Meditation on my 2 years at Caseware

Food for thought for my candidates who are deliberating over a decision to join the company


Do I recommend joining Caseware?

Yes. Absolutely. Otherwise, what would I be still doing here?

In this article I will cover:

  • My candidate pitch
  • Org structure
  • My story of securing the role
  • Why I have chosen Caseware at that time
  • My reasons for being here
  • What’s next

“Hi, this is Chengeer from Caseware. How are you?”

If you are hearing this through your phone, you have decided to jump on a call with me. Congratulations. At least we know you are open to exploring what is possible. And trust me. I am here to delight 🤌 🤣

Small talk. Ice-breaker. But then I will ask you if you have any context on Caseware. We (recruiters) do that to see if you’ve done your research beforehand.

Totally cool if not. Life gets busy and it is my job to provide the information. But you are definitely getting bonus points when you show that you have done your due diligence.

What’s the logic here? Top performers don’t look for jobs. They look for career moves. And you can’t make a strategic career move if you lack information. That is why top talent always do their research. They know that their decision will change their life so they don’t take it lightly.

After the intro part is over, I will proceed with the “Candidate Pitch”. Everyone is doing it differently. But here is mine.

Caseware is the original Canadian Fintech. 35 years of history. Founded and built by accountants for accountants. We are a SaaS shop. We make software for accounting firms and internal audit organizations, but we service not just mid-sized firms but enterprise, governmental, and Big 4 organizations.

But all the fun stuff started for us a couple of years ago. In October 2020, we have secured an investment from Hg — a private equity firm based in the UK and with this injection of capital we have been going through a huge business transformation.

I joined Caseware in March 2021 and we were at about 300+ people at that time. Today we are pushing a 1000. We had 6 acquisitions: Houston, Denmark, Netherlands, UK, Germany/Romania, opened an entity in Colombia, plus there are more deals in the pipeline. The whole executive leadership team is new to Caseware but not new to the game. Many of them worked together in previous organizations.

As you can tell, we are very aggressive on the inorganic growth and there is a capital to deploy for M&A activities so this could be a good indicator for you of the financial health of the company. And we are just getting started.

But let me give you a little bit more context on the role itself…

This is it. That’s my spiel. It’s fast, concise, and unsophisticated.

IMHO company branding is important for candidates but job branding will always hold more weight, so most of my time in the conversation I will be focusing on the role itself.

The roles are different within the organization, so I will just give you a quick snapshot of what the organization looks like.

Why am I sharing this?

I think it is always good to have a bird's view of the org to understand the business plus understand where the role sits within the organization.

Org Structure

At the moment of writing [Jan 2023] the org structure looks as follows (If you are new to SaaS, this would be a good insight for you into how software companies are structured):

Leads the ELT (Executive Leadership team)

Leads Technology groups: Development and TechOps.

Software Development — these are the people who build Caseware products.

We have 4 main verticals:

  • Hybrid Cloud — Caseware Desktop platform. The most mature platform. 35 years of history. Java, C#, C++, JavaScript, WebAPI, Restful APIs, ETL tools. The flagship product — Caseware Working Papers.
  • Cloud Platform — This is what we are talking about when we say we are moving the industry to Cloud. Java, Springboot, Angular, AWS.
  • Smart Engagements — Another Cloud platform. An easy way to think about it is — it is Caseware Working Papers but on Cloud.
  • Data Analytics Solutions — two teams there. Data Ingestion and Data Analytics itself.

TechOps, led by a CIO (Chief Information Officer) — these are the people who enable all developers and overall operations from an IT perspective. We also have 4 teams there:

  • IT Ops
  • Cloud Ops (DevOps and InfraOps)
  • Information / Application Security
  • PMO

Function: Everything M&A

  • Mergers & Acquisitions
  • Integration work

Functions: Everything Product

  • Product teams, Industry Strategists — people who decide what to build and what the product should do
  • UX/UXR team
  • Technical writers
  • Localization & Translation team

Functions: Everything Marketing

  • Product Marketing
  • Corporate Communication
  • Marketing Operations
  • Engagement Marketing / Demand Generation
  • Digital Marketing / SEO / SEM / PPC
  • Brand Marketing
  • Content Marketing
  • Creative Services (Graphic & Video Designers)

Functions: Everything Sales

  • Customer Service
  • Customer Success
  • Direct Sales
  • Technical Sales
  • Training and Education
  • RevOps / SalesOps
  • Pricing

Functions: Everything Finance

  • Legal
  • FP&A
  • FinOps (corporate accounting, financial reporting, AP, AR, royalties & commissions, consolidations, etc.)

