⚡£23M revenue from Organic Growth for SaaS with Content Marketing Sprints | Storytelling, SEO and Content Marketing ⚡️

Your AI content sucks.
Your competitors' AI content sucks.
Everyone's AI content sucks.

And you know what's worse? You're all paying through the nose for it.

While you're sitting there wrestling with prompts like a cat trying to open a doorknob, we've built something that actually works. Because unlike every other "revolutionary AI tool" (looking at you, [REDACTED]), we know it takes more than 10 prompts and a prayer to write content that doesn't sound like it was outsourced to a drunk toddler.

We use 450+ prompts. Overkill? Maybe. But at least our stuff doesn't read like it was written by an AI having an existential crisis.

Some receipts for the skeptics:
↳ Slapped 400 blogs on our site = 10x traffic in 3 months
↳ Halved content budgets while 5x-ing output (yeah, your Content Manager's been lying about costs)
↳ Helped tiny startups pimp-slap Fortune 500s right off page 1

After a decade watching the B2B content circus, I've seen every "game-changing" tool and "revolutionary" AI writer. Most of them belong in the same trash bin as your last strategic plan.

Here's the uncomfortable truth: Your investors aren't buying your "we're playing the long game" BS anymore. They want to see organic traction, and your three LinkedIn posts from 2023 aren't cutting it.

You need Penfriend.ai if:
✓ Your competitors are living rent-free at the top of Google while you're still "building awareness"
✓ VCs are ghosting you because your "organic presence" looks like a digital ghost town
✓ You're burning cash on content that reads like it was plagiarized from a terms of service agreement
✓ You're ready to stop being the industry's wallflower and start being its problem child

Sound familiar? Then you're exactly who we're looking for.

The hard truth? You suck at AI. But it's not your fault. You've been sold a lie by companies who think "AI writing" means letting GPT go wild after a two-prompt foreplay.

We fixed it. Because someone had to.

DM me "PAGE ONE" and I'll show you how we're helping companies terrorize their competition online.

P.S. If you're happy with generic, soulless AI content that sounds like everyone else's, this probably isn't for you. And that's okay. Someone has to keep the internet boring.

Tim Hanson

Jacalyn Beales

⚡️Leading lifecycle marketing @ Copy.ai | On a mission to find the best Moscow Mule | Em dash enthusiast

Hey, I'm Jacalyn 👋 I'm a fractional marketing and lifecycle leader with a passion for emboldening brands and empowering their customers. My focus is helping companies solve common marketing woes with a human-first approach. 

I've spent 10+ years working alongside cross-functional GTM teams—ideating and executing demand-driven strategies that propel growth and brand recognition—to drive over $2 million+ in revenue for B2B and B2C companies. Big advocate for bridging the gap between companies and their customers—and breaking the confines of commonplace marketing 🙌

I believe:

⚡ Everything about a brand should be human-centric
⚡ Em dashes are the elite punctuation mark
⚡ Breakfast for dinner is a highly underrated combo👌 

When I'm not working, I can usually be found hunting down the best Moscow Mule and traveling wherever there are trails and a mountain.

Head of Lifecycle

when i started working for myself, i made a commitment that i would rediscover the things i used to love before my career became my sole focus 😅 



i think anyone who's spent long enough in their career gets it 🫶 

that all too familiar feeling you wake up with one day, when you suddenly realize that you don't really know who you are after years of climbing the ladder, putting work first, and being the "career girl" (or guy) in your family & friend groups. 

it took getting laid off for me wake up and accept that—shockingly—your career truly isn't everything. it's not all that you are. 

example: in my past life, i...
- moved overseas on my own and fell in love with life in stockholm
- spent over 17 years riding horses and show jumping 
- used to do pottery 
- was obsessed with florals and gardening (thanks to my amazing mom)
- would read CONSTANTLY, like to the point where i had a closet just for my books 😂 
-  was a lifestyle photographer (yes, magazines paid me to take pics, it was fun!)
- traveled frequently enough that friends would ask me, "how long are you home for before you leave again?" 

the thing is, i got to a point where i couldn't really remember the last time i truly enjoyed any of those things once my career became "everything".

so, i promised myself that 2026 would be the year i rediscovered what the heck makes me happy (plot twist: career is nowhere near the top of the list). 

