Most SaaS companies have a sharp play of following champions to their next company – because a former champion is good pipeline. Far fewer have any strategy for the person who just landed in the seat the champion vacated.

When a champion leaves, someone else inherits their account, and the onboarding that already ran on the initial user never runs again. The account record doesn't change. The health score still says green. Yet the new human inside it is on day one – and probably lost. And that's why 51% of accounts that lose a champion churn within 12 months.

Jane Portman, co-founder of Userlist, found this pattern in her quarterly customer calls: a handful of people who'd inherited a working account and had never been trained on any of it. We trace this churn risk back to the Identity flag, dig into the trigger Jane built to solve it, get into exactly how the automation is wired, and workshop what else can ride the same trigger.

Along the way, Jane opens her creativity playbook: an onboarding campaign built around a cartoon named Susie – inspired by script writing formulas, customer success emails deliberately styled to look operational rather than marketed, and three teammates sending from one support address. Because the creativity isn't the point – it's what being creative gives your customers.

Ideas you don't want to miss

(00:00) The everyday event that slips past retention dashboards – that puts your account at a 51%-65% churn risk
(04:27) How the same user can suddenly become a completely different user, needing completely different features – and the flag that catches this
(06:08) The trigger that catches a stranger inheriting your product – and why Jane makes it wait two months before firing
(07:28) The simple save you've already written, sitting unused in your sending platform
(10:24) How script formulas became a cartoon named Susie who teaches segmentation
(11:53) The inspiration most of us take away from a creative campaign – and why it's not helpful
(14:07) Why three people at Userlist email you from the same address on purpose
(15:04) The Reddit thread that says every tool in the category is identical – and what I'd say actually separates them
(18:33) How a really happy, really big account can have a secret activation problem

We diagnosed one flag today – score and price yours with the Change Flags quiz

Found your flag and want it closed? That's a sprint

Links

Go deeper on the dismal champion departure stats here and here

Take a look at the adorable-yet-strategic Userlist onboarding emails

Listen in on Jane's excellent swag loyalty playbook episode: Using Swag to Grow Your SaaS Brand with Scott Markovits

About our guest

Jane Portman is the co-founder of Userlist. Her mission is to help SaaS companies leverage the power of email marketing automation. Mom of three, Jane also enjoys scuba diving and rock concerts.

About the show

Every episode of Churn Flags, host Nikki Elbaz hands a SaaS leader one real piece of customer feedback – a 3-star review, a Reddit rant, a survey response – traces it to one of the nine Change Flags behind a customer's reevaluation, then builds the retention experiment that closes it, or unpacks the one the company is already running. For the retention, NRR, and expansion calls that don't have a best practice yet. For VPs of Growth & Product, CMOs, CGOs, CPOs, and heads of product, growth & CS at mature SaaS. New episodes every other Wednesday. Work with Nikki.

I've spent the better part of a year building the Change Flags framework. I use it in every episode of this show, in every client interaction, in every chapter I write for the book. Which is exactly how adoption dies: assuming everyone already knows what you know.

That's a Change Flag – even I'm not immune to them! We're all flying Change Flags, especially on our best work: we've sharpened it so many times internally that we don't unpack it nearly enough externally.

So instead of a regular episode, I'm sending you somewhere better. I'm presenting the entire framework – all nine flags, with the stories – at the Women in Experimentation Summit. My talk is Thursday, September 10, 10am ET: "You Shipped Everything. Why Isn't NRR Moving?"

The summit is meticulously crafted: ten talks curated from 121 applications, all coached start to finish by Michael Aagaard, and the lineup is genuinely unusual – experimental design lessons from dolphins, what happens when AI makes experimentation almost free, the most dangerous moment in any experiment (spoiler: it's when it starts working). And of course, my talk, which #humblebrag, Michael might have said was one of the strongest of the summit.

It's free, and there are 72-hour replays if you can't make it live.

Join us → convert.com/wie-summit-2026

About the show: Every episode of Churn Flags, host Nikki Elbaz hands a SaaS leader one real piece of customer feedback – a 3-star review, a Reddit rant, a survey response – traces it to one of the nine Change Flags behind a customer's reevaluation, and builds a live retention experiment. For the retention, NRR, and expansion calls that don't have a best practice yet – VPs of Growth & Product, CMOs, CGOs, CPOs, and heads of product, growth & CS at mature SaaS. New episodes every other Wednesday. Work with Nikki → nikkielbaz.com/sprints

Topics: Net Revenue Retention (NRR) · Expansion Revenue · Product Adoption · Feature Adoption · Feature Discoverability · Feature Launch Communication · Customer Enablement · Product Perception · Retention Experiments · Growth Experiments · SaaS Customer Retention · Voice of Customer

Penpot's users don't file feature requests. They open the source code, build the fix themselves, publish it for everyone else – and quite often never mention it to anybody. The single most important asset in their whole migration flow, the tool that gets your files out of Figma, arrived exactly that way.

