Designing Success: Designing the Blueprint for Modern CS, from Onboarding to Advocacy

If your renewal strategy starts 30 days before the contract ends…

That’s not a strategy. That’s a fire drill.

In this episode of Designing Success, we break down how world-class CS teams plan for renewals proactively—starting 120 days out, not 12 minutes before the customer ghosts you.

Here’s what we cover:

• Why most renewals fail before they’re ever discussed
• The key moves to make at 120, 90, and 60 days—and who should be in the room
• How to turn QBRs into forward momentum—not flashbacks
• Tactical plays like the “Mini-QBR,” Renewal Readiness Checklist, and internal Renewal Brief

How to shift your mindset from “please renew” to “here’s what’s next”

Because the best renewals?

They don’t feel like events.

They feel like next steps.

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They close the deal.

You keep it alive.

They ring the gong.

You calm the customer after the dust settles.

Welcome to the most complicated relationship in SaaS: Customer Success + Sales.

In this episode of Designing Success, we unpack:

Why the CS/Sales tension isn’t personal—it’s structural

The most common breakdown points (hello, handoffs and overpromises)

What real alignment actually looks like—from pipeline to pre-renewal

Tactical plays you can run today to build trust, not just shared Slack channels

Because when CS and Sales work together?

Retention climbs. Expansion lands. Customers stay.

But when they don’t?

Your customers feel it—and your metrics pay for it.

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Let’s be honest—most job descriptions sound like they were copy-pasted from LinkedIn’s Greatest Hits:

“Customer-obsessed.”
“Collaborative.”
“Strong communicator.”
“Team player.”

And sure, those things matter… sort of.

But if you’re trying to land your next CSM role—or build a CS team that actually moves the needle—those buzzwords won’t cut it.

In this episode of Designing Success, we’re pulling back the curtain.

We’re talking about:

The traits hiring managers actually look for—but rarely write down

The red flags that don’t show up on résumés (but tank interviews anyway)

How to stand out in a saturated market—without sounding like a sales pitch in sneakers

And what separates “nice to have” from “offer letter incoming”

Whether you’re a CSM aiming for your next big leap, or a CS leader looking to make your next hire count—this episode is your cheat code.

Because “good on paper” doesn’t mean good in the role.

And in today’s talent market? Relevance is a strategy.

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Enjoy!

Your executive sponsor was there at kickoff—excited, engaged, fully aligned. And then, suddenly, silence. They’ve gone quiet, delegated downward, or disappeared altogether. Sound familiar?

In this episode of Designing Success, Rob explores why executive sponsors disengage, and more importantly, how to win them back. You’ll learn the strategies and psychology behind re-engaging sponsors who’ve ghosted, how to rebuild alignment when your champion leaves the company, and ways to ensure you never get caught off-guard again.

Listen in to uncover:

• Why most executive sponsors check out—and what you can do about it.
• The four distinct types of sponsor disengagement (and tailored strategies to fix each one).
• Proven plays, like the “Reconnection Brief,” to re-establish relevance at the exec level.
• How to build ongoing sponsor alignment into your Customer Success processes, so you’re never scrambling at renewal time.

Because executive sponsorship isn’t a checkbox—it’s the foundation of long-term customer growth.

Ready to reconnect and realign with confidence? 

Let’s dive in.

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Building your Customer Success team from the ground up sounds exciting—until you’re staring at a blank org chart and wondering who (and how) to hire first.

In this episode of Designing Success, Rob walks you step-by-step through what it takes to build a Customer Success team the right way, from defining your mission and making that critical first hire, to designing roles around your customer journey and setting meaningful metrics that drive impact—not just activity.

You’ll learn:

• Why your first CS hire shouldn’t just “manage relationships,” but build processes, systems, and playbooks that scale.
• How to structure roles around real customer friction points, not generic job descriptions.
• The key metrics to set from day one to avoid vanity numbers and track actual success.
• How to embed Customer Success deeply into your company’s culture, not just around it.

Because the way you start your Customer Success function determines how well (and how fast) it can scale later.

Ready to start building smarter? Let’s get into it.

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Ever wondered why your perfectly planned onboarding hits a wall, or why customers go quiet when everything seemed on track?

In this episode of Designing Success, Rob digs into the psychology behind customer resistance—not as a problem, but as a predictable human behavior.

 You’ll discover why customers hesitate, stall, or suddenly disengage—and more importantly, how to turn that friction into deeper trust and accelerated value.

Tune in to learn:

• The hidden emotional triggers behind customer resistance (hint: it's rarely about your product).
• How to identify resistance early, before it derails the entire relationship.
• Practical frameworks—like the “Customer Change Curve”—to proactively guide customers from hesitation to ownership.
• Real-world tactics for reframing resistance into meaningful conversations and lasting customer partnerships.

Because the best Customer Success teams don’t avoid pushback—they design for it.

Ready to tackle resistance head-on? 

Let’s dive in.

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Forget onboarding as a checklist—this isn’t about account setups and product tours. It’s about first impressions, momentum, and building the kind of customer relationship that fuels retention from day one.

In this episode of Designing Success, Rob dives deep into why most SaaS companies get onboarding wrong, treating it like a phase instead of the critical foundation it truly is. 

You’ll learn how to design an onboarding experience that not only accelerates customer value but actually prevents churn before it starts.

Tune in to discover:

• Why 20–40% of churn happens in the first 90 days (and how to stop it).
• How successful teams segment onboarding to scale impact and efficiency.
• Practical frameworks for setting clear expectations, delivering “first value,” and creating momentum that lasts.
• Real-world insights and examples to turn your onboarding into a competitive growth lever.

Because if your customers aren’t onboarding successfully, they're already thinking about leaving.

Ready to build onboarding that’s a launchpad—not just a phase? 

Let’s get started.

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