Woodruff Sawyer

Woodruff Sawyer is one of the largest insurance brokerage and consulting firms in the U.S., serving more than 4,000 companies from 15 offices across the country.

  • Industry: Insurance
  • Size: 19 Quickskill Assistants

Core Processes We Started With

Calendar Management

Travel Management

Expense Management

Salesforce Management

The Problem

Merely holding on, overwhelmed by a bunch of tiny tasks.

Historically, the company assumed employees would complete all their many administrative tasks themselves, such as scheduling, expense reports, CRM updates, research, and their own travel arrangements. When CEO Andy Barrengos joined the company in 2016, he set in motion a series of important shifts across the organization, with an emphasis on growth. Among the implications, that meant boosting efficiency and productivity by providing support to the company’s producers and executives.

The Goal

Producers wanted to spend more time with clients and prospects, and less time on process-oriented administrative tasks – but they didn’t want or need full time support or in-house staff.

Our Solution

Starting with a pilot project with three Quickskill assistants, Woodruff Sawyer quickly began to see leverage within the team. Phase two of the rollout expanded the service to other top producers as well as sales operations. Within 18 short months, the company has tapped the talent of 19 Quickskill assistants, supporting sales and operations executives across the U.S.

The key to the rollout’s success, says Tom Batchelder, a sales productivity leader for the company, was to start small and slow and to focus on increasing efficiency and productivity from there.

Quickskill has been a game changer for Woodruff Sawyer, freeing hours each day for the company’s top producers and executives. Tasks don’t slip through the cracks, and they have gained back the bandwidth to focus on more value-added work for their clients.

Clark Morton, partner and senior vice president, and Jeff Fenigstein, head of marketing and sales operations, discuss the impact Quickskill has had on the team’s efficiency when Quickskill assistants took ownership of the following tasks.

Calendar Management

Coordinating schedules was one of the biggest challenges at Woodruff Sawyer before Quickskill.

“I spent my days herding cats,” says Clark Morton. “I might need to coordinate with two, three, four, five people from Woodruff Sawyer and several people from the client side. It was a huge time commitment and royal pain. Now I just let the Quickskill assistants coordinate it all.”

Expense Management

Busy schedules left many salespeople and executives struggling to keep up with expense reporting.

“It got to a point where I had to ask my wife to help me with my expense reports because it was just too much for me to do,” says Morton. “Now, I just flip a quick note to my Quickskill assistant Mary Ann, and she takes care of it.”

Travel Management

The planning involved with frequent travel ate up way too much time that could have been spent closing business.

“I was spending too much time making travel arrangements, comparing hotels and flights, and booking everything. Now, I just give parameters to my assistant. She knows what airlines I fly, airports to use, and my hotel preferences, so she can book my travel without much input on my part,” says Morton.

Salesforce Management

Quickskill assistants also play the role of a sales assistant. They drive research, list building, campaigns, Salesforce data management and reporting, ensuring contacts are up-to-date, cleaning up inaccuracies, creating new contacts and opportunities, event support, and even relationship management.

“We can rely on our Quickskill assistants’ expertise in Salesforce. We’re confident that they know what they’re doing and it takes the burden off of the sales team,” says Jeff Fenigstein, head of marketing and sales operations, adding that he credits Quickskill with helping them maximize their investment in Salesforce.


Within 18 months, the company tapped the talent of 19 Quickskill assistants, supporting sales and operations executives across the U.S.

Quickskill assistants provide more than one thousand hours of “productive time” each month back to the firm’s top producers, allowing them to focus more on clients, prospects and the business.

Quickskill helps the Woodruff Sawyer producers and the ops teams maximize their investment in Salesforce by inputting all data / interactions based on company standards and keeping reports upto-date.

All expense reports are now accurate and submitted on a timely basis since busy producers and executives no longer have to worry about them.

Executives leverage their assistants for many admin and sales support tasks, such as inbox management, prospect research, note taking, social media, and helping them become more efficient and organized.

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