Upselling and Cross-Selling

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 warmed up a prospect for 3 months on LinkedIn before our first call. They signed a £75K deal in 3 days. Modern selling demands a new approach: cold outreach fails, warm relationships win. Think about it... That prospect had consumed 47 of my posts. Watched my videos. Read my articles. Engaged with my content. By the time we jumped on that first call? They already trusted me. They already knew my approach. They already understood the value. I didn't have to sell them. They'd already sold themselves. Here's my framework for turning content into closed deals: 👇 1. Build trust at scale BEFORE the pitch Stop spraying and praying with cold messages. Start building relationships through value. Each post builds trust. Your insights mark credibility. Stories create connection. Your content is doing the heavy lifting while you sleep. 2. Let buyers self-educate on THEIR timeline Modern buyers don't want to be sold to. They want to discover solutions themselves. ↳ 70% of the buying journey happens before they talk to sales ↳ They're researching you before you even know they exist ↳ Your content is either attracting or repelling them Give them what they need to make informed decisions. 3. Recognize the REAL buying signals Forget MQLs and SQLs. Think about PQLs (product qualified leads) Here's what actually matters: - Multiple engagements across different posts - Bringing colleagues into the conversation - Asking specific, detailed questions - Moving from public comments to private messages These aren't leads. These are pre-qualified buyers. 4. Keep momentum BETWEEN meetings Here's where most deals die: The 167 hours between your calls. While you're chasing other prospects, your buyer is: ↳ Getting cold feet ↳ Talking to competitors ↳ Forgetting why they were excited Smart sellers stay present even when they're not there. This is where tools like Consensus come in. They let buyers explore demos on their own time. Answer their questions at 10 PM. Share materials with their team. Stay engaged between touchpoints. It's how you keep social selling momentum right through the demo stage. https://lnkd.in/ePVWw-Bi 5. Close with confidence, not pressure When trust is already built? When value is already proven? When buyers are already educated? Closing feels natural, not like a battle. The best deals I've ever closed felt inevitable. Because the relationship started months before the opportunity. Here's what this approach delivers (in my experience): ✓ Significantly faster sales cycles ✓ Much higher close rates ✓ Bigger deal sizes (pre-sold = less negotiation) ✓ Happier customers (they chose you, not the other way around) Stop thinking of social selling as "nice to have." Start treating it as your primary sales strategy. Your next big deal isn't in your CRM. They're scrolling LinkedIn right now. What content are you creating to catch them? #ConsensusPartner

I've analyzed 10,000+ sales calls and discovered something shocking… Elite closers NEVER discount when asked, "Can I get a better price?" While most reps panic and immediately cave, the top 1% have a completely different playbook 👇 Instead, they have a systematic approach that PRESERVES margins while CLOSING more deals. When you're quick to discount, you communicate TWO things that DESTROY trust: 1️⃣ "YOU CAN'T TRUST ME". They'll think: "Why didn't they give me the best price initially?" This makes them suspicious of everything else you've said. 2️⃣ "MY PRODUCT ISN'T WORTH IT". You're telling them you don't believe in your own value. If YOU don't believe it, why should THEY? Before using any strategy, run the objection through my H.E.A.R.T. framework: - H-ear them: "Cari, I appreciate the ask." - E-laborate: "Help me understand why you're asking?" - A-side: “Aside from the pricing, is anything else giving you pause?" - R-eclarify value: "What did you like most about our solution?" - T-ransition: Now use one of these 5 strategies... ➡️STRATEGY #1. THE REDUCTION CLOSE "Let's review everything in your package and remove what's 'nice-to-have' versus 'must-have.' Then we'll recalculate." You're NOT giving a discount. You're reducing what they're buying. Most prospects realize they want everything and end up paying full price anyway. ➡️STRATEGY #2. THE SUBSTITUTE CLOSE "I know we discussed Option X. Another option is Y, it does things 1, 2, and 3 but doesn't have 4, 5, or 6. However, it's $XXX less." Again, NO discount. Just a lower-priced alternative that creates value comparison. When they see what they lose, they often stick with the premium solution. ➡️STRATEGY #3. THE UPSELL VALUE GIVE "I can't discount, but I CAN include Premium Support for 30 days. Normally reserved for our highest tier and costs 30% more." The magic? They often upgrade after experiencing the premium feature! This is my personal favorite with the highest conversion. ➡️STRATEGY #4. THE 3 OPTION CLOSE Present good/better/best options BEFORE the price objection happens. When they ask for a discount, guide them to the lower option. This makes THEM decide between features vs. price. Instead of YOU deciding between discount or no deal. ➡️STRATEGY #5. FLEXIBLE PAYMENT TERMS Instead of cutting price, adjust WHEN and HOW they pay: → Half now, half in 30 days → Payments over 3 months → Net-30 instead of Net-15 One Fortune 500 client increased close rates 32% with this approach alone. ➡️THE LAST RESORT: GIVE TO GET If you absolutely MUST discount, NEVER give without getting something in return: "I can do 10% off if we add 5 more licenses." OR "I can do 10% off if you introduce me to 5 other business owners who could use our solution." You're conditioning how you do business AND maximizing value. — Hey sales pros, want to handle objections better? Go here: https://lnkd.in/g-uJ7ECX