Which leaves a product adoption problem you cannot solve by shipping faster: The capability already exists. It just never went through a launch. No owner, no announcement, no release note — because from the team's perspective, nothing was shipped.

Nikki sits down with Mario Araujo, ex-Head of Growth at Penpot and current Head of Product Growth at Flosum, to trace what happens when your customers close the product gap for free, leaving a wide open communication gap in its place. They get into the one mechanism Penpot ran for telling anyone about anything, why onboarding tours are a stopgap rather than a solution, and what Penpot built instead.

Ideas from this episode you don't want to miss

• (06:06) What half of Penpot's 30,000 monthly signups have in common, and why it makes every launch harder
• (06:40) How nine different first-session use cases across just two personas kills the idea of straight-line onboarding
• (08:28) What Penpot built instead of an onboarding tour, and why it's a better choice for their lifecycle
• (09:25) The surprising reason Mario thinks onboarding checklists exist
• (12:17) The email that a twelve-person team in Ukraine sends that almost no SaaS company sends

Links from the episode

• We diagnosed one flag today — here are all nine, scored against Stagehand and priced in dollars
• Found the flag and want it closed without it landing on your team's roadmap? That's a sprint
• Follow Mario on LinkedIn
• Connect with Nikki on LinkedIn
• Send us your feedback

About our guest

Mario Araujo is a product leader focused on making B2B products sell. $0→$17M self-service + $80M influenced at OutSystems ($10B scale); 3x revenue at Softr; enterprise pipeline at Penpot (Spotify, US Postal Service, Swiss National Bank, US Army). 16 years at OutSystems (developer → trainer → PM → growth). Builds product-growth infrastructure bridging product, community and sales. Mentored by Elena Verna; advised by Andrew Capland; works with Wes Bush at ProductLed (Google, Mozilla, Boomi).

About the show

Every episode of Churn Flags, host Nikki Elbaz hands a SaaS leader one real piece of customer feedback — a 3-star review, a Reddit rant, a survey response — traces it to one of the nine Change Flags behind a customer's reevaluation, and builds a live retention experiment. For the retention, NRR, and expansion calls that don't have a best practice yet — VPs of Growth & Product, CMOs, CGOs, CPOs, and heads of product, growth & CS at mature SaaS. New episodes every other Wednesday. Work with Nikki → nikkielbaz.com/sprints

Topics: Product Adoption · Feature Adoption · Feature Discoverability · Feature Launch Communication · Re-Onboarding Existing Customers · Onboarding Optimization · Customer Activation · Customer Enablement · Product-Led Growth · Churn Reduction

Being famous for one thing is the fastest way to cap your NRR. Your customers are happy, they renew – and they're using a fraction of what they pay for, because the rest of your platform doesn't exist in their mental picture of you.

This episode starts with a G2 review from a Bitly customer asking for a link in bio feature. Bitly has one. It's called Pages, it sits in the main navigation, and it's been there for years.

Together with Tara Robertson, Chief Marketing Officer at Bitly, Nikki traces the review back to the Perception Change Flag underneath it – and to Bitly's always-running product adoption campaign: the drumbeat with no launch date, no over-engineered segmentation, and no end date.

Ideas you don't want to miss:
(03:49) How being famous for one thing introduces churn (in the shape of a customer asking for a product that's been in the nav for years!)
(06:07) Why $8/mo is both expensive and cheap for the same user, depending on how much of the product they know exists
(18:02) How long 8% of Bitly's free users take to upgrade – and the drumbeats that finally nudge them up
(20:55) Why an unsegmented email is the one a CMO forwards to her lifecycle team
(25:46) How National Sneak Some Zucchini Onto Your Neighbor's Porch Day earns its place in a repositioning campaign

Score your nine flags against your competitors' and get the dollar cost of each
Find out which flags are eating your expansion revenue, then fix them

Links from the episode:
Tara Robertson on LinkedIn
Bitly
Bitly Pages
Listen to my Email Swipes interview with Devin here

About our guest:
Tara is the Chief Marketing Officer at Bitly. Prior to Bitly, Robertson served as CMO at Teamwork and has held various key marketing leadership roles over the past 20 years at top tech brands such as Sprout Social and Hotjar. She now leads marketing at Bitly, whose Connections Platform empowers millions of monthly active users globally to use branded links, custom QR Codes and link-in-bio solutions to engage audiences and deliver critical notifications, information and experiences.

