Software

Why We Don't Have Nice Things

By
Steve Hazelton
June 3, 2024
5 min read

I have always been fascinated by how product roadmaps are maintained. So much so that I feel it necessary to pen a bombastic screed on the topic.

(As an aside, when you talk to VC’s, they’ll ask, “What’s your {2-5} year roadmap?” I want to say, “Whatever needs to get built,” but I think better of it. Life Pro Tip: use words like, “disintermediate.”

I find there is little utility in years-long product roadmaps. Unless you ignore your users/customers. If you have a team conducting market research to determine what to build and then put it in a 2-year plan, then you’re ignoring your users. If you have a team advocating for your users and having hard conversations with engineering and sales, you are not ignoring your users.

This is why Gmail, 20 years later, still has the attachments at the bottom of the email instead of at the top, where they belong: the revenue team is filling the roadmap with better ways to sell your data. I digress.)

The three drivers of a company’s product roadmap are:

Things users want;

Things your sellers want;

Things your product team/engineers want.

They don’t overlap as often as you might think.

Your users want usability (and probably a ton of user-permissions stuff). They bought your product missing certain features, and they are OK with that. They primarily want your existing stuff to get better, easier to use, and easier to get data from.

Your sellers want new features. They usually want the best feature that your competitors already have.

Your product team is more complicated. Most teams want insane reliability, security, and speed. Teams run by CTO’s aspiring to wear black turtlenecks build their own UI framework from scratch so that the one thing the new thing does will be 1% better at something.

Where do they overlap?

  1. Your Revenue Teams and Users overlap around UI and reporting. If it looks pretty and has cool reports, it will sell software (1).
  2. Users and Engineering overlap in the desire for performance and reliability (2).
  3. Development and Revenue overlap at shiny things (3). When you hear “Minimally Viable Product,” you’ve found it. When you hear “App Store”, or “I took some screenshots,” you’ve found it.
  4. If you are wondering what happens when they all intersect, I don’t know. I can’t remember all three teams agreeing on a feature.

Your existing customers don’t care about shiny things. But you need to grow revenue, and the CTO is on board, so guess what gets built?

(I would like to say that building shiny things isn’t wholly a bad idea. You need to go for it every now and then. Sometimes, really cool stuff gets built. But, in my experience, that shiny MVP is going to the back of the update line the day it's shipped, and it will suck, forever. Related to this is why your “Admin” area is terrible. Don’t lie, you know it is.)

I have sat in so many board meetings where the CTO presents a roadmap, and the COO/Customer Leader freaks out. I was in an amazing one over a decade ago when the CTO’s priority was “voice enabling the product.”

Everyone blew a gasket.

If your customer falls in the woods, and no one is listening, do they make a sound?

If a user reports a bug or asks for a feature, if someone remembers to do it, it  will be manually logged in a drop-down menu in some silo. It’s also probably logged by someone who has no incentive other than to close the ticket as quickly as possible. In other words, if it gets logged, it will be stored somewhere that’s hard to get to, and no one will read it.

If a user is confused, or says something sucks, someone wraps the user in a warm blanket of apologies and moves on. In the worst case scenario, the user will get something like, “that’s actually how we intended it to work!”

(Once, in a design review, a UI team told me they hid a feature because they didn’t want the users to actually use it. It allowed people to opt in to having a paper check instead of a direct deposit. “How many support tickets did this cause last month?” No one knew.)

It takes hard work to know what the customer wants, or hates. It also requires honesty, and a bit of self-flagellation.

I ran into a CxO who wanted AI to “automatically write knowledge base articles.” I hear this as, “Our product is so confusing that we can’t manage the number of questions about how to use it.”

Get honest: fix the product. No one, ever, renewed because of an awesome knowledge base. Good products don’t need AI knowledge bases. They also don’t need churn prediction or quarterly business reviews, but that’s for another time.

To break this cycle, you must be rigorous about logging every feature request, bug, and UI issue. You’ll need to understand why customers are saying, “how do I do this?” and “that’s confusing.”

(Another data point: track when your people apologize. “What are we apologizing for?”)

How will you gather this brutal truth? You need to put someone in charge of collecting data from your 5-50 systems, organizing it by account, and attaching a cost-benefit analysis to each issue. Then put it in a spreadsheet and review it every week with the Revenue, Ops, Customer and Engineering teams. Soon everyone will develop a healthy anxiety about the quality of your product. Saying “no” to shiny things will get easier.

Do this and your customers will like you again.

End rant.

Do the hard things,

Steve

Similar articles

View all
Software

Have you heard this from your CEO?

Joel Passen
April 29, 2025
5 min read

"How are we using AI internally?"

The drumbeat is real. Boards are leaning in. Investors are leaning in. Yet, too many leaders hardly use it. Most CS teams? Still making excuses.