"Just checking in on that proposal." I sent this email the other day. My 4th "check-in" to this prospect. No response. Frustrated, I called my sales amigo: "I don't get it. Great demo, they loved our solution, but now they've gone dark." He asked a simple question: "What content have they engaged with since your demo?" I had no idea. The truth hit me: I was flying blind. I sent PDFs, presentations, and pricing. But had zero visibility into what they actually viewed. Were they showing it to others? Did they have concerns? Was anything resonating? I had no clue. Last week, I tried a different approach: After a promising demo, instead of attaching files to an email, I created a digital sales room. Inside: - Everything they needed to evaluate us - Organized by their specific priorities - Clear calls-to-action for next steps The difference was immediate: Day 1: The main contact viewed the ROI calculator twice Day 2: They shared it with their CFO (who I'd never spoken to) Day 3: The CFO spent 30 minutes on pricing information Day 4: They downloaded our security documentation Day 5: The main contact viewed implementation timeline 3 times I picked up the phone: "I noticed you've been looking at our implementation process. Any questions about that timeline?" Their response: "How did you know? Yes, actually, we're concerned about..." The objection surfaced BEFORE it killed the deal. Old school selling: Send content. Cross fingers. Guess what's happening. Modern selling: Share content. Watch engagement. Address concerns proactively. The hard truth: 90% of buying happens when you're not in the room. Are you still pretending those blind "check-in" calls are a strategy? Or are you watching how prospects actually consume information when you're not there? Stop asking prospects to update you. Start building systems that show you what's really happening. Agree?

You join the company excited to create content that helps sales close faster, better proof points, cleaner positioning, the kind of messaging that makes a rep’s job easier. But the very first people you need to partner with…have been doing this long before you got here. They’ve closed deals without your decks. They’ve written half the pitch in their heads. And they’ve built trust with prospects in real time, not by waiting for enablement assets to show up in a Notion doc. So when you show up with “help”, even if it’s good, even if it’s asked for, it’s easy for it to land like a correction. A quiet implication that they were doing it wrong. That’s the part no one tells you. Enablement is not a one-way street. And if your work looks even a little too top-down, like instruction instead of support, you will lose trust before you even start. What I’ve learned (and am still learning) is this: building healthy relationships with sales isn’t about proving your value fast. It’s about creating shared momentum, without stepping on the people who’ve already figured out how to win. Here’s how I try to do that: 1. Act like an investigator, not a fixer. In your first 30–60 days, don’t start with “What’s broken?” Start with “What’s already working that we can double down on?” Ask what moments in a deal feel frictionless. What content or stories they always go back to. Map the habits before you map the gaps. 2. Bring ideas, not deliverables. Too often, we show up with an asset in hand — a one-pager, a case study, a pitch update — and ask for feedback. Instead, bring the seed: “I’m seeing X come up in deals. What’s your take on how we should address it?” When a rep contributes to the idea, they’re more likely to adopt the output. 3. Remember your role: scale, not overwrite. The best enablement isn’t a new playbook. It’s a way to scale the instincts and stories your top reps already use. Don’t say, “Here’s what to send.” Say, “This might help reinforce what you just said.” Subtle shift, big difference. This takes longer than building a content repository and calling it done. But the payoff is way better: real trust, faster feedback loops, and enablement that actually gets used. Because the goal isn’t to impress your sales team. The goal is to build with them, so your work feels like a shortcut, not a sidestep.

