Upselling and Cross-Selling

One way I help my clients sell more, faster: Remove friction from the sales process. Most B2B service companies have a horrible sales experience. → booking multiple calls to figure out what a prospect needs → filling out a form and waiting days to book a sales call → custom proposals that take weeks to create → 100's of iterations on that proposal It makes it hard for prospects to choose them. There is an easier way to sell. Yes, even for custom deliverables. Like websites, equipment manufacturing, Salesforce fixes, patent and trademark applications, IOT remote monitoring systems, and the like. It's simple. Turn your discovery process into a paid offer. → systematize it → create a templated deliverable → provide calls to get the information you need → include your proposal at the end of the deliverable → do one final call to present your report and your proposal → make it low-cost enough to feel like an impulse buy One of our clients has achieved a 100% upsell rate to their custom offer. Think about that for a minute. - sell a $1k-$5k offer - that sells your $50k-$500k offer Every. Damn. Time. This tactic has worked for multiple B2B industries: - manufacturing - industrial services - professional services - equipment sales - commodity sales The trick: you need to have the right initial offer. One people want. Priced for an easy sale. Want a product that creates a 100% upsell to your main offer? Shoot me a DM. I've done this for multiple B2B industries. And my clients who implement it make a sh*t ton of money. You could, too. ✌🏼 #shftyourbrand

Your product’s biggest strength? Might be the reason you're losing. Stop me if you've seen this before: A rep walks into a demo, guns blazing with the flagship feature. Patented AI. Endless integrations. Dashboards so pretty you want to frame them. The problem? None of that matters if the buyer doesn’t care. It’s like offering a juice cleanse to someone who just asked for a steak. This is the trap: we confuse differentiation with default positioning. Just because something is unique doesn’t mean it’s useful. Just because something is premium doesn’t mean it’s priority aligned. I’ve lost deals this way. You probably have too. Brian LaManna broke this down during a Sales Assembly course last week. His thesis is that the game isn’t about showing what makes you great...it’s about showing why you’re exactly right for them. Here’s how to make the shift: 1. Start with strategic fit, NOT product strength Before you drop into demo mode, answer this: What strategic priority does this prospect actually care about? - Reduce CAC by 15% - Launch in Europe by Q3 - Retain 95% of enterprise accounts - Improve onboarding velocity for ramping reps If your feature doesn’t map to one of those? It’s window dressing. No matter how powerful it is. 2. Quantify the cost of staying put Sellers love to sell the future. Buyers make decisions based on the cost of the present. If your differentiation doesn’t help them: - Close the gap between current and ideal state - Avoid a known risk - Or capitalize on an urgent opportunity... …it’s irrelevant. Build the business case around urgency, not just capability. 3. Use differentiation to de-risk the decision Great sellers use differentiation to reduce perceived risk. Bad sellers use it to inflate perceived value. “We’re the only vendor with XYZ” Only matters if: That feature ties to a must have outcome AND you make it feel safer to choose you than to stall or default to the status quo Otherwise? You sound like every other overengineered solution they don’t need. 4. Tailor the pitch by segment and stage Early stage startup? They care about velocity, not sophistication. MM? Probably looking for plug and play solutions with high ROI. ENT? Stability, compliance, scale...and political cover. Same feature, totally different framing. Differentiation that doesn’t flex by buyer type fails. Differentiation isn’t about being better. It’s about being the right answer to their very specific problem - right now. You’re not selling a Ferrari. You’re selling a way out of whatever corner they’re currently stuck in.

