Customer success from the Ground Up Podcast

In this episode of Customer Success from the Ground Up, Mike and Deborah are joined by Jonathan Rivers, a Customer Success leader with extensive experience building and scaling CS functions at early stage companies, including a role where he joined with just one trial customer and grew the team to 25 to 30 people.

The conversation digs into one of the most common tensions in startup CS: the pressure to drive expansion revenue while still proving the value of what the customer already bought.

Jonathan shares how heavy discounting in year one creates a trap at renewal, why land and expand is sometimes overused as a strategy, how to remind customers of the value they are getting without it feeling transactional, and why cross-selling into a new business unit is often closer to a brand new sale than an expansion.

We also cover the internal pressure that comes when product teams release new features and expect CS to sell them, why customer satisfaction alone is never enough to guarantee a renewal, and how to build playbooks for different customer segments when you simply do not have the time to treat every account the same.

Plus our Reddit segment this week: a health tech startup asks how to approach customers with expansion potential into other providers within the same practice.

If you are navigating growth at an early stage company, this one will resonate.

Timestamps
(00:00) Introductions
(01:00) Jonathan's background and career journey into CS
(03:00) The tension between customer satisfaction and revenue growth at startups
(05:32) Reddit: how do you approach customers with expansion potential?
(07:00) Understanding the incumbent and the cost of change
(09:00) Using advocacy and referrals to drive expansion
(10:27) Upsell vs cross-sell and what early stage startups actually have to offer
(12:41) Icebreaker: favourite or most hated subject at school
(16:02) Where the tension between satisfaction and growth comes from
(20:00) Internal pressure when product releases features that do not sell
(21:00) Why customer satisfaction is not enough on its own
(24:00) Proving value and staying close to what customers actually need
(27:00) The regulatory tech example: when customers like a product but do not need it
(30:00) You cannot upsell what they are not already getting value from
(31:44) Why land and expand is sometimes overused
(36:00) Heavy discounting and the renewal trap
(38:00) Reminding customers what they paid and what they got
(40:00) The challenge of getting customers to pay full price at renewal
(41:30) Cross-selling into a new business unit is a new sale
(43:00) Multiple playbooks for different customer segments
(45:36) Wrap up

Customer Success from the Ground Up is hosted by Mike Marshall , Global CS Programme Lead, and Deborah Knight from KaptivCX. Find us on Spotify, subscribe on your favourite podcast app, and join the community.

LinkedIn Community - https://www.linkedin.com/company/customer-success-from-the-ground-up/

Customer Success from the Ground Up Programme: https://www.skool.com/cs-from-the-ground-up-9350/about

KaptiveCX Customer Success Consultancy: www.kaptivecx.com

In this episode of Customer Success from the Ground Up, Mike and Deborah are joined by James Mair, Head of Customer Success at HublSoft, an analytics scale-up serving enterprise IT customers.

James joined HublSoft as the founding CS hire in 2018 with no playbook, no team and a portfolio to grow. Seven years on, he has built the function from the ground up and has a lot of hard-won lessons to share.

This episode covers the full arc of what that journey actually looks like. How to build a health scoring model that evolves as you learn more about your customers. Why James restructured onboarding entirely to make it more consultative and strategic. The structural mistakes he made early on, including hiring specialists too soon, segmenting the team by vertical, and holding onto customer relationships too long rather than letting his team develop. How to know whether something is a learning curve problem or a structural problem, and why that distinction matters enormously for when to act. What James now looks for when hiring, and why tenacity and adaptability matter more than a CS background.

Plus the Reddit segment this week covers a question every CS leader faces: who should own the health scoring formula?

If you are building CS from scratch or navigating the messy middle of a growing CS function, this one is essential listening.

