Raises [B] Long Term Incentives (LTI)–often ongoing equity grants [C] Short Term Incentives (STI)–often called a bonus program Today, let’s compare how much differentiation there is across the market for top performers between [A] and [B]. ________________ 𝗠𝗲𝘁𝗵𝗼𝗱𝗼𝗹𝗼𝗴𝘆: We recently took a look at Q1 2025 merit cycle data across 46k+ employees from Pave's dataset. 1st, our data science team grouped and analyzed employees across four groups:  • [1] Promoted  • [2] Above expectations (no promo)  • [3] Meets Expectations or equivalent (no promo)  • [4] Below Expectations (no promo) 2nd, our data science team looked at two dimensions across salary and ongoing equity grants  • [1] What % of employees received a compensation update?  • [2] For those who received, what was the size of the increase? Note that for equity, this was measured by the % increase in net equity value compensation vesting over the next 12 months 3rd, our data science team multiplied “participation” with “amount” to find the “𝗲𝘅𝗽𝗲𝗰𝘁𝗲𝗱 𝘃𝗮𝗹𝘂𝗲 𝗼𝗳 𝗶𝗻𝗰𝗿𝗲𝗮𝘀𝗲” as a method of measuring pay for performance. ________________ The Results: ✅ 𝗣𝗿𝗼𝗺𝗼𝘁𝗲𝗱  => Salary: +9.7% expected value increase => Ongoing Equity: +38.6% expected value increase ✅ 𝗔𝗯𝗼𝘃𝗲 𝗘𝘅𝗽𝗲𝗰𝘁𝗮𝘁𝗶𝗼𝗻𝘀 (𝗡𝗼 𝗣𝗿𝗼𝗺𝗼)  => Salary: +4.5% => Ongoing Equity: +11.0% ✅ 𝗠𝗲𝗲𝘁𝘀 𝗘𝘅𝗽𝗲𝗰𝘁𝗮𝘁𝗶𝗼𝗻𝘀 𝗼𝗿 𝗘𝗾𝘂𝗶𝘃𝗮𝗹𝗲𝗻𝘁 (𝗡𝗼 𝗣𝗿𝗼𝗺𝗼)  => Salary: +3.1% => Ongoing Equity: +3.8% ✅ 𝗕𝗲𝗹𝗼𝘄 𝗘𝘅𝗽𝗲𝗰𝘁𝗮𝘁𝗶𝗼𝗻𝘀 (𝗡𝗼 𝗣𝗿𝗼𝗺𝗼)  => Salary: +0.3% => Ongoing Equity: +0.0% expected value increase ________________ 𝗠𝘆 𝗧𝗮𝗸𝗲𝗮𝘄𝗮𝘆𝘀: 1️⃣ 𝗣𝗿𝗼𝗺𝗼𝘁𝗲𝗱 𝗲𝗺𝗽𝗹𝗼𝘆𝗲𝗲𝘀 𝗿𝗲𝗰𝗲𝗶𝘃𝗲 𝗮 𝗺𝗲𝗱𝗶𝗮𝗻 𝗲𝘅𝗽𝗲𝗰𝘁𝗲𝗱 𝘃𝗮𝗹𝘂𝗲 𝟯𝟴.𝟲% “𝗲𝗾𝘂𝗶𝘁𝘆 𝗿𝗮𝗶𝘀𝗲” 𝘃𝘀 𝗮 𝟵.𝟳% 𝘀𝗮𝗹𝗮𝗿𝘆 𝗿𝗮𝗶𝘀𝗲. This means that for promoted employees, the equity comp is ~4x as outsized from a pay for performance standpoint. 2️⃣ 𝗠𝗲𝗮𝗻𝘄𝗵𝗶𝗹𝗲, 𝘁𝗵𝗲 “𝗲𝗾𝘂𝗶𝘁𝘆 𝗿𝗮𝗶𝘀𝗲𝘀” (𝟯.𝟴%) 𝗮𝗿𝗲 𝗺𝘂𝗰𝗵 𝗰𝗹𝗼𝘀𝗲𝗿 𝘁𝗼 𝘀𝗮𝗹𝗮𝗿𝘆 𝗿𝗮𝗶𝘀𝗲𝘀 (𝟯.𝟭%) 𝗳𝗼𝗿 “𝗺𝗲𝗲𝘁 𝗲𝘅𝗽𝗲𝗰𝘁𝗮𝘁𝗶𝗼𝗻𝘀” 𝗲𝗺𝗽𝗹𝗼𝘆𝗲𝗲𝘀. This suggests that the real LTI/ongoing equity comp differentiation is happening for top performers (both those in the “promoted” and “above expectations (no promo)” buckets. ________________ 𝗣𝗿𝗮𝗰𝘁𝗶𝗰𝗮𝗹 𝗦𝘂𝗴𝗴𝗲𝘀𝘁𝗶𝗼𝗻 𝗳𝗼𝗿 𝗖𝗼𝗺𝗽𝗲𝗻𝘀𝗮𝘁𝗶𝗼𝗻 & 𝗛𝗥 𝗟𝗲𝗮𝗱𝗲𝗿𝘀: Analyze your company’s “expected value” salary and equity raise amounts. How do your outcomes compare to the Q1 2025 benchmarks from this post? And where + how should you consider tweaking your "recommendation logic” to guide your company towards more or less merit cycle differentiation for different cohorts of employees?