so far, that's looked like:
- taking courses for hobbies i once loved (like pottery, baking, textiles, and floral design)
- finding a stable and getting paired with a horse i'm training with (that's Big John in the pic, and yes, that's his actual name 😂)
- buying new copies of all of my fave books and re-reading 'em
- pulling my camera out to get back into photography, and hanging with photographer friends 
- traveling more (and working remotely from new & old places)
- rediscovering stuff i loved about living abroad (like baking my fave kolasnittar and dusting off old recipes)

i don't think any of us really mean to get lost in our careers, and it's not a bad thing to be driven ✨ 

you can also still adore what you do for a living, and not make it your entire identity (spoken by someone who's entire identity was their career for...too long 😅)

but there's something to be said for finding value and worth in things outside of work, and not tying your own self worth to your job 💜 

i'm super fortunate to be surrounded by people who have come to the same conclusion, and who support + cheer each other on to do their best work while living for more than just their careers. 

you might surprise yourself with how much happier you are in and outside of work 🥹 

#marketerlife #marketingthings #marketers #lifelessons

Fractional marketing & lifecycle leader | Says “howdy” a lot | Always on the hunt for the best whiskey sour

btw, this is who you're asking to build a lifecycle program by EOD




(jacalyn, aged 4, toad catcher)

my hot take is a lot of lifecycle marketers don't have a strategy problem—they have a systems problem 🙈 



(if you've ever touched anything in lifecycle, you've probably seen this, too). 

- the tooling works
- the ESP is set up
- your CDP is connected
- maybe there's even a data warehouse humming along in the background

the thing is, nobody built the process around it. 

⚡ asana is used to PM stuff, but there's no intake workflow

⚡ you've got braze, iterable, or customer[dot]io setup, but there's no comms governance or rigour (aka zero guardrails) 

⚡ there's OKRs and KPIs to hit, and yettttt no cross-functional partnerships with product, cs, or sales

meanwhile, lifecycle folks still have to "do lifecycle" (and you're doing a DARN GOOD JOB, too 👏) 

however, if you happen to be looking for some ideas, or just a fun resource, that'll help you put systems or processes in place so lifecycle feels a ✨ little less messy ✨ i created this guide based on stuff i've worked on, systems i've had to build, and how i've tackled creating processes around lifecycle in the past. 

(there's even a bit on ai, too, since we're all using it in some form or other!) 

hope it's helpful 🫶 

#lifecyclemarketing #lifecyclemarketingtips #lifecycletips #lifecyclemarketingstrategy #b2blifecycle #b2bmarketing

A fun guide to closing your lifecycle gaps

i've had about 9 coffee chats with marketers and lifecycle folks since 2026 kicked off, and most of the q&a is the same 💜 



"how the heck do you build for____"

"what if i don't have _____"

"how can i get buy in when_____"

i've walked into enough lifecycle roles to know these questions are ones we ALL have 🥹 

and i've also been in enough situations by now that the pattern kinda becomes the same for us.

- day one: here's the ESP, here's the CRM, here's the product analytics tool. cool!

- day two: why are these segments from 2022?? why is this automation still running? who owns this data? cool cool cool 😅 

i'm gonna be honest: i DON'T have all the answers 😂 

all i can say is that everything i've learned, and done, has been thanks to asking questions, building, experimenting, and trying. i really don't know what i don't know, you know?

in the event that some of those learnings help someone else who might be struggling with the whole, "how the heck do i approach X lifecycle problem??" without tearing your hair out, i put together this nifty guide. 

because the reality is that lifecycle's job can be pretty messy. 

you're figuring out what data to trust, which program to build first, and how to prove that any of it matters to the business, all while the requests keep piling up in Slack 🫠 

i've been through this process more than once now, so i get it 🫶 

so i put together the guide i wish i'd had when i was starting from scratch. 

it covers stuff like:

- auditing what you've got before you build anything
- why your first program should have one objective (seriously, just one)
- segmenting by role and JTBD, not just by company name
- behaviour-triggered journeys that respond to what users actually do
- the middle child problem that you're gonna run into (or already have)
- how lifecycle ABM can work (ex. i used it to drive $300k+ in cross-sell rev)
- measuring impact when your attribution tool was built for lead gen, not lifecycle
- the cross-functional work that gets lifecycle a seat at the table

it's not perfect, but hopefully it's a start 🤗 

#lifecyclemarketing #b2blifecycle #b2bmarketing #lifecyclemarketingtips #lifecyclestrategy #b2bmarketingtips #lifecycletips

The lifecycle playbook you can steal

one of the biggest takeaways of my career has ended up defining every single success i've had with work since.



it's not "be nice", or "be the smartest person in the room", or even "be the first one to arrive and the last one to leave". 