In 2024, we took a radically different approach that drove exceptional net revenue retention (NRR), with all customers renewing and expanding within their first year. Most SaaS companies claim they have a land and expand strategy. But let's be honest—many are just rushing to close initial deals and figuring out expansion later. I’ve seen (and done) this myself as an IC. Here are 3 things we're doing differently to maintain profitability in 2025: (1) Intentional Deal Architecture from Day One We've abandoned the "close now, figure it out later" mentality. Instead, we architect comprehensive deals upfront that map to our customers' growth journey: -Set platform pricing with included user counts -Pre-negotiate expansion user pricing -Define integration pricing tiers -Document future use case pricing This means when a customer starts with Gmail and Salesforce integrations, they already know exactly what adding Microsoft Dynamics or Tableau will cost. No surprises, no painful negotiations – just seamless expansion. (2) Zero Handoffs, Total Accountability. We've eliminated the traditional sales-to-CS handoff that creates gaps in customer experience. The same team that closes your deal stays involved in deployment and ongoing success. This isn't just feel-good stuff – it's practical: -Sales maintains strategic relationships -We deeply understand use cases -We spot expansion opportunities naturally -Early renewal conversations happen organically The result? We're not just vendors – we become strategic advisors helping shape our customers' trial and demo strategies (aka every CRO’s dream state.) (3) Aligned Incentives Drive Better Outcomes Here's something radical: our reps earn the same commission on expansion deals as new business. Why? Because expansion isn't an afterthought – it's core to our strategy. When you remove the artificial divide between new and expansion revenue, teams naturally focus on long-term customer success. 🤙 The Impact Yes, this approach requires more upfront work. You'll spend more time on initial deals. Your sales cycle might lengthen. But the results speak for themselves: >100% customer renewal rate >Every renewal includes expansion >Most customers expand license counts >We're seeing early renewals with expansion The old way of landing deals at all costs then scrambling to expand later is done. Today's market demands intentional, strategic deal architecture that sets both you and your customers up for long-term success. It's time to stop talking about land and expansion and start designing for it from day one.

1 simple strategy increased my client’s revenue by 15.08% in just 3 months. There was this client i worked with in 2022. Few months back he again reached out His store was generating good revenue but he was looking for more So we had a meeting and discussed what we could do to increase his revenue And we ultimately find our solution - Upselling Upselling increased his Average Order Value (AOV) from $176.40 to $203.00, creating a better shopping experience for our customers. Here’s how we did it and how you can, too! 1️⃣ Pre-purchase upsells: We introduced related products right in the shopping cart. For instance, customers buying a blue T-shirt could see an offer for matching blue shoes with a 11% discount if added immediately, and 14% off if they added two products. Tool I am using: Upcart 2️⃣ Post-purchase upsells: After the initial purchase, we offered similar items with an even greater discount. This approach keeps the customer engaged even after the checkout process and increases the likelihood of additional sales. Tool I am using: Aftersell 3️⃣ Thank you page upsells: Our order confirmation page wasn’t just a dead end. We turned it into another sales opportunity by presenting time-sensitive offers on related products, significantly increasing the chances of further purchases. This is how you can implement upsells in your store ◾ Identify related products: Understand your customers' buying habits to offer complementary products. ◾ Use the right tools: Employ apps that facilitate smooth 1-click upsells and offer customizable tiered discounts. ◾ Monitor and optimize: You can always track the performance of your upsell strategies and tweak them based on customer feedback and analytics. If your store runs smoothly, upselling can turbocharge your sales numbers and enhance customer satisfaction through relevant offers. P.S. Drop your upselling experience in the comment box!

2023 and 2024 have been the hardest years to sell in a long time. I've spent 18 months selling every day through it. Here's 11 tips I've learned about selling in bad economic conditions:    1. Building a business case is more powerful when you measure the cost of the status quo than when you measure the ROI of your product.     2. Understand the “need behind the need.” Keep peeling back the onion until you get to its core. The first few things customers share are always surface-level.     3. Agonize over how you phrase questions. “What are the ripple effects of X challenge on your business?” is far more powerful (and less salesy) than “how does that impact you?”     4. You can gain access to power by asking “who else is impacted by this challenge?” When your buyer answers, request that they be involved. This has a high hit-rate.     5. Test your champions. Do they get things done? If so, they’re not a champion. Give them “homework.”     6. Things are always changing. If you don’t stay on top of them, you’ll lose the deal. Start every call with “what’s changed since we last spoke?”     7. Social proof is so much more powerful when the customers you’re showing off are part of your buyer’s “tribe.”     8. You can’t treat discovery calls with inbound deals and outbound deals the same. You have to “earn the right” to discovery with outbound deals.     9. Sell the hell out of next steps. Don’t assume your buyer will show up just because they showed up to the first call. Sell the WHAT, the WHO, and the WHY of the next step you’re proposing.     10. If you’re having trouble quantifying a problem, try asking “what metric would solving this most improve?” Bingo.     11. The best questions you’ll ever ask aren’t pre-planned. They’re based on whatever the buyer just said. LISTEN.   What would you add? P.S. I've watched over 3,000 discovery call recordings in the last six years. Here's a free list of 39 of the best questions that sell: https://go.pclub.io/list

