#90DaysofSaaS
90 days. 90 posts. One SaaS delivery leader writing her way through the noise — CRM roasts, fintech curveballs, and hard-won lessons.
A daily field journal from Heather Jacobs’ 90-day LinkedIn sprint on SaaS, CRM, fintech, and delivery leadership. Read in order for the full arc, or dip in for a single dispatch.
Table of transmissions
- Prelude
Prelude — In honor of the weekend, here’s your warning:
In honor of the weekend, here’s your warning: Next week, I’m kicking off a 90-day LinkedIn posting sprint. There will be stories. There will be hot takes. There may be a CRM roast or two. Topics comin…
Apr 12, 20251 min - Prelude
Prelude — Tomorrow, it begins.
Tomorrow, it begins. 90 days of LinkedIn posts. No fluff. No filler. Just real stories from years of SaaS delivery, CRM adventures, and fintech curveballs. I’ll share: 👉Mistakes I’ve made (and survive…
Apr 13, 20251 min - Part 1
Day 1: Most SaaS onboarding doesn’t suffer from a lack of automation.
Most SaaS onboarding doesn’t suffer from a lack of automation. It suffers from a lack of alignment. I’ve watched teams roll out sophisticated playbooks, AI copilots, and dazzling dashboards—only to re…
Apr 14, 20251 min - Part 2
Day 2: A client ghosted me mid-implementation.
A client ghosted me mid-implementation. No warning. No red flags. Just… silence. Emails: unopened. Project plan: untouched. Phone calls: unanswered. And we had done everything by the book: ✔️ Kickoff …
Apr 15, 20251 min - Part 3
Day 3: I asked ChatGPT what I should do if I ever wanted to shift careers.
I asked ChatGPT what I should do if I ever wanted to shift careers. Here’s what it said: You’ve got the rare combo of product-savvy, client empathy, and operational wizardry. You could: 👩🏻💼Be a Fract…
Apr 16, 20251 min - Part 4
Day 4: SaaS onboarding and delivery managers aren’t just project people.
SaaS onboarding and delivery managers aren’t just project people. They’re product truth-tellers. They know: • Which features trip users up every time • What workarounds are invented before week one en…
Apr 17, 20251 min - Part 5
Day 5: Adoption isn't about capabilities, it's about accessibility.
Adoption isn't about capabilities, it's about accessibility. Aidium Quickstart transforms how our users interact with automations by organizing everything around client journey stages - the way our us…
Apr 18, 20251 min - Part 6
Day 6: Let’s talk about the invisible roadmap no one adds to the pitch deck.
Let’s talk about the invisible roadmap no one adds to the pitch deck. You know, the one with: 🔹The detour for “client changed their mind” 🔹The fork in the road labeled “Sales said yes to what?” 🔹And t…
Apr 19, 20251 min - Part 7
Day 7: I used to think onboarding was about execution.
I used to think onboarding was about execution. Get in, get set up, get out. But the more I led SaaS delivery projects, the more I realized it’s not about tasks. It’s about translation. Translating vi…
Apr 20, 20251 min - Part 8
Day 8: I took the next step in the hashtag#ActionFigure trend—literally.
I took the next step in the hashtag#ActionFigure trend—literally. Meet the walking, talking (well… not really) version of my alter ego, thanks to Kling AI and a little weekend creativity. Big thanks t…
Apr 21, 20251 min - Part 9
Day 9: Ever watched a 15-minute misunderstanding turn into 3 weeks of chaos?
Ever watched a 15-minute misunderstanding turn into 3 weeks of chaos? I have. It starts innocently enough: • Sales calls it a “simple integration” • Product assumes the client knows what they want • D…
Apr 22, 20251 min - Part 10
Day 10: Somewhere between “create kickoff deck” and “enable integrations,” we lost sight of the hu…
Somewhere between “create kickoff deck” and “enable integrations,” we lost sight of the human side of onboarding. Here’s what I wish made it onto every SaaS implementation checklist—because it’s rarel…
Apr 23, 20251 min - Part 11
Day 11: If your QBR feels like a glorified slide show, you’re doing it wrong.
If your QBR feels like a glorified slide show, you’re doing it wrong. A good QBR isn’t a status update. It’s a strategic reset. Try this instead: • What outcomes are we driving toward? • Where are use…
Apr 24, 20251 min - Part 12
Day 12: Product says, “We added this feature for flexibility.”
