Grounded & Steadfast

est. 2008

It’s hard to know where to start with this piece. It’s classic Rands. But it also hits close to home after discussing the validity of product managers recently. There are so many quotable bits from this essay, but let me share those that caught my attention.

Image courtesy of the Wildbit blog.

First, he wisely takes the time to frame the discussion. What is the difference between project, product, and program managers?

A project manager is responsible for shipping a product, whereas a product manager is responsible for making sure the right product is shipped. A program manager is an uber-mutated combination of both that usually shows up to handle multiple interrelated projects like, say, an operating system.

Then he describes some qualities of a good project manager:

A good project manager is one who elegantly and deftly handles information. They know what structured meetings need to exist to gather information; they artfully understand how to gather additional essential information in the hallways; and they instinctively manage to move that gathered information to the right people and the right teams at the right time.


Project managers don’t write code, they don’t test the use cases, and they’re not designing the interface. You know what a good project manager does? They are chaos destroying machines …

Lastly, he describes why a project/product/program manager is important to a team. It’s due to their focus, which is macro and micro at the same time.

Good project managers have a unique insight into the health of the project because it’s their job to have visibility into the entire machine.

If you work as an engineer, this article may help you understand what the people in these types of roles do every day, and how they can help you focus on your coding. A great read!

Note: this article came up recently as Michael Lopp has been sharing older posts from his site on Medium. Although the Medium link came through my circles, I chose to link to the original. If you want to highlight quotes or write a response, the Medium version is here.


The Changing Financial Industry

It’s interesting to watch the finance industry attempt to catch up to the web and technology in general. In my experience of running a business and working on the web, no one struggles more with the shifting landscape than accountants, lawyers, and bankers. Most are firmly stuck in the brick and mortar world they grew up in.

One classic example of this was my US based business account for running Fusion Ads. If I wanted to send a wire transfer, I had to start up VMWare Fusion, load up my virtual install of Win XP, open the banking site in IE, then insert a USB key fob and log in. Painful! But that was the world in 2011–12 and things have improved.

Most banks now allow scanned cheques. And I’ve been impressed with my personal banking officer. He’s young, he understands that current generations want to do things differently and does what he can to enable that. And now we’re seeing new startups attempting to bridge the gap.

One that caught my eye a few months back was a Canadian based startup, Wealthsimple. With a focus on the overall experience, it’s clear that this team is putting good design at the forefront of a financially focused app. It currently exists as a web app, as well as being available on iOS and Android devices.

I signed up and adding a small bit of funds to check it out. So far, it’s more than decent in terms of the experience. Initially, the process is daunting because it’s far different than most SaaS tools or web apps. On signup, you have to start giving out some private details and signing papers. That is a scary first step and goes against the grain of current web products, where an email addy is usually enough to check things out.

But we’re talking finances here, a very regulated industry, so that’s to be expected. But once you complete all that and add some funds, things are very enjoyable.

Compared with traditional options, Wealthsimple is far superior. I’ve had a friend who runs a financial advisory firm who has handled our investments for years. And while I always enjoy chatting with him, I never log into the web portal they offer. It’s butt ugly, plain and simple. Wealthsimple makes the simple act of reviewing the status of your investments daily a pleasure.

It’s too good actually, as I’m a firm believer long term investments should be done with a bit of a “set and forget” mentality. A nice UI makes me want to check in more often, not a good thing in this are … and the screenshot above proves my point. It’s been a bad week for the markets :)

Another area that has impressed is personal banking. As mentioned above, the overall industry is improving. And although Simple is still US only, YNAB has been a joy to use the past couple of years. And that team has been hard at work making the newest version, which is completely web based.

No more Mac desktop app. And I couldn’t be happier. Why? Because now they can sync with my bank! For the past 18 months, I’ve been using YNAB by painstakingly adding in transactions manually, one by one. Along with that major improvement for this Canadian, they’ve improved a lot of the aspects of their app (the goals are great, as is the “age of your money”), as well as tightened up their overall approach to budgeting. It fits very well with modern spending habits.

It makes me happy to see design helping real problems. Let’s hope this trend continues to spread (healthcare, anyone?).


Bethany Heck gives a long, in-depth explanation of why it can be acceptable to go against the widely held opinion of “do not use too many fonts” in a design. She starts by recognizing there is a reason this specific guideline came to be:

We can all point to questionable designs that use an excessive number of typefaces. You can sense when a designer is trying to compensate for a deficiency by throwing more typefaces into a piece.