Growth is still on the table. But most GTM plans only build on last year. Category leaders don't think that way. This year CEOs, sales, and BD leaders I coach are making 5 strategic shifts to unlock partnership-driven revenue. Here’s their thinking: 1. Redesign for revenue leverage → Upgrading incentives → Redefining BD as market-making → Focusing sales on revenue conversion 2. Prioritise the right partners → Evaluating mutual benefit, trust and velocity → Using a “Partnership Potential Score” to focus on high-leverage allies 3. Build a co-sell access gateway → Give BDs fast access to top 3 co-selling partners who are ready to create leverage 4. Reflect on historic momentum → Analyse last year’s top 10 deals for partner impact → Identify where they influenced pipeline, speed or retention 5. Operationalise your partnership system → Codify onboarding, first wins, and partner enablement → Equip champions inside and outside your org The difference between 10% growth and market dominance? Moving from ad hoc deals to a scalable system. Remember this: Partnerships aren't a channel. They’re the strategy your competitors haven’t figured out. Yet. Need to capture growth? Send your team to The Partnership Lab. A 12 week group coaching program delivers the strategy, AI-based tools and community to close 6-figure deals with confidence. Learn more here: https://lnkd.in/etQTiW6u ♻️ Repost to help a BD leader or founder move to category leader ➕ Follow Phil Hayes-St Clair for more like this

Most sellers think the biggest obstacle is the status quo. They’re wrong. I’ve coached 1,000+ reps and closed over $100M in enterprise software deals— And I can tell you firsthand: Your biggest competitor isn’t “do nothing.” It’s fear. Here’s how to de-risk deals and overcome buyer indecision: Buyers don’t lose sleep over doing nothing. They lose sleep over messing up. Because if they do nothing? Nothing happens. If they choose you and it fails? Their job’s on the line. That’s the real reason you get ghosted. Not because they want to stay in the status quo— But because they’re terrified your solution won’t deliver. Here’s how top sellers overcome that fear: 1. Get brutally honest, fast. Read their energy. Watch their face. If something feels off, call it out. “I’m sensing some hesitation. Where do you feel risk?” or “What would make you feel comfortable moving forward?” Don’t wait for objections—extract them. 2. Land and expand. Big deals create big fear. Instead of pushing the whole $1M rollout, start with one team. Prove results, build credibility, then go enterprise-wide. Smaller deal. Faster close. More trust. 3. Get creative with contracts. You don’t have to choose between ‘yes’ or ‘no’. Invent a ‘yes that feels safer.’ Here are 2 ways I’ve done that: A. Carveouts: We put experimental products on a 1-year agreement, while the core was 5 years. Result? They said yes to both—without getting locked into unproven tech. B. Price ramps: Instead of $5M up front, we ramped: $3M → $4M → $5M. They only paid what they could actually use—and that made all the difference. 4. Conservative ROI. Don’t sell the dream. Sell the floor. Buyers don’t want inflated projections—they want numbers they can defend. Let them plug in the ROI and stand behind it. Remember: The real reason deals stall? It’s not lack of urgency. It’s lack of confidence. Help your buyer feel safe— Or watch the deal die in “maybe.” Be the rep that makes saying yes easy. De-risk everything. Win more. P.S. If you're an AE who wants to work with me as your sales coach in 2025, we have a few 1:1 spots left. You can apply here: https://lnkd.in/gf3zQSPy