Product says, “We added this feature for flexibility.” Sales says, “It can do everything!” Clients say, “I’m confused.” Support says, “Here we go again.” Delivery says: “Let me explain…” Implementatio…
Apr 25, 20251 min - Part 13
Day 13: We delivered the platform.
We delivered the platform. We hit the milestones. We trained the users. And yet… it still didn’t feel done. Why? Because we forgot the unspoken deliverable: Confidence. Clients don’t just want working…
Apr 26, 20251 min - Part 14
Day 14: Let’s play a game called:
Let’s play a game called: Guess who has to explain that roadmap decision to the client? Not product. Not sales. Delivery. We’re the ones fielding the “wait, this changed?” questions. The ones who have…
Apr 27, 20251 min - Part 15
Day 15: Between the kickoff call and the "go-live" stage, a common occurrence unfolds: the sudden …
Between the kickoff call and the "go-live" stage, a common occurrence unfolds: the sudden emergence of phantom stakeholders. These elusive figures require a rundown of the project scope despite their …
Apr 28, 20251 min - Part 16
Day 16: In SaaS delivery, “MVP” isn’t just a product thing.
In SaaS delivery, “MVP” isn’t just a product thing. It’s an onboarding thing. It’s a delivery thing. It’s a did-we-all-agree-on-what-done-looks-like thing. If there’s any fuzziness around what “done” …
Apr 29, 20251 min - Part 17
Day 17: Compliance fears keep too many lenders from effective lead capture and follow-up.
Compliance fears keep too many lenders from effective lead capture and follow-up. Our forms solve this by automatically documenting TCPA consent with every submission. Create professional, branded for…
Apr 30, 20251 min - Part 18
Day 18: At the heart of successful project management lies clarity. In the realm of SaaS kickoff d…
At the heart of successful project management lies clarity. In the realm of SaaS kickoff decks, the difference between a mere project and a hostage situation can be as concise as five slides versus tw…
May 1, 20251 min - Part 19
Day 19: In SaaS, when an implementation falls apart, the first instinct is to blame the tool.
In SaaS, when an implementation falls apart, the first instinct is to blame the tool. But here’s the real culprit 90% of the time: • Misaligned people. • Broken or missing processes. • Vague definitio…
May 2, 20251 min - Part 20
Day 20: Weekend Wisdom: Scope Creep Edition
Weekend Wisdom: Scope Creep Edition Scope creep doesn’t usually announce itself. It shows up disguised as: • “Just a quick update.” • “Can we sneak this in?” • “It’s a small tweak, promise.” By the ti…
May 3, 20251 min - Part 21
Day 21: Go-live isn’t the finish line.
Go-live isn’t the finish line. It’s the starting point for the second leg of the marathon. Real SaaS delivery success isn’t just about launching. It’s about adoption, behavior change, and long-term va…
May 4, 20251 min - Part 22
Day 22: Remember that Tootsie Pop commercial with the owl?
Remember that Tootsie Pop commercial with the owl? “How many licks does it take to get to the center of a Tootsie Pop?” CRUNCH. “Three.” Your users are basically asking the same thing—"How many clicks…
May 5, 20251 min - Part 23
Day 23: Late nights. Big ideas. Serious talent. Here’s the Aidium team grinding it out at 11 PM la…
🚀 Late nights. Big ideas. Serious talent. Here’s the Aidium team grinding it out at 11 PM last night during our Hackathon! 💻⚡️ But wait — what’s a hackathon and why are we doing it? At Aidium, we hire…
May 11, 20251 min - Part 24
Day 24: If Day 1 was about caffeine and chaos, Day 2 is all about clarity and creation.
If Day 1 was about caffeine and chaos, Day 2 is all about clarity and creation. The ideas are sharper, the caffeine tolerance is dangerously high. Our teams are pushing boundaries on what’s possible f…
May 12, 20251 min - Part 25
Day 25: I'm hyped up on copious amounts of coffee. But the fun is just beginning. What’s the one f…
I'm hyped up on copious amounts of coffee. But the fun is just beginning. What’s the one feature your CRM is missing that would make your life easier? Drop it below—this might just be the week it goes…
May 13, 20251 min - Part 26
Day 26: Everyone wants AI—but do they actually know why?