What if you had to achieve the same results with half the resources? Years ago, I ran a workshopping exercise with 90 magazine editors. It was called The 8 Page Magazine. I set the scene: a surprise paper shortage had been announced, and the government had decreed that, for the rest of the year, all magazines must be printed on just 8 pages. The editors had 20 minutes to plan their magazine within this extreme constraint. Their reactions were revealing. Some tried to cram everything in — every feature, every column — just in miniature. The result? A cluttered, unsatisfying mess. But the smartest editors made tough choices. They stripped the magazine down to its essence, giving just three or four key elements the space to breathe. Then I asked them: “Now that you’ve decided what’s really important, what happens if you go back to your normal number of pages?” The impact was transformative. Their magazines became cleaner, more purposeful, and more impactful. They focused resources on what mattered — and cut the clutter. This exercise wasn’t just about magazines. It’s a lesson for any business facing constraints: → What if you could only serve half your customers but twice as well — who would you choose? → What if you could only sell one product — what would it be? → What if you diverted half of your budget into a new area — where would you launch something new? Scarcity forces clarity. Constraints drive creativity. Sometimes, the best way to grow bigger is to think smaller. Is there an 8 Page Magazine moment in your business?

Your team should be selling. Instead, they’re drowning in admin work. Sales reps just want to sell. But when we sit down with them, it’s always the same story. They’re buried in 20 screens, clicking through fields that don’t help them close deals. And if it takes that much effort? They’ll stop using the CRM altogether. Not because they’re lazy. But because the system wasn’t built for them. Here’s what we see over and over—and how to fix it: 1) Too Much Manual Data Entry No rep wants to spend their time: • Logging calls • Typing out notes • Moving data between tools They’re here to sell—not push buttons. Fix it by automating everything you can. Use tools like Gong & QuickBooks to log calls automatically and sync invoices. The less manual data entry they do, the more time they have to close deals. 2) Clunky CRM Layouts If it takes 20 clicks to close a deal, they’re not going to use the system. Most CRM setups are bloated with fields that reps don’t care about. Half of them aren’t even for sales. The answer: fewer clicks, better layouts. • Two clicks, max • Only show fields relevant to their role 3) Tools Aren’t Integrated Reps live in: • Outreach • Gong • Slack If none of these tools talk to Salesforce, they’re forced to double their work. That kills adoption. Integrate the tools they already use. If it doesn’t make their job easier, it doesn’t belong in the stack. 4) The CRM Feels Like a Surveillance Tool Managers care about dials. Reps care about closing deals and hitting quota. If the CRM only tracks activity, it’s just another micromanagement tool. Fix it by making the CRM valuable for the rep. • AI-driven next steps • Deal insights • Sales shortcuts that actually help them win It has to feel like a competitive advantage—not a chore. 5) Training That Doesn’t Address Real Gaps Most training is based on gut feelings: “Reps need to know this.” But it doesn’t actually address the biggest problems. Fix it by making training metric-driven. If reps aren’t filling out critical fields, start there. Focus on what actually moves deals forward. Make the CRM work for reps, and they’ll actually use it. Make it a burden, and they’ll find ways around it. Enjoyed this post? Follow Jordan Nelson for more insights on making CRMs actually work for sales teams.

Moving the needle on average order value (AOV) is on every retailers mind right now. One way to offset rising customer acquisition costs (CAC) is to counter this by making customers spend more in one transaction. So many brands attempt to do this by moving free shipping thresholds and this sometimes can result in a higher AOV, but it can also hurt conversion rates. Two new approaches we have seen work really well for retailers/brands: 🥇 If you have a hero product in beauty or supplements, what if you create a "jumbo" version? You may not have as frequent re-purchases potentially but this can be offset by customers being less sparse with the product because it is a larger size. Don't forget when a customer is re-purchasing, this usually comes at a cost to your business in the form of SMS/emails, transactions fees, shipping and packaging costs etc... At times having customers spend more upfront even if they have a longer re-purchasing window can result in greater profitability! 🥈 Can you bundle two or three products plus a free gift? An ideal introductory offer to drive AOV typically converts best at a $100-$150 price point. The price of the bundle needs to represent at least a 20% discount vs buying each product indidually and a "junk" item cannot represent the perceived value if you want it to be a success. Long term though AOV growth comes from exploring adjacent categories and products that have a naturally higher price tag. Upsizing products and bundling are short term fixes and won't support year on year AOV growth. Next time you discuss AOV as a marketing team, I recommend including your product and buying team in the conversation. Collaboration is key to success in any business, retail is not excluded from this. What examples have you seen that moved the needle for a retailer increasing AOV year on year?

