Scaling Trust with Matt Tidwell

Ryan Randall has spent fifteen years in healthcare SaaS carrying the retention number inside health systems — where the buyer is a committee, the margins are razor thin, and a new CFO can wipe out a contract that was performing just fine.

His take: customer success can't promise retention. What it can do is engineer the conditions that make it more likely.

In this episode, Ryan breaks down why health scores are useful for triage but dangerous as a crystal ball, how he thinks about the three things that actually determine whether a health system renews (measurable value, an internal advocate, and budget), and what it looks like to build a coalition inside an account that will defend your investment in a room you'll never be in.

Ryan is VP of Commercial at Vital — an AI-powered patient experience platform deployed across hospital emergency departments nationwide. Before Vital, he spent nearly a decade at Healthgrades building and leading health system relationships at scale.

What we cover: 
- Why churn in healthcare SaaS isn't fully predictable 
- The three-part renewal framework Ryan uses instead of a health score 
- How to build internal advocates who fight for you when budgets get cut 
- What "value on investment" means before a client ever goes live 
- Why the technology's job is to create space for human connection, not replace it

Timestamps:
0:00 — Introduction 
1:30 — Ryan's background and the VP of Commercial framing 
6:24 — Why sales-to-CS handoffs break (and how automation fixes it) 
9:21 — You can't promise retention — here's what you can promise 
9:57 — Why health scores aren't oracles 
12:23 — The three things that actually drive a renewal: value, advocate, budget 
12:47 — Building the coalition that defends you when you're not in the room 
18:26 — Value on Investment: setting the goalpost before you go live 
20:31 — When your customer and your user aren't the same person 
24:06 — How Vital thinks about patient portals vs. the in-visit experience 
26:56 — The pilot-to-expansion playbook in healthcare 
33:28 — Technology creates space for human connection — not a replacement for it 
35:39 — Advice for post-sale leaders going into 2027

Connect with us:

• Connect with Ryan Randall:  https://www.linkedin.com/in/ryan-randall-23517724/
• Connect with Matt Tidwell: https://www.linkedin.com/in/itsmatttidwell/
• Substack: https://itsmatttidwell.substack.com/

Resources:

• Vital.io — vital.io
• ThinkThru — www.thinkthru.co

Scaling Trust is a show for post-sale leaders in B2B SaaS who believe that trust is a system you build, not a feeling you hope for.

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Most companies stumble into partnerships. They get a referral, it works, and they start calling it a channel.

But there's a massive difference between having partners and actually building a partner program — especially one that generates high-trust, high-intent opportunities that scale your business.

Stefano Sengos is a Channel Partnerships Manager at Ramp, one of the fastest-growing fintech companies in the world. He manages the full motion — finding the right partners, enabling them to represent Ramp to their clients, and making sure the first 30 to 60 days of the customer relationship is a success.

In this episode, we get into:
- Why partners are a completely different ICP than your direct customer
- What it actually takes to earn a partner's trust before they ever send you a client
- How Ramp structures the handoff between partnerships and CS
- The 30-60 day activation window and why it makes or breaks retention
- How live events fit into a modern partner channel strategy
- AI in the accounting space — who's excited and who's skeptical

This is a conversation about what it actually means to own the partnership function — and what happens when you build it on trust instead of transactions.

Connect with us:
Connect with Stefano Sengos: https://www.linkedin.com/in/stefano-sengos-5160b5110/
Connect with Matt Tidwell: https://www.linkedin.com/in/itsmatttidwell/
Substack: https://itsmatttidwell.substack.com/

Resources:
More about Ramp: https://ramp.com/
More about ThinkThru: www.thinkthru.co

Most early-stage companies have a land and expand strategy. Very few have anyone actually running the expand part.

Michael Su noticed that gap in 2008 as a sales engineer at a 40-person startup where nobody was calling anything customer success yet.
Instead of moving on to the next deal, he kept going back to his existing customers. Leadership told him to stop. He kept going. One quarter, the Midwest territory, and nearly half of revenue came from existing logos. They handed him a blank check.

What followed was a 15-year career built around one question: how do you align what your company needs to grow with what your customer actually needs to succeed?

