About Underscore VC

Underscore VC is an early-stage, Boston-based venture capital firm backing bold entrepreneurs with an aligned community designed to fit each startup’s unique needs.  

Core Processes We Started With

Calendar + Expense Management

Proactive Daily Schedules

Financial Data Management

The Problem

Need assistance without the hassle of turnover

James Orsillo is Partner and Chief Financial and Operating Officer at Underscore VC, and executive support is one of his responsibilities. When James contacted Quickskill, Underscore had one assistant supporting six executives. While James knew they needed to add support he was wary of hiring and training new executive assistants only to have them quit. 

“We had gone through some of the pain of hiring and training people and they leave, and you start over,” he said. “The executive assistant was a high turnover position in every company I have worked at, and I saw Quickskill’s model as a way to avoid that.” 

The bottom line: “We want to make sure that everyone has adequate resources without adding more management overhead, and a solution that could grow and flex to our exact needs,” James said. “Quickskill’s managed service model gives us a lot of options to tailor administrative services for different executives and can grow with us.” 

The Goal

Accelerate adding executive assistants without the cost and disruption of hiring, training, and frequent turnover. 

Our Solution

Seamless Admin Support

Underscore started with two Quickskill Productivity Assistants (PAs) to schedule executive meetings, coordinate travel and file expenses for two partners. “One of the partners told me how much value the PAs were adding beyond calendar and expense management, doing project work too, so we expanded from there and brought a PA in to support myself too.”  

“There are a bunch of things that are important, and there are things that you need me to do, like wire money” James said. “But I’m not the only person that can send an email to someone to schedule an important meeting.” 

Core Processes 

Calendar and Expense Management

Underscore executives use an assortment of codes for types of meetings, priority levels, how soon it needs to be scheduled, and how long the meeting should be, and theQuickskill PAs learned the codes quickly and ran with the system. PAs also prepare expense reports for executives to save the time it takes to find and copy receipts and enter line items and billing codes. 

Data Management for Budgets and Fund Allocations 

James developed custom processes for uploading financial data for budgets and fund allocation that required the PA to fill out forms, get signatures, and closeout workflows. “This was something new and different and my PA took it and ran with it,” James said. 

Daily Schedules

PAs compile schedules for the next day’s meetings for executives and send them at the end of the previous days so the executives always know what the next day will bring.


“People were so used to doing administrative tasks themselves, we initially had to train ourselves to delegate to the PAs,” James said. “But now that they’ve seen their productivity rise, the value is clear.” 

“We all like that the service is seamless, we don’t have to worry about what the assistants are doing or if they are out of the office because there’s a backup and a team that is managing everything in the background. There’s also huge value in the flexibility to add resources when workloads grow.” 

Getting to “seamless” support took time. “You can’t expect any human to read your mind,” James said. “I had to spend some time creating a cadence for how frequently you check in, a set of objectives for what you need to learn and train on, and then follow up. Once I did that, the service became a lifesaver.”  

Quickskill supports eight Underscore executives, while all include calendar and expense management, the service is tailored to each executive’s preferences and includes travel planning, email organization, and custom workflows. 

“I’m doing the things that only I can do and I’m not doing things that I could train somebody else to do,” James said. “That makes my life so much easier.” 

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