I said this in a webinar recently: The name of the game in DTC is  “whoever can afford the highest CAC will survive.” But to do that, you need a high AOV, a sticky subscription program, or a lot of cash in the bank. We went with focusing on increasing order value. Here are 4 of my favorite ways we’ve found to ⬆️AOV so far… 1. Upsell "more of the same" - Instead of upselling something new, we offer more of the same product the customer with a volume discount. This approach has increased our take rate SIGNIFICANTLY without hurting conversion. Why it works: The customer is already invested in the product - they’ve learned about it through ads, LPs, etc. So we just tap into their existing commitment, making the offer more enticing. 2. Urgency & Scarcity During the purchase flow, we highlight messages like "This product sells out fast" or "For best results, use for 8–12 weeks.” You can also try things like countdown timers and “low inventory” messaging to really drive this home. Why it works: Customers at the bottom of the funnel can be motivated by FOMO —they don’t want to miss out on getting the deal you’re offering, especially one they perceive as beneficial. If a product might sell out soon or if buying more now means they won’t run out later, they’re more likely to purchase right away or more of it. 3. Sequential Offers After someone buys from us, our post-purchase funnel begins immediately with our volume discount upsell. If they skip that, Obvi presents them our cross-sell and down-sell offers in a sequential funnel: First → Volume/bulk discount upsell Second → Complementary product offer Third → Smaller accessory or branded gear Why it works: This structured approach helps avoid overwhelming the customer with too many offers at once. Each step is designed to maximize potential revenue (highest-performing upsell shown first) while maintaining a logical flow. 4. Maximize the Thank You Page This is a simple one that a lot of brands miss.  Your thank you page has a bunch of valuable real estate that every one of your buyers look at it. At Obvi, we maximize this with post-purchase surveys and network offers. Network offers are a complete no-brainer for us. Big brands like Nike and Hulu pay to present offers to our customers on our Thank You page. If a customer opts in, we get some $. Why it works: It’s a win-win-win. The customer gets a good deal, the big brand gets another subscriber, and the seller gets incremental profit. For Obvi, it has resulted in about +$0.45 more per transaction so far. Post-purchase surveys won’t directly add $ to your bottom line, but they give you valuable insights about customer behavior and perceptions. Not to mention marketing attribution. That’s it, you know our ⬆️AOV secrets. BTW, AfterSell by Rokt is the tool we’ve used to test and execute these tactics. If you’re a Shopify brand looking to grow your AOV without hurting your conversion rate, they can help you get there. 

Account Managers.... Cross selling into different business units can be difficult, however there is plenty you can do to maximize your opportunities. It is your job to be aware of the organization's overall goals and initiatives, so tying those to your potential cross sell will be important. In a perfect world, you main POC will refer you to speak with their colleagues, but that is not always the case. If you are doing outreach to tap into different units, trying to find other potential buyers, you need to create a solid gameplan. I personally like to use a 4-step formula in my outreach. 1. Research based opener (tied to the organization 9/10 times) 2. Problem based statement (what they are/may be facing) 3. How we are currently helping, and how the additional solution can help 4. Interest based CTA When speaking or messaging prospects within your account set, you need to tie how the current implemented solution is helping the main POC achieve XYZ. This automatically triggers a sense of ROI, positive impact, value given, etc. From that, then tie in how your proposed solutions helps them achieve XYZ. Mention how other leaders in their space achieved X, how they will get that similar/better ROI, how they will solve X, etc. Build credibility, status, and trust with them, as you already should have this with the clients you support. Never miss out on opportunity with aspects that are in your control. Go make it happen.

One of the most impactful strategies I've learned is the art of upselling to increase revenue and customer value. Done right, upselling benefits both the business and the customer. It's not a pushy tactic - it's about recommending additional products/services that genuinely enhance the customer's experience and enable them to achieve their goals more fully. I always keep a few guiding principles in mind when implementing an upsell strategy: 🗺️ I map the entire customer journey to identify prime upsell windows when buyers are most receptive. Key moments include during live support chats, post-purchase follow-ups, and subscription renewals. 📊 I leverage customer data within my CRM to personalize upsell offers based on the individual's purchase history, interests, and needs. Generic, irrelevant upsells get ignored or spark frustration. 👂 I train my team to actively listen for buying signals and pain points that set up a natural, valuable upsell opportunity. Things like questions about additional features or positive feedback about the product/service. 💡 I craft clear value propositions that articulate exactly how the incremental investment creates a better, stickier experience for that customer's specific use case. At the end of the day, upselling should be a win-win that drives more revenue AND more customer satisfaction/loyalty. 💬 What's your experience with upselling as a business or a buyer? Do you have any tried-and-true upselling tips to add? Any horror stories of pushy, irrelevant upsell fails?