(01:05) James's background — founding CS hire at HublSoft in 2018
(04:59) Reddit: who should own the customer health scoring formula?
(10:28) Why qualitative measures matter as much as quantitative ones
(11:22) Icebreaker — end of summer, Bon Jovi and music festivals
(13:00) James's career journey into customer success
(15:00) What HublSoft does and who their customers are
(17:00) How James restructured onboarding to be more consultative and strategic
(20:00) Moving from productivity metrics to genuine business value
(24:50) Validating customer outcomes as part of the consulting engagement
(25:24) Structural mistakes — what didn't go to plan
(27:00) Why generalists beat specialists at early stage
(28:18) The hardest transition: cutting the apron strings and letting the team own relationships
(30:25) How to know when something is a learning curve problem vs a structural problem
(31:45) Will vs skill — when to give it time and when to act fast
(32:07) What James now looks for when hiring
(34:32) Other pivots — the danger of replicating what works across different customers
(38:45) How AI will drive scale efficiencies in onboarding and consulting
(40:14) Wrap up — frank conversations about value and making decisions fast

Customer Success from the Ground Up is hosted by Mike Marshall , Global CS Programme Lead, and Deborah Knight from KaptivCX. Find us on Spotify, subscribe on your favourite podcast app, and join the community.

LinkedIn Community - https://www.linkedin.com/company/customer-success-from-the-ground-up/

Customer Success from the Ground Up Programme: https://www.skool.com/cs-from-the-ground-up-9350/about

KaptiveCX Customer Success Consultancy: www.kaptivecx.com

In this episode of Customer Success from the Ground Up, Mike and Deborah are joined by Natasha Evans, VP of Customer Growth at Hook, an AI-powered platform built to elevate customer success and account management teams.

Tash has 12 years in CS across LinkedIn, SalesLoft and now Hook, and brings a sharp, practical view on how startups and scale-ups should actually be thinking about AI agents and automation in their CS motions.

We cover what agents really are versus automations, why most teams get it wrong by building before they know what good looks like, the importance of keeping a human in the loop, and how to start small, test, and iterate rather than trying to automate everything at once.

We also dig into the Reddit segment this week, where a team's AI chatbot started giving bad answers because of messy, duplicate documentation.

If you are thinking about bringing AI into your CS function, this episode will save you from some expensive mistakes.

(00:00) Introductions
(02:27) Tash's background and what Hook does
(05:10) Today's topic: AI agents and automation in CS
(06:13) Reddit: AI chatbots going wrong due to messy documentation
(10:39) Human in the loop as the right starting point
(12:07) Icebreaker
(14:00) Automations vs agents: what is the difference?
(17:43) How automations and agents work together
(18:23) When to use each one
(20:45) How agents get triggered in practice
(22:46) Agents vs traditional tech touch
(25:41) Where to start: jobs to be done first, automation second
(28:43) Building new vs unravelling what already exists
(29:13) Getting CSM and customer buy-in
(31:05) Should agents send emails or should CSMs?
(33:33) Cultural differences in accepting AI-led CS
(36:30) Tash's whoops moment at Hook
(38:17) Keeping the human in the loop
(42:32) Impact at Hook: NRR and efficiency
(44:43) Don't build for the sake of it
(46:08) Wrap up

Customer Success from the Ground Up is hosted by Mike Marshall , Global CS Programme Lead, and Deborah Knight from KaptivCX. Find us on Spotify, subscribe on your favourite podcast app, and join the community.

LinkedIn Community - https://www.linkedin.com/company/customer-success-from-the-ground-up/

Customer Success from the Ground Up Programme: https://www.skool.com/cs-from-the-ground-up-9350/about

KaptiveCX Customer Success Consultancy: www.kaptivecx.com

In this episode of Customer Success from the Ground Up, Mike and Deborah are joined by Rohan Tailor, Principal Consultant at ABR Talent, one of the UK's leading customer success recruitment agencies.

Rohan brings a recruiter's view on hiring for CS at early-stage startups, covering what founders consistently get wrong, why the word "toxic" gets thrown around too easily, and why cultural fit can matter just as much as technical skill.

We also dig into the real difference between a £50K and a £60K CSM, how AI is changing both sides of the hiring process, and what candidates can do to genuinely stand out once they're in a process.