But she goes on to give good advice for this “rule” (which can be applied to any other guideline as well):

… don’t let one designer’s opinion affect how you approach solving a problem. Given the right content and the right faces, any number of typefaces can work in a design.

From there she goes on to give lovely, nuanced examples. It’s a long read, but a beautiful one that is worth the time. This is the best the web has to offer: someone with talent and experience takes the time to share their knowledge with painstakingly crafted examples that illustrate their point.

Side note: be sure to check out Bethany’s project of love, The Ephesus League. What an example of a master at their craft.



There’s a reason email is so addicting. Like a roulette wheel or a slot machine, there’s always a chance of something exciting coming your way. On the other hand, there’s also an equal chance that terrible news is coming your way in any given piece of electronic mail. The kind of email that makes it hard to sleep at night as your heart races and anxiety kicks into high gear.

That was the kind of email we received from Loren Brichter when he had decided to sell his company to Twitter.

In an interview with (published on Medium. natch), Matt Haughty gives some “lessons on lifestyle business”. As I read the piece, it brought me right back to the days of running Fusion Ads. Matt’s experience was very similar to our own.

For a year and a half, I waited. The revenues kept trickling down. It was this long terrible process, losing half overnight but then also roughly 3% a month for a year and a half after.

We didn’t not have a precipitous drop of this sort, but I do know the feeling of watching this slow decline. Matt summed it up perfectly:

Two weeks later traffic went back to how it was. But in those two years, the ad revenue market had changed. Even with the traffic, we were making half as much money because the market had kind of died in the interim.

That’s exactly what my experience was. We were blessed to get in the business in 2009. And having our ads in Tweetie for Mac (the ancestor of today’s official Twitter client for OS X) enabled our business to flourish. But, like MetaFilter, we had too much of our revenue generating traffic from one source. When that source went away, it was a punch to the gut.

Fusion Ads survived and went on for another two years before we sold it. But the writing was on the wall, the ad business was changing. We got out because it felt like a race to the bottom.

The important lesson I took away from my first business was what every investor learns about: diversification. When you run a business, you want revenue being generated from multiple sources. Hopefully, with multiple strong sources.

I vowed to never make this mistake again. And even further, I vowed to never run a business that was completely dependent on the work of others. Selling ads based on other people’s traffic worked, but it’s hard to run a business when you're 100% tied to other people’s success.

A freelancer wants clients of different sizes, with some retainers and a good mix of new work. A SaaS team wants a varied customer base with related, but slightly different needs (jobs to be done). It’s cliché, but there’s a lot of truth in the old saying. When it comes to eggs, it’s good to have a few different baskets.


Susan Dominus, writing for the NYT Magazine, writes about the importance of team culture over policy. The focus of the article is to illustrate the point that even when companies tout flexibility through corporate policy, it can take time for team members to feel comfortable allowing their personal life to encroach upon the boundaries of their professional life.

The article is a good one (part of an interesting series titled, “THE WORK ISSUE: REIMAGINING THE OFFICE”). Dominus states that making this type of shift has to start with the employers way of thinking and talking about this subject of work-life balance:

For years, employees and human-resources professionals spoke of the ubiquitous desire for ‘‘work-family balance.’ … at best, balance is perhaps an unrealistic goal: a state of grace in which all is aligned. ‘‘Balance is something you want but can never have,’’ says Cali Yost, whose specialty is helping businesses implement flexibility strategies. She started referring to ‘‘work-life fit’’ to capture the way workers try to piece the disparate parts of their lives together. (The American Psychological Association and the Society for Human Resource Management have started to use this term as well.)

The following point stands out as the most poignant aspect of work that people struggle with:

Workplace stress often is more accurately described as workplace guilt, an especially corrosive form of distress.

Which makes working for a company that includes guidelines such this so enjoyable:

We don’t babysit. Everyone is responsible and accountable for their contributions.


We believe most things are not urgent. Be patient, stay calm, and go home.

I’ve worked in many different team environments and getting the right balance is hard. Our North American sense of self worth is tied to our vocation, so this entire subject is a delicate one. I’m glad to see it getting a lot of attention.


Customer-centric Roles in SaaS

When you're not a full time designer and developer, how do you get started working in the web industry? For many, the way to get a “foot in the door” is to start in a customer facing role. For many, the question to then answer is:

What next?

