Jesse Osborne

Every sales org has a pipeline: Stage 1. Stage 2. Forecast. Commit. You can recite it in your sleep. But when it comes to renewals? Crickets.... There’s no real-time view of customer risk. No weekly trendline. No forward-looking model that projects retention. Isn't that kinda bonkers? You FORECAST growth, but you DISCOVER churn...usually when it’s too late to fix. The big mistake is presuming retention is a lagging indicator, when it would be more accurate to define it as a neglected one. Think about it...most CS dashboards read like a rearview mirror: - Usage metrics. - Ticket volume. - NPS. Useful? Sure. Predictive? Nah. Because churn doesn’t start when a customer says they’re leaving. It starts months earlier when their exec sponsor stops showing up. If you can spot the risk early, you can unlock more levers: - Re-engage power. - Reset the value narrative. - Escalate to commercial. - Offer roadmap visibility. - Re-map success metrics post-reorg. But none of that works if your team can’t see it coming, which is why you need a churn forecast...just like you do for revenue. Build a churn pipeline. Treat it like sales. Some things to build into this: 1. Define churn stages. Just like deals, risk evolves: - Stage 1 (Early): No exec alignment, lagging adoption, stakeholder turnover. - Stage 2 (Mid): Value not realized, weak champion, limited engagement. - Stage 3 (Late): Renewal live, buyer pushing back, pricing/legal blockers. Assign clear criteria. Surface it in Gainsight, CZ, or Salesforce. Manage it like opportunity stages. 2. Assign prevention plays. Each stage should trigger a play: - Stage 1 = exec outreach + roadmap session. - Stage 2 = commercial review + value plan. - Stage 3 = C-level call + tailored retention offer. Codify this. Don’t let reps improvise. 3. Forecast it weekly. Revenue leaders inspect pipeline weekly. CS should do the same with churn. Ask: - How many accounts moved stages? - What’s projected retention by segment? - What % of at-risk logos have exec visibility? Also, share your churn forecast with the CFO. If the CFO sees new logo pipeline every Monday, but doesn’t see churn risk until Q4? That's no bueno. Start sending a weekly churn report with: - Total ARR at risk. - ARR by churn stage. - Stage progression. - Active recovery plays. - Forecasted retention (with confidence levels). This reduces surprises while also forcing accountability. Why? Because churn is rarely a CS failure, but it's often a product gap, pricing mismatch, or sales promise that aged poorly. When churn is forecasted, it becomes EVERYONE'S problem. Which it is. tl;dr = you don’t “discover” churn. You forecast it. You stage it. You act on it. Just like sales.

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Had a fascinating conversation with a new BDR leader at a ~$30M+ ARR SaaS co who spent 6+ years leading teams at a well-run sales org prior. His reality perfectly captures what I'm hearing in dozens of conversations. Here's the stark reality that's quietly killing growth inside many companies today: THE EMAIL CLIFF "Email works next to zero percent," he said. They're calling into healthcare systems with advanced firewalls and spam blockers. What used to be a reliable channel has essentially flatlined. His team still sends emails, but he admits it's "probably a waste of time." THE DIALING SQUEEZE They've invested in better dialing technology for improved coaching and gamification, but their connect rates have dropped to 3.5%. At his previous company, he was hitting 4.5-6%. The trend line is clear and it's not pretty. THE INTENT SIGNAL OVER PROMISE Three weeks into his role, they bought an "intent signal" platforms that promises to identify hot prospects from website visitors and digital signals. The reality? "Once you get only one relevant visitor a week for your specific patch, that doesn't make it engaging." The volume is so low it's barely worth logging in. THE EXPERIENCED LEADER DILEMMA He works under a seasoned CRO with an incredible track record. Very impressive runs. Someone who built successful playbooks at scale across 3 high growth SaaS companies. But those proven plays from 3-5 years ago? They're not working anymore. The CRO is in "learning and absorbing mode" trying to figure out what comes next. What I read from that is he doesn’t know what to do. And he is not alone. This situation isn't unique. It's becoming the norm. Teams are "turning over every rock" looking for pipeline. They're manually building closed-lost re-engagement campaigns. They're increasing dial requirements to 150+ per day just to sniff their numbers. While email isn’t delivering, they are afraid to have their teams stop doing it because they don’t know what the alternative is. NOW WHAT? If email is in trouble, connect rates keep dropping, and signal aggregation doesn’t move the needle unless you have a real inbound machine or massive PLG motion... what happens next? I see three paths: 1. Full-cycle reps become the default       Fewer specialists, more account ownership. Likely nowhere near the 6-7X quota to OTE ratios and cost to acquire customers rise. Outbound deals take much longer to close and these reps begin to master long-term nurture.     2. Outbound shrinks dramatically as a portion of pipeline Companies invest heavily in inbound, partnerships, content, thought leadership, and events instead. If this is true, a lot of the CROs whose value is tied to building outbound functions will decrease (this was me before Champify) 3. Growth slows across the board Companies simply can't scale as quickly without reliable outbound channels. What do you think happens? What am I missing?