Everyone wants AI—but do they actually know why? Here’s the scene: • Executive: “We need AI in our platform!” • Me: “Great! What’s the use case?” • Executive: “…It’s AI?” Don’t get me wrong—I’m pro-AI…
May 14, 20251 min - Part 27
Day 27: Day 3 of the #MAYAI Hackathon, and let’s just say… sleep is optional, but innovation is m…
Day 3 of the #MAYAI Hackathon, and let’s just say… sleep is optional, but innovation is mandatory. The whiteboards look like conspiracy theory maps, the coffee supply is running on sheer hope, and eve…
May 15, 20251 min - Part 28
Day 28: There are plenty of “AI” tools being slapped onto mortgage software right now.
There are plenty of “AI” tools being slapped onto mortgage software right now. Here’s what makes Aidium different: Our AI isn’t just a flashy add-on. It’s a connected stack that actually drives produc…
May 16, 20251 min - Part 29
Day 29: If you’ve ever wondered what happens when you combine jet lag, dangerously strong Spanish …
If you’ve ever wondered what happens when you combine jet lag, dangerously strong Spanish coffee, and a room full of slightly-overcaffeinated product minds… you get THIS: Two new AI-powered superpower…
May 17, 20251 min - Part 30
Day 30: Your SaaS implementation isn’t complete. It’s just unsupervised now.
Your SaaS implementation isn’t complete. It’s just unsupervised now. We love to throw that “Go-Live” party and slap a big ✅ on the project plan—but here’s the uncomfortable truth: Going live doesn’t m…
May 18, 20251 min - Part 31
Day 31: You know it’s a real hackathon when the ideas go from “What’s feasible?” to “What if the C…
You know it’s a real hackathon when the ideas go from “What’s feasible?” to “What if the CRM could sense feelings?” Watching the team go full mad scientist this week has been equal parts inspiring and…
May 19, 20251 min - Part 32
Day 32: Some companies talk about innovation.
Some companies talk about innovation. Others ship it. Our team is in build mode — and the pace is real. In just two weeks of MAYAI, we’ve rolled out: ✅ More than a dozen smart, pre-built Agents — live…
May 20, 20251 min - Part 33
Day 33: You don’t have a tech problem. You have a people and process problem wearing a tech costum…
You don’t have a tech problem. You have a people and process problem wearing a tech costume.” If I had a dollar for every time I heard “The CRM just isn’t working for us,” I’d retire early and launch …
May 25, 20251 min - Part 34
Day 34: Still emotionally jetlagged from the strength of Spanish coffee and the sheer brilliance o…
Still emotionally jetlagged from the strength of Spanish coffee and the sheer brilliance of our product and engineering teams. Last week, we descended upon the charming town of Chinchón, Spain for the…
May 26, 20251 min - Part 35
Day 35: AI isn’t just for research papers and pitch decks.
AI isn’t just for research papers and pitch decks. Last week, I used it to summarize a meeting… while walking through a quaint Spanish town. (10/10 would recommend both.) The magic isn’t in AI doing e…
May 27, 20251 min - Part 36
Day 36: At last week's #AidiumAIHackathon, we reimagined the search bar.
At last week's #AidiumAIHackathon, we reimagined the search bar. Instead of “search by name,” what if you could ask: 🗣️“Who’s most likely to close this month?” 🗣️"Who just got pre-approved?” 🗣️"Which …
May 28, 20251 min - Part 37
Day 37: Mortgage moves aren’t made on luck. It’s timing. Precision. Awareness.
Mortgage moves aren’t made on luck. It’s timing. Precision. Awareness. Aidium Agents don’t guess. They know. AI-powered nudges that hit at the right moment—refis, rate changes, follow-ups—no more “may…
May 29, 20251 min - Part 38
Day 38: A quiet Saturday used to be for catching up on documentation.
A quiet Saturday used to be for catching up on documentation. Now? It’s where I rethink delivery. Because here’s the secret no one wants to say out loud: You can have the best product in the world… Bu…
May 30, 20251 min - Part 39
Day 39: Here’s the truth about SaaS delivery that most people won’t tell you:
Here’s the truth about SaaS delivery that most people won’t tell you: The tech is important, but it’s not the hard part. The hard part? It’s the messy middle—where real people meet new systems. As a P…
May 31, 20251 min - Part 40
Day 40: Today, we pause.