About the show:
Every episode of Churn Flags, host Nikki Elbaz hands a SaaS leader one real piece of customer feedback – a 3-star review, a Reddit rant, a survey response – traces it to one of the nine Change Flags behind a customer's reevaluation, then builds the retention experiment that closes it, or unpacks the one the company is already running. For the retention, NRR, and expansion calls that don't have a best practice yet. For VPs of Growth & Product, CMOs, CGOs, CPOs, and heads of product, growth & CS at mature SaaS. New episodes every other Wednesday. Work with Nikki.

Every SaaS team knows this churn: a user leaves over something your product already does. Most CS teams reply – accurately – that the feature exists and the docs are right there. Meanwhile, the customer's already gone.

In this episode, we take one real churn review and build the fix – all the way through four iterations – until we land on the one that doesn't just get the customer unstuck, but uplevels them to a better workflow and outcome.

Because when we start defining customer enablement as... the true definition of enablement, we don't just save our customers – we grow them.

Ideas you don't want to miss:

• 03:52 Why our featured customer churned, despite Storylane's impressive G2 review workflow
• 08:53 What it looks like to dig underneath a customer's complaint – to give them the outcome they're really looking for
• 13:28 Why tool tip real estate isn't actually something to worry about
• 16:12 How to improve your customer's outputs when they think they know better
• 21:45 The distinction that turns "make your customer the hero" into a referral machine

Links from the episode

We diagnosed one flag today – here are all nine, and how to catch each
Which of your accounts are silently re-evaluating you? Score them
Follow Anand on LinkedIn
Storylane, the interactive demo platform Anand runs demand gen for
Connect with Nikki on LinkedIn
Send us your feedback

Chapters

00:00 — The help doc problem

02:41 — The review

03:52 — Storylane's documentation domino

06:22 — The answer before the question

07:17 — The flag: Mastery (not Features)

08:53 — Usability vs. outcome

10:37 — The constraint

11:15 — The Experiment v1

13:28 — Usability before publish, outcomes after

14:29 — Gamification scoring

16:12 — Borrowing proof to make it stick

16:56 — Why the help doc can't win

19:11 — Make the customer the hero

21:45 — Hero to referrer

About our guest

Anand Vatsya is the head of demand generation and outbound at Storylane. Having gone through multiple 0-1 and 1-10 journeys in B2B SaaS, he brings over a decade of experience navigating the full spectrum of marketing. His approach is rooted in a simple belief — there are many right answers in marketing, but very few that are relevant to your specific stage, motion, and market. Getting to those few and executing them well is the job. Outside of work, he's usually reading a non-fiction, watching a Chelsea game, or going down a rabbit hole on human psychology or a new idea he probably shouldn't be spending time on.

About the show: Every episode of Churn Flags, host Nikki Elbaz hands a SaaS leader one real piece of customer feedback — a 3-star review, a Reddit rant, a survey response — traces it to one of the nine Change Flags behind a customer’s reevaluation, and builds a live retention experiment. For the retention, NRR, and expansion calls that don’t have a best practice yet — VPs of Growth & Product, CMOs, CGOs, CPOs, and heads of product, growth & CS at mature SaaS. New episodes every other Wednesday. Work with Nikki → nikkielbaz.com/sprints.

Topics: SaaS Customer Retention · Product Adoption · Feature Adoption · Customer Enablement · Proactive Customer Success · Time to Value · AI-Driven Product Adoption · Customer Activation · Expansion Revenue · Retention Experiments.

When AI resets what buyers assume your product can do, your most loyal accounts are the last to hear you kept up, and the budget that used to fund you gets re-line-itemed to "AI." Nikki sits down with Michelle Green, Director of Product at Cohley, to trace one real customer review back to the shift underneath it. Then they co-build the cheap, in-product fix that closes the gap before it costs the renewal.

Ideas from this episode you don't want to miss:

(01:45) The one-line response that would've kept Nikki from leaving a product she loved
(03:56) Why "we adopted AI" counts for nothing to the customer who's about to cut you (and what actually moves the needle)
(05:05) How Cohley's AI works for their brands, their creators – and their bottom line, all at the same time
(08:13) The counterintuitive reason your most loyal customers understand your product the least
(13:03) Michelle's Kanban mental model for customer engagement (and the "done" trap to watch for)

Links from the episode:

We diagnosed one flag today — here are all nine, and how to catch each
Which of your accounts are silently re-evaluating you? Score them
Follow Michelle on LinkedIn
Connect with Nikki on LinkedIn
Send us your feedback

About our guest:
Michelle Green is Director of Product at Cohley, where she has spent the past 4 years shaping the platform's product direction. She brings a rich background that spans both media and SaaS: before Cohley, she spent 4 years at Rent. and 8 years at The Weather Company, building deep expertise in marketing and product. In 2018, Michelle made a deliberate pivot from media to SaaS, a move that positioned her at the intersection of content, technology, and brand strategy. Known for her natural curiosity and deep passion for the customer experience, she approaches product development with a simple but powerful belief: the best products are built by listening closely to the customer. Today, she applies that cross-industry perspective and customer-first mindset to help brands and creators connect more effectively through Cohley's platform, with an attention to detail that ensures every touchpoint is thoughtful and intentional.