(all of those tidbits are actually not effective advice, especially the whole "be nice" thing, because...you should always aim to be kind, but i've never seen a male coworker get that advice 😂 iykyk)

the best lesson i learned?

be reliable. 

that doesn't mean being a "yes" person, or taking on everyone's work—although you do have to guardrail against that!

being reliable actually means:
- your team can depend on you to pull your weight
- your direct reports feel safe coming to you, for easy or tough convos 
- your boss doesn't worry about your performance (they know you'll crush it) 
- your coworker knows if they need you, you'll show up 

personally, i think being reliable is one of the more underrated skills any of us can have 🙈 

you definitely don't have to be the smartest, hardest working, highest skilled person in the room...

but being reliable? hella underrated. 

and it doesn't just go for managers or mid-level peeps. 

✨ the best bosses i've had are the ones i could rely on to help me learn, grow, and win.

✨ the best coworkers i've had are the ones i could rely on to help us figure out tough stuff and get through the challenging work.

✨ the best direct reports i've had are the ones where our boss/report relationships were built on dependability, trust, and reliability. 

i also think being reliable is synonymous with being respectful 🤷‍♀️ 

if i show up, i want my team to show up—AND VICE VERSA 👏 

show up. 
give a crap about your work. 
be there for your team. 

reliability is a flex more of us should, well, flex 🫶 

#marketing #b2bmarketing #marketingthings #marketerlife

i'm just going to say it: the tear-downs and analyses of multi-billion dollar companies' lifecycle systems are useless 🫶 



they sound really insightful and helpful on the surface (and honestly, we all want to know how notion, slack, sweetgreens, or starbucks cracked the code on "lifecycle"). 

but there's a few things no one points out...

they don't reflect the reality of most lifecycle marketing teams.

you're probably a team of one, maybe two, and therefore aren't running the types of programs starbucks does. 

it's unlikely your budget is as big as notion's. 

running email sequences doesn't count as lifecycle (there's more to it). 

lifecycle doesn't operate in isolation to drive millions in revenue for these big brands (despite what these tear down posts tell you). 

🥲 

i'm not saying we can't learn a thing or two from these tear downs, it's just that most of the info lacks the [seriously relevant] context behind how these companies run lifecycle. 

- lead lifecycle vs lifecycle marketing
- the tie-in to sales, cs, and continued retention
- what happens beyond emails, in-app messages, and SMS 
- the actual influence these programs have on pipeline vs revenue 
- how these companies track that ^^^^

if you really want to drive impact with lifecycle marketing, it's more useful to go back to the basics.

1️⃣ understand the diff between lifecycle marketing & lead lifecycle 

𝗟𝗶𝗳𝗲𝗰𝘆𝗰𝗹𝗲 𝗠𝗮𝗿𝗸𝗲𝘁𝗶𝗻𝗴 is your STRATEGY for engaging customers across their entire journey with your brand—from awareness to advocacy. 

𝗟𝗲𝗮𝗱 𝗟𝗶𝗳𝗲𝗰𝘆𝗰𝗹𝗲 refers specifically to the STATUS of a lead in your pipeline—MQL, SQL, opportunity, closed-won, or however you track 'em. It's a tracking mechanism for where prospects stand in your sales process.

2️⃣ map out what your user/customer journey ✨ actually ✨ looks like SEPARATE from your lead stages.

3️⃣ answer the basic Q&A of every program you plan out, like:
⚡what emails do users receive? 
⚡what content and messaging should they see? 
⚡what's the experience for DAQ/WAU/MAU?
⚡what will you do you users who aren't ready to buy?
⚡which channels make the most sense to use? 
⚡how will you personalize based on behaviour?

4️⃣ make sure you understand who your users really are (this means you've gotta do user research!).

5️⃣ understand lifecycle marketing's place in your business (what impact, goals, objectives, etc is lifecycle actually meant to drive?).

there's absolutely zero need to comment "COPY" on any post that shares a figma board analysis of X brand's $25 billion dollar "lifecycle engine". 

it's not going to be applicable to your business, your users, your programs, and your goals 💜 

sure, they're fun to read through (and there's probably a neat design tip or hack) but the best thing you can do is build lifecycle around YOUR users. 

#lifecyclemarketing #lifecyclemarketingtips #lifecycletips #lifecyclemarketingstrategy #b2bmarketing #b2blifecycle

Lifecycle marketing in b2b doesn't mean one thing, and i think that's where a lot of the confusion starts 🥹 




just a quick take: lead lifecycle is a status (where someone sits in your pipeline, like MQL, SQL, opp, closed-won)

lifecycle marketing is the strategy for engaging people across their entire journey, from first touch through retention and expansion. 

two very different things, but because most companies never define them internally, everyone ends up talking around each other 😅

buttttt even when we're all saying "lifecycle marketing," what that actually looks like varies wildly from company to company.

