O'Connor Family Law case study: why the CEO invested
O'Connor Family Law serves families across Massachusetts through divorce, custody, and other family law matters. Heather O'Connor, its CEO and founding attorney, describes the firm's billing philosophy simply: "We always err on the side of caution. If we're not completely sure, we'd rather underbill than risk overcharging a client."
That value system has a cost. Her attorneys are pulled in a hundred directions at once, responding to a client's urgent text, reviewing a document from opposing counsel, drafting a custody agreement, and then struggle to reconstruct the day later. As she told us in our first conversation: "I know my team delivers exceptional value, but when we're jumping between urgent matters all day, those quick emails and five-minute phone calls can easily slip through the cracks."
She had tried this category before
O'Connor liked the concept of automated timekeeping and had tried it before Ajax. The execution disappointed: her team found the earlier tool took more time to review and adjust entries than tracking time manually. So she came into the Ajax pilot cautiously optimistic and half-expecting it to be too good to be true.
What she noticed within days was silence. No complaints, no pushback. "This is the first technology I've brought to my team where zero people complained." Even the attorneys who historically resisted change became fans.
The most surprising discovery was about her own habits. Looking at her Ajax dashboard during the pilot, she found 11 billable entries she had forgotten doing entirely, work that would have gone unbilled because it never made it out of her memory.
The pilot numbers
Measure | Result |
|---|---|
Additional billable time captured per user, per day | $162 |
Extra revenue recorded monthly, nine-person pilot group | $30,000+ |
Team ratings across five categories | Mostly 9s and 10s |
Even the firm's most meticulous timekeepers found significant missing time. The lowest score in the firm's internal survey was a single 7, from the most meticulous timekeeper, on the prompt asking whether Ajax caught work they would not have otherwise tracked.
Then she invested
When Ajax opened a round to customers, O'Connor put her own money in. Her reasoning, in her words: "For me, investing wasn't about taking a chance on unproven technology. It was about backing a solution I'd already validated with my own practice - one that pays for itself many times over every month."
She is one of several Ajax customers who became investors after running the product inside their own firms.
Frequently asked questions
Does Ajax fit a firm that deliberately underbills? Especially well. Ajax does not inflate anything; it documents work that actually happened, so a cautious firm can bill accurately instead of rounding down out of uncertainty.
What if my team resists new technology? O'Connor's team had already rejected one automated timekeeping tool. Ajax was the first rollout with zero complaints, because it asks nothing of the user: entries draft in the background and each person reviews their own.
How fast do results show? Her pilot surfaced $162 per user per day, measured within the pilot itself. Here is what to expect from an Ajax pilot week by week.
If your firm underbills out of caution, book a demo and see what accurate looks like.
