Clawing Your Way Back From Embarrassment & Client-Facing MistakesFeatured

Our VP of Sales was looking across the board room table at me, deeply concerned.

“Was it not clear that these were doctors?”

I melted into the table.

Fuck. Fuck. Fuck. “No, that was clear.”

“Okay, so what happened?” It was my first enterprise kick-off call, and I just blew it. Our biggest client by ARR and headcount, and I just. Completely. Blew it.

I didn’t always have a passion for healthcare, or workflows, or SaaS, tech, or any of it. I wasn’t from Saas. I didn’t go to business school. I wasn’t from healthcare. I had an Honours BA in Sexuality Studies, a certificate in gender and women’s studies, and 5 years of experience as a server and a bartender. I’d done one internship as a PR Coordinator which turned into a 3-month stint followed by 3 months of burnout. I got a job at an LMS startup that ran out of money in 8 months, the catalyst for which was our founder spending $2000 on merchandise for a conference (out of the initial $70K runway) that generated no sales.

I applied to work at OnCall on Indeed. The woman who did my phone interview had left the company by the time I had my second round interview. She was the only woman who had worked at OnCall at the time I joined. I was interviewed by the CEO and a Customer Success Manager, and thankfully I got the job. I was employee #6, the only woman, and had only worked for one other tech company.

When they offered me a starting salary of $40K, I was elated. It was more than I was going to ask for, and it was more than I had been making in my previous role. The hiring CSM made a remark about this salary being a sacrifice in start-up land; I nodded and tried to hide my excitement, thinking about how thrilled my partner would be when I told him I’d landed my first job with a salary, and I wouldn’t go back to bartending.My desk was under the mini basketball net that the other team members would shoot at when they were in the mood. I was too excited by the opportunity of the job and the role to want to rock the boat by saying anything about that. In hindsight, that was a mistake. I find myself thinking now of all of the times I made myself smaller to fit in in those early days when I would’ve been more valuable if I had made myself bigger. Not just for the company, but for myself. Lesson #1: Don’t make yourself small because of perceived social pressure.

It wasn’t until the second year of working for OnCall that I was our Enterprise CSM. I had been promoted and had started to build an understanding of what our clients were looking for, and how we could support them.

We didn’t have any true enterprise clients at that point, or at least none that were looking to grow with our current tools. I was given several accounts that had difficult characters to manage – these were my favourites. There was always a psychological reward for me in being able to handle people who seemed unreasonable or tricky, or particular. If it hadn’t been for that mentality, I wonder if I would have been able to stick it out for as long as I have. I prided myself on being able to build relationships with businesses and clients that the team felt were lost causes. I think to me it meant even if I didn’t know anything else, I could build relationships and that would mean I wasn’t a failure. Lesson #2: Eat the frog; you’ll learn the most that way.

We signed a huge hospital network, and their biggest location was going to be our stomping ground for the initial rollout. I spent an hour or so prepping with our VP of Sales and our CEO, where they downloaded their notes to my brain, and I was meant to take it all in (reading this in hindsight I think “an hour is basically no prep time”). There were so many terms I had never heard before, acronyms for staff and programs that they had spent weeks becoming familiar with, and I was meant to learn them in a few sessions preceding the kick-off they had scheduled. Lesson #3: Build your own framework for understanding.

Our kick-off structure was still being built (by me and the Director of CS), and it wasn’t completely clear what the best way was for creating our white-labeled product just yet. We had only just figured out how the logic for matching providers and patients could work on complex accounts thanks to a medical device company that wanted an incredibly cumbersome logic that I’d spent hours upon hours figuring out how to execute. There was no clear language established for talking to clients about the process for setting up, how could there have been? We were still inventing it. Lesson #4: Get in the weeds of your product and that makes up for lacking in process (to a point).

CS was technical support, and implementations, and customer success at this point, so I was always able to get my hands dirty with customer problems and solutions. I started to love figuring out those problems and presenting solutions, but the actual healthcare behind all of these process questions was still revealing itself to me. Who are all of the players at a mental health org vs primary care? What does an IME do? Why is every other company a weed start-up (hello 2019)?