Plus our usual Reddit segment, this week looking at a candidate who left a "toxic" startup CS role and asking what they should do next.

Whether you're hiring your first CSM or thinking about your next move, this one is full of practical advice.

(00:00) Introductions
(03:22) Reddit: I got let go from a toxic CS job, what now?
(05:46) Why "toxic" is often the wrong word — it's about fit
(09:48) AI skills and startup vs established business expectations
(11:49) Icebreaker
(29:30) The shift toward digital and scaled CS motions
(31:12) Where CS and account management are converging
(33:01) Advice for candidates who've fallen out of love with CS
(35:21) The real difference between a £50K and £60K CSM
(38:00) AI in the hiring process — wins and watch-outs
(40:25) Do hiring managers give candidates honest feedback?
(42:34) Cultural fit and why it's critically important
(43:50) Wrap up

Customer Success from the Ground Up is hosted by Mike Marshall , Global CS Programme Lead, and Deborah Knight from KaptivCX. Find us on Spotify, subscribe on your favourite podcast app, and join the community.

LinkedIn Community - https://www.linkedin.com/company/customer-success-from-the-ground-up/

Customer Success from the Ground Up Programme: https://www.skool.com/cs-from-the-ground-up-9350/about

KaptiveCX Customer Success Consultancy: www.kaptivecx.com

In this episode of Customer Success from the Ground Up, Mike and Deborah are joined by Jamie Levy, a customer experience leader and accidental consultant based in Los Angeles, who has built CS programs at Shopify, Magento and Simpro Group.

Jamie shares why she is allergic to playbooks, why QBRs should be outlawed, and what she believes is the single most powerful thing a CSM can do in any customer conversation.

We also dig into how Jamie built the Embassy team at Shopify Plus, why she created an event called Unboxed to get customers talking to each other, and how the concept of the Alter Ego can help CSMs show up with confidence even when they are not feeling it.

Plus — our Reddit segment this week covers a team who stopped running QBRs completely and watched their renewal rate climb from 87% to 91%.

If you are building CS from scratch, leading a team, or just trying to get better at the human side of customer success, this one is for you.

(00:00) Introductions(03:20) Reddit: We stopped running QBRs and renewals went up(05:17) Why QBRs should be outlawed(09:28) Why playbooks are a dirty word(11:08) The "this meeting will be successful if..." tip(12:32) Icebreaker(14:12) Jamie's accidental career into CS(16:04) 350 accounts on day two — sink or swim(17:32) What makes a great CSM(18:20) Why unhappy customers are the best conversations(20:30) Building the Embassy team at Shopify Plus(22:10) Creating Unboxed — customers talking to customers(25:09) The power of saying less(26:38) Keeping the customer hat on across your org(30:00) The Alter Ego concept(32:33) Jamie's mini formula for CS(34:41) Why AI will never replace great CS(35:34) Wrap up

Customer Success from the Ground Up is hosted by Mike Marshall , Global CS Programme Lead, and Deborah Knight from KaptivCX. Find us on Spotify, subscribe on your favourite podcast app, and join the community.

LinkedIn Community - https://www.linkedin.com/company/customer-success-from-the-ground-up/

Customer Success from the Ground Up Programme: https://www.skool.com/cs-from-the-ground-up-9350/about

KaptiveCX Customer Success Consultancy: www.kaptivecx.com

Before the guests, before the frameworks, before the Reddit escalations — this is where it all starts.

In this episode, your hosts put themselves in the hot seat. Mike Marshall and Deborah Knight interview each other: where they came from, how they got into customer success, what they love about it, and — most importantly — why they decided to build this podcast.

Because here's the honest answer to that last question:

People kept asking for help.

Early CS hires landing in startups with no structure. Experienced leaders stepping into companies where the CEO was doing CS on gut feel. People who were good at their jobs but had no one to ask, no playbook to follow, no community of people who'd been through the same thing.

