Chelsea MacDonald of Ada: “Know what you’re trying to accomplish”

Automate — If something is repetitive, a machine can likely do a better job than a human. Humans are not actually that great at repetitive tasks. Bored minds make mistakes. Automate to reduce error, increase efficiency and generally make your humans less bored. Can you automate client conversations? Automate who an upsell talks to based on data? […]

Thrive invites voices from many spheres to share their perspectives on our Community platform. Community stories are not commissioned by our editorial team, and opinions expressed by Community contributors do not reflect the opinions of Thrive or its employees. More information on our Community guidelines is available here.

Automate — If something is repetitive, a machine can likely do a better job than a human. Humans are not actually that great at repetitive tasks. Bored minds make mistakes. Automate to reduce error, increase efficiency and generally make your humans less bored. Can you automate client conversations? Automate who an upsell talks to based on data? Automate a follow up? Can you automate the personalization of those free users?


As part of our series about “How To Use Digital Transformation To Take Your Company To The Next Level”, I had the pleasure of interviewing Chelsea MacDonald.

Chelsea MacDonald is SVP, Operations at Ada, where she is responsible for Operations, Analytics, IT, HR and Recruiting. She specializes in helping fast growing organizations scale, with a focus on creating new digital experiences for employees and clients. She’s won awards for best workplace and best culture over her 15 year career and was a member of the team that was awarded the Best Intranet in the World by Nielsen Norman twice.


Thank you so much for joining us in this interview series. Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I started my first business when I was 12 and my first non-profit when I was 13. I’ve had a super varied career. I’ve been a part of every department in an org at some point for at least 3 months. The thread for me is always about finding a gap: in the market, in the community, in the business, and figuring out how to fill that gap to provide more value. It means I get to learn a whole lot, and I’m almost always doing something I’ve never done before which I find pretty exhilarating.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘take aways’ you learned from that?

I remember the first time I was a part of a company’s leadership team, I didn’t really understand what that really meant. When you’re a Director or a VP, often times the thing you’re rewarded for is being “the best”. You want to be the best VP or Director so that you can get promoted. When I first joined a leadership team, I set out to be the best. And I was! I was the only exec meeting their targets, and I felt so proud of my accomplishments. But the deal was, so what? Your job as a leader is to make the company reach its full potential, and that means spending a lot more time helping and whole lot less time shining.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I have ADHD. At my first corporate job, I was constantly being asked to be “less ADHD”. It was really tough. At my next career, two of my three co-founders also had ADHD, and it was a true liberation. I could talk as quickly as I wanted to. I could say out loud the weird and wonderful things my ADHD brain does. And those things were rewarded. It gave me the confidence to really be myself, and to understand that my ADHD was a gift and not just a curse. I still have to think about how my ADHD behaviour appears to the more neurotypicals amongst us, but I make that choice without shame, and I think that is a gift I was given I hope I can give to other folks with differences out there.

And very specifically, the two co-founders with ADHD had no filter. Every decision that got made or didn’t get made, I knew why and how. I got to listen to the inner workings of their brains constantly, and I learned so quickly that way. It’s a thing I try to emulate as a leader today. I over communicate, both because I think it’s valuable, and also because I don’t have enough norepinephrine in my brain to stop it.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I read 40–60 books a year. Reading has pretty much always been a big part of my life. I choose stories that are about people that are different from me, to try and understand how the life that I live is influenced by the body and brain I find myself in. Some of the most impactful have been The Magic Mountain, which is about nothing, the original Seinfeld (I am definitely a go-go-go person) and Tara Brach’s Radical Acceptance. I get hung up on injustice a lot in the world, and I find her ability to move through acceptance of things to action is helpful for keeping me mentally healthy and still fighting every day.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

Ada started with Mike and David (our co-founders) answering customer service inquiries themselves. They wanted to understand what it was like to be an agent, and what it was like for a business to try and keep up with the ebbs and flows of customer service inquiries.

The company first started around solving that problem: how do you scale customer support? Customers spend 43 hours of their lives on hold. How do we make that problem go away?

As we grew, the mission and vision evolved. It wasn’t just about scaling customer support, but scaling the entire customer experience. As a customer, you don’t care if you’re talking to marketing, sales or customer support, you just want what you want from the brand. We want to make that easy for customers, and easier for clients to deliver a consistent, enjoyable experience at scale.

Are you working on any new, exciting projects now? How do you think that might help people?

Yes! We have POCs running on no fewer than 6 projects right now. We are always working on something new!

Thank you for all that. Let’s now turn to the main focus of our discussion about Digital Transformation. For the benefit of our readers, can you help explain what exactly Digital Transformation means? On a practical level what does it look like to engage in a Digital Transformation?

Digital transformation is about creating new experiences using technology. Oftentimes, people think that Digital Transformation is taking something analog, and making it digital.

It might still be where you start, but it shouldn’t be where you end.

Here are 2 examples: a form and a customer support conversation.

So, let’s take a look at something as simple as a paper form. If you simply take that paper form, and you scan it, you benefit a little. It’s easier to store. It’s easier to share. It’s easier to recover if you lose it. Multiple people can look at the form at the same time. It’s a slightly better version of a paper file.

