A conversation with Kara Wilson Oliver, VP of People & Operations at DealMaker
About DealMaker: A Fintech Company Scaling Talent and Performance Management
When DealMaker scaled past 120 employees, it was time to upgrade its spreadsheet-based review process. Calibration meetings consumed hours of leadership time, and the information leaders had to work with was incomplete. The system tracked outcomes like sales and project delivery, but not behaviors such as adaptability and tenacity. By adopting Incompass Labs, DealMaker introduced a system that was quick to implement, gave leaders broader behavioral data to work with, and streamlined calibration into a more efficient process.
DealMaker built its early review system in Google Sheets, with a lightweight 360 process layered on top. For a smaller team, it worked. As headcount rose, tracking performance across dozens of employees became cumbersome and calibration sessions exposed the approach’s weaknesses. Leaders were often forced to rely on recent memory or the most vocal voices in the room rather than a consistent, statistically defensible dataset.
“You get 16 people in a room, a giant spreadsheet, and exhaustion sets in. Our brains could only remember the last few people, and the process didn’t feel statistically significant.”
The bigger issue was what the system left out. Sales numbers and project deadlines captured outcomes, but they didn’t reflect the qualities DealMaker saw as predictors of long-term success: adaptability and tenacity. While managers tried to uncover these traits during hiring, yet there was no reliable way to measure them in everyday performance conversations.
“Performance management is non-negotiable. It’s the founding layer for HR to prove itself as a business function.”
- Kara Wilson Oliver
Rather than accept an HRIS module that lacked calibration capabilities, DealMaker adopted Incompass Labs to move calibration out of the back room and into the workflow. The platform widened who could give feedback, weighted that feedback by expertise, and used machine learning to detect and correct rater bias in real time. Together, these changes broadened the dataset and moved calibration from a post-cycle reconstruction into a live, evidence-based activity.
That change flipped the power dynamics of calibration. Anyone could give anonymous feedback, which broadened the data set; the system could detect whether a rater was conservative or generous and nudge them; and feedback from recognized experts in a particular domain carried more weight. For example, if two people comment on the CEO’s communication and one is rated by the crowd as an expert in communication, that person’s assessment should matter more.
Crucially, adoption didn’t require heavy training. Kara’s team needed a solution people would “just get,” and Incompass proved intuitive in practice. Managers began using the system without lengthy rollouts, and early feedback described the platform as straightforward and helpful in producing clearer reviews.
“We’re not a company that spends a lot of time on training, so I needed a system people could just get. Incompass delivered on that - it was intuitive from day one, and people immediately saw the value.”
With Incompass, DealMaker was able to:
With calibration embedded in the system, leaders stopped rebuilding assessments in long post-cycle meetings. Instead of spending hours in exhausting calibration meetings, managers worked with pre-calibrated data that had already taken into account crowd feedback and rater tendencies. The platform “takes the weight off of the post cycle calibration and moves it live,” Kara said, freeing people to focus on the 20% of cases that actually need human judgment.
The system also forced managers to make distinctions they previously avoided. Where legacy tools allowed the same score to be given to many people, Incompass required finer gradations — a tenth of a point here or there — which turned blanket ratings into real, defensible rankings. That subtle pressure to specify differences reduced the post-cycle grunt work and made the final calibration conversation more strategic.
“Even the skeptics realized this was a better way. We actually got kudos from people who don’t normally give kudos. That never happens. The weight of the work had already been done - we didn’t have to burn mental energy on the basics.”
For DealMaker, the move to Incompass Labs wasn’t an incremental upgrade — it was a change in how the organization treated talent decisions. Rather than letting calibration be a time-consuming, memory-dependent ritual, DealMaker now operates with live, evidence-based assessments that scale. That shift protects trust, surfaces the behaviors the company values, and strengthens HR’s role as a business partner making high-stakes people decisions.
As Kara put it, performance management isn’t a side task: it has “the highest cost implications,” and getting it right enables leaders to make clearer, fairer decisions — and to spend their energy where human judgment matters most.
“Performance management is the most expensive thing we do. Getting it wrong undermines trust and engagement. Getting it right changes everything,”
With Incompass, DealMaker turned performance reviews from a time-consuming process into a competitive advantage: faster, fairer, and built to scale.
Curious to see how Incompass can help you? Schedule your demo today.