That gap is what Customer Success from the Ground Up is for.

In this episode you'll hear:

Mike's story — from sales disillusionment at Adobe to finding his home in CS, leading teams across EMEA, and why building a community of 100+ CS leaders eventually led to this podcast

Deb's story — from the drinks industry to financial services to scaling Perkbox from £5m to £28m, building CS from scratch in global markets, and founding KaptivCX

Why they're doing this together — and why one host with corporate scale-up experience and one with early-stage startup experience makes for a better show than either could do alone

What great customer success actually means — including Deb's favourite framework from her Perkbox days: the power of nudge, and why CS is ultimately a human psychology problem disguised as a business process

Who this podcast is for — founders thinking about when to invest in CS, early CS hires building from nothing, and experienced leaders stepping into a startup world for the first time

This is the episode to send someone when they ask what the show is about. And if you've arrived here first — welcome. You're in the right place.

0:00 Welcome — Why we started Customer Success from the Ground Up1:23 Meet Mike Marshall — 10 years in CS, Adobe, WalkMe and why CS felt like home3:18 Deb grills Mike — from skateboarder to CS leader6:00 Mike's light bulb moment — leaving sales and finding his home in CS8:30 Why this podcast exists — the early CS hire with nobody to ask11:30 Mike grills Deb — travel dreams, Japan and Patagonia13:16 Deb's career journey — drinks industry to Perkbox to founding KaptivCX16:12 What keeps Deb motivated — CS as a people psychology problem18:15 Who this podcast is for — founders, early CS hires and everyone figuring it out

Customer Success from the Ground Up is hosted by Mike Marshall , Global CS Programme Lead, and Deborah Knight from KaptivCX. Find us on Spotify, subscribe on your favourite podcast app, and join the community.

LinkedIn Community - https://www.linkedin.com/company/customer-success-from-the-ground-up/

Customer Success from the Ground Up Programme: https://www.skool.com/cs-from-the-ground-up-9350/about

KaptiveCX Customer Success Consultancy: www.kaptivecx.com

Most CS teams are set up to absorb the pain of a product that isn't quite working. That's not customer success — that's damage control.

In this episode, we're joined by Alastair Doig, CEO at Tiller, for a perspective you don't often get on a CS podcast: the founder's view on when to invest in customer success, what it should actually do for your business, and what he wishes he'd figured out sooner.

Alastair brings hard-won experience from scaling Perkbox — where CS, sales and product either pulled together brilliantly or didn't — and he's refreshingly direct about what separates a CS function that drives growth from one that's just firefighting.

We cover:

When to make your first CS investment — and why getting the timing wrong costs more than you think

Why your CSMs getting battered is a product problem, not a people problem

How to make CS a strategic voice — feeding product, energising sales, and building the kind of retention that compounds

Managing a big book of business — practical advice for the CSM drowning in 300 accounts wondering where to start

What Tiller does — and how in-call AI guidance is changing the way CS teams capture and use customer insight

Plus the usual chaos from Mike and Deb in the intro, including a party recovery, some strong opinions about 300-account CSMs, and a section we forgot to record properly.

If you're a founder wondering when CS becomes a priority, or a CS leader trying to get your voice heard across the business — this one's for you.

0:00 Welcome & Intro — Sunny afternoons and croaky voices2:08 Well That Escalated Fast — Managing 300 accounts: chaos or normal?8:15 Meet Alastair Doig — CEO at Tiller & the founder's CS perspective11:30 When should a founder invest in Customer Success?17:45 Product-market fit is the foundation — not your CSM team24:00 CS as a strategic voice across sales, product and the business29:30 What Tiller does — in-call AI guidance for CS teams33:00 What I learned too late: it shouldn't be that hard40:51 Wrap up & final thoughts

Customer Success from the Ground Up is hosted by Mike Marshall , Global CS Programme Lead, and Deborah Knight from KaptivCX. Find us on Spotify, subscribe on your favourite podcast app, and join the community.