I've been browsing through a bunch of online stores (part of the job, part of the fun), and something caught my eye: A lot of stores do try upselling, but many don’t do it strategically. Some even give up on it completely after a while, thinking it doesn’t work. This is a shame because upselling – when done right – is one of the coolest tools you can use to grow your store. It’s not just about adding more stuff to the cart. It’s about creating a smarter, smoother shopping experience and boosting your AOV at the same time. Here’s how to actually launch upsells the right way—from scratch 👇 𝗦𝘁𝗲𝗽 𝟭: Understand your product journey You can’t upsell what you don’t understand. Start by mapping your bestsellers. ➝ What products do people buy first? ➝ What naturally complements them? 𝗘𝘅𝗮𝗺𝗽𝗹𝗲: Selling protein powder? The logical upsell might be a shaker bottle, creatine, or a higher-value bundle. 𝗦𝘁𝗲𝗽 𝟮: Look at the data (even if it’s limited) You don’t need a full analytics department. Check your orders: ➝ What are people buying together? ➝ What’s your most frequent cart combo? ➝ What’s the average order value? This gives you a baseline for what to promote and where to push. 𝗦𝘁𝗲𝗽 𝟯: Choose the right moment to upsell There’s a difference between annoying and helpful. Start with one of these: ✔ Pre-purchase upsell: On product or cart page ("Upgrade to a bundle and save 20%") ✔ Post-purchase upsell: After checkout but before confirmation ✔ Follow-up email upsell: A week after purchase ("You might also love…") Start small – test one placement at a time. 𝗦𝘁𝗲𝗽 𝟰: Use smart logic, not just discounts An upsell should feel like a natural next step, not a sales pitch. ✔ Offer more value (“Add this for just $9 and get free shipping”) ✔ Offer convenience (“Subscribe now, and you won’t run out”) ✔ Offer upgrades (“Switch to a 2-month pack and save 15%”) 𝗦𝘁𝗲𝗽 𝟱: Test and refine (even if it's not perfect) Watch how people interact: ➝ Is it being ignored? ➝ Is it increasing AOV? ➝ Are you seeing better conversions or just more noise? Tweak copy. Try different placements. Use urgency or testimonials. Upselling is 80% iteration. 💡 One more thing Don’t see upselling as an “add-on tactic”. It’s a core part of a growth-oriented customer journey. Do it right, and you’ll see: ✅ Higher AOV ✅ Better retention ✅ A store that sells more without more traffic #shopify #ecommerce

Refresh and cross-sell are simply THE most neglected revenue engines in vendors and the channel at large. They’re not underperforming because they don’t work. They’re underperforming because leadership doesn’t prioritize them or more often they are simply too hard to launch. Net new logos get the spotlight. Legacy accounts and install bases get ignored. Partners aren’t enabled. Customer data isn’t centralised. And no one is held accountable for driving these motions with urgency. Fact: System refresh is THE low-hanging revenue. Fact: Cross-Sell is a margin multiplier. The effort-to-reward ratio is significantly better than any new logo acquisition, yet it’s treated as an afterthought. Organizations that win here don’t wait for perfect signals. They trap installed base. They assign ownership. They simplify offers. They operationalise partner touchpoints. They launch automated sales campaigns at scale. I’ve seen buried accounts turn into 7-figure wins, just by giving people the mandate and organisations the tools to act. Forget the “new logo” obsession. The real growth is in what you already own. iasset.com

The shift from Customer Success to Account Management isn’t just a title change. It’s a complete mindset shift. Top organizations are walking a tightrope - realigning incentives, enabling their teams, and making tough calls on who truly fits this new hybrid role. Incentives? It’s not enough to say, “go sell more.” Comp plans need to strike the right balance between rewarding customer retention and driving revenue growth. Here’s what works: 1. Base + Variable: Maintain a stable base salary but introduce a variable component tied directly to upsell and expansion targets - typically 10-20% of total OTE. 2. Retention Bonus: Reward CSMs for renewals with a lower commission rate (2-3%) to maintain focus on customer success. 3. Expansion Accelerator: Upsells and cross-sells should have a higher commission rate (5-10%) to encourage revenue-generating behaviors. 4. Team Targets: Consider overlaying team-based bonuses to promote collaboration between CSMs and AEs on complex deals. The key? Make sure incentives don't push CSMs to prioritize revenue at the expense of customer trust. It’s a fine line. Enablement? It’s not just about product knowledge anymore. CSMs need: - Sales Training: Discovery skills, objection handling, and negotiation techniques. - Commercial Awareness: Understanding pricing structures, contract terms, and how to position upsell opportunities naturally during success calls. - Playbooks: Clear frameworks that outline when and how to introduce commercial discussions without derailing the customer relationship. And the hardest part? Tough calls. Not every CSM will thrive in this hybrid role. Some are natural relationship builders who shy away from sales. Others will embrace the challenge and flourish. The best orgs are upfront about this and are offering distinct career paths: - Customer Advocate Path: For CSMs who want to deepen relationships and focus solely on retention. - Commercial Growth Path: For those eager to take on upsell/expansion responsibilities and earn variable compensation tied to revenue. Balancing customer happiness with revenue growth isn’t easy. But when done right? It’s a force multiplier.