How WSS Took Timekeeping from the Flintstones to the Jetsons with PointOne

CUSTOMER

Founded in 1993, Winget, Spadafora & Schwartzberg, LLP is a nationally recognized litigation firm operating across 10 offices. WSS represents leading insurance companies and financial institutions, as well as businesses, nonprofit organizations and professionals.

PRACTICE MANAGEMENT SYSTEM

SurePoint

TIMEKEEPING BEFORE POINTONE

SurePoint

FIRM SIZE

50-100

WEBSITE

https://wssllp.com/ 

Choosing a first AI use case people would actually want

When WSS began exploring its first AI product, Co-Managing Partner Benjamin Biard did not start with the flashiest use case. He began with a problem nearly every lawyer shares, one he was candid enough to admit he had not solved himself.

“Entering time contemporaneously has always been a challenge for me.”

Biard was co-managing the firm, leading its Florida office, and carrying an active caseload. On a typical day, 500 to 1,000 emails could pass through his inbox because he remained copied on the work moving through the office. 

By the end of the day, finding another 30 to 45 minutes to reconstruct every call, skim through all the emails, and write time entries felt like a second job.

He knew he was not alone. Everyone hates timekeeping.

Evaluating technology like the person who would use it

Biard followed the AI timekeeping market and evaluated several platforms. He looked for an advanced software, but sophistication alone was not enough. The product had to truly understand and address the reality of a lawyer’s day: constant context switching, an overflowing inbox, and no appetite for another tool that demanded neverending attention.

Initially, PointOne’s capture depth stood out. It could account for activity across both received and sent emails, along with connected applications, to create a more complete record of the work behind a matter. Retro Capture helped Biard reconstruct earlier uncaptured periods, while automatic entries were then drafted going forward.

However, one categorical differentiation made the difference. Certain products required users to pause capture whenever they moved to nonbillable activity, but Biard knew exactly how that would end.

“I’m never going to remember to hit a pause button.”

With PointOne, all time capture occurs passively, as work happens. He could exclude a news site, personal email address or another category once, then keep working normally without having to filter through those non-billable time entries at the end of the day. The rule stayed in place without interrupting his day again. Attorneys can shape the output through their own rules, filters and minimum-activity settings rather than conforming to one rigid workflow.

PointOne’s integration with SurePoint LMS Cloud, paired with its connection with Microsoft Outlook, SharePoint, and NetDocuments, also allowed the firm to introduce automated timekeeping without replacing any of its current systems.

That combination—advanced capture, practical controls, and an easy integration into the firm’s existing environment—made PointOne the strongest contender.

Learning the workflow before asking anyone else to change

Biard knew that success would partially rely on internal champions that people would listen to. A small group, including himself, used PointOne before onboarding the initial cohort of lawyers. Throughout the first week, they defined preferences, corrected suggestions and taught the platform how they worked. PointOne quickly picked up on each attorney’s work patterns. Soon after, the daily exercise of retracing emails, documents, and calls began to disappear.

For Biard and the early users, that meant recovering the 30 to 45 minutes per day they had routinely spent reconstructing their time.

Being the first to adopt was important to him. The choice reflected lessons from technology rollouts he had seen at other firms, where he had personally experienced unprompted firm-wide mandates of new tools that triggered immediate resistance. The message attorneys heard was simple: leadership had chosen another tool, and now everyone had to adapt. 

By learning how to use and customize PointOne’s workflow, he could pass on personal tips as someone who knows exactly how WSS attorneys operate.

Building a cohort that represented the whole firm

For the first broader cohort, Biard resisted the temptation to choose 15 technology enthusiasts. He wanted to truly put PointOne to the test. This involved a mix of attorneys who entered time consistently and attorneys who struggled with it, people who embraced new technology, and people who approached it cautiously.

He also understood that not everyone experiences technology in the same way. He remembered helping a family member who would call because her phone or computer had “broken,” when what she really needed was someone patient enough to walk through the same steps again.

It reminded him that a rollout designed only for confident users is not a successful rollout. The people most likely to need support had to be included from the beginning, while there was still time to learn from them.

That decision produced credible internal advocates from very different starting points. Attorneys who had struggled most with manual timekeeping were among the quickest to see PointOne’s value. Technology-oriented users adopted it readily as well.

Their shared experience gave WSS proof that the platform could work across different habits and levels of technical confidence.

Letting colleagues build the case

Biard then used the firm’s existing experiences to make the rollout transparent, providing a space for early users to share firsthand learnings. Lawyers saw their own people test, challenge, and benefit from PointOne. WSS built support around demonstrated value.

“On average, our attorneys are capturing 5 to 10% more billable hours with PointOne.”

Seeing the work as well as capturing it

PointOne now does more for Biard than reduce the burden of entering time. Its Intelligence view condenses thousands of time entries into an easy-to-navigate picture of where his time is spent across cases, clients, and firm responsibilities.

He can look back at a month and see which matters he dedicated his time to—something that was difficult to discern when the evidence was scattered across the platforms he uses everyday. That visibility is crucial for a Managing Partner whose time is split between practicing law and running a firm. 

“In July, when I was in trial for two weeks, PointOne captured 265 hours of my work. Reviewing the output gives me a clear understanding of where my time was being allocated, including time spent in trial that month to better understand the responsibilities that were handled while in the midst of a two week trial.”

A practical playbook for firmwide AI adoption

WSS’s experience offers a useful lesson for managing partners deciding where to begin with AI. The best first use case does not have to be the most uprooting one. It should solve a problem people already feel, produce value they can immediately recognize, and give the firm a reason to believe the next change can work too.

Biard made that lesson real by going first. He chose a problem he understood personally, learned the workflow before asking others to adopt it, included both advocates and skeptics, and let their experience carry the story across the firm.

It gave WSS a human approach to introducing AI: start with trust, prove the value in daily work, and bring people with you.

When asked to describe the change, Biard put it simply:

“Before PointOne, timekeeping was painful. Now it’s easy.”