When we asked attendees at the start of our September webinar about their biggest challenge in managing a flexible workforce, one answer came out on top: reporting and workforce visibility.
In What Breaks When Flexible Workers Are Managed With Disconnected Systems, we sat down with Diane Padilla, a former AVP at a global consumer enterprise brand and, importantly, someone who experienced that challenge firsthand. She ran a flexible workforce of more than 6,000 people, and that number climbed higher every holiday season.
Joined by AllWork’s CEO, Glenn Laumeister, and moderated by AllWork’s VP of Marketing, Laura Dutile, Diane walked us through the whole journey. She covered the cracks in a patched-together system, the business case she built for leadership, the pilot, and the results years later.
Here’s a line from the session that particularly stuck with us:
“The success of a system—it’s corporate, it’s the software, but it’s also your users.”
Diane’s team had worked with the same payroll partner for more than 10 years, and the contract had never gone out to a competitive bid. About 90% of the workers were W-2, and 10% were 1099. Nearly everything else ran on Excel, from budgeting to scheduling to time and attendance, handled brand by brand and manager by manager.
That setup sufficed while the program was small. But as it grew to thousands of retail locations nationwide, managers were often in different states from the stores their teams worked in.
“Not one thing was broken,” Diane explained. The problem was the gaps between systems that weren’t connecting, “and that’s where things really started to fall apart.”
A compliance audit brought those gaps into focus. It showed that workers weren’t always being paid correctly for the time they spent completing state-mandated trainings, and completion records were inaccurate. In addition, store location numbers were entered by hand and didn’t match across systems, so sales teams and leadership couldn’t trust the data. Lastly, payroll fixes sometimes took weeks, and vendor response times slowed after support moved offshore.
The team first tried layering a scheduling tool from their existing vendor on top of its payroll. But the promised budget integrations never materialized, and the team lost six months of time and resources before stopping the project. Luckily, it never reached the field.
To make the case for change, Diane built a package that showed leadership exactly what wasn’t working. It included:
Then came the vision: one place and one source of truth, where leadership could pull numbers at any time “and trust that those numbers were correct,” she said.
Importantly, Diane brought HR, finance, sales, and the field teams into those conversations. After approval, the team held weekly status calls with leadership for the first six months.
“We obviously didn’t want this to be a gut call,” Diane said.
Before looking at vendors, the team set clear targets: a 60% reduction in manager time and 98–99% reporting accuracy, all in one system. They then scored several types of options against those targets:
In the end, said Diane, AllWork scored highest across the board. She pointed to built-in scheduling, mobile tools, dashboards for both managers and talent, and one login.
“You go in. Everything is right there for you,” she said.
Just as important was who sat in on the scoring. Along with corporate, leadership, and finance, Diane brought in the account executives and managers who would use the platform every day.
“They’re the ones putting this data in,” she explained. “They’re the ones who have to adopt this.”
That group came with a list of about 20 scheduling and timesheet scenarios, Glenn recalled. AllWork could handle 19 of them, and the generic tools could handle about four. The team then built the 20th.
Glenn’s advice for anyone evaluating options is to ask who owns the software, who builds it, who modifies it, and who controls the code. When several providers pass data back and forth, he said, “you’re probably not going to get that one clean data set.”
Instead of switching everyone at once, Diane’s team ran a three-month pilot in early 2023. It covered:
The team deliberately included managers who were quick to adopt new tools alongside some who were “a little technology-shy.”
The pilot also meant listening to the talent.
“Changing a payroll provider for talent is very scary to them,” Diane pointed out. “It’s their paycheck.”
Workers’ biggest concern was GPS verification—they didn’t want to feel tracked. Diane’s team reassured them that location is captured only when they clock in and clock out. They also explained what’s in it for the workers: accurate pay for all the time they work, with breaks recorded automatically.
The pilot hit both targets: 60% time-savings for managers and 99% reporting accuracy. It also created a group of managers who became advocates for every region that followed. Only two pilot participants initially refused the mobile app over privacy concerns, but both came around within three months, Diane noted.
According to Glenn, the cracks usually show up first in two places.
Reporting: Reports are inaccurate, they’re missing data, they’re slow to run, or they’re out of date. The root cause usually sits further upstream, with several systems capturing data that either syncs poorly or not at all.
Payment issues: Workers call in about late paychecks, missed overtime, or breaks deducted incorrectly. Manual uploads of payment data to a payroll provider are a common source of delays and errors.
“When you see it in those two places, it’s kind of a systemic problem,” Glenn said. “It’s not like a one-off.”
The full launch went live Oct. 1, 2023, across seven brands, 250 managers, and 9,100 flexible workers, just ahead of the Q4 retail peak.
Preparation started early that summer. The team sent a launch packet and FAQs, held office hours, shared weekly previews, and rolled out brand by brand across August and September. Onboarding was redesigned during the pilot to cut down on paperwork, which helped when thousands of workers needed to start within weeks.
Once the platform was live, other teams asked for access too. Finance wanted the reporting suite, and the user count grew to 375.
Two years on, Diane described one connected platform in place of “a patchwork of manuals and spreadsheets.” She shared these results:
Importantly, the app also gave the brand a direct line to its field talent. Workers now share photos and notes from their shifts. Training can go out on the spot, so a rep can read a one-page product brief right after clocking in instead of waiting for training a couple times a year.
In turn, feedback from the field kept improving the platform. Glenn noted that new features typically took about 60 days, configuration changes about two weeks, and bug fixes a couple of days.
“It wasn’t just about software,” Diane said. “It was about how our workforce interacted with this software.”
How long did it take to get leadership approval? About a year and a half, Diane said, counting the attempt to make the original vendor’s tools work. Proposing a pilot helped leadership move faster because they could see clear results before committing to a full change.
How long did implementation take? About six months, including the pilot, Glenn said, with the full rollout taking about three months.
We have a small field team today. What should we do now to avoid pain later once we expand? Don’t wait for something to break, Glenn advised. He recommended choosing a platform that can grow in both size and complexity. Diane added that time-savings and a stronger connection with workers matter at any size.
How do you avoid reporting overload? Start with the top five reports you need to run the business, and automate them, Glenn said. Ad hoc analysis can come from a BI analyst, and AllWork’s customer success team builds a reporting package around what each team needs.
Want to see what one connected system looks like for your flexible workforce? Schedule a demo of the AllWork platform.
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