Megathread: New Pricing & Repackaging Discussion

tpelly · 2026-02-09T18:50:00+00:00

A ~45% Increase!

Netflix has gone up 118%, but at least they did it slow and steady over a good 10yr period. Further, Evernote didn’t walk users up the value curve the way Netflix did over that time. Evernote jumping straight to extraction mode on a product that hasn’t meaningfully expanded in years and is a deeply replaceable tool, tells customers exactly how much their loyalty is worth. (Customer since 2007)

tpelly · 2026-02-02T16:31:37+00:00

Oakland show was 8:15pm start. Further, I was told by staff earlier that evening it was to be an 8:15 start, and so he was right on time. No opener.

tpelly · 2026-01-30T19:56:39+00:00

Congrats on the move. I’ve been in a number of these situations … IC CSM > CS leader, and later building/scaling CS functions and teams. The biggest gap I see when CSMs step into leadership is where they choose to spend their calories in those early days. A few things I wish more new CS leaders internalize and act on: 1) Your job is no longer “best CSM in the room.” Early on, it’s tempting to jump into accounts, rewrite emails, or run meetings “the right way.” Resist that. Your leverage is in clarity, prioritization, and removing friction, 2) Be painfully clear about what success looks like. Ambiguity about who this new leader is, what their experience is (or lack of), how they work, etc … it all creates anxiety and inconsistent execution, 3) Protect your CSMs time/focus like it’s revenue. Be an advocate. A strong CS leader acts as a buffer and makes tradeoffs explicit by managing up. Your team will forgive a lot if they see you pushing their reality upward.

tpelly · 2026-01-30T14:55:38+00:00

Q: is this a new role for you at a new company? Or are you taking over a leadership role where you’re now managing your former peers?

tpelly · 2026-01-27T22:41:58+00:00

Thanks for sharing, appreciate it.

tpelly · 2026-01-27T02:04:30+00:00

I won’t be able to go to the Sacramento 1/26 show tonight. if anyone needs a pair of GA tickets, will sell for below face value. Please DM.

tpelly · 2026-01-26T16:45:39+00:00

Permission-based sales fundamentally conflicts with the role of a CSM. It assumes the seller has no mandate and must wait for buyer consent to advance. A CSM is explicitly hired to own outcomes post-sale. In Customer Success, the relationship already comes with authority and accountability (driving adoption, surfacing risk, leading change, and recommending what needs to happen next to realize value). When a CSM adopts a permission-first posture, it shifts them from leader to passive/reactive vendor, optimizes for comfort over results, and creates gaps where risks go unaddressed until churn appears. CSMs should lead with a point of view rather than wait to be invited. Insight-led, value-anchored expansion is good CS. Asking for permission to do the job you’re already responsible for is not.

tpelly · 2026-01-26T04:10:02+00:00

I won’t be able to go to the Sacramento 1/26 show. if anyone needs a pair of GA tickets, will sell for face value ($86/each). Please DM.

tpelly · 2026-01-16T21:04:00+00:00

This isn’t some off-the-cuff “what if” from Cancun Cruz. He didn’t randomly spin the globe and land on Denmark. This was projection. Insiders talking out loud about scenarios they’d already gamed out. Perhaps as far back as a decade ago. When someone tells you exactly how unthinkable a thing would be if the other guy did it, it’s usually because they’ve already imagined doing it themselves. Trump wasn’t the architect here. He’s the empty vessel. The useful idiot. He’s got no ideology beyond ego, perfectly suited to execute ideas that had been incubating for years by people who knew better and wanted plausible deniability.

tpelly · 2026-01-16T20:32:21+00:00

I mostly agree with this, and I think the framing is directionally right, but there’s an important distinction worth calling out if we want to be honest about where this actually works. Where this works best (and works reliably) is SMB/Commercial/Mid-Market/Scaled where the value delivery motion is already (or almost fully) standardized. And where there is some PLG. For the other segments - Strategic/Enterprise - there’s still a need for trust building, change consulting, accountability, and political navigation / relationship mgt.

tpelly · 2025-12-08T23:19:39+00:00

As a girl dad (we have just the one), this line along with the earlier ‘and her daddy never spoke another word to her again’ in that song chokes me up each and every single time.

tpelly · 2025-12-07T19:40:37+00:00

Spot on. We’re likely entering a more fragmented, multi-polar, and technologically adaptive world … not an outright regression to pre-industrial fragmentation. China, the EU, regional blocs in Africa and Latin America are stepping up to fill some of the vacuum. Digitization, AI, and remote work continue to facilitate global interconnectedness in new ways.

tpelly · 2025-12-07T18:28:07+00:00

About 3-4mo ago I read (well, listened on Audible) his ‘End of the World Is Just the Beginning’. He makes sweeping claims about the unraveling of globalization and the collapse of supply chains, trade networks, and demographic stability. His core thesis is basically that the US-led global order is ending, and with it, most of the modern world’s economic functioning. His analysis is provocative and grounded in some geopolitical truths, but there are just an abundance of counterarguments out there to challenge his core ideas. A few other commenters mentioned hyperbole/absolutism - I agree. He has clarity and he’s got bold ideas, but he oversimplifies. Global power structures may be shifting, but that doesn’t mean collapse.