LinkedIn Community - https://www.linkedin.com/company/customer-success-from-the-ground-up/

Customer Success from the Ground Up Programme: https://www.skool.com/cs-from-the-ground-up-9350/about

KaptiveCX Customer Success Consultancy: www.kaptivecx.com

Most CS functions fail not because of the wrong technology — but because they bought it too early, built too much too fast, and forgot that good people following simple frameworks beat a 40-page playbook every time.

In this episode we're joined by David Lane, Senior Customer Success Manager at WalkMe, who has one of those CS careers that covers everything: first CSM hire at a startup, scaling the function, building out EMEA and APAC, and making every classic mistake along the way so you don't have to.

David is refreshingly honest about what he got wrong — and what he'd do differently if he was walking into a startup CS role today.

We cover:

The crawl, walk, run framework — what to build first, what to save for later, and why doing too much too soon is one of the most common startup CS mistakes

People, process, technology — in that order — why buying a CS platform before you're ready is an expensive way to learn a lesson

Owning your positioning internally — why letting sales introduce you to customers is a mistake, and how to control the narrative from day one

The AI strategy conversation nobody's having — why having a vague plan isn't enough, and what embedding AI properly actually looks like at an early-stage CS team

Don't make it cookie cutter — why comprehensive playbooks sound great and fall apart in practice, and what to do instead

Plus: should CSMs own expansion quotas when the sales team disappears? Mike, Deb and David weigh in — and the answer might surprise you.

If you're a first CS hire, a founder building out your post-sales function, or a CS leader trying to scale without throwing headcount at the problem — this one's packed with the kind of practical thinking you won't find in a certification course.

0:00 Intro — Deb's secret radio DJ past3:29 Well That Escalated Fast — CSMs with expansion quotas: too much or fair game?8:00 Meet David Lane — from first CS hire to Director at Ciara11:00 People, Process, Technology — in that order, always16:30 The crawl, walk, run framework for early-stage CS21:00 Don't let sales introduce you to your customers26:30 Managing CS across EMEA and APAC — what changes by market31:00 Owning your positioning internally as a CS leader35:00 Don't buy a CSP until you're ready37:40 Future-proofing your CS function — having an actual AI strategy41:00 Wrap up — key takeaways from Mike & Deb

Customer Success from the Ground Up is hosted by Mike Marshall , Global CS Programme Lead, and Deborah Knight from KaptivCX. Find us on Spotify, subscribe on your favourite podcast app, and join the community.

LinkedIn Community - https://www.linkedin.com/company/customer-success-from-the-ground-up/

Customer Success from the Ground Up Programme: https://www.skool.com/cs-from-the-ground-up-9350/about

KaptiveCX Customer Success Consultancy: www.kaptivecx.com

You've got data everywhere. In spreadsheets, in your CRM, in QBR decks nobody reads twice. Some customers are WhatsApping your team. Others want 20 fields of metrics every month and have no idea what any of them mean.

Welcome to CS at an early-stage startup.

In this episode we're joined by Olivia House, Customer Success at Dynarisk, who's been in the thick of building CS across multiple products, multiple territories and multiple stages of a business lifecycle — often at the same time. She's honest, practical and refreshingly unbothered about not having all the answers.

We cover:

Step one when the data is a mess — why simplifying your dashboard before doing anything else is the most underrated move in early-stage CS

Too much data is a real problem — how to know when your metrics have become noise, and how to educate internally when the business doesn't want to hear it

Managing CS across territories — why what works in North America falls flat in APAC, and why some of your most important customer relationships happen entirely on WhatsApp

The corporate vs startup leap — why so many experienced CS people last three months at a startup and go straight back through the revolving door, and how to know if you're actually built for it

Giving data context — why sending customers 20 numbers a month without telling them why they should care is worse than sending them nothing

Plus: stale bread, Farmer J's, and a genuinely useful debate about whether CS should own expansion quotas when the sales team disappears.

If you're building CS at an early-stage company and feel like you're making it up as you go — you're not alone, and this episode is for you.