Functions: Everything People Operations

  • Total Rewards & Compensation
  • Payroll
  • HR (Talent Retention, Talent Development)
  • TA (Talent Acquisition)

At the moment of writing, we have 766 people on the org chart (not everyone might be reflected as some integrations are still on the way).

My Story

Ok, well, my story of getting a job at Caseware is actually pretty funny.

I was on a hunt after finishing my contract with the previous organization. Lots of networking, tons of applications, dozens of interviews.

Browsing on LinkedIn, I find this Slack community for HR/TA folks called The People People Group (TPPG) led by Martin Hauck.

I sent a request to join followed by a message on LinkedIn to Martin: “Hey! Just applied for TPPG. Let me in please.” We connected but nothing happens.

A few weeks later I get a message from Martin: “Hey, are you in?” “Still waiting.” “~ Ok, hold on.” And so I join TPPG.

Within 1–2 weeks I see somewhere a posting from Martin: “If you are a recruiter, I want to talk to you.” I comment. Send DM. Nothing happens.

One day my PC rings. A call from Martin. Normally, I am groomed up, dressed up, my resume printed, and I am ready to rock the interview. This time I thought it was just a coffee chat. I am in my home t-shirt, my hair is messy, I am severely underslept, but we are chatting. 20–25 min into the conversation it hits me: “Hey…. this guy is interviewing me.” ~ “Hey are you interviewing me?” “~ Yeah. I actually have some openings on my team.

Oh good. We chat a bit more but in the end, I say: “Hey, Martin. I truly enjoyed the conversation but I don’t want to give false hopes and set wrong expectations. I am actually sitting on 3 offers. Got verbals.” And I was indeed. “~ No problem, man. All cool.” We say our goodbyes.

6 pm in the evening I get a text: “Hey, I don’t want you to text me next week and say you accepted another offer. Mind if I arrange some calls for you?” Sure. Conversations never hurt.

I met Martin on Tue. Dipinti on Wed. Lorena on Thursday. By Friday I had an offer.

I have turned down the other 3, accepted the offer with Caseware, and never looked back.

Why I have chosen Caseware at that time

I chose people.

Caseware is the only company that made me feel that they really want me. I’ve met so many companies and I was feeling that I am going through scrutiny — I am being selected for the role. The Caseware team made me feel that it is their privilege that I have chosen them over all others. I still remember that feeling, and this is the feeling I want to give to everyone. It is a special feeling indeed for a human — to be recognized, to be wanted. If you choose to join us, it is our honor to share this ride with you.

I didn’t fully understand what exactly was the product and the business model at that time. I still don’t think that everyone fully understood that at that time. We are not accountants by trade and the company has been around for 30+ years.

I am 2 years in, and I barely scratched the surface to understand the intelligence behind the Caseware machine. I know enough to be dangerous (in my function), but the complexity of the Caseware product suite is very hard to grasp even for seasoned professionals.

When I was making my decision, I looked at the caliber of people I was joining. I knew that they have done their due diligence and they see reasons to join that I don’t yet see.

Sheryl Sandberg, the COO of Facebook, once was asked about the best piece of career advice she can give. She said:

“If you’re offered a seat on a rocket ship, don’t ask what seat!”

Based on the conversations I had, my instincts told me that Caseware was a rocket ship. So I jumped in. What happened next confirmed what became one of my main decision-making rules:

Always trust your instincts.

2 years later, why am I still here?

There are two sets of reasons. First — the business side. Second — the people side.