⚡at a PLG org, lifecycle might mean onboarding and activation flows, like getting users to value fast 

⚡at an enterprise SLG company, it could mean renewal enablement, expansion plays, and working alongside CS to reduce churn 

⚡ at a hybrid? some combo of both, usually with one person trying to figure it all out 🙃

the function itself shifts depending on motion, company stage, team structure, and (honestly) what leadership actually means when they say "we need lifecycle."

and that's where things get tricky.

a lot of companies hire for lifecycle but scope the role as "email person." 

(they say they want retention but measure acquisition metrics, or they build a lifecycle function and sit it so far from Product, CS, and Sales that it can't actually influence the customer experience in any meaningful way).

this isn't a chirp! 🫶 

it happens because lifecycle is still a relatively new function in b2b, and there's no universal playbook for how to build it. the shape of it depends on what your business actually needs, and figuring that out is half the work.

to avoid burning lifecycle marketers out, and creating a lot of directionless work, the first thing to do is get clear on what lifecycle should mean for YOUR biz (based on your customers, data, growth motion, and where the biggest gaps are) 👀 

it's easy to say "we need lifecycle," but a lot of lifecycle peeps burn out quicckkkk when they're brought on to solve customer marketing, cross-sell, activation, NRR issues, upsell, etc all at once. 

lifecycle is truly a crawl - walk - run thing 💜 

#lifecyclemarketing #b2bmarketing #b2blifecycle #lifecyclestrategy #lifecyclemarketingtips #lifecyclemarketingstrategy #fractionalmarketing

Lifecycle can do a lot, but it can’t do everything…and when it’s asked to, things get messy 😅




a while back, i was reviewing an expansion and renewal motion for a client, and on paper, it looked 🫰 

- usage hit 80% of plan limits = an expansion email fired
- renewal window was 60 days out = triggered a pre-renewal sequence 
- feature adoption lags = triggered in-app nudges

everything looked like you’d expect it would for lifecycle comms, but revenue was barely moving. 

expansion emails were going out while accounts had open support escalations, re-engagement nudges were firing even after CSM reports showed that their accounts were still working to get buy-in, and renewal comms read like automated billing reminders instead of a recap of the value the team actually got from the platform. 

“on paper”, a lot of our lifecycle systems look solid, but the actual message gets totally missed. 

and IMO that’s the line more teams need to define.

lifecycle marketers own stuff like systems, behavioural triggers, activation & usage optimization, expansion signals, all that rigmarole. 

(it’s how we help create readiness)

but when lifecycle is asked to “own revenue” without customer context, we end up optimizing workflows instead of outcomes.

there’s two reasons for that:
1. readiness alone isn’t meaning
2. meaning alone doesn’t scale

i like to think of it like a handshake, where lifecycle can help create readiness, but customer marketing and insights help create the meaning 🤝 

for example, if lifecycle can prove that an account is showing expansion signals, then on the customer side, you can better explain how expansion helps that account. 

or, if users aren’t logging in or their activity is lagging, lifecycle and customer marketing can work together to figure out what’s missing (priorities, education, whatever the case!)

that’s why Maylee Jacob and i ground a lot of our work in what’s actually happening with the customer 👀 

if you can connect lifecycle and customer marketing back to what they’re trying to prove internally, what pressures they’re under, what success really looks like in their world…it becomes a handshake motion where programs aren’t just launching, but landing. 

you can do a quick audit right now to figure out if you’ve got a handshake motion by looking at:

⚡your expansion triggers: are they firing purely on usage thresholds, or layered with account context?
⚡your renewal sequence: does it sound like a workflow…or a relationship? 
⚡your re-engagement motion: are you suppressing based on CS activity and insights?

if you’re asking lifecycle to do the whole job, it can’t.

butttttt when lifecycle systems and customer marketing are designed as a handshake, both functions get to do what they’re best at.

#lifecyclemarketing #customermarketing #b2bmarketing #retentionmarketing #customerjourney #growthstrategy

p.s. if that sounds like a roadblock you’re bumping into, might be worth chatting with Maylee and I 🥳

Everyone wants to automate lifecycle—automation is exciting, it scales, and it makes you look like you have your act together 💁‍♀️ 




but automation without a foundation is just noise at scale. 

i've seen this happen both with companies that have some lifecycle work in place but no real strategy, and companies starting from zero.