Today, we pause. It’s easy to get caught up in the day-to-day of building, delivering, and solving in the world of #fintech. The next feature. The next milestone. The next client call. But today, it’s…
Jun 1, 20251 min - Part 41
Day 41: Ever heard of a project that took nine years to fully implement?
Ever heard of a project that took nine years to fully implement? Yeah… I lived it. My first experience in implementation wasn’t in a sleek corporate office. It was while working as a correctional offi…
Jun 2, 20251 min - Part 42
Day 42: Let’s talk about onboarding (again. I know...😉). So often, we treat it like a checklist: S…
Let’s talk about onboarding (again. I know...😉). So often, we treat it like a checklist: Set up the account, upload some logos, import a few CSVs, and… done. But if you think onboarding is just about …
Jun 3, 20251 min - Part 43
Day 43: That One Coworker Who Just Gets You...
That One Coworker Who Just Gets You... You know the one I’m talking about. That coworker who just gets you. They’re the first to slide into your DMs when they see a bug in production. They know exactl…
Jun 4, 20251 min - Part 44
Day 44: We’ve all heard it:
We’ve all heard it: “We bought a CRM... but no one used it.” The first post in our Mortgage Executive Insights series with Ryan Grant dives into why that’s so common—and what to do differently. At Len…
Jun 5, 20251 min - Part 45
Day 45: I used to think hobbies were a nice-to-have. Something you pick up when the emails stop an…
I used to think hobbies were a nice-to-have. Something you pick up when the emails stop and the to-do list is finally empty. Spoiler: the list never empties. The emails never stop. And hobbies? They’r…
Jun 6, 20251 min - Part 46
Day 46: Please join me in welcoming Bill Lage to the team as our new Senior Training and Enablemen…
Please join me in welcoming Bill Lage to the team as our new Senior Training and Enablement Specialist! 🎉 Bill brings a wealth of experience in crafting training programs that actually stick—the kind …
Jun 7, 20251 min - Part 47
Day 47: You write bad prompts on ChatGPT.
You write bad prompts on ChatGPT. You commit the 7 deadly sins of prompting: 1. No context ("Analyze this" with zero background) 2. Vague instructions ("Write about marketing") 3. Treating it like Goo…
Jun 8, 20251 min - Part 48
Day 48: Stillwater, MN—encapsulated. (Yes, the pun is fully intentional and entirely satisfying.)
Stillwater, MN—encapsulated. (Yes, the pun is fully intentional and entirely satisfying.) After stumbling on this visual technique from How to GenAI I knew exactly which city deserved the capsule trea…
Jun 9, 20251 min - Part 49
Day 49: I didn’t ease into tech—I was thrown into it.
I didn’t ease into tech—I was thrown into it. My first corporate job after leaving corrections? It was a buffet of roles, titles, and chaos. I was: 🎨 The UX designer (with zero Figma experience) 🧠 The…
Jun 10, 20251 min - Part 50
Day 50: SaaS and fintech will humble you faster than a code freeze on a Friday.
SaaS and fintech will humble you faster than a code freeze on a Friday. Just when you think you’ve nailed a rollout, someone forgets a permission toggle and suddenly your “seamless launch” has custome…
Jun 11, 20251 min - Part 51
Day 51: Geriatric millennials in SaaS are a very specific breed:
Geriatric millennials in SaaS are a very specific breed: We remember dial-up. But also how to customize HTML and CSS. We build product strategies by day and cry about knee pain by night. We were raise…
Jun 12, 20251 min - Part 52
Day 52: My dad, Steve, worked in a printing press bindery for over 40 years.
My dad, Steve, worked in a printing press bindery for over 40 years. No glamour. No corner office. Just honest, hard work done well. He’d come home with glue on his hands and stories about machinery t…
Jun 13, 20251 min - Part 53
Day 53: Everyone in fintech crosses paths eventually
Everyone in fintech crosses paths eventually SaaS feels massive until you work in fintech—and then it’s basically one big Slack channel. Mortgage tech, banking SaaS, regtech… the players move around, …
Jun 14, 20251 min - Part 54
Day 54: Must read post. AI is not going to replace humans. It's helping to enhance us, but we need…
Must read post. AI is not going to replace humans. It's helping to enhance us, but we need to know how to utilize it and make it work for us. You can't just type in a prompt and away you go. It takes …
Jun 15, 20251 min - Part 55
Day 55: It’s not glamorous.