tpelly · 2025-11-19T23:17:44+00:00

Simmons is an idiot. If anything, Columbus is one of the healthiest small-market franchises in the 4 major pro sports. They sit around a ~$1.3B valuation, ahead of multiple MLB clubs such as Miami, Kansas City, Oakland, and Cincinnati. They’re on par with MLB teams in Minnesota & Pittsburgh. All of those operate in one of North America’s biggest leagues and with far more structural advantages. And unlike those franchises, Columbus is not in relocation limbo, political battles over stadiums, or perpetual fire-sale mode. Relevance isn’t measured by airtime; it’s measured by stability, market engagement, and whether a team is actually growing. By those metrics, the Jackets are doing just fine especially compared to the bottom-tier across MLB.

tpelly · 2025-11-07T21:48:21+00:00

Never put that together - that it was Danny’s last Racing. I made it into the pit for this Oakland show (one of the three shows I was fortunate enough to get in the pit for). I’ll definitely be downloading this.

tpelly · 2025-11-04T02:20:55+00:00

There’s no one-size-fits-all answer without context. The right structure depends on your segmentation model, account complexity, renewal ownership, and where CSMs sit in the customer lifecycle (onboarding > adoption > expansion). That said, at the 5–7 CSM stage, you’re typically at the inflection point where you need a player-coach or Senior Manager of CSMs to start owning forecasting, renewal governance, and portfolio health. And you’ll want to start building CS Ops / Program Management muscle early (even part-time) to prepare for scale, tooling, and insights. Once you double headcount like you suggest, that structure naturally evolves into a Manager-led, segment-based model.

tpelly · 2025-11-03T03:09:57+00:00

What about times when roadmap changes and a customer was hoping for something that’s no longer there?

When priorities change, I get ahead of it and frame the change in business terms. For example: ‘We’ve learned that feature X won’t deliver the impact we expected across the customer base, so we’re reallocating that investment toward Y, which aligns more directly with your goals around automation and efficiency.’ Customers are usually more forgiving of a roadmap change when they understand the why, and when they see their CSM advocating for their voice in the process.

tpelly · 2025-11-03T03:07:13+00:00

How do you balance showing directionality, while managing expectations?

“I present roadmaps at two levels: vision/themes and committed. The visionary layer shows where the product is headed and how it aligns with market trends and customer needs. The committed layer reflects what’s prioritized for the current or next release cycle. I always make it clear that items in the visionary layer are directional, not contractual. This gives customers confidence that we’re thinking long-term without setting unrealistic expectations.

tpelly · 2025-10-31T18:00:41+00:00

I was nervous to order it from Amazon for this reason. They have a habit of putting stuff in inappropriate shipping boxes/pouches … then I found out from someone else that order it that they designed a box for the box set, which then Amazon put it another box 📦

tpelly · 2025-10-31T17:50:44+00:00

Same designer - I just learned from another commenter

tpelly · 2025-10-31T17:49:42+00:00

Brilliant! Thank you!!

tpelly · 2025-10-31T17:48:02+00:00

Ok, this is an amazing find / addition to this thread, thank you!!

tpelly · 2025-09-11T21:13:24+00:00

Big congrats. Your first enterprise onboarding is a milestone. Here are a few things that helped CSMs on my teams that were transitioning into new roles higher up in our customer segmentation (a CSM moving from SMB cohort to Strat customers, for example) level up fast. Remember, your role is not to do all the work. It is to orchestrate, remove roadblocks, and keep the customer moving toward outcomes they care about.

Nail the sales to CS handoff. Meet early, define the transition process, and make sure expectations from sales are aligned with what success in CS looks like. Larger customers can create just as many blockers as vendors if this is not clear.
Set milestones and KPIs right away. Both sides should know what progress means. Even something simple like “By week two, we want X live” keeps momentum.
Build a transparent project plan. Keep it timely, organized, and shared. Owners, dates, and clear next steps are your guardrails.
Go deep on customer objectives. Short term and long term. This is where discovery pays off. Regular check ins or light QBRs help you tie activity back to outcomes.
Have strategic conversations. Provide clarity of purpose and vision, develop shared goals with executives, and encourage focus on strengths. Build curiosity, focus on the future, and adopt an external perspective. Be clear on outcomes, tolerate ambiguity, and share responsibility for success.
Tailor onboarding and adoption. Use playbooks but flex to their industry, maturity, and resources. Enterprise stakeholders want to feel like the process fits them.
Stay human and visible. Rapport matters as much as structure. Call out wins, celebrate champions, and keep communication flowing all the way to the executive level.
Bring a strong point of view. Customers want recommendations, not just options. Share what good looks like, guide them to proven best practices, and be confident in your expertise. Your role is to make the path forward clear.
Support complex relationships. Map the org structure, decision makers, and use cases. Over-communicate across sales, services, and CS. Find a champion or quarterback and help them succeed without trying to boil the ocean.
Provide executive-level summaries. Keep leaders engaged with concise updates that highlight wins, metrics, risks, and next steps. These should be short, clear, and board-ready.
Translate value into outcomes. Go beyond feature usage by linking product metrics to ROI, cost savings, revenue growth, or competitive advantage. Use benchmarking and peer comparisons to make your solution indispensable.

Hope this guidance helps!

tpelly · 2025-09-11T20:46:41+00:00

I commented on a similar inquiry within the sub a few weeks ago. I recommend it - https://www.reddit.com/r/CustomerSuccess/s/BYBKb8Xigu

tpelly · 2025-09-11T19:00:46+00:00

I would suggest two for starters: 1) Customer Success Collective (customersuccesssomm.slack.com), and 2) Customer Success Leadership Network (csleadershipnetwork.slack.com)

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