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I’ve reviewed 100s of discovery calls. The #1 difference between AEs converting 40% and AEs converting 70%+ of first calls is the number of problems discussed. And the top reps discuss fewer. Reps that don’t convert go wide, trying to find anything and everything to tie their product to. They think: “The more problems I find, the better chance I have of solving some of them.” Reps that convert go deep into the most important problems uncovered. They think: “I need to attach to a problem worth solving.” I built a discovery capture sheet that will help “guide” your conversations to go deep, instead of wide. You can get it here in this blog post (ungated and no cost - just make a copy): https://lnkd.in/gCaUJ4ZD

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Please, for the love of revenue, stop opening your pricing call by pulling up the proposal and running through the price. You’re not a waiter dropping the check at the table. If the prospect says, “We just want to review the price,” that’s your signal to slow down and give context to the conversation. Every pricing call should start by confirming: - current challenges or problems to be solved - desired outcome for their business - how your product or service is going to deliver the outcome for them Once you are aligned on these three things, you can move forward with showing the price. This is especially important when a new evaluator joins the call. For example, you have been working with a champion who gets to the point where they want to see the price. You schedule the call to review the commercial terms. They invite the CFO or the economic buyer. That CFO has no context for value that you are going to deliver. They haven’t felt the pain you’ve been unpacking over the last few weeks. That's your job to give them the right context. Price only makes sense when you understand the current challenges and desired outcomes. That’s why I always start pricing calls the same way: “Before we jump into numbers, I just want to make sure we’re aligned on the goals of this partnership. Can we quickly revisit the challenges you’re solving and the outcomes you’re targeting? I want to make sure the proposal maps to that.” It’s a hard thing to say no to. And it does two important things: It gives you a chance to reinforce the value. It opens the door for new information or things the buyer hasn’t told you yet, but that will matter in the decision. I have lost many sales opportunities in my career by rushing to show the pricing. I thought moving fast meant being efficient. But I skipped the context. So the next time you have a pricing call, slow down. Frame the conversation. Align on the value of the partnership. Then move on to the commercial terms. ______ If you need help structuring that conversation, I’ve got an executive summary template that makes this easy. Comment "Summary" and I'll send it to you.

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When did 40-50%+ attrition rates on SDR teams become okay? "It's part of the grind running an SDR org." And the kicker...it's mostly voluntary attrition. Reps are choosing to leave the org. From our work with dozens of SDR teams, attrition happens for a few reasons: ⛔️ Toxic culture You know...the smile and dial stuff everyone's always talking about. Fear-based leadership. Unrelenting focus on hitting dial activity. Strict adherence to scripts and cadences. This is the obvious one. ⛔️ Lack of role-specific enablement I see this all too often. Enablement is strapped on bandwidth, so SDRs never get role-specific training. The "last mile" training/coaching around what to do when a prospect picks up a cold call and says "hello." How to write great emails, subject lines, etc. SDRs attend enablement sessions meant for AEs, then have to translate that into their outbound approach. ⛔️ No career track (a big one) SDRs are no longer getting promoted to AE in 10-12 months. Orgs are struggling to hold onto SDRs for 1-2+ years because there isn't a place for them to go. Ideas: - Create a "belt system" where reps can earn promotions: SDR 1, SDR 2, etc - Give them extra responsibility (like owning the playbook) - Make them a team lead - Build an AE development program to start AE training when they're still SDRs ⛔️ Inexperienced front-line managers 99% of sales orgs spend 6-7 figures on rep training every year, but ZERO on manager training. You have managers that don't know how to run proper 1on1s, weekly team meeting, coach around skills, etc ⛔️ Poor AE/SDR alignment Still seeing this one a lot. Alignment is basically three AEs bossing around one SDR on what accounts they should reach out to. There has to be specific guidance that allows SDRs to work autonomously. What helps an SDR hit quota vs. pleasing their AEs is often in conflict. Fix that immediately. ~~~ What would you add to the list?

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Biggest challenges in sales by year: 2020: Spray-and-pray: “What's the maximum number of BDR's we can hire? 2021: “How can we keep spray-and-pray but make it look personalized?” 2022: “Why are open rates tanking and nobody picks up anymore?” 2023: “Buy another intent data tool or pretend this one works?” 2024: “How do we stop reps from pasting ChatGPT into DMs?” 2025: “My AiSDR brought in $0 qualified pipeline last quarter.” Spray and pray is dead. It died a while ago, but the market seems to now have caught up to the idea that the Orbb team realized a while ago. If you teach one rep how to send 1000 emails per day If you teach one rep how to make 200 dials per day Even if you teach one person how to close on a call, you didn’t build a repeatable system. A true system needs input from access, messaging, trust, product, customers - everything blending together. If your strategy still includes the belief that volume matters above all, it might be time to re-evaluate.

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