It’s not glamorous. It’s not flashy. It rarely makes the roadmap. But the glue work? ✅ Chasing down clarification on a JIRA ticket ✅ Translating tech for non-tech folks ✅ Making sure someone actually …
Jun 16, 20251 min - Part 56
Day 56: The "One Feature" Trap: Is Your CRM's Low Adoption Costing Your Business Its Future?
The "One Feature" Trap: Is Your CRM's Low Adoption Costing Your Business Its Future? We've all been there: Your current CRM might offer one or two features that your team genuinely loves. It feels "go…
Jun 17, 20251 min - Part 57
Day 57: In SaaS startups, something is always on fire.
In SaaS startups, something is always on fire. Not metaphorically. Literally sometimes (hi, prod bugs). The goal isn’t to make the chaos stop. It’s to build better smoke detectors. 🔥 Incident processe…
Jun 18, 20251 min - Part 58
Day 58: Tired: “Support is expensive.”
Tired: “Support is expensive.” Wired: “Support is the reason people stay.” Your support team is your front line. Your early warning system. Your brand stewards. Your feedback loop. If you treat suppor…
Jun 19, 20251 min - Part 59
Day 59: Right product, wrong time = no traction
Right product, wrong time = no traction I’ve seen brilliant ideas fail in SaaS. Not because the product was bad—but because the market wasn’t ready. The tech was solid. The pitch was tight. The team w…
Jun 20, 20251 min - Part 60
Day 60: I have an open-door policy.”
“I have an open-door policy.” Cool. I also have a "locked file drawer policy" for my own peace. Great leadership doesn’t mean 24/7 availability. It means being present when it matters, not available f…
Jun 21, 20251 min - Part 61
Day 61: Did you know there are still organizations using paper and pen for critical system trackin…
Did you know there are still organizations using paper and pen for critical system tracking? In the mid-2010s, I worked with a law enforcement agency still logging correctional activity in giant leath…
Jun 22, 20251 min - Part 62
Day 62: Let’s talk Microsoft.
Let’s talk Microsoft. They’ve started replacing human roles with AI. And sure, I work in tech. I build AI into solutions. But I’m going to say it louder for the folks in the server room: AI isn’t here…
Jun 23, 20251 min - Part 63
Day 63: 95% of LinkedIn posts die at 500 views.
95% of LinkedIn posts die at 500 views. And posting daily means nothing... Unless you're doing it with strategy. So many people confuse "being active" with "making progress." Especially on LinkedIn. T…
Jun 24, 20251 min - Part 64
Day 64: You know what gets SaaS orgs stuck?
You know what gets SaaS orgs stuck? Living in the weeds. You can be amazing at tracking tickets, delivering training, or updating dashboards—but if you can’t connect those micro-actions to the macro g…
Jun 25, 20251 min - Part 65
Day 65: We're hiring! 🚨
🚨 We're hiring! 🚨 Our Marketing team is looking for a Strategic Communications Specialist. If you're passionate about creative thinking and impactful messaging, this is your opportunity to help shape …
Jun 26, 20251 min - Part 66
Day 66: If your core system hasn’t evolved since before Y2K, you don’t need a rebrand.
If your core system hasn’t evolved since before Y2K, you don’t need a rebrand. You need a technical intervention. Shiny new features are great. But if your platform is built on spaghetti code, all the…
Jun 27, 20251 min - Part 67
Day 67: You want ARR to grow?
You want ARR to grow? Your CS/AM team better be more than a glorified helpdesk. Customer Success/Account Management is your retention engine. They’re the difference between a customer who renews and o…
Jun 28, 20251 min - Part 68
Day 68: Canva + D-ID = Magic in a Slide Deck
Canva + D-ID = Magic in a Slide Deck Have you played with Canva’s AI avatars powered by D-ID yet? If not—prepare to never give a boring training presentation again. Upload a script, pick a friendly AI…
Jun 29, 20251 min - Part 69
Day 69: Every project has that one moment where someone says, “Wouldn’t it be cool if we also…?