  1. Anti-fragility. At the moment of writing, we are going through a recession. New day — new layoff in tech. This sucks. Times are hard for everyday people like you and me. Now, I am not saying that Caseware is recession-immune. Nobody is. But Caseware is well-positioned and relatively recession-proof. Accounting was here 600 years ago and will be here 600 years later. People who enable accountants would probably find their place under the sun. We know this time will be challenging. I am under no illusion that Caseware too can sustain losses. I can lose my job tomorrow for that matter. Talent folks are in the worst position — if the business is not doing well we are the first through the door. But for an individual, this should not be a concern. We deliver our best work, focus on how to make ourselves recession-proof, and remain intentional about keeping a positive outlook.
  2. Exposure to the Private Equity. Being in a PE-backed private company has its very strong advantages. This is not a VC business and not a public company. Caseware is a fairly nimble business and has a high degree of autonomy. A normal Private Equity run is 4–7 years depending on the company's performance. Some form of exit is obviously a potential endgame for us. But many players joined Caseware understanding that if they deliver for the PE, they can get invited for the next ride. Hg Capital has a portfolio of 40+ software companies and they are truly a powerful ally to have.
  3. Strong ELT. Many of the ELT members worked together before. This is not their first rodeo. It's a well-glued team, they are very smart, and the collective intelligence and experience give them a solid foundation for sound executive decision-making.
  4. Canadian FinTech. There are not many original Canadian software companies that are successful. There are even fewer fintech companies among those. If you have a patriotic sentiment about supporting a Canadian business, Caseware will be a great organization to join.
  5. It is SaaS/Tech. Not sure what industry you have been working in but in my world (HR/TA) tech is King. You will see not only the most high-functioning People Operations team but also the best-in-class talent. A lot of smart people come to build tech companies and you will learn a lot from those smart people. Look at PayPal for example, they were a bunch of geniuses and now they are all multi-millionaires.
  6. Flexibility & Autonomy. Caseware is a flexible work environment. Some teams are set to work in a hybrid mode because of the nature of the business. Some are working remotely. But Caseware is truly a ROWE (Results-Oriented Work Environment). No micromanagement. No drama. No nonsense. Need to go see a dentist or drop kids off at school? NP. Act like an Owner. Deliver. And no questions will be asked.
  7. Largely Acquisitive Business. 6 acquisitions in the past 17 months — this is a lot for any software company. More to come. This is just the beginning. Where there is growth, there is an opportunity to make an impact. You make an impact — you build your reputation. And from that reputation new opportunities stem. This is not a sales pitch. This is my personal experience.
  8. International Presence. Regardless of the function you get a chance to get international exposure. This will be great for your career development. From a Graphic Designer to a Software Developer, to even someone like me in a Talent Function — your work will be seen across the globe.
  9. New office. Our head office is located at 351 King St E., Toronto, 🇨🇦, 5 min from Distillery District. The office is an amazing space. Fresh, clean, and minimalistic, with a lot of space for collaboration, deep work, and brainstorming meetings. If you are in GTA and having a productivity zone matters to you, you will enjoy coming to the office.
  10. Compensation. We have a robust but constantly evolving compensation philosophy. Do you know how some companies out there are trying to lowball you? This is not the case with Caseware. We leverage statistical tools to gain insight from the market to understand what the 25th, 50th, and 75th percentile within the salary bands look like. This data, the level of the candidate, and the ability to drive enterprise value inform our decisions at the offer stage. Our Offer is a product of a lot of smart people working together to find an alignment that works well for both parties. We don’t just acquire Talent. We work hard to retain it.
  11. A Complex Problem to Solve. I know that even for many accountants accounting is not sexy. But you know what is sexy? Solving a real systemic problem that exists in the world. The problem is huge and the opportunity that comes with it is gigantic as well. Automation and Software as Leverage is a solution that is created by people for people — it exists to liberate humans from thoughtless mind-numbing work and unleash human potential and creativity. Plus, if the software exists in the fintech space it enables and promotes economic growth. And this is the first problem we need to solve. We will probably have to get rich before we have the capacity to think deeply about our spiritual problems as a race.

Our CTO Matt Baxter writes about “Why Caseware?” much better than I do. Read it HERE. 👈

My favorite reason of all is People. I can talk about Culture all day. So Why?

  1. First, this was important for me. I was looking for the right bunch of people. I wanted to place myself in an environment with a high density of Extremely Intelligent Problem-Solvers. Those who leave their ego at the door and come together to solve complex problems. I found them at Caseware.
  2. Second, relatively flat org structure. Executive leaders are communicative and open to conversation. Senior leaders and mid-level management embody the standards we are looking for in the talent we acquire. Ideal Team Players: Hungry, Humble, Smart. High Energy, High Intelligence, High Integrity. They will elevate your game just by being with you in one room.
  3. Third, I was blessed with an opportunity to personally impact the culture here. 75+ external hires to date and counting. I have certain principles when it comes to hiring: I don’t hire people I wouldn’t hire for my own company and I don’t hire people I wouldn’t feel comfortable working for. So I can tell you with an honest heart: all the people are bar-raisers second to none. They all operate at the next level. This is another reason why I love Talent Acquisition. I get to work with crème de la crème top 1% talent, build meaningful relationships, and learn from them.

What’s next

Well, hope I didn’t bore you with my stories. As I said, my job is to provide you with maximum information so that you could make an informed decision.

Whether Caseware is for you or not is your choice. My job is to show you a variation of reality that can be materialized should you choose to step into that door 🚪

If you are interested in exploring an opportunity with Caseware, our opportunities are posted HERE.

Make sure that you reside and are eligible to work in the region where the job is opened.

If there is something that interests you, you know where to find me.

DM me on LinkedIn or email me at:


If you want to be more successful as a candidate, with Caseware or not, feel free to check my library of resources. I update it daily. 👇


👋 Thanks for reading!

I’m on a mission to enable 1M humans to actualize their full potential and live a Purpose-Driven Life.

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