Yesterday, I had an insightful conversation with a VP of Customer Success from a well-known SaaS company based in Bangalore. We were discussing strategies around upsell and cross-sell, and she shared a fantastic example of the power of subtle nudges. Her team noticed one of their long-standing customers was steadily increasing their use of automation features—a strong indicator that they might benefit from more advanced capabilities. But rather than pushing an upsell directly, her CSM decided to take a softer approach. During a regular check-in, the CSM casually shared a success story about a similar customer who had upgraded and saw a significant boost in productivity. 𝐓𝐡𝐞 𝐬𝐭𝐨𝐫𝐲 𝐫𝐞𝐬𝐨𝐧𝐚𝐭𝐞𝐝. 𝐈𝐧𝐬𝐭𝐞𝐚𝐝 𝐨𝐟 𝐟𝐞𝐞𝐥𝐢𝐧𝐠 𝐥𝐢𝐤𝐞 𝐚 𝐬𝐚𝐥𝐞𝐬 𝐩𝐢𝐭𝐜𝐡, 𝐢𝐭 𝐟𝐞𝐥𝐭 𝐥𝐢𝐤𝐞 𝐚 𝐠𝐞𝐧𝐮𝐢𝐧𝐞 𝐭𝐢𝐩. The CSM even highlighted a few specific premium features that would align with the customer's current growth phase, like advanced analytics and additional integrations. This was all done in a way that showed they understood the customer’s journey and were there to support it. The result? Within a quarter, the customer upgraded, excited by the potential impact on their operations. They even went on to explore cross-sell options in other areas. The VP and I both agreed: 𝐬𝐮𝐛𝐭𝐥𝐞, 𝐭𝐢𝐦𝐞𝐥𝐲 𝐧𝐮𝐝𝐠𝐞𝐬 𝐛𝐚𝐬𝐞𝐝 𝐨𝐧 𝐠𝐞𝐧𝐮𝐢𝐧𝐞 𝐜𝐮𝐬𝐭𝐨𝐦𝐞𝐫 𝐢𝐧𝐬𝐢𝐠𝐡𝐭𝐬 𝐜𝐚𝐧 𝐛𝐞 𝐠𝐚𝐦𝐞-𝐜𝐡𝐚𝐧𝐠𝐞𝐫𝐬. Upselling and cross-selling don’t have to be about pushing products—it’s about helping customers realize the full potential of what’s available to them. We explored on how to make the above a playbook across all their 62 CSMs who are spread across 3 continents and what kind of nudges can be incorporated. #CustomerSuccess #Upsell #CrossSell #CustomerJourney #CustomerSuccessStories

I get this question a lot - "How can I increase revenue?" The answer is simple. As the "Sales Doctor" for over 1,400 portfolio companies at Right Side Capital, I have a unique vantage point in the sales strategies of early-stage companies. One of the most significant opportunities I see frequently overlooked is the art of upselling existing customers. There are two primary types of upsells to focus on: 1. Existing Customer, Existing Contact: This is a straightforward yet powerful opportunity. By deepening your relationship with current customers, you can enhance your product's footprint within their organization. Focus on understanding and solving their problems, demonstrating a strong return on investment (ROI), and progressively increasing your engagement. This approach not only boosts sales but also reinforces customer loyalty. 2. Existing Customer, New Contact: Leveraging your success with an existing customer to reach new contacts within the same organization can be incredibly effective. Although you can request introductions from your current contacts, a proactive approach is often more fruitful. Identify different divisions and build relationships with key contacts in each. Having a case study and reference from within the company gives you a warmer entry point, making your pitch more compelling. To capitalize on these opportunities, follow these simple steps: 1. Create a comprehensive case study of your success with the existing customer.  2. Identify potential new contacts across their global operations. 3. Craft a strategic outbound engine involving calls and an automated email sequence(I prefer the agoge sequence) to engage them. By doing so, you can systematically expand your pipeline and drive sustained growth. Focusing on upselling existing customers is not just about increasing sales; it's about building deeper, more resilient relationships that can weather market changes and foster long-term success.