About the show: Every episode of Churn Flags, host Nikki Elbaz hands a SaaS leader one real piece of customer feedback — a 3-star review, a Reddit rant, a survey response — traces it to one of the nine Change Flags behind a customer’s reevaluation, and builds a live retention experiment. For the retention, NRR, and expansion calls that don’t have a best practice yet — VPs of Growth & Product, CMOs, CGOs, CPOs, and heads of product, growth & CS at mature SaaS. New episodes every other Wednesday. Work with Nikki → nikkielbaz.com/sprints.

Topics: SaaS Customer Retention · Net Revenue Retention (NRR) · AI Agents · AI-Driven Product Adoption · Feature Adoption · Re-Onboarding Existing Customers · In-App Onboarding · Customer Activation · At-Risk Customers · Retention Experiments · Voice of Customer.

This G2 review looks like a feature request and… it is. Paperform co-founder Diony McPherson kills my flag diagnosis two minutes into the episode, then drops another one right into my lap. We run through three experiments to address the flag — a rename, a template filter, and a weekly case-study series — and Diony picks the one she'd actually run. Along the way she reframes what a launch even is, staying intentional about what you build, and keeping the customer relationship close as you grow.

About our guest

Diony McPherson: Bootstrapped SaaS Founder | Co-Founder at Paperform.co, Stepper.io and Dubble.so, with Dean McPherson | Proud Boy-Mum of 5 under 9

Links from this episode

• Build "your definition of a form" with Paperform — take 50% off Paperform Pro and Stepper Pro with code SP+PF&STEPPER2026 (expires June 30, 2026)
• Automate all your busywork with Stepper
• Run your own product through the Change Flags rubric and find the one quietly costing you customers → nikkielbaz.com/rubric
• Connect with Diony on LinkedIn
• Connect with Nikki on LinkedIn
• Send us your feedback

Ideas you don't want to miss

• 00:00 — The launch you missed on vacation
• 04:24 — How Diony killed my first diagnosis in two minutes
• 09:23 — The aside that flipped the episode: a whole product this power user didn't notice
• 19:02 — The three experiments: rename, direct, or weekly case studies
• 21:12 — When renaming is a real lever, and when it torches years of recognition
• 24:44 — Today's launch: AI-forward onboarding
• 27:37 — The payoff: perception is static, placement is the fix
• 29:07 — Bonus: 2 a.m. alarms and staying close as you scale
• 30:45 — The instinct that never expires (grab the rubric)

About the show: Every episode of Churn Flags, host Nikki Elbaz hands a SaaS leader one real piece of customer feedback — a 3-star review, a Reddit rant, a survey response — traces it to one of the nine Change Flags behind a customer’s reevaluation, and builds a live retention experiment. For the retention, NRR, and expansion calls that don’t have a best practice yet — VPs of Growth & Product, CMOs, CGOs, CPOs, and heads of product, growth & CS at mature SaaS. New episodes every other Wednesday. Work with Nikki → nikkielbaz.com/sprints.

Topics: SaaS Customer Retention · Product Adoption · Feature Adoption · Feature Discoverability · Re-Onboarding Existing Customers · Product Perception · Feature Launch Communication · AI-Driven Onboarding · Customer Activation · Retention Experiments.

Peek behind the scenes at the retention moves that earn their place in the playbook of $50M+ ARR SaaS – the ones lifecycle flowcharts and QBR reviews miss.

Every episode, host Nikki Elbaz hands her guest a real piece of customer feedback – a 3-star review, a Reddit rant, a puzzling survey response. Together, they trace it back to one of nine Change Flags that trigger user reevaluation – then map out a growth experiment that turns churn into expansion.

Nikki Elbaz is the retention strategist behind NRR and activation work for SaaS companies at the scale where best practice runs out and judgment takes over.

New episodes every other Wednesday with guests from Bitly, Storylane, and SparkToro.

Topics: SaaS Customer Retention · Net Revenue Retention (NRR) · Expansion Revenue · Product Adoption · Feature Adoption · Customer Activation · AI-Driven Product Adoption · Retention Experiments · Voice of Customer.