From IBM Account Executive to Enterprise Customer Success Manager

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Call me a nerd, but working at Convictional feels like stepping into a grand library where everyone around you has maxed out their library card as well. 

Hi there, I’m Kyle. I lead our customer success team as we enable seamless B2B trade for our customers

Before Convictional, I worked as an Account Manager at IBM.

After getting my bachelor’s degree from Queen’s Commerce in 2018 and exploring Europe I began IBM’s sales training program. This involved a year of learning the IBM sales method and putting those lessons into practice. The goal was to learn the tried-and-true sales playbook and execute it repeatedly. 

Through that experience, I realized that the right environment for me would be someplace I could strategize going from 0 to 1 rather than from 99 to 100. I wanted to study the first principles of the areas I was looking to master (like key account management) and learn to write my own playbook in a place where none existed. 

In this article, I’ll break down what the customer success manager (CSM) job description looks like for Convictional, why (or why not) working at a startup like Convictional will be a good fit for you, and what makes us a unique place to build a customer success career.

But when I first started at Convictional, I didn’t even understand Shopify or ecommerce.

From IBM to a startup

These days, my best hours as Head of Customer Success are focused around enabling the CS team to be successful. But when I first started full-time, to say that there wasn’t a lot of information available is an understatement. 

At that time, I did not hold any domain knowledge and barely knew what Shopify was. The market opportunity was completely unknown to me. To this day I still rarely buy things online, and I’ve never returned an item I’ve purchased online. 

Even with the excitement of joining a startup, it was hard departing from a “sure bet” career – sales at IBM, or “Big Blue” as our grandparents call it  – to join a small tribe of people crazy enough to pursue an overwhelmingly massive market. 

And small we were. When I joined Convictional, I started as a business development representative on the sales team. The rest of the company was composed of:

  • Two top-notch Shopify salespeople crazy enough to leave the company in its heyday
  • A programmer who went to school with one of the founders
  • Another programmer who I couldn’t find anywhere on the internet

We’re now a few multiples bigger than that initial stage. We have customer success team members who were former VPs of Merchandising, DTC ecommerce experts, developers-turned-account-managers, and the human equivalent of a Swiss army knife.  

I also know more about the market opportunity we’re hoping to capture. Behind the billions of dollars transacted each day are people who could benefit from a new method of trade, people whose lives could improve if we streamlined the process. 

Convictional’s customer success manager job description

There is a tendency to conflate CSM roles with reactionary work to help customers. This might be standard across other SaaS startups, but at Convictional, this is far from the truth. 

Our goal is to enable the best possible B2B trade experience in the modern era. To do this, we are setting the standard for what “seamless” B2B truly looks like. 

For our customers, partnering with us often means implementing dropship or a marketplace in their ecommerce strategy. 

For most of our customers, this is an entirely new business model. Thus, they rely on their Convictional point of contact – a CSM or key account executive – to guide them through setting up their online B2B marketplace. This might mean...

Our CSMs must be able to use their daily context of the customer experience to guide the  customer. They must have the project management skills to build customer relationships with new accounts until their marketplace launches. They must also have the communication skills to become a trusted advisor for executives and key stakeholders.

Another misconception is that the playbook for successful projects at Convictional is written in stone. The truth is, the customer support playbooks we use at Convictional evolve every quarter.

Each new customer brings a unique set of requirements and demands nuance. 

Each new account has a different set of metrics in mind when they think about “customer satisfaction”. Thus, our CSMs need to proactively identify problems we may not have solutions for, and build the plan needed to solve them. 

A Convictional CSM must be able to look across the projects, people, and products involved and pull together resources in ways that may not have been done before.

Being “above the line”: Tips on succeeding in a startup environment

The interpersonal traits you need to succeed in a startup are the basic requirements you need to succeed as a human being. 

Success as a startup employee is less about business models, market analysis, and 2x2 matrices. These are commodities, freely available online, and can be drawn up by anyone.

Instead, the true drivers of success in a startup environment are interpersonal vulnerability, a beginners’ mindset, and psychological safety needed to ask the tough questions in the right moments. 

