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Coffee With Kelly Gaskin of Workday

Before it became one of the biggest names in cloud-based HR and finance, Workday was a startup competing against industry giants – and Kelly Gaskin was there, pushing the then-fledging company toward success. Now an Implementation Strategy Director, we recently caught up with Kelly over a virtual coffee to talk about her background, get some professional advice and discuss The National, her favorite band.

Tell us about what you do.

I’m currently a leader in the Workforce Management space with a focus on our global payroll offerings. Most recently, I spent a lot of time traveling to London, helping bring our U.K. payroll to market and supporting our largest U.K. payroll deployment. I initially went to school to become a CPA, which really prepared me well for this payroll-centric role. This enabled me to easily cross-over and support our Workday Financial solution while also supporting our ecosystem and customers throughout the entire Workday platform. It’s so exciting to see our customers harness the power of one and solve for the most super complex business requirements; truly realizing the value of Workday from HCM, to Payroll, to Financials.

What is your favorite part of your role?

I love helping others and solving problems. I’ve learned that the problem as presented is rarely ever the actual issue at hand. There are multiple layers to it, and I enjoy discovery and completing the root cause analysis to identify the real issue that needs resolve.

I also love making a difference. Be it supporting our product management and adding value to our features; or creating a better experience for our customers. Back in the heyday of PeopleSoft you had separate functional and technical architects. In the SaaS space they’re one and the same. It’s critical you have the ability to marry the two and be both technical and functional.  You need to understand the business requirement and know how to architect the solution within the product to provide the best customer experience.

Talk about a big challenge you had to navigate at Workday.

No attention is paid to payroll when everything is going well, but when it doesn’t, the underlying complexities come to light.  There was once a customer set to go live April 1. A week before go-live they realized there was a significant error with payroll history/prior taxable wages. We had to quickly pivot, correct, and recover.  It required teamwork & sacrifice in working over Easter weekend.

In another case, we had a customer set to go live July 1, and there were concerns about losing critical weeks within the project timeline. One recommendation was to go live mid-quarter, but that added effort, complexity and a lot of risk, especially around accurate W-2s.   My deep background in payroll allowed me to quickly suggest pushing that July pay date back a couple  days into June. This was an easy decision for the customer.   Super simple solution that saved a lot of time and effort.

Are you often able to transfer those learnings between clients?

Yes, because we see similar challenges in how certain issues are approached across our customer base. There’s this YouTube clip I like to reference sometimes in these challenging situations, in which a mother tells her 2-year old not to try the baking cocoa because it’s not sweet and they’ll be disappointed if they’re expecting it to taste like NesQuik – which can be a hard point to make, since the two look the same.

During projects, our customers sometimes experience these “cocoa moments,” meaning they can continue with their desired approach, although Workday may suggest differently. I’d like them to benefit from our experience and our advisory.  Conversations three or six months down the line are always more difficult, as there is likely some level of rework needed.  

It’s so important to balance a best-of-breed configurable Workday approach with extensively customized legacy solution and processes. I’ve realized that what constitutes “best practice” (and I always think those words should be placed within quotes!) for one organization might not be the same for another. You really have to understand the unique dynamics of each customer.

Making a project work is kind of like finding the right car for a buyer. There are often trade-offs to going down any particular route, just as there are with a vehicle that has a nice UI but isn’t very fuel-efficient. Each customer will vary in what trade-offs they will accept, what budget they have available and what priorities they’ve set for the project. You have to work within the defined principles for the project.

A customer coming off PeopleSoft for example has a lot of historical pay slips. It’s not efficient to store those PDFs within Workday, so a solution like CIC Plus is something they would want to seriously consider. It simplifies access for terminated workers and is an overall better solution for historical data storage.

How do you judge success in your role?

Is our customer happy?  Do they believe like they made the right decision in selecting Workday?  Do we add value to their business?   Did I add value to their project?

And what’s the secret to your success?

Hard work, determination and grit. My fearlessness certainly helped, too, since I joined Workday in 2008, we were deploying payroll customers number 1 & 2.  I was building a house and had three kids whose college education needed funding. Knowing Dave Duffield and Aneel Bhursi were leading the charge of course reduced my anxiety, but it was still a big move to go from my previous role at Hewitt directly to a startup. I remember sending my resume from a hotel room on a Friday before Memorial Day, right before my daughter participated in an Irish dancing competition that weekend, and feeling confident that Workday was going to be a big game changer in the industry and knowing that I wanted to help make it happen.

Has a lot changed over the years in how you approach customers at Workday?

No, not at all, and that’s what I love about Workday – it’s always been an incredible group of people who are very customer-centric. There have been some surprises and changes along the way, in part because I never had a defined career path, I just went where I was needed most. I didn’t set milestones like “I need to be X by the time I’m 25” but instead focused on doing work I felt good about and being recognized for it.

What trends have you seen in the industry the last five years, and where do you see it going in the future?

Cloud solutions are becoming the norm, and that trend is going to continue as Zoomers enter the workforce.  They expect a consumer-like experience. The youngest have grown up with devices like iPads, and now expect that level of streamlined, on-demand consumer experience in every context.

We’re already seeing that in the rise of daily pay, which might become a key competitive advantage for firms offering it to their employees. If at 25 I had asked my boss to get paid every day I would probably have been laughed out of the room, but now it’s a realistic way to acquire and retain talent.  Software providers will be expected to respond with the right solutions and to help customers manage their workforce more effectively, again with the consumer type experience.

What advice would you give to others in the industry?

Learn what you like to do and throw yourself into it. Finding groups like the APA, which can provide the support you need and help build your network, makes it easier to have a rewarding career, too. Also don’t forget where you came from, and to thank the people who supported you and helped your growth.

If you could have dinner with three people who would you choose?

  • Lori Lightfoot, Mayor of Chicago – She’s a Chicagoan through and through, she’s direct, real, and adds a flair of humor in her humility & leadership.
  • John Gallagher, former Honeywell CFO – One of the smartest leaders I know. He was tough but very fair.  He measured and rewarded effort; and taught me it’s okay to challenge when it’s the right thing for the company. 
  • Aaron Dessner, guitar, piano, keyboards and contributing songwriter of The National – I’d love to learn about his process for putting together their setlists and lobby for a few of my favorites too.

If You weren’t at Workday, what would be your ideal job?

Something that really helps make a difference in people’s lives and represents what comes after Workday. So maybe that looks like an onboarding program for non-traditional candidates, one that combines training folks in operational functions like accounting and payroll and then builds that with the technical architecture of Workday solution. Marrying the functional with technical, filling a resource demand, and improving lives.

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