(i've also been super tempted to automate as much as i can, which hasn't always worked 😅)

here's how i'd approach building the lifecycle foundation first BEFORE automating stuff (steal this if it helps):

⚡ audit what exists
- what programs are running?
- what data do you have?
- what's broken, what's working but no one's measuring, and what's just... there? 

you'd be surprised how many flows are running in the background that no one's looked at in months, so it's helpful to know what you're working with.

⚡ talk to the humans 
- CS, Sales, Product—these folks know things your dashboards don't. 
- dig into the WHY behind what's happening with customers and users
- look at usage patterns, churn signals, common threads in win-backs and lost opps, retention trends, yada yada

it'll save you from building programs based on assumptions.

⚡ pick your source of truth
- where does your customer data actually live, and what can you trust? 
- CRM, product analytics, CS platform—pick one and build around it

trying to reconcile five tools will eat your week alive (trust me!)

⚡ surface the biggest leaks
- where are people dropping off, disengaging, or churning?
- prioritize 2-3 of those instead of fixing everything at once

⚡ map the journey
- i treat journey mapping as its own step, but it's informed by everything above 
- you want to map based on real patterns you've already surfaced

⚡ Build ONE program around your biggest drop-off
- behaviour-triggered, not time-based
- target the leak that's costing you the most and build something focused

you can expand later (ship useful now, perfect later)

⚡ define how you're measuring behavioural impact
- this is the part most people skip, and it's the part that matters most
- before you launch, get clear on what downstream behaviour you're trying to influence
- feature adoption, activation, retention lift, expansion signals—not clicks, not open rates. 

l ifecycle wins when you can show it changed what people actually did.

one caveat here: every company treats lifecycle differently. 

some have pieces of this in place already, and some are starting from scratch. so, these steps might look a little different depending on where you're at (but the thinking applies either way) 🤗 

tbh, the reason i care so much about foundations is because the companies that skip this step end up automating a mess. 

the foundation is what lets you actually track and prove lifecycle's impact on downstream user and customer behavior. 

that's where the function earns its seat at the table 😊

#lifecyclemarketing #b2blifecycle #lifecyclemarketingtips #b2bmarketing #lifecyclestrategy #lifecycletips

There's a pattern I keep running into with lifecycle programs that aren't performing (and it's almost never that teams aren't doing enough).


it's usually that they're doing too much 🫶 

when the strategy underneath isn't clear, the natural instinct is to compensate with more:
- more sequences
- more channels
- more triggers
- more tools

when you're not sure what's working, it feels safer to cover every angle than to make a bet on one thing.

but what ends up happening is complexity without clarity, which is a really pricey place to be 🫰 

you’ve probably seen this happen IRL: 

- a dozen active sequences nobody's reviewed in months—some overlapping, some contradicting each other, a few still referencing messaging that's since changed
- three tools doing overlapping jobs with data living in three places, none of them telling the same story
- campaigns launching without baselines, so when someone asks "how's it doing?" the best answer is "people are opening them"
- “personalization" that's really just different subject lines on the same message.

building more is basically just covering your bases, and trust me, I GET it. 

(i’ve been there 🥹)

what I’ve found, though, is that the fix is almost always subtraction, not addition.

⚡ start with an inventory of every active sequence and map each one to a specific behaviour you're trying to drive
- if you can't name the behaviour, that's a candidate for cutting or rethinking.

⚡ consolidate your tools where there's overlap
- pick a source of truth and commit to it
- half the battle with messy lifecycle programs is that teams are spending more time reconciling data across platforms than actually acting on it.

⚡ build measurement into what remains
- not opens and clicks, but behavioural outcomes
- did the user take the action?
- did it stick after 7 days? 14? T
- track the behaviour change, not just the email engagement.

⚡ simplify your segmentation
- if your branching logic requires a flowchart to explain, your customers are probably getting a more fragmented experience than you think
- start with fewer, cleaner segments and expand from there once you can see what's working.

on paper, this looks super unimpressive 😂 but it’s actually more effective in practice.

honestly, one of the best ways to know whether you've simplified enough? 

look at what the customer is actually experiencing on the other end. 

that's where Maylee Jacob and I work together—customer insight meets lifecycle systems. 

if any of this sounds familiar, happy to chat through how we can help☺️

#lifecyclemarketing #b2blifecycle #lifecyclestrategy #retentionmarketing #b2bmarketing #lifecyclemarketingtips

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Jacalyn Beales

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