We had a call with myself, the executives and some front-line people, and our VP of Sales. Their team were all extremely serious, and it had been made clear to me that they were the ‘come correct’ type of clients. I honestly felt like I had grasped the information that had been presented to me – until it came time to do the call. It fell apart nearly right away. I started using the wrong terminology, calling their providers therapists, instead of using primary care language (it sounds like a tiny thing, but it’s not, trust me). I tried to brush it off like the terms were interchangeable even though they weren’t. It became clear I didn’t understand what they were trying to achieve and what they would care about. I didn’t lead the call smoothly. I was trying to claw my way back to the shore, but saw quickly that any hope of there being an island was a mirage. Lesson #5: Don’t give up.

I didn’t ask nearly enough questions in advance of that call. I let the rest of the team dictate how information would be shared with me, and the call ended up being defined by that. I didn’t take ownership of the client relationship and show them that I was invested in who they were; not just the information sales had gathered during the initial process, but what they were really trying to do. Lesson #6: It’s your name on it.

You could have cut the embarrassment with a knife in that conference room. I had no idea at the moment what had just happened. I had been thrown into the deep end of a pool only to realise I’d been practising my golf swing thinking it was swimming. I was mortified. I could only promise that nothing like that would ever happen again, and then figure out how to make that true.

I made it my responsibility to get to the heart of the matter on their workflow, and everything they were trying to accomplish. It started to become clear that front-line staff loved talking about their workflows, and how they wanted to deliver patient care. They wanted to be involved in the process, and to be asked a million questions. My claim to fame in bartending was that I could memorise a 4-top’s orders including soup/salad, appetizers, drinks, and mains without missing anything, even the lemon slice on your diet Coke. This proved to be extremely helpful in working with clients looking to download an enormous amount of field-specific information about their jobs to be done. Lesson #7: Find your niche.

A few months later, I was on-site with the client leading a training session in front of 30+ employees at a time for 3 days straight with our VP of Sales and CEO. I was prepared. I had determined how I would be prepared. The staff loved it. We went out to celebrate as a team, and I really felt like I had accomplished something.

A year or so later, we signed a new client. Similar deal, huge opportunity, client in behavioural health, big network, lots of potential. I was still an Enterprise CSM. This time, my approach was completely different. I asked the sales team much more in-depth questions. I had the knowledge base to fill in the gaps from hundreds of other customer calls. I was an expert on the platform from hours and hours of doing support calls, workflow calls, and troubleshooting with coworkers. I had re-done the talk track for the kick-off call with our team, and I asked everyone for their input when putting together the deck to make sure there was alignment and nothing was missing.

Our VP of sales DM’d me on Slack after the kick-off.

“Jesus Christ Alex.”

Fuck. Fuck. Fuck.

“You crushedddddd that.”


Our Director chimed in to the chat, “best KO at OnCall to date.”

omg. I was spinning.

“+1 to that. That was the best OnCall KO I’ve personally seen. Great job prepping!”

Thinking back on that moment, I remember the feeling – sweet external validation. I belonged. I was a woman in tech. I was doing the thing. I was promoted to Manager, Enterprise Customer Success the next year. The following year I became Director, Account Management. Now, I’m Director, Professional Services, and building a department (DM me for workflow chats). I’ve tried to never lose my sense that all of this is fragile and that I could get ousted at any moment for being an imposter. It’s not a perfect system, but it definitely drives me forward to earn everything. Lesson #8: Everyone is an imposter.

So relatable! Wow. "Lesson #3: Build your own framework for understanding." THIS!
Thank you Courtney! I'm so honoured you read it.
Save that. You think you'll remember it forever, but those are amazing details to keep.
Definitely! All the more reason to keep writing, I suppose.
What a great read, thank you! Excellent advice and more power to you! 💪👌🙌
Thank you so much for reading! I really appreciate it.
Love this! Such valuable insights you've distilled from your experience and introspection!
Thank you so much! I'm so glad it was valuable for you.
Just started a new job this week and even though I haven't made any embarrassing mistakes yet, reading this has really given me the confidence to take my time to learn so that I can add value and grow in the long run
I’m so glad to hear that! ❤️ congrats on the new job