Where digital transformation really starts to get magical is if you use machine learning to extract data from your file. Now you are able to do some things you couldn’t do before with that same information. You can recognize earlier that a field has been missed. You can reuse the same information on the next form. You can segment. You can recommend. You can translate it into a new language. It’s suddenly moved beyond a form and into a tool that can have real value both for your business and for your customer.

Now let’s look at a customer interaction with your brand.

So in the first step, maybe you move this conversation over to live chat. Live chat allows your employees to interact with multiple people at once. They can copy and paste. They can serve people faster than the phone.

Now, let’s add some digital transformation magic and think about what you can automate. Those copy-pastes, a machine can handle those for you. A small team can now handle millions of inquiries. You can segment. Recommend. Adjust based on the type of customer, what you need them to do. And if you need to adjust it, you don’t need to train tens, hundreds or thousands of agents. You can update it once and you’ve got a new experience minutes later. It speaks 100+ languages. And you get real time feedback on how it’s doing. And if it can’t handle an inquiry, it can seamlessly connect an agent and the customer doesn’t need to repeat themselves.

Which companies can most benefit from a Digital Transformation?

I don’t think there is a company that can’t benefit from digital transformation. Every single business today is in danger of being disrupted digitally. The question isn’t if they’ll be disrupted, but how quickly and to what extent.

So let’s look at a few examples to understand. I’ll throw in some personal experiences for colour.

Example A: Retail

I’m an avid hiker. I’m also a woman. I’m also cheap and mostly buy on discount. This means I look like an easter egg in the wild, because about 95% of all unsold outdoor apparel on the clearance rack for women is pink, purple or yellow.

The reason this happens? A mix of sexism and analog systems. Most brands don’t connect directly with their customers. They connect with a retailer. The data on what sells and how doesn’t get back to the brands. Retail buying in the outdoor space is still dominated by men and the biases that go with that. They have bad data, and they haven’t invested in digital transformation to get better data and get closer to their customers through live chat. So they’ll continue producing too much pink and purple merchandise, and miss the broader market opportunity.

Example B: Services

Services seems like an area where digital transformation wouldn’t be so impactful. Afterall, your business is about one human delivering something to another.

So what can you do? You can make those humans more efficient with digital transformation. Let’s say you’re a dentist. You can digitize patient records to automate bookings. You can invest in machine learning imaging technology to recognize cavities. You can increase the number of patients you can see. You can increase the amount of time you spend with your patients to prevent churn.

Or you can be my dentist, who has done all of that, found out that I’m an SVP of Operations with a view over the budgeting plan and spend time showing me her cool toys so that I’ll increase our budget on dentistry and recommend her practice to all of my “AI-appreciating friends”.

Example C: Telco

Right before I joined Ada, I had an experience with my telco provider, Koodo.

I dropped my phone and my screen shattered in such a way that made me understand the term, “smithereens”. I had bought the phone myself, and started to look at purchasing a new phone. I wanted a new phone, and I wanted a deal. I also wanted to keep my existing plan and I’m very, very impatient.

I opened live chat with Rogers, Telus, Bell and Koodo, and I figured I’d get myself a true round robin competition for my business going. Except the experience with Koodo and Telus was different. While I was still waiting on hold for both Rogers and Bell, I already knew that for $15 a month, I could get a new phone, keep my outrageous plan I’d negotiated with Koodo and save myself some time. I signed up without talking to a human, stayed a Koodo customer, and have yet to have to call Koodo in the last 2.5 years since.

We’d love to hear about your experiences helping others with Digital Transformation. In your experience, how has Digital Transformation helped improve operations, processes and customer experiences? We’d love to hear some stories if possible.

Digital transformation starts with a decent business hypothesis. If only we could… And then you need a healthy dose of change management.

So let’s take a look at my very first job. I started off as perhaps the world’s worst executive assistant. The only thing I was good at was technology, so I leaned into that, and that’s how I became so focused on digital transformation: I was really bad at making coffee and scheduling. I thought my job was to make the executives more effective, and what I noticed was a lot of politics, pettiness and poor decision making.

At first, I thought my bosses were idiots, as any 20 something does surrounded by a bunch of boomers. But I realized I was wrong. My bosses weren’t idiots, they just had poor tooling. So I set about trying to add more tooling to their years of experience and qualitative experiences. I measured everything I could find. I took the existing digital processes and I figured out ways to modernize them without IT resources. I volunteered to help with anything and everything, trying to figure out how the business worked. I wrote queries. I had others write queries. I was scrappy and imaginative and I had a blast. I had the fervour that only a powerless 20 something has when faced with the opportunity to impact.

I wish I could tell you that I was super successful, and that I digitally transformed that business. I had some modest success. I was voted a top performer. My boss thought I was a “hacker”. But did I digitally transform that business? No. For a few years, I helped my executive team make better decisions, but most of my work died when I left. That job came back to me 10 years later with a proposal for digital transformation where we’d be a vendor that was strikingly similar to the one I’d written a few months before I’d left.