In this episode, Michael and Matt talk about:
- How Michael built the case for CS inside an organization that thought there was no gap to fill
- What breaks first when you scale something you invented on the fly
- How to build a renewal conversation around a product that works best when nobody notices it
- Why the line between customer success and product is disappearing, and what CS teams need to do to be ready

Michael currently serves as Director of Customer Success at Astrix Security, where he leads customer strategy for enterprise security teams. He's built and scaled CS organizations across cybersecurity, fintech, martech, and edtech — from early-stage startups to global teams of 60-plus.

This is a conversation about what it actually means to own the expansion function, and what happens when someone finally does.

Connect with us:
Connect with Michael Su: https://www.linkedin.com/in/michael-su-cs/
Connect with Matt Tidwell: https://www.linkedin.com/in/itsmatttidwell/
Substack: https://itsmatttidwell.substack.com/

Resources:
More about Astrix Security: https://astrix.security/
More about ThinkThru: www.thinkthru.co

Most customer success teams will tell you they lead with empathy. It's in the mission statement, it's in the job description, it might even be on a poster in the office. But empathy as a value and empathy as a practice are two completely different things — and the gap between them is exactly where customer relationships start to fall apart.

Akila Giridharan has spent 15 years building learning ecosystems across SaaS, manufacturing, media, and energy. In this conversation, she makes the case that great customer education isn't about checking boxes or moving completions through an LMS. It's about transformation — taking customers from where they are to where they want to be, faster and more confidently than they thought possible.

As a consultant and director of learning and development with 15 years of experience building learning ecosystems across SaaS companies, global manufacturers, media conglomerates, and energy companies including Warner Bros. and Sonnen Inc., Akila has done what most L&D leaders only talk about: she made a deliberate shift from internal talent development into customer education because she didn't want to be adjacent to growth. She wanted to be responsible for it.

We got into what changes when you stop building training from the office and start building it from the field — and why the program her leadership asked her to build looked nothing like the one her customers actually needed.

In this episode:

• What Akila found when she left the office, went into the field with installers, and ran an actual performance gap analysis — and why it changed her entire strategy

• Why empathy isn't something you feel about your customers — it's something you build into systems before a single piece of content gets created

• The real difference between customer education and customer enablement, and why getting it wrong costs you product adoption

• How to make the case for L&D in a boardroom full of people who only speak numbers

• Why the next generation of customer success professionals need to lead with empathy and an eye on performance metrics — not one or the other

Connect with us:

• Connect with Akila Giridharan: www.linkedin.com/in/akilagiridharan 
• Connect with Matt Tidwell: itsmatttidwell  
• Substack: https://itsmatttidwell.substack.com/

Resources:
More about ThinkThru: www.thinkthru.co

In an era of AI agents, automated health scores, and tech-touch everything — the CS teams actually retaining customers are doing something that looks almost old-fashioned. They're calling people.

In the first episode of Scaling Trust, I sat down with Aidan Murphy, Enterprise Customer Success Manager at Slope — an AI-native B2B lending platform backed by JP Morgan with partnerships at Amazon and Walmart. Before Slope, Aidan built customer relationships at Ramp, Zoe Financial, and Fidelity Investments. 

Every stop in his career has one thing in common: trust isn't optional. You're not selling software. 
You're asking someone to trust you with their money and their business.

We got into what that actually looks like in practice — the signals he tracks, the questions he asks, and why his direct cell number is in every client's email signature.

In this episode:

• What Aidan learned about matching people to financial advisors entirely over the phone — and why that skill transferred everywhere. 

• Why "tell me about your business" is the most important first question in any new customer relationship

• How Slope is leveraging AI agents in their CS motion — and why they waited longer than they could have before releasing it.

• What enterprise customer success actually looks like when it's working — and how you know which version you're building.

• Why the next generation of CS professionals needs to be "comfortable being uncomfortable". 

Connect with us:

• Connect with Aidan Murphy: https://www.linkedin.com/in/aidan-murphy-9037b01b4
• Connect with Matt Tidwell: https://www.linkedin.com/in/itsmatttidwell/
• Substack: https://itsmatttidwell.substack.com/

Resources:

• More about Slope: https://slopepay.com/
• More about ThinkThru: www.thinkthru.co