Startup operators work with tight deadlines, lofty goals, and intense pressure. You move fast, together. Investing time into building core skills such as integrity, accountability, and honesty (especially with yourself) are the ones that have made a difference in my time at Convictional. 

I love the idea of “being above the line” that our COO Chris shared. This entails having a growth mindset, being genuinely curious, open to growth, and inviting new experiences as lessons. 

For me, this means asking for honest feedback when I knew I had areas for improvement. This required me to drop a layer of protective ego in order to truly hear what was being said and trusting that my teammates would continue to support me as I sought to improve. 

This also led to a bi-weekly learning sync with our CEO Roger to whom I would pose increasingly deep questions. This was my attempt to download his decade of industry experience into my own brain. 

Despite never learning this in business school, the concept of “above the line” has been the most impactful idea I’ve learned at Convictional to date. 

Onboarding & building a career in a hypergrowth startup

Convictional isn’t for someone who is afraid of being wrong and of letting go of their most deeply held beliefs.

We’re looking for people who draw inspiration from seeing a teammate reading a complex book or working on a hard problem. Every team-wide weekly update gives new ideas for learning, new rabbit-holes to dive into, and new opportunities to learn from someone else who shares your interests. 

Call me a nerd, but working at Convictional feels like stepping into a grand library where everyone around you has maxed out their library card as well. 


Learning involves making judgement calls (“should I branch into this new area of knowledge?”) and enlisting the help of others (“who can I share my dreams with who will support me?”). True learning is a hard process that is made much more enjoyable when you’re part of a larger tribe of learners. 

Convictional is a learning-first company. This commitment compressed years of career growth into months and forced me to level up as a person. 

Working with avid learners in an environment supportive of learning is the perfect place to work early in one’s career. 


Part of Convictional culture is being introspective, self-aware, and authentic. Any time I’ve shared a half-baked thought or question I was pondering, whether work-related or personal, my teammates were more than willing to talk through the idea with me or their lend support.

Compound time

At Convictional, we encourage everyone to dedicate 10% of their work hours to work “on” their careers, instead of “in” it. We call this compound time. This means investing time into skills that will compound over the course of one’s career,

Personally, I dedicate 9:00 am - 10:00 am on weekdays towards learning skills that increase my impact within Convictional. I used this time for a number of career-growth activities:

  1. Interviews with those 3 years ahead of me in career development
  2. A shelf’s worth of books expensed and borrowed
  3. Programming lessons through 
  4. Online courses on Coursera

An environment of focus

Convictional’s leadership team emphasizes a strong reduction of “noise” during the work day. 

There are no Slack pings, no unnecessary 10 paragraph emails, and no superfluous projects. Having sat in on 10-person meetings that could’ve been 3-line emails, I enjoy having control over my own calendar. 

We’ve deliberately created the space to say “no” to the unimportant and focus on projects that move the needle. If there are meetings, there are fewer things on the agenda, and all of them matter. This makes work far more enjoyable. 

Infinite games: How to know if the Convictional job description fits you

I had 3 reasons for joining Convictional:

  1. The sense of “what if”? What if we found sustainable customer relevancy? What if we captured even 0.5% of a trillion dollar market? What if we could be like those other software companies that always seemed a step ahead?
  2. Accelerated learning. I knew I’d learn 3x the amount in ½ of the time. The two co-founders crazy enough to leave were exactly the type of people I want to spend my days learning from. 
  3. A trillion-dollar, untapped market opportunity. Every day I work on a non-sexy, non-obvious problem that has the potential to free up hours in the day for tens of thousands of people. 

The task of building an organization fit to meet a trillion-dollar opportunity is no small feat. It involves rapid iteration with a tightly-knit team, and a commitment towards becoming the best versions of ourselves. This involves action, reflection, trust, and a higher-degree of self-awareness than I’ve encountered elsewhere. 

I would wholeheartedly recommend Convictional, but only to those who are passionate about living life as an infinite game

If the pursuit of improvement is exciting to you, then I recommend that you check out our open postings and apply.

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