🤦🏼 "We’re not ready."Translation: We don't know where to start, so I'm waiting to run into someone who has done something with it.

🤦🏼 "We need cleaner data."Translation: We’re still hoping bad inputs from fractured processes will magically produce good outputs. Everyone's data is a sh*tshow. Trust me. 🤹🏼♂️ "We're playing with it."Translation: We have that one person messing with ChatGPT - experimenting.

😕 "Just don't have the resources right now."Translation: We're too overwhelmed manually building reports, wrangling renewals, and answering tickets forwarded by the support teams.

🫃🏼 "We've got too many tools."Translation: We’re overwhelmed by the tools we bought that created a bunch of silos and forced us into constant app-switching.

🤓 "Our IT team won't let us use AI."Translation: We’ve outsourced innovation to a risk-averse inbox.

It's time to put some cowboy under that hat 🤠 . No one’s asking you to rebuild the data warehouse or perform some sacred data ritual. You don’t need a PhD in AI.

You can start small.

Nearly every AI vendor has a way for you to try their wares without hiring a team of talking heads to perform unworldly 🧙🏼 acts of digital transformation.

Where to start.

✔️ Pick a use case that will give you a revenue boost or reveal something you didn't know about your customers.

✔️ Choose something that directs valuable work to the valuable people you've hired.

✔️ Pick something with outcomes that other teams can use.

Pro Tip: Your CEO doesn't care about chatbots, knowledgebase articles, or things that write emails to customers.

What do you have to lose? More customers? Your seat at the table?

CX Strategy

Talent gets you started. Infrastructure gets you scale.

Joel Passen
April 29, 2025
5 min read

We obsess over hiring A-players. But even the best GTM talent will flounder if the foundation isn’t there.

I’ve seen companies overpay for “rockstars” who quit in 6 months—not because they weren’t capable, but because they were dropped into chaos. No ICP. Bad data. No process. No enablement. No system to measure or coach.

Great GTM teams aren’t built on purple squirrels. They’re built on a strong foundation.

That foundation looks like this:

✅ A crisp, written ICP and buyer persona (not just tribal knowledge)

✅ Accurate prospect data to target the right ICP

✅ A playbook that outlines how you win—and how you lose

✅ A clear point-of-view that your team can rally around in every email, call, and deck

✅ Defined stages, handoffs, and accountability across marketing, sales, CS

✅ A baseline reporting system to see what’s working—and what’s not

When this exists, you can onboard faster, coach better, and scale smarter. It's not easy, and it’s not sexy, but it works.

Want to cut CAC and increase ramp speed? Start with your infrastructure. Hire into a structure.

Software

The Three Biggest Problems Facing B2B SaaS in 2025

Joel Passen
April 29, 2025
5 min read

Most B2B SaaS companies still operate like it's 2020. Everything changed: customer expectations, growth efficiency, and competitive dynamics have flipped.

Here’s what’s changed:

Net-New Growth is Slowing: Recent benchmarks show it’s not just a feeling—it's a trend. The 2024 SaaS Capital Performance Metrics Benchmark report notes a pivot from "growth at any cost" to "lower growth at reduced efficiency," with CAC Ratios, Payback Periods, and Net Revenue Retention all trending in the wrong direction. The biggest slowdowns? Private SaaS companies in the $10-$20M ARR range, where growth rates dropped sharply from 2022 to 2023.

Real-Time Expectations: Today’s customers don’t wait for a QBR. They expect immediate action when things go wrong—or when their needs change. When ignored, they escalate quickly. If your team is still relying on survey responses or notes from a quarterly meeting, you’ve already lost.

Lower Switching Costs/More Competition: SaaS is saturated. Data portability, budget flexibility, and competitive pricing mean your customers can and will leave. Loyalty isn't dead—it just has to be earned every day.

The old playbooks are outdated. In the past, churn was a problem you could try to fix before renewal. Now? It’s a daily risk.

📌 The solution isn’t more headcount (flesh) or more software (abstraction layers). It’s visibility and intelligence/insights. Business need knowledge that uncovers what customers are actually saying—across every channel/silo—and turns it into action before the renewal is at risk.

The playbook is changing fast. AI is raising the bar by transforming how teams detect realtime revenue threats, identify cross-sell opportunities, and respond to customer signals/behaviors beyond just login/usage data, opinions, and surveys. The delta between AI-powered companies and everyone else is widening very fast.

SaaS teams that win in 2025 will focus on minding GRR and stop reacting to churn—and start preventing it.

How many customers will you have to lose before you try Sturdy?

Schedule Demo
A blue and gray logo with a black background
A number of different types of labels on a white backgroundA white background with a red line and a white background with a red line andA sign that says executive change and contact request
A white background with a red line and a blue lineA number of different types of logos on a white backgroundA pie chart with the percentage of customer confusion and unhappy
A number of graphs on a white background