So where did I go wrong? I’d digitally transformed! I’d taken gut feels and turned them into data. But I hadn’t brought anyone along with me. I was an island of one, and I’d spent more time trying to make myself look smart and being indispensable than actually transforming the business. I needed to evangelize, and make what I was doing accessible. I needed to put the needs of the business ahead of my need to look smart.

So years later, hopefully a bit wiser, when I think about digital transformation, I focus on what I’m trying to achieve. What’s that “If only we could…” and I think about how to bring everyone else along. How to make it easy for everyone to participate in digital transformation. It’s not about me, it’s about the company. If I leave tomorrow, I want to feel like this place is different because I am here, but because I was there.

Has integrating Digital Transformation been a challenging process for some companies? What are the challenges? How do you help resolve them?

Yes. If it wasn’t, we’d all be there already. Digital transformation is applicable everywhere, but it’s not a silver bullet.

Digital transformation will not change the outcome if the original goal is wrong. I once had a mentee reach out asking for advice on how to use NLP to figure out if a goal was SMART or not, with the assumption that more SMART goals would improve performance. I asked if the data they had suggested that SMART goals had a significant impact on performance. They did not. It might have still been the right thing, but they could have gone through the entire digital transformation, and arrived at the conclusion that SMART goals had no correlation to performance.

In this scenario you spend a good amount of time refining your problem. If you can’t, maybe you still take the risk, but you parcel it off into small chunks to check in. Is my hypothesis worthwhile? Is this still worth doing?

Sometimes digital transformation’s results aren’t worth the effort you put in. If you have many types, you won’t have economies of scale. I once worked for a company that wanted to build software, but when we tried to classify intents, we had 67 types in 100 use cases, and the trend was to add more use cases. Digital transformation doesn’t make as much sense in this scenario because the effort to digitize for each type was greater than the reward from the digitization.

In this scenario, you focus. You choose the top 5 most typical use cases, and you focus your digital transformation there. You learn as you’re going, and you figure out if there’s enough value as you go along to continue to add new use cases.

And sometimes, you just don’t know. I have a friend who works at a major bank. We chatted about digital transformation, and I asked her what’s the hardest part. She told me a story about her first week, where she noticed a ticker machine in her otherwise modern office. “What does it do?” she asked. “No one knows. Everyone is too afraid to turn it off, so we just keep letting it run.” was the response.

Digitizing that requires the risk of unplugging that machine in the hopes that what you can achieve is greater than the risk you’re taking. You have to be willing to take those risks. If you don’t, someone else will. In the case of a bank, they might have more time because it’s a highly regulated industry. They have so much money, maybe they can just buy anything that threatens them. But eventually, the customer will ask them for more. The customer always asks for more.

Ok. Thank you. Here is the primary question of our discussion. Based on your experience and success, what are “Five Ways a Company Can Use Digital Transformation To Take It To The Next Level”? Please share a story or an example for each.

  1. Start with a hypothesis — Know what you’re trying to accomplish. Use step 2 to validate your hypothesis where you can. 
    I want more of my users to convert from free to paid.
  2. Measure — Measure everything. Data is the number one friend of digital transformation. Measure to confirm your assumptions. Measure to conflict with your assumptions.
    What percentage of my current users convert from free to paid? What are the characteristics of those that do convert? Of those that don’t? Which users that should have converted didn’t? Which users that shouldn’t have converted did? Where? Why?
    If you don’t have this data in an easy way, think about what data you do have. I once stacked all of the paper files we had and measured the average height of the paper files. I got the phone logs. I didn’t know what got said, but I could tell if the call was incoming, outgoing and for how long.
  3. Automate — If something is repetitive, a machine can likely do a better job than a human. Humans are not actually that great at repetitive tasks. Bored minds make mistakes. Automate to reduce error, increase efficiency and generally make your humans less bored. Can you automate client conversations? Automate who an upsell talks to based on data? Automate a follow up? Can you automate the personalization of those free users?
  4. Augment — Use your humans wisely. Give your teams digital tools that augment their abilities.
    Can you use tools to support your teams to better answer sales questions? Can you give them dynamic pricing? Can you automate the “speak to a manager” to give them that autonomy?
  5. Predict — Use data, automation and augmentation to predict what your customers will do and want. They change their minds so often. What if you knew what they wanted before they did?
    Can you predict when a customer is considering upgrading based on behaviour? Can you predict which customers are more likely to churn? To stay?

In your opinion, how can companies best create a “culture of innovation” in order to create new competitive advantages?

This one might be the shortest answer for me. Assume that you can do anything, and add some sandboxes to make sure you don’t burn the barn down.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Don’t complain to people who agree with you, complain to the people who will change it with you.

Everyone vents. I want to work with the people who want to make the change they need.

How can our readers further follow your work?

Follow Ada. We’re doing great things!

Thank you so much for sharing these important insights. We wish you continued success and good health!

You might also like...

Community//

Cody Miles of ‘Ashore’: “Automate menial and repetitive tasks”

by Jason Hartman
Community//

Seth Lively of PA Consulting: “Automate your processes”

by Jason Hartman
Community//

Bruce Orcutt of ABBYY: “GROWTH OF PROCESS INTELLIGENCE”

by Phil La Duke
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.