(Part 2) Bundles that actually move the needle on AOV In Part 1, we covered layout, positioning, and small UI tweaks that reduce friction and increase conversions on the product page Now let’s talk strategy, specifically how to use bundles to drive higher average order value without relying on random upsells or blanket discounts The right bundle strategy doesn’t just increase cart size It helps you launch new products, clear stale inventory, and create a better customer experience Here are 3 proven ones you can start with 👇 1. “Try me” launch bundles 💡 Perfect for: new products, seasonal collections, or early access drops Pair your new release with a proven bestseller to get attention and lower the risk of trying something new How to do it: • Use “Buy X, Get Y” (e.g. Buy our hero product, get the new one at 25% off) • Add a limited-time tag or countdown badge to drive urgency 2. Inventory busters 💡 Perfect for: slow-moving SKUs, returned items, or high-CTR but low-converting products Have stock you want to clear without discounting it to the ground? Bundle it How to do it: • Fixed bundles or BOGO formats work well • Combine with top-selling products to make the offer more attractive 3. Mix & match builder 💡 Perfect for: apparel, beauty, wellness, and giftable products Give customers a way to create their own bundle, it feels more personal and increases perceived value How to do it: • Let shoppers choose 3-5 products from a collection • Offer tiered pricing (e.g. 3 items = 15% off, 5 items = 25% off) These aren’t gimmicks. They’re practical tools to boost margin, move stock, and give customers more of what they want 📌 Next up: 3 more bundle ideas to increase cart size and personalize the experience. Stay tuned #shopify #ecommerce #growth

FOMO works in B2B! Behavioural studies on scarcity show a clear pattern: when something is both desired and genuinely limited, people decide faster, assign it higher value, and are more likely to commit. When demand is weak, though, layering on urgency – countdown timers, “last few spots”, fake limits – tends to backfire, creating scepticism rather than sales. Humans don’t just respond to scarcity itself; they respond to what scarcity signals. Limited access suggests that others value it, that capacity is constrained for real reasons, or that the opportunity won’t be available in the same form again. In that context, FOMO doesn’t create demand from thin air; it nudges already-interested buyers out of indecision and into action. Practically, this means scarcity tactics are most effective when they sit on top of clear intent signals: people are visiting the page and returning, asking questions, joining a waitlist, or engaging with your content. In those moments, stating real constraints – a fixed cohort size, genuine capacity limits, a true deadline – helps buyers make a confident choice instead of endlessly circling the decision. What that means for your brand: FOMO should be a spotlight, not a smoke machine. Use scarcity to highlight real demand and real constraints, protect trust by avoiding artificial pressure, and design your campaigns so urgency accelerates good-fit decisions instead of trying to manufacture interest that isn’t there.

Most sellers misuse discounts. They drop them too late. Talk to the wrong person. Add pressure. Miss their number. I’ve taught 1,000s of reps how to do it right. Here are 7 ways to use incentives without looking desperate: I’m not anti-incentives. I’m anti-commission breath. And that’s exactly what shows up when sellers drop a 30% discount on the 29th of the month…only to find out their champion still needs two more approvals and a legal review. It doesn’t close the deal. It just creates pressure. On you and your buyer. Here’s a better way. 1. Incentives are not discounts Don’t pitch 30% off like a used car dealer. Offer something valuable with a story behind it: → A month free → Preferred pricing → Bonus feature access It has to be legit—and tied to a reason (like quarter-end, new logo program, etc). 2. Talk to the decision maker If your buyer can’t actually sign, an incentive won’t help. You need someone who can say yes—or who can push it through. 3. Ask about their process first “What’s your timeline for getting this done?” If it’s next quarter, ask if an incentive would help them pull it forward. If they say yes, you might have a deal to accelerate. 4. Don’t offer anything if the timing isn’t natural You’re not trying to force urgency. So say: “I don’t want to show you this if it’s not something that’s realistic for you.” Let them opt in. 5. Always qualify timing “If we were able to offer something strong, do you think you’d be able to move forward this month?” You want buy-in before they see price. Not after. 6. Map the path to signature Lay out the mutual action plan: - Who needs to review the proposal? - When does legal need it? - How long does procurement take? If it’s not doable, don’t offer it yet. 7. Bring it up early in the month Waiting until the end will kill the deal. Even motivated buyers run out of time. So if you’re going to offer an incentive—do it with 2–3 weeks to spare. Not 2–3 days. TAKEAWAY Discounts don’t create urgency. Timing does. Know their process. Earn the yes. Stay out of panic mode. Close without pressure. Sell with trust.