Every project has that one moment where someone says, “Wouldn’t it be cool if we also…? Cue the internal scream. Let’s be honest—scope creep isn’t always malicious. Sometimes it’s excitement, a good i…
Jun 30, 20251 min - Part 70
Day 70: A CRM isn’t just a place to store names and numbers.
A CRM isn’t just a place to store names and numbers. If your sales team is treating it like a glorified Rolodex, you’re leaking revenue. CRMs should be active ecosystems—segmenting leads, triggering a…
Jul 1, 20251 min - Part 71
Day 71: Nothing says “SaaS go-live in 3 days” like simultaneous celebration and panic.
Nothing says “SaaS go-live in 3 days” like simultaneous celebration and panic. Everyone’s asking: • Is the data clean? • Is training done? • Do we even remember the original business problem? Here’s y…
Jul 2, 20251 min - Part 72
Day 72: No thoughts. Just gratitude, grilled things, and one day off the calendar.
No thoughts. Just gratitude, grilled things, and one day off the calendar. Reminder: it’s okay to rest. Even your favorite SaaS won’t crumble if you step away for 24 hours. Go outside. Or don’t. Just …
Jul 3, 20251 min - Part 73
Day 73: One of my first lessons in project management came from working in a jail.
One of my first lessons in project management came from working in a jail. You want stakeholder management? Try balancing the needs of inmates, guards, and nurses. You want process improvement? Try ge…
Jul 4, 20251 min - Part 74
Day 74: Day 84 of #90DaysofSaaS
Day 84 of #90DaysofSaaS This is the final week. When I started this challenge, I wasn’t chasing virality. I was chasing clarity. Clarity around what I believe. Clarity around what I know. Clarity arou…
Jul 5, 20251 min - Part 75
Day 75: What’s your #1 CRM headache right now?
💬 What’s your #1 CRM headache right now? We work with mortgage teams every day who tell us some version of the same thing: > “We’re using three systems to try to do the job of one.” > “Our top produce…
Jul 6, 20251 min - Part 76
Day 76: I went to a startup networking event at a brewery, and honestly? 10/10 would recommend. 🍻
I went to a startup networking event at a brewery, and honestly? 10/10 would recommend. 🍻 There’s something magic about being in a room full of people who are deep in the trenches—whether they’re buil…
Jul 7, 20251 min - Part 77
Day 77: In SaaS delivery—and honestly, in life—most success isn’t built in breakthrough moments.
In SaaS delivery—and honestly, in life—most success isn’t built in breakthrough moments. It’s built in: • The meeting you almost rescheduled (but didn’t) • The ticket you documented with just enough d…
Jul 8, 20251 min - Part 78
Day 78: You ever sit through a strategy presentation that’s 80 slides long and still walk out aski…
You ever sit through a strategy presentation that’s 80 slides long and still walk out asking… “Wait, what are we actually doing?” Same. We throw around the word strategy like it’s sacred. Like it live…
Jul 9, 20251 min - Part 79
Day 79: It starts the same way:
It starts the same way: “We just want to set up the CRM.” “It’s a basic integration.” “No major workflow changes.” Lies. All lies. (Said with love, of course💛) Every single SaaS implementation is a tr…
Jul 10, 20251 min - Part 80
Day 80: You ever sit through a strategy presentation that’s 80 slides long and still walk out aski…
You ever sit through a strategy presentation that’s 80 slides long and still walk out asking… “Wait, what are we actually doing?” Same. We throw around the word strategy like it’s sacred. Like it live…
Jul 11, 20251 min - Part 81
Day 81: It starts the same way:
It starts the same way: “We just want to set up the CRM.” “It’s a basic integration.” “No major workflow changes.” Lies. All lies. (Said with love, of course💛) Every single SaaS implementation is a tr…
Jul 12, 20251 min - Part 82
Day 82: We’ve built entire tech stacks around the idea that we can scale trust.
We’ve built entire tech stacks around the idea that we can scale trust. Smart CRMs. Conversational AI. Sequenced outreach. All designed to mimic that magic moment when a customer says, “I feel like th…
Jul 13, 20251 min - Coda
Coda — 90 posts.
90 days. 90 posts. 90 chances to show up, say something real, and see what sticks. I didn’t start this to go viral. I started it because I wanted to write my way through the noise. And here’s what I f…
Jul 14, 20251 min