0:00 Intro — Stale bread, Farmer J's and London lunches2:33 Well That Escalated Fast — Big corporate to startup: should you make the leap?7:15 Meet Olivia House — CS at Dynarisk and building across multiple products10:30 Joining a startup at three different lifecycle stages — what changes each time15:00 Step one when the data is a mess — simplify before you do anything else19:30 Health scores with incomplete data — how to build one that's actually useful23:00 Managing CS feedback loops across multiple products26:30 CS across territories — why WhatsApp is a data problem nobody talks about29:45 Too much data is a real problem — giving numbers context and meaning32:10 Wrap up — key takeaways from Mike & Deb

Customer Success from the Ground Up is hosted by Mike Marshall , Global CS Programme Lead, and Deborah Knight from KaptivCX. Find us on Spotify, subscribe on your favourite podcast app, and join the community.

LinkedIn Community - https://www.linkedin.com/company/customer-success-from-the-ground-up/

Customer Success from the Ground Up Programme: https://www.skool.com/cs-from-the-ground-up-9350/about

Kaptive CX Customer Success Consultancy: www.kaptivecx.com

What do you do when you're the first employee at a pre-seed startup, you've never done customer success before, and nobody's written a playbook because nobody's been there long enough to write one?

You figure it out. And then you do it again at the next startup. And the one after that.

Iram Cook-Monie has spent the last seven years joining early-stage companies at pre-seed through Series A — often as the sole CS person, often before the product is fully formed, almost always before anyone has agreed on what customer success is actually supposed to do. She now brings that hard-won experience to Visa Sustainability Solutions.

This episode is one of the most practical we've recorded. No theory. No enterprise frameworks that don't apply to a team of one. Just honest, specific advice from someone who's been in the thick of it repeatedly.

We cover:

The North Star conversation every early CS hire needs to have — why getting aligned with your founders on the single most important objective before you do anything else changes everything

The maturity matrix — Iram's own framework for taking a CS function from putting out fires to proactive to predictive, and how to walk founders through it without losing them

QBR yourself — why reviewing your own priorities quarterly is the most underrated habit in early-stage CS, and how it helps you push back when founders get excited about the next shiny thing

Don't over-engineer the health score — why building a complex scoring system before you have meaningful data is one of the most common early-stage mistakes

Imposter syndrome is normal — even with 10 years of CS in your title, if you've never done true CS work before, the feeling of not knowing what you're doing is almost universal

Plus: the elevator pitch for early-stage CS in under 60 seconds, and why attending networking events beats reading every book and listening to every podcast combined.

If you're the first CS hire at a startup, a founder trying to work out what to do with your post-sales function, or a CSM wrestling with imposter syndrome — Iram's story will feel very familiar, and her advice is immediately usable.

0:00 Intro — "I'm a CSM and I don't know what I'm doing. Help!"3:41 Well That Escalated Fast — Imposter syndrome, AI anxiety and upskilling yourself7:11 Meet Iram Cook-Monie — 7 years as first CS hire at pre-seed startups10:30 Employee number one: what do you actually do first?14:00 Don't over-engineer the health score before you have meaningful data18:30 The personal QBR — reviewing your own priorities before anyone else does22:00 Managing founders — keeping them focused on the North Star when they get excited about shiny things28:50 Aligning CS strategy to what founders actually care about (NRR, investor references, product market fit)31:19 The maturity matrix — from putting out fires to proactive to predictive34:11 Elevator pitch — the three things every early CS hire must do

Customer Success from the Ground Up is hosted by Mike Marshall , Global CS Programme Lead, and Deborah Knight from KaptivCX. Find us on Spotify, subscribe on your favourite podcast app, and join the community.

LinkedIn Community - https://www.linkedin.com/company/customer-success-from-the-ground-up/

Customer Success from the Ground Up Programme: https://www.skool.com/cs-from-the-ground-up-9350/about

KaptiveCX Customer Success Consultancy: www.kaptivecx.com