But before looking at the various options available to those in customer-centric roles, let’s cover some verbiage. What type of roles am I referring to here? Well, if you work on a customer service, success, or support team, I’m talking about you. Customer experience? That can be more of a design focused role or team, so let’s stick with the 3 S’s for now.

As I’ve mentioned before, there is a growing focus on customers, period. And although different companies approach the idea differently, there is a trend towards focusing on the entire experience a customer has with a business/brand. The people who work in service, success, and support are there to ensure the needs of those customers are met.

A career unto itself

The first option is to stay where you are. Although traditionally treated as a stepping stone to other paths, customer-centric roles can make a satisfying career.

Unfortunately, many companies also see these roles as basic and less vital to their overall success. As such, they treat the employees in these roles accordingly. Backchannel published a recent piece that highlighted this fact amongst the “Valley elite”:

As unicorn startups send customer service gigs to the hinterland, is Silicon Valley exporting its prosperity, or just dead-end jobs?

So if you want a career in a customer facing role, it’s important to recognize that finding the right company is the key to your job satisfaction. A low salary combined with being treated as a lesser contributor to the company’s success is not usually a recipe for happiness in the workplace.

But if you can find the right company and enjoy solving people’s problems, a support or service role for the long term may be a great option.

And if you choose to make this a career, how should you focus your time? I would argue that even those who take great delight in solving people’s problems need to find proactive activities to focus on over the long haul. Answering questions over Twitter, email, and live chat all day long, every day is a recipe for burnout. So good teams give their support staff time away from the inboxes to work on other things.

Creating documentation, educational materials, or test projects can help you learn your product better and are some good ways support staff can spend their time. Some of the best SaaS support people I’ve seen were those who were good at support in general, but over time they developed a focus in one area of the product they supported and became the go-to expert in that “thing”.

How to move into other roles

I hear this question from people from time to time. If you start in a support or service role, how do you move on to something different?

Again, this often comes down to finding the right company. I prefer companies who do their best to hire from within and are willing to provide the environment and opportunity for team members to follow their desired career path. However, this is not always an easy task.

Despite being a great company, a primary reason for my leaving Campaign Monitor was because it became clear that there was a mentality of “once support, always support”. It was not easy to move on from the support team to other teams. When a new position was posted, the desire was to hire someone who was already performing that same role somewhere else, rather than groom someone who was already on the team.

That type of thinking is understandable, to a degree. A company cannot always afford to train people for a new position. And so if you're looking to shift from customer support or success, it’s good to give yourself the best chance by acquiring some of the skills required in your desired role.

Many technically strong customer support staff would love to transition to being developers. If that is the case, working on your own side projects is a great way to both get experience and showcase your skills. Contributing to open source projects is another. The same approach could be true for design, writing, or marketing.

The issue with this approach is that you have to carve time out of the rest of your life to achieve the new skillset. The same hustle that is required to be able to start your own lifestyle business may be required to switch roles in the SaaS world. If you're single or married with children, this switch may be easier to achieve. But for many people, time for side projects is in limited quantity. So if you choose to take this path, do so with wisdom and plenty of caution.

Otherwise, your hustle can lead to burnout as well.

You may have noticed I haven’t mentioned Customer Success as much as Support or Service. This is partly because it’s a role with a slightly different emphasis. I’d tie Success more closely with product management than anything else. It involves a lot of research, product strategy, and writing. And it’s the type of role that can vary greatly from one company to the next. How does one move from the reactive work to the proactive? Again, working in the right place will help. From there, show your willingness to identify opportunities to improve your customer’s journey.

Writing: have a blog

And that is my other point of focus. I’m a firm believer that any type of role on a SaaS team benefits from writing. It helps every person clarify and hone their opinions, as well as improve their ability in their specific role (designers, developers, and everyone else). But this is most especially true for product managers, customer success managers, and marketing types.

Where as a designer can have a portfolio showing their work, and a developer can share their GitHub profile, the rest of us can showcase our skills and expertise with our own blog. Getting words “to paper” is the best portfolio you have.

And so I’d put reading and writing high on the list of priorities if I was looking to switch from customer support to customer success or product management. Start a blog, join the right community, and start sharing your knowledge.

Working in the SaaS industry can be very enjoyable. Challenging, but enjoyable. Finding the role you enjoy the most can take some time, but persist. It’s worth it!